They entered HR tech at the worst possible moment: the remote-work boom was over, the category was overcrowded, and every keyword was already taken. Yet BuddiesHR still managed to grow, because they tested every hypothesis so radically that, at one point, they even built a competitor to themselves.

This episode focuses on J.Y. Delmotte, the co-founder of BuddiesHR. He explains how they chose to bootstrap after raising $6M in VC funding.

J.Y. shared his sharpest insights — what they did, why they did it, and what results it led to:

• how they entered one of the most overcrowded HR markets in 2023 — when the remote-work boom was over, Slack apps looked interchangeable, and every relevant keyword was already dominated
• why they stayed a two-founder team in a market where everyone hires early — and how this constraint forced them to design a cleaner, faster GTM
• why they spoke to more than 40 HR leaders before writing a single line of code
• how a tiny birthday-automation app became their entry point — and why this lightweight product helped them break through marketplace noise
• how cold outreach collapsed for them from day one
• how Slack Marketplace became their strongest early channel — and why this ecosystem rewarded focus, not breadth
• how they crafted a meme first, a culture-driven tone of voice that speaks only to their best HR buyers, something radically unusual in the corporate HR tools space
• why their AI SEO strategy backfired — thousands of programmatic pages that hurt domain health — and how switching to topic clusters revived their organic traffic
• how their first Google Ads attempt resulted in ~$500 per signup with no ROI, and why their later shift to competitor-keyword campaigns and “X vs BuddiesHR” pages finally started showing early positive signals
• how they improve messaging by watching real visitors interact with the site and letting a 10-member ICP board critique the copy
• how they divide marketing and product between two founders — and why this structure prevents slowdowns even with zero full-time hires
• how ChatGPT became a practical tool for editing, clarity, and risk-control — and why they use it selectively to avoid brand damage
• why they rely on small, fast experiments instead of big, resource-heavy bets — and how this mindset keeps their growth steady while staying fully bootstrapped

Connect with J.Y. on Linkedin. Learn more at BuddiesHR.com