From Flip-Flops to a $500M Exit as CRO: Lessons Learned from Taking a Startup From $0 to a Successful Exit with Martin Roth

Former Levelset CRO Martin Roth takes you down nan scenes of scaling a institution from $0 to complete $25 cardinal ARR and a successful exit to Procore. With earthy honesty, he shares cardinal mistakes made on nan measurement and invaluable lessons learned astir building a winning income playbook, culture, and squad structure. 

The early days and profession beginnings

In 2012, Martin Roth joined Levelset (formerly ZLien) arsenic 1 of nan earliest employees, a clip erstwhile nan institution was a specified broadside business for its founder, Scott Wolf. Roth’s travel began arsenic a 23-year-old grounded entrepreneur, caller from a stint pedicabbing successful nan French Quarter of New Orleans for rate aft his user merchandise startup fizzled out. His way to Levelset was serendipitous – he had tried to waste Wolf wellness insurance, reasoning nan institution was overmuch larger than it really was.

Martin’s early years astatine Levelset were a whirlwind of learning and overcoming challenges. With nary inheritance successful package sales, he had to quickly prime up nan ropes of B2B selling, making galore mistakes on nan way. However, his competitory tone and willingness to study fueled his determination to succeed. As he puts it, “I for illustration to win. I’m competitive.” 

Building nan income organization

In nan formative years, Levelset lacked a general income playbook. It wasn’t until 2018 – 5 years into his tenure – that they developed a system attack to guiding prospects done nan income process. 

The worth of “been there, done that” came retired arsenic Martin expressed:

“If I could do it again, knowing what I cognize now, I cognize we could spell faster.”

As nan institution scaled, Martin recognized nan value of coaching and actively managing nan income team. He shifted from a hands-off attack to embracing what he calls “micro-coaching,” moving woody by woody pinch reps to guarantee compliance pinch nan playbook and supply support. 

He besides realized nan value of fluidity and iteration. 

“Think of merchandise improvement for illustration collaborative design: a surviving process wherever mini adjustments compound into transformative outcomes.”

Scaling from $1M to $10M ARR

The travel from $1 cardinal to $10 cardinal successful yearly recurring gross (ARR) was arduous, spanning astir six years. Martin attributes this extended timeline partially to early missteps but besides to nan inherent challenges of this maturation phase. 

“0 to 1’s really hard. 1 to 10’s really hard. 10 to 20. They’re each different versions of hard.”

A captious inflection constituent came erstwhile Martin and Levelset’s VP of Customer Success recognized nan untapped imaginable successful their existing customer base. By transitioning nan upsell and description mobility to a dedicated income team, they were capable to summation monthly upsell gross from $30,000 to $500,000 wrong six months.

Hiring and squad description decisions were driven by a operation of top-down request modeling and bottom-up capacity planning. Martin emphasizes nan value of maintaining capable quota sum to meet gross targets while accounting for factors for illustration rep attrition and ramp time.

Preparing for nan adjacent stage: $10M to $20M ARR

As Levelset approached nan $10 cardinal ARR milestone, nan COVID-19 pandemic struck, forcing nan institution to reevaluate its maturation strategy. Initially, location was uncertainty astir nan pandemic’s effect connected nan building industry, prompting Levelset to propulsion backmost connected fierce income hiring temporarily.

However, arsenic nan manufacture proved resilient, Levelset was capable to accelerate its maturation trajectory successful 2021. This play saw nan institution optimizing its income processes, doubling down connected nan upsell motion, and yet positioning itself for acquisition by Procore successful a $500 cardinal deal.

3 pieces of proposal and lessons learned

While wide debated, from Martin’s acquisition he stands by these 3 beliefs:

1. Remote income environments are often suboptimal for early-career professionals. In-person training and improvement are highly effective for fostering maturation and skill-building successful these roles.
2. Cold outreach remains a foundational strategy for master success, emphasizing highly personalized outreach and nan improvement of targeted lists. Avoiding nan communal “set it and hide it” attack is important for meaningful connections. 
3. A hybrid strategy that combines integer outreach pinch periodic in-person events aliases “road shows” successful cardinal markets tin create immersive experiences that deepen connections pinch customers and prospects, driving marque consciousness and pipeline generation.

Listen to Martin explicate much discourse astir this successful episode 125 of The GTM Podcast.