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.
From the Pharmacy to the Fundraiser: My Unexpected Journey to Stupid Cancer
At the age of 15, I worked as a Pharmacy Technician for the local mom and pop, Islip Pharmacy. A job at CVS followed, then our community hospital. I loved it, however, I knew I wasn’t going to be a Pharmacist when I got a 62 in high school chemistry. Even my failing grade had a bit of creative curving upward. It was obvious that my pharmacy career would have a ceiling and an eventual stopping point. Luckily, I was pretty good on the computer, and tech became my primary focus.
I’m writing this from 35,000 feet—somewhere between Austin, TX, and New York City—as I head to Toast, Stupid Cancer’s annual fundraiser. It’s been a while since I’ve reflected on how I got here, and this flight feels like a good time to look back.
When I was 15, I got my first job as a Pharmacy Technician at the local mom-and-pop Islip Pharmacy. I loved it. I loved helping people, loved the structure, and even kind of liked the hustle. That led to a job at CVS, then at our community hospital. For a while, I thought I’d be a pharmacist—until I scored a 62 in high school chemistry. Even that was curved up. I started to see that maybe my future wasn’t behind the counter, but somewhere else. Thankfully, I was also pretty good with computers. Tech quietly became my Plan B.
In fall 2009, during my fifth year of undergrad (yes, fifth), I was sitting in a Grant Writing class without a clear idea of what came next. That’s when Cyndy, a guest speaker, introduced us to the “I’m Too Young For This! Cancer Foundation,” or i[2]y for short. My dad had been diagnosed with cancer in 2005, so the mission immediately caught my attention. I couldn’t help myself—I started browsing their website during her talk and even shot off an email to the CEO asking about internships. I got in trouble for it, but it turned out to be the right kind of trouble.
Around the same time, I applied for a Community Coordinator job at the hospital where I worked in the pharmacy. It was an entry-level marketing role—perfect for someone about to earn a degree in Communications. I didn’t get it. It stung at the time, but in hindsight, I’m grateful. That “no” cleared the path to something better.
On January 23, 2010, I started an internship at i[2]y with founder Matthew Zachary. I used my PTO from the hospital to spend Fridays in i[2]y’s Lower Manhattan office, bouncing between my pharmacy life and a new world in nonprofit startup life. In April—just two weeks before Matthew’s twins were due—I got the call: a full-time offer. I accepted immediately.
The next couple of years were foundational. We were scrappy but focused. We had a vision and were determined to build something that mattered.
In 2011, we rebranded from “I’m Too Young For This!” to “Stupid Cancer.” Almost instantly, our Facebook numbers shot up, thanks in part to a bold awareness ad that took off and got hundreds of thousands of likes. We leaned into that momentum.
That same year, we took our annual conference, the OMG! Cancer Summit, to Las Vegas. With support from Volkswagen, John Sabia and I jumped into a tiny coupe and hit the road. We visited hospitals, met patients, hosted meetups, and ultimately circled back to Vegas. We’d go on to do five of these road trips over the years—logging over 35,000 miles and leaving a trail of awareness, community, and purpose. Big thanks to GM/Chevy and Michael Savoni for helping keep us rolling.
From that point on, there was no slowing down. Stupid Cancer had found its stride, and we were all in.
Between 2013 and my departure in 2016, I focused on scaling areas of the organization that hadn’t yet been fully realized. One of my proudest achievements was growing the Stupid Cancer Store—from less than $5,000 in annual revenue to over $150,000. More than just a revenue stream, our apparel became a badge of identity for our community. We even spotted it on national TV. (Shoutout to Italia Ricci for that.)
Today, as I head back to NYC for Toast, I’m reminded of the winding road that brought me here—from a pharmacy counter in Long Island to co-leading a national movement for young adults affected by cancer. The journey was anything but linear, but it was exactly what I needed.
Did you spot the @StupidCancer logo in last night’s #ChasingLife? Here’s @italiaricci modeling a #StupidCancer tee! pic.twitter.com/KVNueba9PV
— Chasing Life (@ChasingLifeTV) July 3, 2014
MZ and I also sat through hours of choppy WebEx meetings with our offshore development company and created Instapeer, a mobile app for survivors and caregivers to connect and chat about their experience with cancer. It was the first of its kind.
