Kyle Racki

Kyle Racki is co-founder and chief executive of Proposify, a company in Halifax, Nova Scotia, that makes software for writing, sending, tracking, and signing sales proposals. Born in Calgary and raised in Cole Harbour, Nova Scotia, he is a designer by background and is known for talking frankly about the hard years of building the company.

A designer with a better proposal

“I was brought up a Jehovah’s Witness and, in my early 20s, I became a designer and preached the gospel door to door,” he told Entrevestor. At a Halifax design agency he met Kevin Springer, and in 2008 the two started their own firm, Headspace Design. Springer said Racki “was thinking about a better way to write proposals” even then, and in 2013 they co-founded Proposify.

A year of hell

The early period nearly broke him. Proposify struggled for traction, the agency carried debt, his father died, he separated from his wife, and after he left the church his mother and sister cut off contact. At one point he could not pay the toll on a bridge into Halifax, TIME reported. “It’s just tenacity,” he said of how he got through.

Proposify raised a $250,000 seed round in 2014, and its customer count began doubling every month that fall. “Now, I believe life is not a training session; I make the most of it,” he told Entrevestor in 2015.

Growing to 110 people and back

Proposify bootstrapped to about $3 million in annual recurring revenue before raising a Series A, then grew to 110 people. When costs ran ahead of revenue he cut the team to about 55 and rebuilt Proposify’s software, he said on the Small Team Big Scale podcast in April 2026, when Proposify was past $9 million in annual recurring revenue.