The short answer is: whenever you've demonstrated solid product-market fit. But when is that? Product-market fit happens when you're gaining real, sustained, repeatable traction from those who drive revenue. For example, if you build a marketplace, traction comes when you have many end-consumers or demand channels actively using your platform for transactions. While having the right supply base is crucial, it's customer demand that truly signals product-market fit.
Investing in any commercial role before reaching this milestone would be like throwing your hard-earned seed money out the window. This means, however, that you have another set of important tasks on your to-do list: attract and sign supply partners, convince demand customers (in a B2B environment) to take a leap of faith and try your product, build your brand, and develop a suitable yet scalable pricing strategy. The good news? You'll be the best person for these tasks. As the driving force behind the company, you're passionate about your big idea, which makes you the best salesperson—even if sales has never been your strong suit, like me.
Of course, you've got to find ways to do all this efficiently (meaning cheaply). In my experience, a successful commercial start hinges on two factors: a live product and an engaging story. With these in place, you'll be able to open doors to key supply partners, industry press, and pilot customers. Don’t travel around or make calls until you’ve got this in place.
Despite early challenges with product execution, the first flyiin was a marketing and sales success. Many major airlines embraced our vision of a new consumer-facing platform that would challenge traditional online travel agencies and flight search engines. Our timing was perfect—we offered airlines a way to justify their substantial investments in their new distribution APIs.
In less than 18 months, we had convinced over 10 major airlines to join our Air Travel Marketplace concept. The trade press was writing about us, and we had secured a large, founder-friendly investor to finance our live product development and go-to-market strategy. We achieved all this without a dedicated budget or role—our compelling story and prototype product did the trick.
After our failed seed investment and pivot to a pure tech solution, we had to start anew. While most airlines remained on board, some were less enthusiastic about the pivot. Our new challenge was finding "demand" customers—consumer-facing brands or tech players who would use our platform for booking transactions with our partner airlines. We signed two pilot customers in 2019–2020 (one of whom shut down just two months after going live with us). Yet, the reality was that our story lacked sufficient appeal, and our product wasn't quite ready to execute our strategy effectively.
I brought on board a more experienced commercial person in the middle of the COVID-19 pandemic. In denial of our reality—we were going nowhere—I wanted to establish the foundations of proper sales and account management early on. Not a very smart decision (to say the least). I had to let this person go just five months after she had joined our team.
Key Takeaway #26
Prioritize product-market fit before hiring sales and marketing people . Focus on building your product, attracting customers, and crafting a compelling story. As the founder, you're the best salesperson to initially drive growth.