Chapter 5: Building a Team Out of Software

I had no dedicated ecommerce team. No warehouse staff. No customer service department. No marketing manager. No inventory analyst.

What I did have was a carefully assembled ecosystem of apps that performed those functions for me.

Looking back now, more than a decade later, the specific apps I used matter less than understanding why I chose them and what burden each one lifted from my shoulders. Some of those tools still exist. Others have been acquired, sunset, or replaced by better alternatives. But the problems they solved haven't changed.

Every lean operator faces the same fundamental challenge: how do you do the work of five people when you're just one person? The answer isn't working five times harder. It's building systems that free you to focus on what matters most.

Email Marketing Without the Data Entry

Email marketing felt like a second job.

A customer would place an order on Bigcommerce. I'd need to manually add them to Mailchimp. Then I'd check their order history to decide which email segment they belonged in. New customer? Returning buyer? High-value customer who deserved a personal thank-you?

By the end of each week, I'd have a backlog of customer data that needed processing. And while I was catching up on administrative work, I wasn't writing the kind of emails that actually built relationships with our community.

I found a platform that connected directly to Bigcommerce and synced every customer, every order, and all the behavioral data to Mailchimp automatically. More importantly, it segmented customers based on their actual behavior—purchase history, engagement, lifetime value—without me having to think about it.

This freed me to do the work that actually mattered: writing emails that told stories, sharing updates about our mission, creating content that made customers feel connected to something bigger than a transaction.

The tool didn't replace my voice or my judgment about what to say. It just handled all the data management so I could focus on the creative work of building community through email.

What it does today: Similar functionality exists in platforms like Klaviyo, Omnisend, and others. The principle remains: automate the data management so you can focus on the message.

Inventory Planner: Math I Didn't Want to Do

Inventory management was my least favorite part of running the store.

Before Inventory Planner, I'd look at sales from the previous month, make rough calculations about reorder points, and hope I was ordering the right quantities. Sometimes I'd run out of popular items. Sometimes I'd over-order and tie up cash in slow-moving inventory.

Inventory Planner took over this entire headache. It analyzed sales velocity, tracked seasonal patterns, and told me exactly when to reorder and how much to order. It accounted for lead times from suppliers. It warned me when items were at risk of stockout. It identified dead stock that wasn't moving.

This freed me from constantly worrying about inventory levels. I could trust that the system would alert me when action was needed, and I could spend my mental energy on deciding what new products to create based on community feedback instead of calculating reorder points.

What it does today: Inventory Planner still exists under Sage. Modern alternatives include tools like Cin7, Ordoro, and even Shopify's native inventory features have improved dramatically. The principle remains: let software handle the math so you can focus on product strategy.

Lexity: Seeing What Customers Actually Do

Understanding what was happening on the website in real-time was critical, especially during the platform migration.

Lexity let me see who was browsing the store, what products they were viewing, and where they were getting stuck. During the migration, it caught 404 errors before customers even reported them. When someone seemed confused about sizing, I could proactively initiate a live chat to help them.

But the real value wasn't just fixing problems. It was understanding what products people were interested in before they bought. If I noticed several people viewing a product that wasn't selling well, I knew the issue wasn't interest—it was something about the product page, pricing, or description that needed work.

This visibility informed product decisions and helped me understand what resonated with the community.

What it does today: Lexity was acquired by Yahoo and evolved into different tools. Modern equivalents include Hotjar, Microsoft Clarity, Lucky Orange, or LiveSession. The principle remains: you need real-time visibility into customer behavior to catch problems and capitalize on opportunities.

Trello: An External Brain

Running a store generates hundreds of small tasks.

Without a system, these tasks lived in my head or scattered across email, sticky notes, and half-remembered conversations. Things fell through the cracks constantly.

Trello became my external brain. Every task got a card. Every card lived in the appropriate list (To Do, In Progress, Waiting On, Done). I could see at a glance what needed attention, what was blocked, and what had been completed.

