How Levelset scaled to $25M ARR, then sold for $500M

Hello and welcome to The GTM Newsletter by GTMnow – read by 50,000+ to scale their companies and careers. GTMnow shares insight around the go-to-market strategies responsible for explosive company growth. GTMnow highlights the strategies, along with the stories from the top 1% of GTM executives, VCs, and founders behind these strategies and companies.

Former Levelset CRO Martin Roth takes us behind the scenes of scaling a company from $0 to over $25 million ARR and a successful exit to Procore. One shift unlocked $500k per month in expansion revenue. They also had no sales playbook for 5 years, then had a $500M exit.

The early days

When Martin joined Levelset (formerly ZLien) in 2012, the company was a far cry from the high-growth SaaS business it would eventually become. At the time, it was a side business for its founder—a bootstrapped, transactional platform helping contractors file construction liens online.

Martin himself wasn’t the obvious choice for a sales leadership role. At just 23 years old, he had already experienced the highs and lows of entrepreneurship. His first startup—a consumer product company focused on group gifting—never gained enough traction, leaving him scrambling for work. In the months before joining Levelset, he was pedicabbing in New Orleans’ French Quarter and selling insurance, trying to find his next step.

His introduction to Levelset was pure chance. While selling health insurance, he mistakenly assumed that the company was much larger than it was and attempted to pitch the founder. Instead of a policy, the founder offered him something unexpected: a job building out Levelset’s sales motion from scratch.

Building a sales organization from the ground up

Like many early-stage startups, Levelset didn’t start with a well-oiled sales machine. There was no structured playbook, no hiring blueprint, and certainly no quota capacity planning. In those early years, Martin was carrying a bag himself, closing deals while figuring out enterprise sales on the fly.

For the first five years, the company lacked a formal sales playbook.

“If I could do it again, knowing what I know now, I know we could go faster.”

In 2018, everything changed. Martin led the charge in implementing a structured sales process, shifting from an instinct-driven approach to a disciplined, repeatable system. He embraced what he now calls “micro-coaching”—getting deep into the details of each deal, guiding reps through every stage, and ensuring full compliance with their new playbook.

It wasn’t about controlling reps. It was about eliminating inefficiencies and ensuring consistency in execution.

“I used to think you just hire good people and let them do their thing. That’s a mistake. Great leaders get in the weeds—they listen to calls, they review pipeline deal by deal, and they coach relentlessly.”

This shift set the stage for Levelset’s next phase of growth.

Related resource: How Outreach Scaled from $0 to $230M ARR

$1M to $10M ARR: The grind

Scaling from $1M to $10M ARR was one of the hardest phases of Levelset’s journey and a process that took nearly six years.

“Zero to one is really hard. One to ten is really hard. Ten to twenty—they’re all different versions of hard.”

One of the biggest unlocks came when Martin and Levelset’s VP of Customer Success (CS) recognized a massive gap in their revenue strategy: they weren’t monetizing their existing customers effectively.

At the time, expansion and upsell were handled by the CS team, whose primary focus was retention and customer success, not sales. The result? Expansion revenue was trickling in at just $30,000 per month, a fraction of what it should have been.

The fix: moving upsell and expansion to a dedicated sales team.

Within six months, Levelset’s monthly upsell revenue exploded from $30,000 to $500,000.

“We took a traditional account management role, turned it into a true sales function, gave them quotas, comped them like salespeople, and built a structured playbook. That single change drove a half-million in new revenue every month.”

Beyond upsell, hiring decisions during this period were driven by top-down demand modeling and bottom-up capacity planning.

Related resource: How Asana & Calendly Scaled Their PLG to SLG Motion

$10 to $20M ARR: Navigating it and a $500M exit

Just as Levelset was hitting its stride in early 2020, the COVID-19 pandemic threw everything into uncertainty.

The company had just raised a $30M Series C at the end of 2019 and was aggressively hiring. On March 16, 2020, two days after lockdowns began, a class of 14 new reps was supposed to start onboarding in person. Instead, the company slammed the brakes.

But as the construction industry proved resilient, Levelset was able to re-accelerate hiring in 2021, refining its sales processes and scaling its upsell motion even further.

The result? By the time Levelset was acquired by Procore for $500M, they had:

A well-defined SMB and mid-market sales motion.
A high-velocity upsell engine generating $500K+ in expansion revenue per month.
A culture of managerial durability, where key leaders stayed with the company through scale.

While aggressive hiring can be tempting, a learning from Levelset’s growth was the importance of hiring for leverage, not headcount. This is related to Price’s Law, states that “the square root of the number of employees in a company do about half the work.” Meaning, it’s actually a small fraction of people who drive half the productivity. For example, in a 100-person company, 10 people will be doing half the work.

