E92: The journey from web agency to proposal expert with Kyle Racki

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Show Notes:

Kyle Racki is the co-founder and CEO of Proposify, a software-as-a-service (SaaS) company based in Halifax, Nova Scotia, Canada. Proposify currently serves more than six thousand customers worldwide. He started his first business, a web design company, at age twenty-four and sold it after five years. Kyle has blogged extensively about his journey through the ups and downs of entrepreneurship, and was the subject of a 2016 article in Time Magazine.


  • What made Kyle see a need for Purposify—and how he got started building it.
  • The challenges of going from an agency to a software company.
  • How a grant helped Proposify get past a rough patch.
  • Kyle’s philosophy on sales, and how it’s changed over time.
  • The best timeframe to send a proposal.
  • Best advice ever received:  Get rid of the agency.
  • Habit that contributes to success: The 5-minute journal
  • Favorite tool:  The Calm App and Productive
  • Book recommendations:  Rand Fishkin’s Lost and Founder
  • Run time:  41:52



  • “We were kind of in this limbo state.”
  • “A big saving grace….was applying for a grant program.”
  • “We’re helping solve a big problem.”
  • “There’s the graveyard of failed side projects.”
  • “Get the agreement in front of the prospect.”
  • “Once they’re basically saying, shut up and take my money.”
  • “You make us look like a rockstar.”


  • Review your sales and proposal process. When do you send the proposal? Are you able to track the process?
  • If you aren’t using something that allows for electronic signature, increase your close rate by starting now.