Proposify’s Unlikely Partnership Works
Kevin Springer and Kyle Racki have forged an unusually successful partnership — forming two businesses and exiting one — despite a 20-year age gap and early religious differences.
Springer, 51, is president of Halifax-based PitchPerfect Software, the parent company of Proposify.biz.
Proposify is a software-as-a-service, or SaaS, product, which allows members of an agency to collaborate on client proposals.
Racki, 31, is PitchPerfect’s CEO.
Before Proposify, the two built the web-design firm Headspace Design, which they sold in 2014.
They first met a decade ago while working for a Halifax design agency.
The two got on well, even though Racki was at the time a Jehovah’s Witness and Springer was an atheist environmentalist.
“I was brought up a Jehovah’s Witness and, in my early 20s, I became a designer and preached the gospel door to door,” Racki said as he sat in the Proposify office at Volta, Halifax’s startup house on Spring Garden Road.
A U.S.-raised entrepreneur, Springer had already created several businesses, including one that raised funds to help save the endangered Florida manatee.
Springer saw Racki’s potential.
“Kyle was already a great user-experience guy and designer,” said Springer.
“He was thinking about a better way to write proposals. He already had the seed of Proposify.”
In 2008, the two began working on Headspace. Their connection has evolved since then.
“You have to nurture the relationship,” said Racki. “If you go too long without saying, ‘Good job,’ the other feels unappreciated.”
Both say building a business has been smoother the second time around.
This is partly because they are now selling a product, not a service. That means they have been eligible for more government support.
A funding round of $670,000 included an investment from Innovacorp and a loan from the Atlantic Canada Opportunities Agency.
ACOA also helped them employ Jonathan Down, who built the Proposify prototype and is now their chief technical officer.
“With Headspace, it was a constant challenge to get business. Our clients were mostly regional,” said Springer.
“Now with a SaaS product, most of our clients are in the U.S., the U.K. and Australia.”
Second time around, the duo knew to focus on refining their product and finding their market niche.
Still, leaving Headspace to focus on Proposify was not easy. The two tried to work on both, but found themselves having to drop Proposify when Headspace clients came in.
“We had to make a decision. It was hard. The Headspace employees had become our friends, and it was difficult to find the right buyer,” Springer said.
But Proposify now has hundreds of customers who collectively pitch over $1 million every month.
With wildly different backgrounds and experiences, they have different skill sets.
Springer grew up near Boston, moving to Nova Scotia in 2001. A musician and athlete, he is well-known in Halifax as an athletics and ball coach.
He has a degree in fine-arts management, worked in museums and the music industry and ran a live music club in his hometown.
“A background in non-profits taught me how to market something on a shoestring,” he said.
“I love athletics and sports. When I’m with those kids, I don’t think about anything else. And dealing with parents has taught me communication and leadership skills.”
Racki was born in Calgary and raised in Cole Harbour.
He left the church after his father died, losing many friends and contacts. He has now rebuilt his life and personal and business networks.
“I’ve changed in a lot of ways,” he said. “Now, I believe life is not a training session; I make the most of it.”
Springer said Racki’s new philosophy helps them align their goals.
“I’m thinking of my legacy,” he said. “I want to build a solid company and live a great life.”
Racki grinned. “Yeah, we want to provide the best proposal software in the world.”