Why I'm Investing in Structured Data (And Why You Should Care About Schema Markup)

This week, I took a hard look at the structured data on my website. Not because I'm chasing some technical SEO checklist, but because I realized something important: if I don't tell search engines who I am, they'll figure it out on their own. And when there are two other people with my exact name competing for the same search results, I can't afford to leave that interpretation up to chance.

Structured data, specifically schema markup, is how you give search engines the context they need to understand your identity. It's not about gaming the system. It's about clarity. When someone searches for Kenny Kane, I want Google to know exactly which one I am. The CEO and author in Austin, not the comedian in Los Angeles or the rapper in Memphis.

The Problem with Ambiguity

Search engines are good at making educated guesses, but they're not perfect. When you share a name with other public figures, those guesses can go sideways fast. Without structured data, Google has to infer who you are based on scattered signals across the web. Sometimes it gets it right. Sometimes it mixes you up with someone else. And sometimes it just shrugs and shows a little bit of everyone.

That's what was happening to me. My site had basic schema markup, which is better than nothing, but it wasn't doing enough to differentiate me. It listed my roles and my books, but it didn't emphasize the things that make me distinct. My location. My career timeline. My specific affiliations with organizations that have their own authority and recognition.

The more I thought about it, the more I realized that structured data isn't just a technical nicety. It's a strategic asset. It's how you control the narrative before someone even clicks on your site.

What Structured Data Actually Does

Schema markup is a language that search engines understand natively. It's a way of saying, "Here's who I am, here's what I do, here's where I'm based, and here's how I'm connected to these other entities you already recognize." When you implement it properly, you're not just optimizing for search. You're building a knowledge graph that connects you to the rest of the web in a structured, verifiable way.

For me, that means connecting my name to Firmspace, the Testicular Cancer Foundation, and Gryt Health. It means linking my author profile to my books on Amazon and Goodreads. It means specifying that I'm based in Austin, Texas, which immediately sets me apart from the other Kenny Kanes. And eventually, when I have a Wikipedia page, it means linking that page directly into my schema so Google knows it's the authoritative source.

This isn't about vanity. It's about precision. When someone searches for me, I want the results to reflect the work I've actually done, not a blended average of three different people.

Why Location Matters More Than You Think

One of the simplest but most powerful additions I'm making to my schema is geographic information. Adding Austin, Texas as my home location seems almost too obvious, but it's one of the strongest differentiators I have. The comedian is in Los Angeles. The musician is in Memphis. I'm in Austin. That single data point cuts through a lot of confusion.

Location isn't just a detail. It's context. It tells search engines where I operate, what markets I'm connected to, and what communities I'm part of. It also helps with local search, which matters more than people realize. When someone searches for "Kenny Kane Austin" or "Austin CEO," I want to show up. And I want to show up as the definitive result, not as one of several possibilities.

Geographic data also supports other parts of my digital strategy. If I'm speaking at an event in Austin, writing about the Austin tech scene, or getting covered by local media, that location context reinforces the connection. It's one more signal that tells search engines, "This is the Kenny Kane who's based here, who works in these industries, and who's connected to these organizations."

The Role of Disambiguation

There's a specific schema property called "disambiguating description" that I'm adding to my markup. It's exactly what it sounds like: a short statement that clarifies who you are when your name might be confused with someone else's. For me, that description is simple. "American business executive, CEO of Firmspace and Testicular Cancer Foundation, author of The Accidental Nonprofiteer."

That one sentence does a lot of work. It immediately distinguishes me from the comedian and the musician. It highlights my primary roles and my most recognizable credential. And it gives search engines a clear, structured way to categorize me when they're building knowledge panels or answering queries.

Disambiguation isn't just for people with common names. It's for anyone whose identity might overlap with someone else's in search results. If you're in a crowded field, or if your work spans multiple industries, disambiguation helps search engines understand which version of you to show in which context.

Connecting to Authority

One of the most valuable things structured data does is connect you to entities that already have authority in Google's knowledge graph. For me, that means linking to Firmspace, which has its own Wikipedia page. It means linking to the Testicular Cancer Foundation and Gryt Health, both of which have established digital footprints. And it means linking to my books on Amazon, my articles on Forbes, and my profiles on LinkedIn and Crunchbase.

Each of those connections is a signal. It tells search engines that I'm not just claiming to be a CEO or an author. I'm verifiably connected to organizations and platforms that validate those claims. The more of those connections you can establish in your schema, the stronger your knowledge graph becomes.

This is also why pursuing a Wikipedia page is so important. Wikipedia is one of the most authoritative sources in Google's ecosystem. When you have a Wikipedia page, and when that page is linked into your schema, it becomes the anchor for your entire digital identity. It's the single source of truth that everything else connects back to.

Why This Matters for AI Search

There's another reason I'm prioritizing structured data right now, and it has to do with the future of search. AI-powered search engines like ChatGPT, Claude, and Perplexity are becoming more prominent, and they rely heavily on structured data to generate answers. When someone asks an AI, "Who is Kenny Kane?" I want the response to be clear and accurate. Not a guess. Not a blend of multiple people. Just me.

Structured data is how you ensure that AI systems have the right information to work with. It's how you make sure that when these tools pull information about you, they're pulling from authoritative, verified sources rather than making inferences based on incomplete data.

The Long Game

Implementing structured data isn't a one-time project. It's an ongoing process. As my career evolves, as I take on new roles or publish new work, my schema needs to be updated to reflect that. It's part of maintaining your digital presence, just like updating your LinkedIn profile or refreshing your website copy.

But the payoff is worth it. Structured data is one of the few things in SEO that you can control directly. You can't control how other sites link to you, and you can't control how search engines rank your content. But you can control the information you provide about yourself. You can make sure that when search engines are trying to figure out who you are, they have all the context they need to get it right.

For me, that means being deliberate about the details. Adding my location. Clarifying my roles. Connecting my work to the organizations I lead. Linking to authoritative sources that validate my credentials. And eventually, once I have a Wikipedia page, making sure that page is woven into my schema so it becomes the definitive reference point.

If you're in a similar situation, whether it's name confusion or just a lack of clarity in how you show up in search results, structured data is one of the most effective tools you have. It's not flashy, and it's not something most people will ever see directly. But it's foundational. It's how you take control of your digital identity and make sure that when people search for you, they find the right version of your story.

And in a world where your online presence is often the first impression you make, that clarity matters more than ever.

I Asked Lindy AI to Write My Wikipedia Page

This week I asked Lindy AI to generate a Wikipedia page about me. Not to publish on Wikipedia itself, just to see what it could create from my public footprint.

The result looked surprisingly real. It built a full article with an infobox, clean sections, and a references list that linked to my site, Forbes articles, and even my books. It read like something that could actually live on Wikipedia.

Initially, it wasn’t perfect. A few dates were wrong and some sources were thin, but that was the value. It showed me what the internet already says about me, how consistent my story is, and where I could improve the trail of verified information behind it.

I used it as a checklist to tighten my own online narrative. If an AI can build a convincing profile in seconds, it’s a good reminder that your digital presence is always being written, whether you’re involved or not.

AI isn’t just a writing tool anymore. It’s a mirror that reflects your public story back to you. The best thing you can do is make sure it’s reflecting the version you actually want people to see.

Kenny Kane

Kenny Kane

Born

Islip, New York, U.S.

Education

Farmingdale State University (Communications)
LSU Shreveport (MBA)

Occupation

Business executive, entrepreneur, nonprofit leader, author

Known for

CEO of Testicular Cancer Foundation
CEO of Firmspace
Co-Founder of Gryt Health
Author of "The Accidental Nonprofiteer"

Website

kenny-kane.com

Kenny Kane is an American business executive, entrepreneur, author, and nonprofit leader known for his work in healthcare advocacy, technology, and commercial real estate. He currently serves as Chief Executive Officer of both the Testicular Cancer Foundation and Firmspace, and is Co-Founder and Chief Technology Officer of Gryt Health.

