Hard Lessons from a Previous Startup Pivot

On this episode of The SaaS CFO Podcast, host Ben Murray welcomes Brett Carlson, co-founder and CEO of ServiceUp, to share his entrepreneurial journey and the story behind his latest venture. Brett’s background spans over 25 years in tech, with experience founding and scaling startups on the business side. With ServiceUp, Brett turned his focus to the vehicle repair industry, spotting a massive, underserved $250 billion market ready for modernization and disruption. 

Brett dives into how ServiceUp started by offering digital car repair solutions directly to consumers before pivoting to serve fleet operators and insurance companies. He explains the pain points that large fleet owners—think Amazon, UPS, and major rental car companies—face with outdated repair processes, and how ServiceUp’s platform streamlines transactions and increases efficiency for both fleets and repair shops. Brett also shares how thoughtful use of technology and automation, including AI-powered voice agents, has accelerated their reach and operational effectiveness. 

Throughout the conversation, Brett offers an inside look at ServiceUp’s rapid growth and successful fundraising journey, including securing a $55 million Series B. He discusses the evolving expectations of investors, the importance of backing up metrics at each funding stage, and key lessons learned from navigating both the highs and lows of startup life. Whether you’re an aspiring SaaS founder or just curious about the intersection of technology and traditional industries, Brett’s insights into building ServiceUp are sure to inspire. 

Show Notes: 

00:00 Switching Focus to Fleet Services 

04:20 Major Retailer Faces $175M Collision Costs 

08:43 Frugal Growth and Investment Strategy 

12:30 "Investor Monetization Contradictions" 

15:21 DoorDash's Missed Market Opportunity 

20:30 Advanced AI in Voice & Shop Tech 

21:16 Automated Market Entry Strategy 

Links: 

SaaS Fundraising Stories: https://www.thesaasnews.com/news/serviceup-secures-55-million-in-series-b 

Brett Carlson’s LinkedIn: https://www.linkedin.com/in/brettcarlson418/ 

ServiceUp’s LinkedIn: https://www.linkedin.com/company/serviceupio/ 

ServiceUp’s Website: https://www.serviceup.com/ 

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