Former Levelset CRO Martin Roth takes you behind the scenes of scaling a company from $0 to over $25 million ARR and a successful exit to Procore. With raw honesty, he shares key mistakes made along the way and invaluable lessons learned about building a winning sales playbook, culture, and team structure.
The early days and career beginnings
In 2012, Martin Roth joined Levelset (formerly ZLien) as one of the earliest employees, a time when the company was a mere side business for its founder, Scott Wolf. Roth’s journey began as a 23-year-old failed entrepreneur, fresh from a stint pedicabbing in the French Quarter of New Orleans for cash after his consumer product startup fizzled out. His path to Levelset was serendipitous – he had tried to sell Wolf health insurance, thinking the company was much larger than it actually was.
Martin’s early years at Levelset were a whirlwind of learning and overcoming challenges. With no background in software sales, he had to quickly pick up the ropes of B2B selling, making numerous mistakes along the way. However, his competitive spirit and willingness to learn fueled his determination to succeed. As he puts it, “I like to win. I’m competitive.”
Building the sales organization
In the formative years, Levelset lacked a formal sales playbook. It wasn’t until 2018 – five years into his tenure – that they developed a structured approach to guiding prospects through the sales process.
The value of “been there, done that” came out as Martin expressed:
“If I could do it again, knowing what I know now, I know we could go faster.”
As the company scaled, Martin recognized the importance of coaching and actively managing the sales team. He shifted from a hands-off approach to embracing what he calls “micro-coaching,” working deal by deal with reps to ensure compliance with the playbook and provide support.
He also realized the importance of fluidity and iteration.
“Think of product development like collaborative design: a living process where small adjustments compound into transformative outcomes.”
Scaling from $1M to $10M ARR
The journey from $1 million to $10 million in annual recurring revenue (ARR) was arduous, spanning nearly six years. Martin attributes this extended timeline partly to early missteps but also to the inherent challenges of this growth phase.
“0 to 1’s really hard. 1 to 10’s really hard. 10 to 20. They’re all different versions of hard.”
A critical inflection point came when Martin and Levelset’s VP of Customer Success recognized the untapped potential in their existing customer base. By transitioning the upsell and expansion motion to a dedicated sales team, they were able to increase monthly upsell revenue from $30,000 to $500,000 within six months.
Hiring and team expansion decisions were driven by a combination of top-down demand modeling and bottom-up capacity planning. Martin emphasizes the importance of maintaining enough quota coverage to meet revenue targets while accounting for factors like rep attrition and ramp time.
Preparing for the next stage: $10M to $20M ARR
As Levelset approached the $10 million ARR milestone, the COVID-19 pandemic struck, forcing the company to reevaluate its growth strategy. Initially, there was uncertainty about the pandemic’s impact on the construction industry, prompting Levelset to pull back on aggressive sales hiring temporarily.
However, as the industry proved resilient, Levelset was able to accelerate its growth trajectory in 2021. This period saw the company optimizing its sales processes, doubling down on the upsell motion, and ultimately positioning itself for acquisition by Procore in a $500 million deal.
3 pieces of advice and lessons learned
While widely debated, from Martin’s experience he stands by these three beliefs:
- Remote sales environments are often suboptimal for early-career professionals. In-person training and development are highly effective for fostering growth and skill-building in these roles.
- Cold outreach remains a foundational strategy for professional success, emphasizing highly personalized outreach and the development of targeted lists. Avoiding the common “set it and forget it” approach is crucial for meaningful connections.
- A hybrid strategy that combines digital outreach with periodic in-person events or “road shows” in key markets can create immersive experiences that deepen connections with customers and prospects, driving brand awareness and pipeline generation.
Listen to Martin explain more context around this in episode 125 of The GTM Podcast.
The post From Flip-Flops to a $500M Exit as CRO: Lessons Learned from Taking a Startup From $0 to a Successful Exit with Martin Roth appeared first on GTMnow.