Early Life and Education

Kane graduated from Islip High School in June 2005.^[1] He attended Suffolk County Community College (2005-2007) and Binghamton University (2006) before completing his undergraduate studies in Professional Communications at Farmingdale State University of New York (2007-2010).^[1] In 2023, Kane earned his Master of Business Administration (MBA) from LSU Shreveport while continuing his full-time executive roles.^[1][2]

Kane began his career at age 15 as a Pharmacy Technician at Islip Pharmacy & Surgical in Islip, New York, where he worked from 2002 to 2007. He continued in pharmacy roles at CVS Health (2007-2008) and Northwell Health (2007-2010).^[1]

Career

Nonprofit Leadership

Stupid Cancer (2010-2016)

Kane's entry into nonprofit work was inspired by his father's diagnosis with stage 2b testicular cancer.^[3][4] In 2010, while attending a guest lecture at his university, Kane emailed the founder of "I'm Too Young For This! Cancer Foundation" during the presentation and secured an internship.^[5] He joined the organization full-time later that year.

The organization rebranded as Stupid Cancer in 2011, and Kane held progressively senior roles, ultimately serving as Co-Founder and Chief Operating Officer (November 2014 - May 2016).^[1][6][7] During his tenure, Kane helped scale Stupid Cancer into a nationally recognized voice for young adults affected by cancer, launching e-commerce operations, producing national conferences, and leading multi-city awareness campaigns.^[8]

Testicular Cancer Foundation (2016-Present)

In May 2016, the Testicular Cancer Foundation announced the hiring of Kenny Kane as its new Executive Director (later CEO).^[9][10] Kane relocated from New York City to Austin, Texas, to assume the role on June 1, 2016.^[9][10]

Under his leadership, TCF has:

• Expanded digital infrastructure and online reach^[11]
• Modernized fundraising operations^[12]
• Grown the annual TCF Summit into a major resource hub^[13]
• Introduced innovative programs including the world's first AI-powered testicular self-examination tool (2025)^[14]

Kane's role encompasses overall strategy, fundraising, digital transformation, and program execution, with a focus on delivering resources to young men and their families.^[11]

YNPN-NYC

Kane served on the board of Young Nonprofit Professionals Network of New York City (YNPN-NYC), holding positions as Partnerships Chair (August 2014 - December 2015) and Board Chair (January 2016 - June 2016).^[1]

Technology and Healthcare

Gryt Health (2016-Present)

Kane is Co-Founder, Chief Technology Officer, and Board Member of Gryt Health, a survivor-led healthtech company.^[1][15] In this role, he advises on technology strategy, governance, and scaling patient-centered digital health solutions. Gryt Health connects cancer patients globally to community support, clinical trials, and real-time resources.^[15]

Commercial Real Estate

Firmspace (2017-Present)

Kane joined Firmspace, a premium flexible workspace provider, as a Technology and Operations Consultant in May 2017.^[1] He has held multiple leadership positions:

• Technology and Operations Consultant (May 2017 - December 2017)
• Director of Operations (January 2018 - August 2019)
• Vice President of Operations (September 2019 - June 2020)
• Chief Operating Officer (July 2020 - September 2022)
• Chief Executive Officer (October 2022 - Present)^[1][16]

As CEO, Kane oversees all aspects of national operations including finance, HR, IT, AV, security, and facilities for Firmspace's network of premium workspaces across the United States.^[1][16][17]

Writing and Thought Leadership

Kane has been a prolific writer on business operations, digital strategy, and nonprofit management:

Forbes Councils

• Forbes Nonprofit Council Member (March 2017 - February 2018)^[1][18]
• Forbes Business Council Member (July 2020 - June 2022)^[1][19]

Publications

• Practical Ecommerce - Columnist (May 2015 - March 2016)^[1][20]
• BigCommerce - Columnist (October 2014 - November 2015)^[1]

Kane has authored articles on topics including donor cultivation, digital transformation, e-commerce for nonprofits, and operational efficiency.^[18][20][21] His work has been featured in Forbes, Practical Ecommerce, BigCommerce, and other business publications.

Notable articles include:

• "How You Can Get Past Barriers That Keep Potential Donors From Giving" (Forbes, May 2017)^[18]
• "Five Morale-Boosting Tips To Use In A Fundraising Slump" (Forbes, May 2017)^[22]
• "Book Excerpt: Mission-Driven Ecommerce" (Practical Ecommerce, October 2025)^[20]

Books

The Accidental Nonprofiteer (2025)

Kane's first book, "The Accidental Nonprofiteer: Building Systems That Serve Your Mission (Not the Other Way Around)", was published on August 10, 2025.^[23] The book draws from Kane's experience building nonprofit infrastructure from the ground up, beginning with his internship at I'm Too Young For This! Cancer Foundation in 2010.

The book addresses leaders who "never planned to run a nonprofit" but found themselves building organizations to solve problems they encountered personally. Kane shares practical insights on building systems, empowering volunteers, and maintaining mission focus while scaling operations.^[23] The book is available on Amazon and Google Play.

Mission-Driven Ecommerce (2025)

Kane's second book, "Mission-Driven Ecommerce", was announced in October 2025.^[24] The book focuses on e-commerce strategies specifically designed for mission-driven organizations and nonprofits.

Awards and Recognition

• Forbes Business Council Member (2020-2022)^[1][19]
• Forbes Nonprofit Council Member (2017-2018)^[1][18]
• Featured in "Band of Ballers" series by A Ballsy Sense of Tumor (2019)^[4]

Personal Life

Kane is based in Austin, Texas.^[1][10] His career has been significantly influenced by his father's testicular cancer diagnosis, which motivated his dedication to cancer advocacy and patient support.^[3][4]

Philosophy and Leadership Style

Kane describes his approach as "building with purpose, leading with systems, and staying focused on the people we serve."^[1] He is known for his ability to apply cross-industry experience to create innovation, combining tech startup savviness with corporate operational expertise.^[25]

In "The Accidental Nonprofiteer," Kane emphasizes building technology and systems that serve people rather than processes, drawing from lessons learned in customer service, email marketing, and organizational infrastructure.^[23]

External Links

• Personal Website
• LinkedIn Profile
• Amazon Author Page
• Goodreads Author Page
• Testicular Cancer Foundation
• Firmspace
• Gryt Health

