A founding principle of our Enduring GROWTH System™ Research Program is that we’re learning from people who have experienced company growth from very different vantage points.
Few people have seen it from as many angles as Jeff Wald.
Jeff is a serial technology entrepreneur, investor and board director who has founded and exited multiple companies. He’s best known as the co-founder of WorkMarket, which grew to approximately $30M in revenue before being acquired by ADP. Today, he’s back in founder mode as Co-Founder of BoomerangHR. He’s also been on the other side of the table — as a venture investor, angel investor and board member — evaluating companies, founders and growth opportunities.
So I was particularly interested in his answer to a deceptively simple question:
After building company after company, what does Jeff now understand about growth that he didn’t understand the first time?
His answers were refreshingly practical. Here are four ideas from our conversation that have stayed with me since our interview.
1. Eventually, you have to build the machine.
Jeff used this phrase repeatedly during our conversation:
“What’s the machine?”
At WorkMarket, founder-led effort could get the company only so far.
Eventually, marketing had to reliably create opportunity. Sales had to convert it. Customers had to be onboarded successfully. Usage had to be visible. Problems had to surface before customers left. Renewals couldn’t depend on someone remembering to check in. The work had to become a system.
Jeff described company growth in three broad phases.
Phase 1: Founder-land. Few customers. Extraordinary individual effort. People doing whatever needs to be done.
Phase 2: Customers arrive. Complexity increases. Processes and systems start becoming necessary.
Phase 3: The machine increasingly takes over. Policies, procedures, tooling and organizational capability replace individual heroics.
That’s not bureaucracy for bureaucracy’s sake. It’s what makes growth repeatable.
Because if success depends on exceptional people remembering everything, noticing everything and personally making everything happen, you haven’t really built a scalable company yet.
2. Don’t confuse “sell-to” with “sell-through.”
This may have been my favorite distinction from our conversation.
Companies can buy your product without actually using your product. WorkMarket learned that firsthand. Executives could understand the business case. They could approve the purchase. They could deploy the technology. But the people who actually had to use it were being asked to change how they worked — sometimes without seeing much personal benefit from doing so. So WorkMarket had customers who had bought the product but weren’t really using it.
Jeff and his team had to get extraordinarily close to those users.
They went onsite. Brought pizza. Trained people. Sat beside them while they worked. Watched where they struggled. Changed the software. Went back and watched again. Two days of hands-on onboarding eventually became one day. Then an hour. Eventually, they didn’t need to be onsite at all.
Those were what Jeff called the “hard yards.” And they expose an important growth trap:
A signed contract proves someone will buy. It doesn’t prove you’ve created enduring customer value.
Utilization matters. Engagement matters. Retention matters. Renewal matters.
Revenue can look like validation before customer behaviour proves that it actually is.
3. The founder eventually has to stop being the router.
Jeff was remarkably candid about this one.
Earlier in his career, he often believed he could do things better himself. And maybe sometimes he could. But eventually he realized something much more important:
It doesn’t matter. It doesn’t scale.
If every meaningful decision, customer issue or piece of institutional knowledge has to pass through the founder, the founder eventually becomes the constraint. Jeff described the necessary transition as moving from a “cult of personality” to a “cult of systems”.
His test is wonderfully simple:
Can important things happen without you?
At WorkMarket, he remembers reaching the point where a deal could be sourced, sold, implemented and supported without him even knowing about it. That wasn’t a loss of control. It was evidence that they had built a company.
The founder’s job changes from creating the outcomes personally to creating the systems, culture and people capable of producing those outcomes without them.
4. Capital buys you a window. Know what has to become true before it closes.
Jeff is unapologetically comfortable with venture capital.
His first startup was bootstrapped. It failed and left him penniless. Since then, he’s generally preferred taking a smaller piece of a potentially larger pie while investors help underwrite the financial risk.
But that doesn’t make him casual about capital. Quite the opposite.
Jeff thinks of every raise as creating a finite capital window. You raise a certain amount of money. That gives you a certain amount of time.
The important question becomes:
What are the two or three things that absolutely have to become true before that window closes?
- Better unit economics?
- A repeatable acquisition channel?
- Proof of customer retention?
- The underlying machine?
More capital isn’t automatically the answer when those things aren’t working. In fact, Jeff has resisted pressure to accelerate BoomerangHR, even when early signals looked promising, because he didn’t believe they’d built the underlying machine yet.
His shorthand is hard to forget:
“Cash is oxygen. When it runs out, you’re done.”
So capital discipline isn’t simply about conserving cash. It’s about knowing exactly what the cash needs to prove.
What struck me about Jeff’s perspective is how little of it is really about finding a growth “hack.” It’s almost the opposite.
- Find the customer.
- Figure out what actually works.
- Do the hard yards required to create real customer value.
- Turn what works into a machine.
- Build a culture and organization that don’t depend on the founder to keep that machine running.
- And use capital deliberately enough to give yourself the time to get there.
That’s company building.
And perhaps that’s the bigger lesson from someone who has done it repeatedly: enduring growth isn’t created by doing more. It’s created by progressively turning what you’ve learned into organizational capability.
A sincere thank you to Jeff Wald for sharing his experience, candour and perspective with the Enduring GROWTH System™ Research Program. Jeff brought the perspective of someone who has built, funded, scaled, sold, invested in and advised technology companies — and who is still actively putting those lessons to work as a founder today. His willingness to talk openly about both what worked and what didn’t made this an especially valuable conversation, and his insights are helping shape our understanding of what it takes to build companies that don’t just grow — but endure.
To learn more from Jeff, connect with him on LinkedIn:
https://www.linkedin.com/in/jeffwald/
To learn more about BoomerangHR, visit their website here: https://boomeranghr.com/