Levelset’s leadership team stayed intact throughout the company’s rapid growth.

Related resource: Hiring, Scaling, and the Impact of Price’s Law

3 lessons for the journey

Reflecting on the experience, three tactical lessons stand out:

1. Remote sales environments are suboptimal for early-career reps — remote reps miss out on the osmosis learning that happens in an office.

2. Cold outreach is still a foundational GTM strategy — it’s not dead, it’s just poorly executed.

3. In-person field events drive outsized impact — don’t avoid in-person, that’s where relationships are built and deepened.

The overarching takeaway: Strategy matters, execution matters, and there’s no shortcut to scale.

Related resource: What’s Actually Working for GTM Leaders

👂 More for your eardrums

Jessica Gilmartin has nearly 20 years of go-to-market leadership experience, most recently serving as both the Chief Revenue Officer and Chief Marketing Officer at Calendly. Prior to that, she led marketing teams at an impressive array of companies, including Asana, Honor, Google, and Microsoft. As the cherry on top, Jessica also built and sold a successful frozen yogurt chain in San Francisco.

GTM 136: How Asana & Calendly Scaled: PLG to SLG Playbooks That Work | Jessica Gilmartin

Listen on Apple, Spotify, YouTube, or wherever you get your podcasts by searching “The GTM Podcast.”

🚀 Startup to watch

Tavus – launched AI with emotional intelligence. AI isn’t just responding anymore – it’s thinking, perceiving, and evolving. This is a big step closer to feeling like true face-to-face communication. The system is powered by huge leaps forward in AI research:

Phoenix-3: now with full-face rendering, emotions, & micro expressions
Raven-0: Real-time perception of movement, gestures, and emotion
Sparrow-0: Transformer-based turn-taking for natural dialogue

Default – announced both an additional $4M in funding and a huge launch around their new inbound orchestration platform. The launch of Default 2.0 unlocks endless new capabilities via website intent and session tracking, AI routing agents, waterfall enrichment, and much more.

Spekit – launched a completely refreshed brand identity. This brand refresh is far more than just a new look. It represents their growth and leadership as an AI innovator in the enablement industry and their unwavering commitment to delivering intuitive, AI-driven enablement solutions, specifically designed for what they call the ‘Change Economy.’

👀 More for your eyeballs

The State of Marketing and AI Report. The report reveals why marketing and creative leaders are making strategic investments in generative AI to pull ahead of the competition.

YouTube now has over 1 billion monthly viewers of podcast content. In 2024, users watched more than 400 million hours of podcasts each month on living-room devices.

Sales reps are not fine wine or cheese. They don’t get better with time, they get better with more at bats.

🔥 Hottest GTM jobs of the week

Revenue Operations Lead at Patch (San Francisco)
Market Development Representative at Patch (San Francisco)
Director, Customer Marketing at Writer (Hybrid – San Francisco)
Product Marketing Manager at Marqii (Hybrid – New York)
Head of Marketing at Ask-AI (Hybrid – Toronto / Tel-Aviv)
Enterprise Account Executive at Patch (London, UK)
Enterprise Account Executive at ModelOp (Remote)

See more top GTM jobs on the GTMfund Job Board.

If you’re looking to scale your sales and marketing teams with top talent, we couldn’t recommend our partner Pursuit more. We work closely together to be able to provide the top go-to-market talent for companies on a non-retainer basis.

See more top GTM jobs on the GTMfund Job Board.

🗓️ GTM industry events

Upcoming go-to-market events you won’t want to miss:

The GTM Workshop for AI Founders (GTMfund event): March 25, 2025 (San Francisco, CA) – private registration
GTMfund Dinner: March 25, 2025 (San Francisco, CA) – private registration
More GTMfund events TBA
Spryng by Wynter: March 24-26, 2025 (Austin, TX)
Pavilion CMO Summit: April 17, 2025 (Atlanta, GA)
Web Summit: May 27-30, 2025 (Vancouver, CAN)
Pavilion CRO Summit: June 3, 2025 (Denver, CO)
SaaStr Annual: September 10-12 (San Francisco, CA)
Pavilion GTM Summit: September 23-25, 2025 (Dallas, TX)

Subscribe now

This newsletter was entirely written and edited by Sophie Buonassisi and Scott Barker (not AI!).

Sophie Buonassisi is the Vice President of Marketing at media company GTMnow and its venture firm, GTMfund. She oversees all aspects of media, marketing, and community engagement. Sophie leads the GTMnow editorial team, producing content exploring the behind the scenes on the go-to-market strategies responsible for companies’ growth. GTMnow highlights the strategies, along with the stories from the top 1% of GTM executives, VCs, and founders behind the strategies and companies.