References

1. Kane, Kenny. "About Kenny Kane". kenny-kane.com. Retrieved October 23, 2025.
2. Kane, Kenny. "How I Earned My MBA Without Pressing Pause on Life". kenny-kane.com. Retrieved October 23, 2025.
3. "Kenny Kane – CEO of Testicular Cancer Foundation". A Ballsy Sense of Tumor. September 6, 2019. Retrieved October 23, 2025.
4. "Band of Ballers: Kenny Kane – CEO of Testicular Cancer Foundation". aballsysenseoftumor.com. Retrieved October 23, 2025.
5. Kane, Kenny. "From Intern to CEO, and Still Fighting Cancer Like Hell". LinkedIn. Retrieved October 23, 2025.
6. "Kenny Kane - Crunchbase Person Profile". Crunchbase. Retrieved October 23, 2025.
7. "Kenny Kane's Biography". Muck Rack. Retrieved October 23, 2025.
8. "Ecommerce and Building a Thriving Community with Kenny Kane of Stupid Cancer". INspired INsider. Retrieved October 23, 2025.
9. "Non-Profit Expert and Advocate Kenny Kane Tapped as The Testicular Cancer Foundation Executive Director". PRWeb. May 9, 2016. Retrieved October 23, 2025.
10. "Non-Profit Expert and Advocate Kenny Kane Tapped as The Testicular Cancer Foundation Executive Director". Testicular Cancer Foundation. May 9, 2016. Retrieved October 23, 2025.
11. "Testicular Cancer Foundation Donor Cultivation". CauseVox. Retrieved October 23, 2025.
12. Kane, Kenny. "How You Can Get Past Barriers That Keep Potential Donors From Giving". Forbes. May 15, 2017. Retrieved October 23, 2025.
13. "TCF Summit 2025: A Transformative Weekend". Testicular Cancer Foundation. April 28, 2025. Retrieved October 23, 2025.
14. "Introducing: The World's First AI Testicular Self Exam". Testicular Cancer Foundation. August 21, 2025. Retrieved October 23, 2025.
15. "Kenny Kane - Gryt Health". The Org. Retrieved October 23, 2025.
16. "Kenny Kane - Firmspace". The Org. Retrieved October 23, 2025.
17. Kane, Kenny. "What Commercial Real Estate Leaders Need To Know About the Hybrid Work Era". Forbes. July 19, 2021. Retrieved October 23, 2025.
18. Kane, Kenny. "How You Can Get Past Barriers That Keep Potential Donors From Giving". Forbes Nonprofit Council. May 15, 2017. Retrieved October 23, 2025.
19. "Kenny Kane's Profile". Muck Rack. Retrieved October 23, 2025.
20. Kane, Kenny. "Book Excerpt: Mission-Driven Ecommerce". Practical Ecommerce. October 23, 2025. Retrieved October 23, 2025.
21. "Kenny Kane's Articles". Muck Rack. Retrieved October 23, 2025.
22. "Five Morale-Boosting Tips To Use In A Fundraising Slump". Forbes Nonprofit Council. May 18, 2017. Retrieved October 23, 2025.
23. Kane, Kenny. "The Accidental Nonprofiteer: Building Systems That Serve Your Mission (Not the Other Way Around)". kenny-kane.com. August 10, 2025. Retrieved October 23, 2025.
24. Kane, Kenny. "Announcing My Second Book: Mission-Driven Ecommerce". kenny-kane.com. October 18, 2025. Retrieved October 23, 2025.
25. "Testimonials". kenny-kane.com. Retrieved October 23, 2025.

See Also

• Testicular Cancer Foundation
• Stupid Cancer
• Young adult cancer advocacy
• Healthcare technology
• Flexible workspace industry
• Nonprofit management

Beyond the Platform: What GoFundMe Taught Us About Nonprofit Tech Ownership

This week, headlines broke that GoFundMe quietly created fundraising pages for 1.4 million nonprofits across the U.S. Most of those organizations had no idea the pages even existed. It’s a perfect, if uncomfortable, illustration of where nonprofits stand today in the digital landscape. Tech platforms are moving faster than most organizations can keep up with, and if you don’t actively manage your digital presence, someone else will.

That’s not a dig at GoFundMe. Their intent was to make it easier for donors to find and give to nonprofits. But it highlights a bigger truth: digital transformation isn’t optional anymore. It’s not just about adopting tools; it’s about owning your identity, your data, and your narrative in an increasingly automated world.

When platforms create something on your behalf without asking, it’s a sign that your digital footprint isn’t fully under your control. For many nonprofits, that’s the wake-up call. If you’re running a nonprofit today, you have to ask yourself who controls your donor data, where your stories live, and what happens if a platform changes the rules or shuts down tomorrow. For years, we’ve relied on “free” or convenient tech to manage fundraising, communications, and volunteers. But convenience can come with a cost: loss of visibility, fragmented data, or misaligned branding that confuses your supporters. The GoFundMe situation reminds us that digital transformation starts with digital ownership. Before you chase new technology, make sure you truly own the assets that represent your mission online.

Let’s be clear: digital transformation isn’t about buying software. It’s about restructuring how your organization operates around technology that works for you, not the other way around. It means automating what’s repeatable so staff can focus on mission-critical work, connecting systems so fundraising, communications, and program data actually talk to each other, and making decisions based on insight, not instinct. Most importantly, it’s about protecting donor trust by managing data responsibly.

When I started my nonprofit career, we used to duct-tape systems together—email lists in one place, event registrations in another, donor CRM halfway updated somewhere else. It worked, sort of, but it wasn’t transformation. It was survival. True digital transformation is when technology becomes your infrastructure, not your headache. It’s when your organization operates seamlessly, with staff empowered by tools that make their work more meaningful instead of more complicated.

At the heart of any modern nonprofit technology strategy are five ideas: ownership, automation, security, scalability, and literacy. Data ownership means not relying solely on third-party platforms as your donor database and making sure your records are secure, accessible, and exportable. Automation means freeing your team from repetitive administrative tasks so they can focus on building relationships and delivering programs. Security means treating donor information with the highest level of care and transparency, ensuring your supporters know their trust is earned and maintained. Scalability means choosing cloud-based systems that can grow with you rather than hold you back. And digital literacy means making sure your team (not just one tech-savvy person) feels confident navigating and adopting new systems.

If all of this feels overwhelming, start small. Begin with a technology audit to understand where your data lives and who controls it. Then, take back ownership of your digital profiles, including any GoFundMe pages that might have been created without your knowledge. Clean up your logins and security, and identify one process to modernize: maybe automating thank-you messages, consolidating donor records, or streamlining communications between departments. Transformation doesn’t happen overnight. It happens one workflow at a time.

The nonprofits that thrive over the next decade will be those that move as fast as their cause deserves. They’ll understand that “digital” isn’t a department or a project; it’s part of how we lead. If GoFundMe can spin up a million nonprofit pages overnight, imagine what your organization could do with that same energy, but with intention, alignment, and full ownership.

Don’t wait for platforms to define your presence. Define it yourself. Digital transformation isn’t about keeping up with technology; it’s about taking back control of your mission’s digital future.

The Rise and Flux of the Chief Automation Officer

When I first wrote about the Chief Automation Officer a couple years ago, it felt like a defining role for the next decade. Someone had to connect the dots between all the apps, processes, and platforms that were supposed to make work smarter. And for a moment, that was true — automation was the next big thing.

But in tech, “the next big thing” doesn’t stay still for long.

From Big Thing to Background Process

The Chief Automation Officer was meant to be the bridge between operations and technology — a translator of efficiency. Yet, as AI raced onto the scene, automation became less of a job title and more of a feature. What was once a dedicated role is now baked into every SaaS platform, marketing suite, and CRM. Everyone’s an automator now, whether they realize it or not.

That’s not failure — it’s evolution. When a technology matures enough to become invisible, it’s usually a sign it succeeded.

The Flash Analogy

If you ever learned Adobe Flash, you know the feeling.
It was the future once — interactive websites, animations, multimedia experiences. Then browsers changed, standards shifted, and a whole generation of Flash developers had to reinvent themselves almost overnight.

The lesson? Specialization has a shelf life. The web kept evolving, and those who thrived were the ones who understood why things worked, not just how.

Automation is having its Flash moment. The tools are still there, but the world has moved on. What used to be a skill is now an expectation.

Generalists Win the Long Game

This is where being a generalist matters.
If you understand systems, logic, data flow, and human behavior — you can adapt. If you only know one platform or one way of doing things, you’re in trouble.

The best operators today don’t just build Zaps or workflows. They ask better questions:

• What problem am I really solving?

• What happens when this tool disappears?

• How can I design for resilience, not just convenience?

AI didn’t kill automation. It absorbed it.
And that’s the same wave that will roll through dozens of other job titles in the coming years.

Watch for the Signs

You can always tell when a role is about to shift. Suddenly the conferences get quiet. The LinkedIn titles start changing. The tools you used to evangelize start using AI to replace the very thing you were doing manually.

That’s when you know it’s time to evolve again.

Automation isn’t over — it’s just automated. The people who saw that coming are already working on the next layer: intelligence, integration, and insight. The rest are still learning Flash.

So What Do You Do? Here's My Real Answer

What Do You Actually Do?

