What Happens After It Works?
How thoughtful systems—and the discipline to wait—create companies that don’t collapse under growth.
In my experience running a creative agency, I’ve noticed a pattern: companies don’t just hire us for the work—they hire us instead of hiring in-house. Not because they’re patching holes, but because they’re making strategic decisions about how to grow. We’re not a stopgap. We’re a structural choice. One that allows them to scale capabilities without scaling headcount.
That kind of decision—what to build internally, what to outsource, when to hire, when to wait—isn’t just operational. It’s philosophical. It forces a company to define its center of gravity. What’s truly core to its success? And what’s simply weight?
When growth is on the line, it’s tempting to solve every problem with more—more people, more tools, more motion. But the best operators don’t add. They refine. They don’t confuse activity with progress. Instead, they build carefully, patiently, and with discipline.
Jeroen Corthout is one such operator. As the co-founder of Salesflare, he has spent the past decade scaling a technology company without relying on the common crutches of overfunding or overhiring. What sets him apart isn’t just what he built—it’s how he built it. With systems that scale, a team that stays lean, and a mindset that puts clarity above complexity.
His story is a reminder that growth isn’t always about reaching further. Sometimes it’s about tightening your grip on what matters most.
Architecting the Advantage, it’s Jeroen Corthout
Jeroen Corthout didn’t set out to build just another CRM—he set out to build a better way to work. After starting his career in corporate marketing, he quickly realized that the traditional path—stacked with hierarchy, inefficiency, and bloat—wasn’t for him. So he took the long road to something simpler.
That road wasn’t smooth. Like many founders, Jeroen cycled through a number of failed startup attempts before Salesflare ever took shape. But each misstep helped sharpen his approach. When he and his co-founder saw how sales tools routinely collapsed under the weight of user friction and manual entry, they didn’t just spot a problem—they reimagined the system entirely.
Today, Jeroen leads Salesflare, a lean, automation-driven CRM designed for small B2B teams that need power without the overhead. But more than the product, what stands out is his way of operating: bootstrap when you can, hire only when it hurts, and always start by designing processes that make people better—not just busier.
Build the Machine Before You Feed It
The temptation to grow fast is everywhere. More people, more features, more everything. But Jeroen Corthout shows us another way: build slowly, but build right. In our conversation, he shared a number of clear-eyed truths about what it means to scale without sprawl, and how thoughtful systems can outperform premature staffing every time.
“Every hire is a big bet. And if you get it wrong, the damage is more than financial—it’s cultural.”
The insight: Hire only after you’ve done the work yourself. Knowing what excellence looks like in a role helps you hire for it—and avoid bringing in the wrong fit too soon.
“Most CRMs expect you to fill them out perfectly. We just wanted something that helped us do the actual work.”
The insight: Choose tools that reduce complexity, not add to it. Ask yourself: is this system saving time, or just tracking it?
“We didn’t get paid until 13 or 14 months in. That forced us to think really hard about what was essential.”
The insight: Delay comfort. Build processes that can survive without early revenue so your product—and your discipline—gets stronger before it scales.
“We were accepted into an accelerator, but only on the condition that we go full-time. That’s when things got real.”
The insight: Let pressure shape progress. Sometimes the right constraint—like a funding requirement or a timeline—can force clarity and commitment.
“Just because you can hire doesn’t mean you should. We turned over every decision twice.”
The insight: Add intentional friction to your decision-making. Implement a pause or second review for any hire, subscription, or major change. Growth should earn its way in.
“Automation isn’t about replacing people. It’s about letting them do the part only they can do.”
The insight: Audit your workflows: where are smart people doing dumb work? That’s where automation belongs.
“You don't need more people to grow—you need better systems. Otherwise, you’re just scaling the chaos.”
The insight: Before expanding your team, document your processes. If you can’t train someone with a one-pager, you’re not ready to hire yet.
Build Like you Mean it
The path to growth doesn’t have to start with a funding round or a flurry of hiring. Sometimes it starts with subtraction—with fewer moving parts, fewer dependencies, fewer distractions. Jeroen’s approach is a reminder that real scale doesn’t come from adding—it comes from designing something that works before you layer anything on top.
The question isn’t just “Can I build this?” It’s “Can I build this in a way that doesn’t break when it works?” That’s the quiet discipline behind sustainable companies: not chasing every opportunity, but structuring the business so that when success arrives, it has somewhere to land.
Thanks for reading,
—Ryan
Ready for more?
Catch Jeroen Corthout’s interview in its entirety on Eggs! The Podcast.
Don’t miss a show! Subscribe on Spotify, Apple Podcasts, or really anywhere great podcasts are found.
Path Picks
Cool stuff to help you forge your path to greatness.
Note: The Path Weekly is reader-supported. As such, I may be using affiliate links below. If you want to support the newsletter at no additional cost to you, please consider using the links below. If you’d rather not, most items below are widely available anywhere you want to shop. Thanks! –R
Reading list
If you're looking to go deeper on the themes from this week's newsletter, here are a few books that pair well with the conversation and offer a broader perspective on learning, systems, and the future of work:
The Lean Startup by Eric Ries: A foundational read on building products iteratively and efficiently, with systems designed to adapt and learn. A modern classic for any founder building without a safety net.
Company of One by Paul Jarvis: An argument for staying small, focused, and profitable—challenging the assumption that growth is always the goal. This one pairs especially well with Jeroen’s mindset.
Shape Up by Ryan Singer (Basecamp): A practical, opinionated look at how to build software (or really any project) with clear constraints, tighter teams, and less waste. Great for founders building processes that scale.
More to explore
Jeroen Corthout’s Links:
https://about.me/jeroencorthout
https://salesflare.com/
https://medium.com/@jeroencorthout
https://blog.salesflare.com/author/jeroencorthout
Work with me
Ryan Roghaar - Fractional CMO/Creative Director/Art Director: https://rogha.ar/portfolio
R2 - Creative Services for Agencies and SMBs: https://www.r2mg.com
Eggs! The Podcast: https://www.eggscast.com
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