What happens when you grow from 3 people to 110 people and then back to 55 people? All the while growing mostly bootstrapped with a bit of funding?

Kyle Racki is the co-founder and CEO of Proposify, a proposal and contract management platform for agencies and service businesses. In this episode, Kyle shares the full arc of building Proposify over 12 years — from a solo designer at an agency to running a $9M+ ARR SaaS company with ~55 people.

The conversation covers the real leverage moves that made the leap possible: raising a small seed round to afford salaries while finding product-market fit, bootstrapping to $3M ARR, and then taking on growth capital that changed everything — including growing to 110 people, hitting cash concerns, and making the hard decision to cut the team in half and rebuild the company's culture and platform f ...