Hello to Canada’s SaaS and AI Community,
From humble beginnings to leading a 400-person global company, Simon De Baene’s story is what happens when sustainable growth meets a relentless focus on solving real customer problems.
At SAAS NORTH, the Co-Founder and CEO of Workleap (formerly GSoft) shared how his bootstrapped SaaS and AI journey led to $100M+ ARR (without a single pitch deck until year 18) and how that journey positioned them to acquire Barley.io just last week.
Simon’s insights are packed with dry humor, tactical advice, and a healthy dose of humility, showing that this isn’t a story about chasing unicorn status but about building a business that works for customers, employees, and the long term.
Key takeaways:
- Workleap raised capital for the first time after reaching $100M ARR, just to accelerate M&A.
- Product success came from falling in love with the problem, not the pitch.
- Culture evolved with the company but never replaced strategy.
Co-Founder/Producer, SAAS NORTH Conference Editor, SAAS NORTH NOW
Simon de Baene shared how Workleap scaled, no funding, no fluff. Get real stories and tactics live in 2025.
Simon De Baene built a $100M+ SaaS company by focusing on what most overlook: real problems, simple products, and strategic patience.
If you’re growing a SaaS business without a roadmap, this journey might be exactly what you need to hear.
1. Solve Real Problems
Fall in love with the problem, not the solution. When you focus on the problem, the solution becomes secondary. What matters most is solving something that truly needs fixing.
That’s exactly how Workleap found success with its first hit, ShareGate. It didn’t tackle a flashy challenge. Instead, it addressed a frustratingly common issue: moving files in SharePoint. It wasn’t glamorous, but it was painful, and no one else was solving it well.
This problem-first mindset became the company’s guiding principle.
“We became so obsessed with the problem that we became the best at solving it,” said Simon and that obsession paid off.
It’s a reminder to listen more than you build. If customers are annoyed by something and willing to pay to make it go away, you’re on to something, even if it doesn’t sound exciting.
2. Build Less. Deliver More.
“There’re always too many features and most features are useless.”
Simon learned this one the hard way: building 18 different products over the years, many of which flopped but the ones that succeeded had one common denominator; they kept things simple.
Launching with fewer features isn’t just a lean tactic; it’s a reality check.
“It needs to be uncomfortable,” Simon said of shipping early. “If it feels complete, you’ve waited too long.”
Simon emphasized how you need to force yourself to release before you’re ready. Then talk to your users. You’ll get more value from real feedback than another month of “polish.”
3. Don’t Confuse Culture for Strategy
“Culture eats strategy for breakfast… but the culture will starve if there’s no strategy.”
In Workleap’s early days, the perks were legendary: in-office baristas, a skate ramp, wild holiday parties. “We even had a coffee shop,” Simon said, laughing.
But those things became distractions.
Some applicants just wanted to work there because it looked cool, not because they believed in the mission.
Simon’s team eventually realized that culture must support strategy and not replace it. “A culture should support your mission, not the other way around,” he said. “The culture will starve if there’s no strategy.”
Perks don’t build alignment but clarity does. Define your mission and reinforce it constantly, especially as the team scales.
4. Be the Painkiller, Not the Vitamin
“It’s very difficult to do a go-to-market when it’s just a nice to have.”
Simon categorized products as either painkillers (must-haves) or vitamins (nice-to-haves). The former are obvious to customers and easy to sell. The latter require education and often get cut from budgets.
At Workleap, the team chose painkillers every time. They wanted products that showed up in Google searches, not ones that required explanation.
You have to ask yourself: If your product disappeared tomorrow, would your customers panic or shrug?
Build things that solve immediate, budget-worthy problems.
5. Your Business Is Not Your Identity
“It’s just a business. It’s not your whole identity… I used to be my business.”
Simon got real about the emotional rollercoaster of entrepreneurship. In the early years, he felt every high and low viscerally. “Every time my business was suffering, I was suffering,” he admitted.
But perspective brought peace. “The day I decided to put myself out of the business a little bit more, I made better decisions. And mentally, I’m much healthier.”
He ended with a note of humility: “Don’t let success, fame, or money change you. Appreciate the success and don’t take it for granted.”
The overriding message was clear; you have to build boundaries, celebrate wins, and protect your mental health.
The business is what you do, not who you are.
Simon De Baene’s journey is a powerful reminder that consistency, intentional growth and an obsession with solving real problems can be a truly winning formula for success.
And sometimes, that starts in the printer room.
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