It's a question I've been asked countless times at parties, networking events, and even by family members who nod politely while clearly having no idea what I'm talking about. For years, I'd fumble through some variation of my job title or rattle off a list of technologies I work with, watching eyes glaze over in real-time.

But recently, after fifteen years in tech, something clicked. The answer was there all along, hiding in plain sight across every role, every team, every project I've touched.

I enable productivity.

That's it. That's what I do.

The Pattern I Didn't See

Looking back, I can see it everywhere. At Stupid Cancer, I wasn't just managing systems—I was making it possible for a small team to punch way above their weight class. In commercial real estate tech, I wasn't just implementing solutions—I was translating complex systems into tools people could actually use. In every role, the through-line was the same: take something complicated and make it work for real people doing real work.

It turns out my strongest value add isn't any single technical skill. It's technological intuition—that ability to look at a complex system and understand not just how it works, but how to make it work for people. To see the gap between what technology can do and what end users need it to do, and then bridge that gap.

I've always been the person teams come to when something isn't clicking. When a new tool isn't being adopted. When processes feel harder than they should be. When there's a sense that "there has to be a better way to do this."

The AI Moment

Which brings me to where we are right now.

We're standing at the edge of the biggest productivity shift in a generation. AI isn't coming—it's here. But here's what I'm seeing: most teams are either paralyzed by uncertainty or rushing in without the right safeguards. They're stuck between "we need to do something with AI" and "we have no idea where to start" or worse, "we can't risk the security implications."

And this is exactly where fifteen years of making complex systems accessible becomes incredibly relevant.

I know how to help teams adopt transformative technology in a smart, secure way. I understand both the possibilities and the pitfalls. I can translate between the technical and the practical. I can help teams move from anxiety to execution, from complexity to clarity.

This is the next chapter of what I've been doing all along—just with stakes that are higher and possibilities that are bigger than ever before.

What This Actually Looks Like

In practice, this means I'm the person who:

• Sees the bottleneck in a workflow that everyone else has accepted as "just how it is"

• Knows when to implement a sophisticated solution and when a simple one will do

• Can explain technical decisions in ways that make sense to non-technical stakeholders

• Understands that the best technology is the one people will actually use

• Stays ahead of what's coming so teams don't fall behind what's already here

It means I'm not just building or implementing—I'm enabling. Every past and present team I've been part of has been more productive because I was there. Not because I'm the smartest person in the room, but because I have this particular intuition for making technology serve people instead of the other way around.

Why This Work Matters to Me

Here's what makes this deeply satisfying: I've done this across wildly different sectors—nonprofit cancer advocacy, commercial real estate, e-commerce, startups—and the mission never mattered less because of it. In fact, it mattered more.

When I was at Stupid Cancer, making systems more efficient meant our small team could reach more young adults facing cancer. In commercial real estate, simplifying complex workflows meant professionals could focus on serving their clients instead of fighting their tools. Every time I've made technology more accessible, I've amplified someone's ability to do meaningful work.

That's what drives me. Not the technology itself, but what it enables people to accomplish.

Whether it's mission-driven work saving lives or mission-critical work driving business results, the satisfaction comes from the same place: watching teams go from frustrated to empowered, from bottlenecked to flowing, from "we can't" to "we did."

After fifteen years, I've realized this skill set—the combination of deep technical understanding, people-focused thinking, and the intuition to bridge the two—is exactly what organizations need but rarely find. And I'm lucky enough to find fulfillment in work that spans any industry, any mission, any team that needs to do more with what they have.

The Next Chapter

So when someone asks me what I do now, I have clarity: I enable productivity through technological intuition and by making complex systems accessible to the people who need to use them.

We're living through one of the most exciting moments in the history of work. AI is rewriting the rules of what's possible, and watching teams figure out how to harness that potential—thoughtfully, securely, effectively—is genuinely thrilling. The barriers that have slowed us down for years are starting to come down, and the possibilities for what teams can accomplish are expanding faster than ever.

After fifteen years of doing this work in different forms, I'm more energized than ever about what comes next. Not just for me, but for everyone who's willing to embrace the change and do the work to get it right.

Your Tech Stack Shouldn’t Require a Decoder Ring

Between 2010 and 2016, when I was building the nonprofit I co-founded, I treated our tech stack like a puzzle only I could solve. If there was a tool with advanced features, hidden settings, and a learning curve steep enough to scare off the average user, I was all in.

Zapier with multi-step filters? Love it.
Custom-coded WordPress plugins? Yes, please.
Google Sheets with so many formulas it looked like mission control? Absolutely.

And here’s the problem: it worked… as long as I was the one running it.

The moment I went on vacation, got sick, or handed something off to a volunteer, the whole system ground to a halt. Not because the mission was complicated—but because I’d made the tools unnecessarily complex.

Over time, I realized this wasn’t just inconvenient—it was risky. If something happened to me, a lot of the organization’s institutional knowledge and access would disappear overnight. That’s not leadership; that’s gambling with the mission.

Here’s what I learned the hard way:

1. Share passwords like the organization depends on it—because it does.

Stop keeping logins in your head or on scraps of paper. Use a shared password manager like 1Password so anyone with the right permissions can access what they need without emailing passwords around. I’ve seen weeks wasted because a critical account was locked and the only person who knew the password was unreachable.

2. Create internal reference documents while you work.

Every time you run a process—publishing a blog post, sending a Mailchimp email, updating the website—write it down in plain language in a shared document. Not polished manuals. Just clear, step-by-step notes. Over time, you’ll build an internal library that makes onboarding easier and keeps operations from grinding to a halt when someone leaves.

3. Favor adoption over optimization.

Squarespace, Mailchimp, Google Drive—these aren’t “basic,” they’re accessible. Your mission isn’t to impress other tech nerds; it’s to keep your systems usable by the widest number of people. The best tool is the one your team can actually use, even if it’s missing a few features you love.

4. Avoid single points of failure.

If you’re the only one who can update the website, send an email blast, or pull a report, you’re not building a sustainable organization—you’re building a bottleneck. The goal is that someone else could run the core operations tomorrow without calling you for help.

5. Think of operations as a risk management tool.

Your tech stack isn’t just about efficiency—it’s about derisking the mission. Staff turnover, illness, vacations, and even emergencies shouldn’t take the organization offline. If your systems are simple, documented, and accessible, the work can continue seamlessly no matter who’s in the chair.

The fancy tools might make you feel like you’re operating on another level. But the real test of your tech stack isn’t how impressive it looks—it’s whether the mission keeps moving when you’re not at the keyboard.

The Chief Automation Officer

I signed up for Zapier on March 5, 2014. I was Chief Operating Officer at Stupid Cancer at the time. Back then, I couldn't tell you what a cloud computing stack was, but I had one, and Zapier unlocked many doors and flipped on many light switches for me, professionally.

Three months after joining Zapier, Slack hit the market, and I was off to the races with automation. Suddenly every business data point was funneling into Slack as it quickly became the brain of Stupid Cancer. I have blogged in the past about Slack, so I will avoid doing that here. As a result, Slack dinged all day long at Stupid Cancer, and it still does in my various current roles.

When Wade Foster, Zapier CEO, posted this on LinkedIn, I felt seen:

Without realizing it, I have spent most of the past decade becoming a well-tuned Chief Automation Officer. It’s subtly been the hallmark of my career.

One of my favorite byproducts of automation is just how amazed people are at the very nature of it. There is little budget or margin of error for trying things out in the nonprofit world, especially with fundraising tools. Most fundraising platforms are awful and siphon much-needed funds out of charities to line their pockets. They would argue that they make it possible for nonprofits to be successful, and that's a debate I would love to have. I digress. People are amazed when you connect multiple apps, and data moves around 24/7.

With Zapier, we could suddenly do more than our out-of-the-box fundraising platform could do alone. I was not left wanting seven features and having to settle for four. I could have it all.

• I didn't need to export donors and import them into Mailchimp.

• I didn't need to watch my email for Stripe donations; I could get a Slack notification.

