Repositioning Proposify for larger customers
Kyle explains why moving into the midmarket required security features, integrations, and messaging centered on control over sales proposals.
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How We Fixed Our Growth After Getting Stuck At $7m ARRMoving upmarket with security features and new positioning, then cutting burn from $400K a month to profit
Kyle Racki · Proposify
Published September 6, 2024Explore the lesson. Sign in to access the slide download.
Kyle explains why moving into the midmarket required security features, integrations, and messaging centered on control over sales proposals. Kyle describes the cash warning from his COO and CFO, the subsequent headcount reduction, and the shift toward cash-flow break-even.
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Kyle explains why moving into the midmarket required security features, integrations, and messaging centered on control over sales proposals.
Kyle describes the cash warning from his COO and CFO, the subsequent headcount reduction, and the shift toward cash-flow break-even.
Kyle discusses replacing an overly comfortable culture with candid conversations, more experiments, and a focus on delivering customer value.
Kyle describes how a new engineering leader combined a practical technical vision with a focus on the shortest path to solving customer problems.
“ProductClosed some gaps (Salesforce, SSO, SOC-2) Positioning around control + visibility (hired April Dunford) Pricing Moved to per-seat, CSM, professional services How We Moved Upmarket 3 things allow us to have mid-five and six figure customers TAKEAWAY 1 TAKEAWAY 2 TAKEAWAY 3”
“Growth by Segment Small segment began declining rapidly in 2022 Large segment grew steadily and now same in ARR as small Our initial growth was driven by small self-serve customers”
“Yearly Net Income Loss From Burning $400,000/month to profitable in 2 years Headcount over time by department”
“Fixing Our Culture Debt Building a performance-driven culture Getting scrappy again Making tough conversations the norm”
“Solve for your biggest constraint Leaders are your leverage SaaS is a marathon, not a sprint Takeaways Momentum is hard to rebuild once you lose it. TAKEAWAY 1 TAKEAWAY 2 TAKEAWAY 3”
Video
How We Fixed Our Growth After Getting Stuck At $7m ARR - Slide Deck

Co-founder & CEO of Proposify, a software that helps companies streamline their proposal creation and management process.
Mark Abbott · Ninety.io
Alex Quilici · YouMail
Savneet Singh · PAR Technology Corp.
Nicolas Vandenberghe · Chili Piper
Jay Ackerman · Reveleer
Aleksandr Yampolskiy · Security Scorecard
Find a passage in the slides and open the original deck.
14 passages
SaaSOpen, September 2024 How We’re Fixing Growth Our After Getting Stuck At $8m ARR Kyle Racki CEO & Co-Founder, Proposify
The good old days High growth, high NPS
ProductClosed some gaps (Salesforce, SSO, SOC-2) Positioning around control + visibility (hired April Dunford) Pricing Moved to per-seat, CSM, professional services How We Moved Upmarket 3 things allow us to have mid-five and six figure customers TAKEAWAY 1 TAKEAWAY 2 TAKEAWAY 3
Growth by Segment Small segment began declining rapidly in 2022 Large segment grew steadily and now same in ARR as small Our initial growth was driven by small self-serve customers
How We Got Here Product stagnation started around here Growth slowed during 2021
Yearly Net Income Loss From Burning $400,000/month to profitable in 2 years Headcount over time by department
One of the Toughest Days of My Life Helped us get to profitability Reset the culture Got us back to startup mode But also one of the best things we did
2023 Financials We became profitable in 2023 Buying us time to innovate our product 2023
Fixing Our Culture Debt Building a performance-driven culture Getting scrappy again Making tough conversations the norm
Meeting My New VP Engineering One developer changed everything Shout out to Mathieu 2023
Fixing Our Technical Debt
We’re Not Out of the Woods Decline flattening out Most new product features haven’t launched yet External market conditions still tough It takes time to fix things when you’re stuck
Solve for your biggest constraint Leaders are your leverage SaaS is a marathon, not a sprint Takeaways Momentum is hard to rebuild once you lose it. TAKEAWAY 1 TAKEAWAY 2 TAKEAWAY 3
SaaSOpen, September 2024 Thank you! [redacted email] Kyle Racki CEO & Co-Founder, Proposify