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Timestamps
3:08 External workforce grew from 20% to 50% of headcount. The software never caught up.
4:46 Why AI agents finally make workforce automation possible.
5:51 The shift from managing employees to orchestrating work.
7:44 How Sherpa attracted global pharma customers before even launching.
7:53 Why professional services is next in line for AI disruption.
9:23 The vision for total work orchestration, from intent to value.
10:32 "Find investors more passionate about your business than you are."
13:43 Pre-seed fundraising advice: don't chase every VC diligence request.
Last week, we shared why we invested in Sherpa. This week, we sat down with Tristan, co-founder and CEO, to unpack the market, the vision and the founder lessons behind the company.
One thing that stood out from our conversation wasn't just the size of the market, it was how invisible the opportunity is.
External workers now make up 30-50% of the workforce in many large organisations, yet the software managing them hasn't fundamentally changed in decades. That's exactly the kind of overlooked market we love: massive, painful and hiding in plain sight.
A few founder lessons stood out:
- Look where nobody else is looking: the biggest opportunities are often hidden inside "boring" industries with broken workflows.
- Develop founder-market fit: deep customer insight is hard to replicate and often becomes your biggest competitive advantage.
- Build conviction, not consensus: great founders don't try to answer every investor request. They focus on the vision and find partners who genuinely believe in it.
- Think beyond today's product: Sherpa isn't building another workflow tool. It's building towards a future where work is orchestrated seamlessly across employees, contractors and AI agents.
The next generation of category-defining companies won't just automate work, they'll redefine how work itself gets done. That is why we backed Sherpa.
For founders, this conversation is packed with practical lessons on identifying overlooked markets, developing deep customer insight, articulating a category-defining vision, and raising a pre-seed round with conviction instead of trying to satisfy every investor.
Whether you're building an AI company, raising your first round, or looking for the next big opportunity, this episode is for you.
Learn more about Sherpa:https://sherpahq.ai/