• I didn't need to create a to-do list task manually; Zapier took care of it.

My pivot to the private sector has created more meaningful automation opportunities in recent years. Now operating a membership-based company, my automation is focused on moving people through different states, such as lead, contact, active member, and former member. These states affect how we interact with you and your place in our cloud stack.

I wish I could say I spent a lot of time making flow charts and thinking about the end-to-end journey of my data. The reality, though, is most of my Zaps are born out of acute necessity and team inspiration. Perhaps one day, I’ll start keeping notes.

One consideration when running through the paces of creating automation is where Zapier fits alongside an app’s internal workflow system. Zoho Campaigns comes to mind in this example. I might use Zapier to get you from Facebook Leads to a Zoho Campaigns Mailing list with additional information. Still, I will let Zoho Campaigns read your contact record and qualify you for an email workflow. Keeping track of these relationships is essential so you don’t create loops or unforeseen automatic enrollment.

Automation can be daunting if you don’t know where to start. Services like Upwork have professionals for hire on a short-term basis to get you started. Once you start seeing what’s possible and connecting the dots between your workflows and cloud apps, you’ll get back those wasted hours doing things manually.

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Further reading:

• The emergence of the chief automation officer

• Chief Automation Officers Are The Answer … But What Is The Question?

My Smart Home

Years ago, sophisticated home automation seemed like an unattainable reality without the help of an electrician, networking expert, or a nerdy friend. The reality is that the market has a lot of options to smarten up your home. They range from the plug and play to flip-the-breaker installs.

A lot of these items come with different degrees of sticker shock. The configuration I am going to outline below was accumulated over many months, out of need and curiosity. When my wife and I bought a house earlier this year, it became clear that while not essential, these tweaks could significantly improve our quality of life. Onward!

Getting Started with Climate Control & Security

When we bought our home in May 2020, the first upgrade was swapping out the old Honeywell thermostat to a Google Nest Learning Thermostat. The home was unoccupied and temperatures in Central Texas were rising. I figured if I was going to be doing some form of pre-move manual labor, the thermostat was critical to cool off the house before I got there. Dropping the temps on moving day made the t-stat worth it.

As we settled into the new home, we realized that our bedroom ran hot at night. Our house is made of brick and gets sun on three sides. To solve this we put a Google Nest Temperature Sensor in the bedroom. During the day, I’ve got Nest prioritizing the hallway temperature, and overnight I’ve got the bedroom sensor controlling the system.

To round out our Nest install, I added two Google Nest Outdoor Cameras and a Nest Doorbell. I found this video really helpful when installing my cameras. With my Google Nest configuration set up to my liking, I moved on to the front door.

My three beautiful nieces live 500 feet away and often will come over to swim in our pool. I began to see a trend forming of us running through the house, dripping water, having to unlock or lock the front door. It became clear that, like the Nest Thermostat, a new August Wi-Fi Smart Lock would quickly pay for itself.

Keeping the Lawn Green

In Central Texas, your Bermuda grass can quickly go from green to white/yellow/brown if you’re not careful. Our new home came with a Hunter X-Core manual sprinkler controller. Between a broken dial and not knowing if the sprinklers were actually coming on at 5 am, I was ready for something a little nicer. Enter the Hunter Hydrawise WiFi-enabled controller. It’s got a great app to set up your programs and read reports on actual watering.

Network Coverage & IoT

As I began accumulating smart home devices, It was clear that my AT&T router wasn’t going to consistently support the diversity of devices both on the 5 GHz and 2.4 GHz. For those unfamiliar with the differences, Netgear sums it up well: 

The 2.4 GHz band provides coverage at a longer range but transmits data at slower speeds. The 5 GHz band provides less coverage but transmits data at faster speeds. The range is lower in the 5 GHz band because higher frequencies cannot penetrate solid objects, such as walls and floors.

As I began to flirt with the idea of upgrading my home network, I was quickly pointed in the direction of Unifi.

With a little bit of false confidence and a few hundred feet of cat6 cable, I began planning my wireless access point (WAP) plan. This was prior to Cardi B. ruining that acronym forever.

I decided to install two Ubiquiti Networks Unifi 802.11ac Dual-Radio PRO Access Point (UAP-AC-PRO-US) in the house. One in the hallway, visible from most of the large interior rooms in the house, and one on the back porch, ensuring full coverage over the pool and patio.

Once I had installed these two WAPs, I identified an opportunity to fill in the front part of the house by adding a Unifi Beacon HD Access Point.

In all, this setup has proven able to support all of my devices. One critical step is to turn off the internal WiFi in your cable modem as these are doing a much better job.

Lights. Cameras. Apple HomeKit.

Having done everything prior and paying the related credit card charges, I was ready to put a cherry on top of my smart home with some smart light switches. 

At my day job, I oversee commercial office space facilities, among other things. A couple of years ago, I was introduced to the Lutron Vive product line. It is an incredibly flexible solution in an environment with 100+ switches. The residential application, Lutron Caseta, is total overkill that is well worth the price of admission.

As with the rest of my smart home devices, I started with solving a problem before moving to non-essential purchases. First up was getting my Lutron Smart Start Kit to lay the foundation for what was to come.

With my Lutron environment established, I was free to begin expanding as I saw fit. My priorities were as follows:

• Turn exterior lights on at sunset; Turn off at sunrise

• Turn select interior lights on upon arriving at home

• Create scenes based on time of day or event

With this strategy in mind, I was able to use the Lutron app and Apple HomeKit to create some slick automation. When my wife or I arrive home, certain lights come on to welcome us. When we both leave, all of the lights shut off, with the exception of the exterior lights.

Along with this home occupancy logic, I have also programmed a few scenes in Apple HomeKit: 

• Party City: All common area lights up to 100%

• Relax: 7-9 pm lighting down to 30%

• Max Chill: Most lights off, one at 20%

• Leave Home/Goodnight: All lights off, except front exterior. (They run on Lutron sunrise/sunset schedule)

• Fans On: Sometimes the smoke detectors go off or the humidity level in the house rises, this quickly circulates air with the HVAC fan on and ceiling fans spinning.

Utilizing Apple HomeKit, I am able to have the majority of my products under one control panel. There are times when I will use a native app, such as the Lutron sunrise/sunset integration. There has also been one instance where I had to buy something to connect two devices that didn’t want to play nice together: Google Nest & Apple HomeKit. Of course, these two would not want to have their products integrate. Luckily, there is an aftermarket bridge that warms up this cold war and connects Nest to HomeKit. The Starling Home Hub plugs in to your network switch and with a quick configuration connects all the devices seamlessly.

All Projects Have a Finish Line

As I mentioned earlier, this didn’t happen overnight, nor do I feel a sense of completion. I still have light switches I would like to switch to Lutron, devices I could tell Alexa to control, and ways to turn our app-controlled devices into more passive experiences through motion detectors and geofencing.

For the holidays, I received two MyQ Smart Garage Door Openers and some Wemo Smart Outlets, both indoor and outdoor. With these recent additions, I am nearly done with my smart home conversion.

I hope this narrative inspires you to finally start your smart home project and align with a product line. In a crowded market, it’s important to make smart decisions early on before finding yourself with multiple brands of smart home products.

Nurture Fundraisers Using CauseVox, Zapier, and ConvertKit

Fundraising is a crucial part of a non-profits existence. The biggest opportunity for a non-profit is leveraging its community to fundraise on its behalf. The hardest part is maintaining the attention of community members and empowering them to feel confident in their efforts.

For a year now, I've been using CauseVox as my primary fundraising tool for the Testicular Cancer Foundation. I really enjoy CauseVox because it puts a lot of the controls on the admin side, rather than having to go through an account manager or some other contact on the provider side.