More importantly, Zapier could create Trello cards automatically. When inventory dropped below threshold? New Trello card. When a customer sent a wholesale inquiry? New Trello card. This meant tasks were captured automatically instead of relying on me to remember to write them down.

What it does today: Trello still exists and is even more powerful. Alternatives include Asana, Monday.com, Notion, ClickUp, and dozens of others. The principle remains: externalize your task management so nothing lives only in your head.

Evernote: Capturing Ideas Before They Disappear

Ideas don't arrive on a schedule.

Without a capture system, these ideas would evaporate before I had time to act on them.

Evernote became my idea repository. I'd clip interesting designs, save customer feedback that suggested new products, and maintain running notes about what was working and what wasn't. The mobile app meant I could capture ideas immediately, wherever I was.

This created a library of insights I could reference when it was time to make decisions about new products, design updates, or strategic direction. The community's voice was preserved and accessible instead of lost in the chaos of daily operations.

What it does today: Evernote still exists but faces stiff competition from Notion, Apple Notes, Google Keep, Obsidian, and others. The principle remains: capture ideas immediately in a system you can search and reference later.

Grasshopper: A Professional Presence

Phone calls were rare but important.

Grasshopper gave us a professional toll-free number with extensions and voicemail transcription, but it all rang to my cell phone. Caller ID showed the business number so I knew it was a customer call, not personal. If I couldn't answer, voicemails were transcribed and emailed to me.

This let us appear more established than we were while maintaining flexibility. I didn't need a dedicated business phone line or office setup. The system worked wherever I was.

What it does today: Grasshopper still exists. Alternatives include OpenPhone, Google Voice (for simpler needs), or RingCentral (for more complex operations). The principle remains: give customers a professional way to reach you by phone without being tied to a physical location.

SurveyMonkey: Asking Instead of Guessing

The community told us what they wanted, but only if we asked.

SurveyMonkey made it easy to create quick polls and detailed surveys. Should we make hoodies? Which color options do you prefer? Would you buy this design? The responses guided product decisions and made customers feel heard.

These weren't just research tools. They were community engagement tools. By asking for input, we strengthened the relationship between the brand and the people supporting it.

What it does today: SurveyMonkey still exists alongside Typeform, Google Forms, Jotform, and others. The principle remains: make it easy to gather structured feedback from your community.

99Designs: Democratizing Product Creation

Creating new products required design work, and I'm not a designer.

99Designs let me launch design contests where multiple designers would submit concepts. I could share these submissions with the community to get feedback, then work with the winning designer to refine the final product.

This democratized the design process and ensured we were creating products that actually resonated with the community, not just products I personally liked.

What it does today: 99Designs still exists and has evolved significantly. Alternatives include Fiverr, Upwork, Dribbble hiring, or Behance. The principle remains: access design talent without hiring full-time staff, and involve your community in the selection process.

Building Your Own Ecosystem

The specific tools I used were right for 2013-2016. Your ecosystem in 2025 and beyond will look different. New tools emerge constantly. Old tools get acquired or shut down. Features that required separate apps get built into platforms.

But the principle never changes: identify the work that's stealing your time and energy, then find tools that can handle that work reliably so you can focus on what actually builds your brand.

Ask yourself:

●  ​What repetitive work drains my energy?

●  ​What data management tasks could be automated?

●  ​Where am I making mistakes because I'm trying to remember too much?

●  ​What analysis am I skipping because it takes too long to do manually?

For each answer, there's probably a tool that can help. The investment in software—usually $20-100 per month per tool—returns that money immediately in time saved and quality improved.

When I left Stupid Cancer in 2016, all these tools kept running. The data kept syncing. The tasks kept organizing. The infrastructure remained operational.

But without someone who understood the ecosystem—why each tool existed, how to interpret its outputs, how to make decisions based on its data—the system couldn't sustain the store long-term.

That's the limitation: tools multiply your effectiveness, but they don't replace your judgment.

You still need the human in the loop. But with the right ecosystem, that human can accomplish far more than should be possible. The tools handled the routine so I could focus on the exceptional.

And that made all the difference.