When I think back to just how different life was from 2010 up to my departure in 2016, there are so many watershed moments for the organization. It was an incredible ride to be on.
Tonight, I am receiving the “Stupid Cancer Recognition Award” from the current Board of Directors and staff. It’s an honor that I could not have imagined receiving when I started out in the non-profit world 10 years ago.
When I think back to my motivation for inquiring about the internship, the feeling of being a helpless caregiver prevails most. Watching dad go through surgeries and chemo. We were bound to the process. Helpless.
If you are feeling helpless, help someone.
– Aung San Suu Kyi
I love this quote.
Productivity Apps that distract me all day long
An ever-growing list of apps and platforms I use every day in my Chief Operating Officer role at Stupid Cancer, client work, and blogging.
I’m always fascinated when I read what apps people use on a regular basis in different industries. Here is my list:
Sunrise Calendar I’ve been using Sunrise for almost two years and it has really changed everything, starting from the moment I wake up. Honestly, though. The email digest in the morning is fantastic and gives me an idea of what I’m up against. I have several calendars shared with me, which I hide on the desktop and mobile app. I get it all in the email which limits alerts.
Slack Slack, my Slack. If you’re reading this, I’m preaching to the choir. Maybe we could have a brief discussion below on how terrible the Ryver ads are on Twitter.
Trello Organized. Elegant. Slack integrated. Nuff said.
Calendly I wear a lot of hats. Calendly is the first solution that lets me put scheduling time in the hands of the other person. Saves so much time and is great for new clients.
Appear.in Love Google Hangouts but hate needing to login and invite someone with a Google account? Try this. It’s lovely.
Curated.co Curated.co is a email service provider that helps you build elegant, roundup emails. You can use a submit stories via email or bookmarklet. Compile collected stories for distribution at will. (Currently getting 50% open rates consistently with the list we’ve built.) Check it out
TripIt Helping me organize travel plans for years. Also has tracking metrics on distance and what not. Forward your itineraries to plans@tripit.com to get started.
Zapier Wade and his team have helped me professionally in ways they will never know. Zapier is the ultimate GSD app.
IFTTT If This Then That could be viewed as a competitor of Zapier, but it’s more of a Coke and Pepsi relationship. They are both super helpful.
iDoneThis This quirky app has changed things at Stupid Cancer. With a cool Slack integration, employees can type /done xyz and have it logged. IDT pings you at 9am and 5pm with what’s happened recently among the staff in a email digest format.
Mint Hit recommend if checking Mint to see how little money you have is a favorite pastime.
Bigcommerce What’s to say. The only game in town. Love BC. Love the people. Shoutout to Mitchell, Ron, Tracey and everyone else on Medium.
Skubana Skubana is an all-in-one cloud management platform for all things e-commerce. It helps me manage my Amazon seller account.
Inventory Planner Oleg has built something amazing here. It’s a Bigcommerce bolt on that has helped me more than I would have thought since enlisting the services of a third-party fulfillment company. It’s my window into the warehouse.
BaseCRM Base is relatively new for Stupid Cancer but works with Zapier (duh) and helps us funnel everyone into the app. Have it connected with just about every entry point to the organization.
Confluence We use Confluence for document retention. I wish we used it more, but we’re a small staff. Adoption has been difficult versus Google Drive or Dropbox.
Zendesk Gone are the days of responding to inquiries via shared gmail account. Zendesk helps us help people and fast.
Iconosquare Perfect Instagram desktop browsing tool. Love tracking our hashtags on it.
SumoMe I just rolled this out on my personal site to grow my list. I am optimistic it will help me beef up my email list.
FileZilla Free FTP client. I’ve been using it since I converted to Mac in 2010.
BBEdit The perfect notepad/html editor. Keep up the good work.
Email Permutator Want to email the CEO of a company but don’t know their email address? Use this.
Assembla We built a mobile app with an India-based dev company. We use Assembla to track app functionality requests and bug fixes.