Exploring CauseVox Zaps on Zapier

About 6 months ago, CauseVox began teasing their Zapier beta integration. As a Zapier lover and full-blown nerd, I'd been waiting for the integration to go live to see what kind of pathways I would have access related to fundraisers. A few weeks ago, the news came through that the integration was live. Excitement ensued.

The CauseVox options are simple and to the point. Did we A) Get a new fundraiser or B) Get a new donation?

With this info, I can do a lot of cool things.

One of the main features that really (I mean really) expensive fundraising platforms up-charge for is communicating with fundraisers within the platform. Campaign updates, direct emails, drip emails, etc. There's a ton of options.

My first Zap using CauseVox is to bridge the gap between a lack of communicating with fundraisers and using an email marketing platform I live in all day long, ConvertKit.

Using ConvertKit

With ConvertKit, I can create drip email sequences to walk my fundraisers along a series of emails that convey important information, emotion, and reinforce why they are so important to our organization. (Fundraisers...if you are reading this, we love you!)

CauseVox has the ability to send a welcome email, which is fantastic. I haven't yet decided if I will keep this email active or send them all to ConvertKit for the entire email series. (On one hand, it's a safe bet that the email will always send, but on the other hand, I would love to have the open rate and click metrics that ConvertKit provides.)

Creating a Drip Email Sequence

Currently, our email series is broken up like this:

Email 1: Welcome to Fundraising

Email 2: More about CauseVox and tactical points around fundraising (includes link to proprietary PDF about fundraising)

Email 3: Where the money goes / why this is so important

Final Thoughts

I am curious to see how the response is to our new series of emails. With all communications, the last thing you want to do is be over communicative and have someone lose interest entirely. By looking at my ConvertKit open and click rates, I'll see which emails are most effective and which need some fine tuning.

3 Automations to Make Year-End Fundraising a Breeze

It's that time again: year-end fundraising and the race to December 31st. While this can be the most wonderful time of the year, it's also the most tedious, data-intensive, drive-you-to-drink time of the year. Unless you have the right tools in place.

Luckily, there are options when it comes to funneling all the data your donors are generating. Enter, Zapier automations.

If you're unfamiliar, Zapier is a subscription service that connects different online apps to one another using API and other means. With a few simple clicks, you can connect the majority (read: relevant) of your apps and be on your way.

The Approach

For me, architecting my Zapier arsenal is a problem-first approach. What do I need in the future and where do I need it?

Let me pause here and give you a word of caution. With too much automation, you can enter a data redundancy wormhole, wherein you have exhausted your monthly Zap limit and reached the task limit. If you have no idea what I am talking about, great. If you're as nerdy as I am, you will be at 80% of your task limit in no time.

Without further suspense, here is my list of essential automations to get from here to listening to U2 on January 1st.

Stripe to Slack

Stripe is currently my primary payment gateway. Using the direct Slack integration, I send payment success, payment fail, and daily deposit information into an #incoming-money channel. On the Zapier side, I send customer and transaction metadata to the same channel. It's duplicative, but helpful for providing donation context in the moment. The input and output looks something like this:

If I donate $5, there will be an #incoming-money message that says "Kenny Kane (kennykane@gmail.com) has donated $5 to campaign x."

By including the customer email field in my Zap, I can very quickly send a new email, instantly, from Slack to thank or learn more about them. I also use it to look them up on social media and try to get background info on them. I typically do this for donations larger than $250. If it's an interesting email domain, I will do it for less.

Stripe to Wunderlist

One of the places you can set yourself up for failure the most in donor cultivation is the process of thanking them. For me, a Slack notification can fly by and be lost forever. To mitigate this problem, I set up a handy insta-to-do list.

Using a similar formula to my Slack message, I create a new Wunderlist task for each successful Stripe transaction. At certain time intervals (instantly – 24 hours), I check my 'Donor Thank You' Wunderlist and clear out the donations less than a certain amount. From there, I prioritize biggest donations first. This integration helps me sort through the madness of my donation notification emails, Slack alerts, and any kind of reports Stripe might give me.

Stripe to Google Sheets

I use Google Sheets to create a running table of all donations. This is helpful in running some quick analytics around donations and drawing conclusions without digging through information from multiple sources.

As you may know/come to find out, things break and I don't expect this integration to work 100% of the time. If I am creating any sort of enduring report, I would go right to Stripe for an export.

In Conclusion

The year-end season of giving can be a noisy time. By leveraging the backend APIs of your platforms, you can create a nice system of checks and balances to ensure you won't have incomplete reports, or a donor who feels like they don't matter.

These are just 3 quick automations. If you were looking to get really automated, you could use Zapier's (relatively) new multi-step Zaps to access existing information and update it, such as adding lines to your CRM.

Good luck!

ConvertKit Makes Me a Better Non-Profit CEO

What makes a good marketing email? For years, I thought it was a combination of colors and images, font types and social icons. I remember when Mailchimp released their drag and drop editor in November 2012 and everything changed for the amazing.

Four years later, I find myself running away from what I once worked on so hard on. Sending flashy emails seeking to dazzle constituents. Don’t get me wrong, I still use said editor and send branded emails, but it is my belief we’re on the verge of a new communication style in the non-profit sector that compliments the main email list.

Last year, I stumbled upon Authority & Nathan Barry and immediately went down this author, creator, entrepreneur rabbit hole. (Shout out to Nathan, Paul, Jason et al) While entrenched in Nathan’s drip email sequence about his book, I found myself looking forward to the next email from him. It was a non-annoying batch of emails that added value to my inbox every few days. What I didn’t realize was that he was actually selling me on his product, ConvertKit.

ConvertKit strips away the fancy drag and drop editor and provides you with the ability to send personalized plain-text emails, fast. Gone are the days of the bulk BCC, replaced with the ability to let my network decide on how they want to engage with me, and the organization I run.

With ConvertKit, I can tag subscribers by donation tiers, campaign affiliation, etc. What’s more, I can change up who the email comes from quickly. If I want to send the email from a fellow staff member or Board Member, it’s a two second switch before the email goes out.

What I really love about ConvertKit is that I can create links within the email that allow people to tag themselves using automations. In the past, a subscriber would have to visit a preference page to do what they can now do right from their inbox. By giving people options on what they want to hear about on the front end, I’m reducing the number of people who might go right for the unsubscribe link in the footer. If they do unsubscribe, that’s fine. "Engage or die."

Uncle Ben said “With great power comes great responsibility.” He’s right. As your ConvertKit database grows in size, you have to maintain strict segmentation of messages and resist the urge to send to everyone at once. That’s what your other list is for.

Since implementing ConvertKit, I’ve seen a ton of conversion and interest from my outbound emails. With the built in analytics, I can see who is opening my emails and interacting with them. These insights are helpful when knowing which donors to pursue, or volunteers to activate. As time progresses, I am discovering new and exciting ways to incorporate ConvertKit into my day to day. With CK starting at $29/month, I can’t help but think back to all of the Salesforce add-ons, priced astronomically, to achieve something similar.

Creating opportunity through self-service

On January 1st, I assumed the role of YNPN-NYC Board Chair. It has been a great first month, taking a 35,000-foot view of the chapter and its operations.

One of the value-adds of YNPN-NYC in the past has been a job board. Previously, anyone could post, just so long as they were a member. This was a great funnel to grow membership, engender community, and create a cycle of brand awareness and retention among employer and employee.

At the start of the year, our Board roster was a little light. Part of the “steep” learning curves of assuming my role, has been to figure out band-aids to carry the organization until we’re whole again.

As I set out to reimagine some of our tech infrastructure, including how we billed membership dues, the job board was a priority to sort out. At the very least, YNPN-NYC must continue to support the nonprofit community which we aim to serve in this capacity.

Through a bit of googling, and some luck, I stumbled upon JobBoard.io. It’s a turnkey solution that allows employers post jobs, candidates to find employers, and board operators to collect a fee for the service. For YNPN-NYC, this is found money around-the-clock.

What really sold me on the platform beyond the customer service from its CEO was that it’s inherently self-service was and we could brand it. Now, jobs.ynpn.nyc is the place to start your nonprofit career in New York City.

Sure, there are other big names out there. How cool would it be, though, to start a job interview talking about your mutual connection through YNPN-NYC and doing good in NYC.

Since the implementation of the new job board, we’ve had 36 jobs posted. Postings begin at $25 for a 30-day listing. Employers have the option of featuring the post for an additional $25. To celebrate, the launch of the board, I utilized the embedded couponing functionality. Until the end of the month, you can save 25% by using coupon code “launch” at checkout.

I’ve enjoyed watching the jobs come through during the work day. I have an integration through Zapier that posts to my Slack channel in real-time. There’s another automation that tweets new job postings to @ynpnnyc.

Thus far, postings have translated into $820 in found revenue for the organization that will be reinvested into expanding our reach and programming for members.

I’ve learned from this experience that sometimes the best way to capitalize on opportunity is to put it in the hands of the person on the other end of the transaction.

Why We Switched to Recurly at YNPN-NYC—and How It’s Already Paying Off

When I stepped into the role of Board Chair at YNPN-NYC earlier this month, one of my first priorities was upgrading our recurring membership payment system. We’d been using a mix of PayPal and SquareSpace purchases, and while functional, it lacked the modern tools needed to streamline operations and improve member experience.

My familiarity with Recurly actually goes back to 2015, when I was a customer of a SaaS platform that used it to manage their subscriptions. I had a good experience—especially with the added bonus of a discount—which left a lasting impression. That experience stuck with me when I started looking for a better solution for YNPN-NYC.

The Payment Patchwork We Inherited

Historically, YNPN-NYC managed recurring dues through PayPal. Then, after a website redesign, new memberships were processed through SquareSpace and synced with Mailchimp. That approach kept the process seamless on the front end but fragmented things behind the scenes. By the end of 2015, we had members split between PayPal and SquareSpace, with no central system to manage them.

Why Recurly?

I needed a solution that was:

• Low-friction for users

• Self-managing on the backend

• Elegant and modern

Recurly’s ecommerce-like experience won me over: members check out once, and the system handles renewals annually. Simple, clean, and scalable.

One of the biggest wins? Recurly syncs active subscriptions to Mailchimp twice a day. No more manual exports. And if someone cancels, they’re automatically removed from the list. Even if that integration didn’t exist, I could have used Zapier—but luckily, I didn’t need to.

Implementation

I approached this rollout with a “day-one” mentality—something I’d recently done with a CRM overhaul at Stupid Cancer. I knew legacy members might be affected, but new signups wouldn’t feel a thing. The setup process for Recurly took less than 30 minutes, and once everything was configured, I pulled down the old form and waited for signups to begin.

January was the perfect time to launch—right in line with New Year’s resolutions—and the response was strong from day one.

After verifying that everything worked, I uploaded legacy members into the new Mailchimp list using their name, email, and membership anniversary date. That allowed me to begin mapping the past to the present.

Migrating Legacy Members

Recurly adds two private fields to Mailchimp. Since we only offer one plan, everyone has the same data in those fields. That made it easy to identify which 2016 members were new and which ones were legacy holdovers.

With Mailchimp’s segmentation tools, I created lists of legacy members based on their anniversary date. That allowed me to identify those who were expired but hadn’t yet been imported into the new system. I haven’t finalized how many reminders these members will get before being moved to the inactive list, but the goal is clear: win them back.

We’re experimenting with coupon codes and other incentives to reactivate lapsed members. Some may not even realize their membership expired. While we know we won’t win back 100%—life moves on for many—it’s worth the effort to retain who we can.

Why Members Love It

What makes Recurly so effective is how it puts the power back in the hands of members. Seven days before their renewal, they get an email reminder. They can cancel, update their billing, or do nothing and let it renew. If a payment fails, Recurly will attempt to fix it automatically (like updating an expired card) before notifying the member. It’s hands-off but thorough.

Looking Ahead

Migrating a membership base sounds like a heavy lift, but modern tools make it manageable—and worthwhile. Retaining a member is always cheaper than acquiring a new one. But more importantly, not spending time managing things that can be automated is a win for any organization.

The Results (So Far)

In the first 18 days of launching Recurly, we had over 75 new members sign up—strong validation that this was the right move.

Non-Profits: Technology is The Biggest Donation You Aren’t Leveraging

Any non-profit COO or CTO will tell you that finding the technology that appropriately addresses their needs is tough to come by. The existing platforms with the non-profit in mind often cost upwards of $25,000 to engage. There are several problems with this situation. First, it is impossible to know that a CRM/donor database/360° fundraising platform will meet your needs long-term. Second, these platforms will lock you in for a year at least, and the much-needed updates will never come. Lastly, these platforms are insular systems without API or any means of connecting them to other solutions. (San Francisco, feel free to help us out here.)

I’m lucky to work in a non-profit vertical that spans from the tiny side-project to the multi-million dollar behemoth fundraising machine. In a space where we’re all working towards the same goal, it’s interesting how organizations leverage technology to carry out their mission.

Over the past six years at Stupid Cancer, we have stopped and started with so many different platforms my staff now cringes any time I tell them I’ve found something new. It’s true that I’ve probably worn out my welcome by having them help me test new things, but old habits die hard. When it was just Matthew and myself, we had to compensate for the lack of staff. It was the wild west of free trial exploration, and I learned a lot from it.

As we’ve grown over the past few years and hired staff to help us, my instinct remains to take a tech-forward approach.

I am also a big believer in putting automated systems in place where appropriate and removing the human element. There is no reason to try to do things better than computers. I see it way too often in this community of limited resources. It will only reduce your capacity for upward growth.

We recently did an internal exercise where we measured how much time each staff member spent on their respective duties. While they mostly landed as we thought they would, there were some instances where outside forces were pulling us away from getting out jobs done. In any company — especially a growing one – this is bound to happen. Ultimately, we took a look at the results and have begun to figure out how to mitigate these distractions by adding articles to our Zendesk FAQ, for example.

In this world of highly scrutinized non-profit budgets, there is so much time and money that can be saved by utilizing low-cost platforms like Zapier or IFTTT (Which doesn’t cost anything at all). I actually find most SaaS-based companies are willing to give deep discounts just based on your merit.

Google and Slack are two examples of companies that reward 501(c)(3) organizations with a lifetime subscription to their platform for free. If a platform doesn’t offer free or discounted services, offer to create compelling content for them that will be mutually beneficial.

We recently received a lovely donation from a platform we had used in the past that was in transition. The temporary separation was a mutual agreement, as they changed their core product offering. When the dust settled on their end, we jumped right in line to sign up.

As the maturation of Stupid Cancer continues from a tiny startup non-profit to million dollar organization, I remain vigilant in making sure we stay nimble and unburdened by the unnecessary.

Drinking from the Data Firehose

When I started with Stupid Cancer in late 2009, the organization had just invested in a SugarCRM database to manage relationships. I had used pharmacy management software since ’02 in my former life as a Pharmacy Tech, so I was familiar with the core functionality. SC had just hired a dev company and spent a considerable amount of money on what was then a worthwhile investment.

Being new to the organization, I didn’t want to rock the boat by accelerating development in ways I knew it could go. I also knew that at any given moment something could happen that would result in some kind of database related disaster. I didn’t have the keys to back up the database regularly. I probably didn’t think back then that I should have been.

Long story short, our self-hosted CRM wasn’t the right fit. We could have made that instance of Sugar work for us, but it was kind of doomed from the start. Before long, we landed on Mailchimp and our Sugar lead forms were replaced by Mailchimp signups. Our contacts became more valuable as subscribers and their journey with us carried on as such.

In 2011/2012, we began to see an uptick in traction across the board due to a corporate rebrand. Suddenly, our lists were growing. In March 2012, we launched an online store and began down an interesting e-commerce journey. All of a sudden, we had rich customer data. For the first time in organizational history, we had an influx of physical addresses. We had real people, spending money and willingly giving us data.

Mailchimp, along with Volusion, were our first two SaaS engagements. We were able to negotiate non-profit pricing which was in the 20–25% off range or sometimes free.

Very quickly, we faced another dilemma. Our email marketing platform and online store weren’t communicating with one another. Luckily, I caught wind of a cloud connector called Kevy. Up until this past summer, Kevy functioned solely as an integration platform. It moved large amounts of data from one cloud-hosted platform to another via API. They have since discontinued their integration service to focus on email marketing. We look forward to utilizing their service at the end of our current ESP contract.

Before we knew it, we were generating a ton of rich data every single day, from all sides. So much so, we couldn’t keep up with it. We had analytics and longitudinal information but were only in a position to glance at it and move on. With a small staff, there was no sound way to compile reports and make informed decisions, for the most part, other than from 35,000 feet up.

Last Summer, Slack was brought to market and changed everything for Stupid Cancer, and team communication everywhere.

Slack isn’t the first team communications platform that our organization has ever used. We were loyal users of Yammer, before it was acquired by Microsoft and the platform didn’t keep up with our needs. We put our best effort into Bitrix24, which only lasted until we caught wind of Slack.

Slack was new and interesting. It came with a lot of bells and whistles that we didn’t know we needed. Slack pointed me in the direction of Zapier, an integrations company. By this point, I had already experimented with IFTTT (If this, then that). Zapier connected Slack with platforms we didn’t even know it could.

Slack became the soul of Stupid Cancer overnight.

A year ago, I wrote this post about Slack. Since then, Slack has helped us refine a lot of our internal processes by making us take a tech-first approach. Throughout our work day, we track projects, finances, social media, customer service, customer feedback, event registration, and more.

After 7 years of creating data, we’re relaunching a traditional CRM on theBase platform. Using the same workflows that we have with Slack, we’ll be able to focus less on the minutiae and have a tool that serves us well.

Case Study: How Stupid Cancer manages all the moving parts with Klipfolio Dashboard

I recently sat down with Klipfolio to chat about how Stupid Cancer uses their service.  This is a repost.

What is Stupid Cancer?

Kenny Kane: Stupid Cancer is a not-for-profit organization that provides a support network for young adults affected by cancer. When our founder, Matthew Zachary, was diagnosed with a brain tumour in 1995, he realized that there were actually very few resources available to the 15-35 age category. Stupid Cancer was founded in 2007 to address this gap, and has grown to include a vast support network that includes local meet ups, online forums, social networks and even an online radio show.

What is your role with the organization?

KK: I was Matthew's 2nd intern and 1st employee. Back then, we were called "I'm Too Young For This!" but decided to adopt one of our campaign taglines, "Stupid Cancer." I am a Co-Founder and Director of Social Media, eCommerce and Supply Chain.

Can you tell us a little bit about your data and reporting needs?

KK: There are a lot of moving parts here at Stupid Cancer. We have a large social footprint and need to track data from our various revenue channels and supply chain. For us, it's about centralizing data from all these channels into one place.

How are you using Klipfolio?

KK: Right now, I have about 8 or 9 tabs on my dashboard. I use Klipfolio to bring all the data together in one place, which makes it convenient when I'm talking to our board of directors and need to rattle off lots of facts and figures. Klipfolio saves me a lot of time and energy when I'm preparing for meetings and it's definitely nice to have it 24/7.

Could you tell us a bit about the metrics you are tracking on your dashboard?

KK: My financial tab tracks donations, revenue vs expenses, and campaign performance, while my store tab tracks revenue by month, shipping costs, number of order shipped by state and I have a chart that tracks sales tax and shipping costs. My operations and social tabs show metrics like number of Facebook, Twitter, and Instagram followers, mail list subscribers, web visitors, and I even have a snapshot taken from Zendesk that shows opened and closed issues, as well as customer feedback.

My conference tab (pictured below) tracks the number of attendees to conferences over the past 4 years – it's actually really cool to see the growth of the conference. And the outreach tab tracks the literature we publish and send out to hospitals and shows data such as number sent, where they are sent to, and the frequency of sends.

Why Klipfolio?

KK: After checking out another solution, a friend referred me to Klipfolio. When I found out it was $20/mth, I didn't think it was real. *Laughs*

I have a basic knowledge of XML and what I like to call web accessible data sources. I've had a lot of fun setting up my dashboard and learning about the capabilities of the platform.

How has your experience been with Klipfolio staff?

KK: Yvonne is the best. Ever. She was absolutely instrumental in helping set up the dashboard and answering any questions I had.

What features would you like to see in the future?

KK: I'd love to see more data sources. I've definitely tweeted to Klipfolio to introduce you to services that I use. We'd definitely love to set up an integration with SoundCloud to get data about radio show attendees.

What's one piece of advice you'd give to a team preparing to deploy their own dashboard?

KK: Think of who you're sharing the dashboard with. A dashboard is only as good as the audience it's intended for. With all the information on my dashboard, I could pull open 8 or 9 chrome tabs in my browser and flip through them to get the same information. But think of how impressive it is to open the dashboard and have all your data flash, update and populate.

Zendesk, a Non-Profit's Dream.

I’ll generalize a bit: most nonprofits just aren’t set up to experiment with their tech stack. That’s not a knock—it’s just the reality. They’re busy doing the work, and let’s face it, most aren’t super nerdy.

As I write this from a JetBlue gate at San Diego International Airport, I find myself daydreaming about... closing tickets. The kind that get triaged to my team and me through our helpdesk. It's second nature now. Any time I check my iPhone, I might see a Zendesk notification waiting for me.

Wait—what’s Zendesk?

Back in 2012, when our team doubled from two to four, I pitched Zendesk as our helpdesk solution. It's simple: an inquiry comes in, a ticket is created, we get notified, we respond, and eventually, we resolve it. It also doubles as a powerful FAQ platform—customizable and user-friendly—with the added bonus of blog-style conversations at the bottom of each article.

But can’t we just stick with a shared Gmail account?

Sure, you can. We did. In fact, we had multiple shared inboxes and aliases, all leading into a messy Gmail catchall. If that sounds familiar, you’re not doing it wrong—but you could be doing it better. Zendesk brings structure, clarity, and scalability to your inbound chaos.

And if your setup is even more duct-taped than that... well, you might already know you need help.

So, why Zendesk?

Here’s what I was hoping for when we signed up:

• A single inbox to rule them all. I wanted a central place for inquiries that wasn’t my personal or work email.

• Smarter routing. No more time-wasting email threads—just reassign a ticket to the right person with a click.

• Better service. We run an online store and get plenty of “Where’s my order?!” messages. Zendesk helps us respond faster and with fewer dropped balls.

• A real, dynamic FAQ. Finally, a place to post policies and reduce repetitive questions.

And here’s what we’ve learned:

• It’s worth the investment. Zendesk isn’t free, but it pays off.

• You still have to drive. It’s not a magic wand. You’ll need to create macros, set rules, and stay on top of it.

• Know your users. Some people won’t love getting a ticket number. Legacy folks might be confused. Communicate the shift clearly.

• Don’t overuse it. We once tried scheduling a meeting via Zendesk. Ten messages later... we switched to email. Know when to step outside the system.

• Use the feedback. Zendesk can automatically send follow-up surveys after tickets are closed. Critical feedback helps us improve fast.

• Crowdsource your FAQs. Don’t write them in a vacuum. What seems obvious to you might be confusing to others.

• Make your FAQ pages fun. They don’t have to look like a dusty helpdesk relic.

• Track performance. Zendesk gives great data—who’s crushing it, who’s not, and how fast your team responds.

Bottom line: Zendesk isn’t a silver bullet, but it’s been a game-changer for us. Like anything else in your tech stack, you get out what you put in.