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The GTM Tactics Behind A $500m Exit
Land & expand your way to scale.
Owen Drury
April 16, 2025 • Estimated Reading Time: 15 minutes
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BEFORE WE START…
The GTM Tactics Behind A $500m Exit
Before we dive into this week’s deep dive insight!!
We’ve just finished a lengthy mini-series on Go To Market within AEC tech, interviewing the top GTM leaders who have built and scaled sales teams to the hundreds of millions.
The episodes will be released from 22nd April 2025 and will be accompanied by a GTM guide to help you:
Master the "land and expand" strategy that scaled PlanGrid from $5M to $100M in 4 years
Implement the GTM approach specifically designed for construction's unique buying cycle
Access battle-tested frameworks for identifying champions and building winning business cases
Avoid costly hiring mistakes that drain capital and waste critical market timing
Learn directly from executives who've built billion-dollar construction tech companies
Over the next few weeks on this newsletter, we will be releasing some eye opening stories, frameworks and lessons taken from the insights contained within the guide.
To confirm your interest in receiving a copy of this guide once released, please click here.
In the meantime, enjoy the content below:
INDUSTRY INSIGHTS
TLDR - The $10M Revenue Wall
How did Levelset go from $20K/month to a $500M+ acquisition by Procore?
By doing the opposite of what most startups are told.
Here’s what worked:
🧠 Built demand before the product — with 100s of articles on lien law
📬 Landed $100K+ deals using handwritten notes + bubble mailers
💸 Closed deals by pricing pragmatically, not perfectly
🎯 Picked one GTM focus (SMB) and scaled like hell
🔥 Hired for grit, not resumes — then trained a sales army in-house
📈 Grew slow, then fast — with zero funding
The playbook is old-school, unpolished, and ridiculously effective.
And it still works today.
From $0 to $500m Acquisition: Levelset's Battle-Tested Sales Playbook
When we interviewed Martin Roth and Scott Wolfe, the key leaders behind Levelset's growth from $20K in monthly revenue to a $500M+ acquisition by Procore, we were struck by how refreshingly honest they were about the messy reality of building a construction tech sales machine.
"We didn't even know what ARR was when I started," Martin laughed. "We couldn't even spell it."
Meanwhile, founder Scott Wolfe described the company's origin: "At its core, what Levelset was is we looked at this problem, which is that it took too damn long to get paid in construction. Wherever you looked across the construction chain, suppliers, subcontractors, general contractors, owners, they all had stress around cash and cashflow."
It's this kind of transparency that makes Levelset's journey so valuable for founders and go-to-market leaders in construction tech today. Here's how they built their sales playbook from scratch.
Chapter 1: The Founder's Content Foundation
Before Martin joined in 2013, Levelset (then called ZLean) had already laid crucial groundwork. Scott's background uniquely prepared him for this venture - he had experience in software development, law, and entrepreneurship.
"I was one of like five construction law bloggers in the country," Scott recalled. "Content was just the way I saw the world. I read all the laws state by state related to construction payment and I published them."
This approach wasn't a calculated marketing strategy but stemmed from Scott's inherent understanding of the power of helpful content. "Levelset actually probably started as basically a blog or content and then became a product," he explained.
"Scott had already generated demand," Martin added. "He'd written hundreds of articles and built a ton of resources around how to file liens, what is a lien waiver, and how to send a preliminary notice."
Chapter 2: The First Million in Revenue
Martin's arrival marked the beginning of a structured sales approach. With just a headset and a copy of Chet Holmes' "The Ultimate Sales Machine," Martin and Scott implemented the "Dream 100" strategy – identifying 100 target enterprise customers and persistently pursuing them with weekly touchpoints.
Their approach was delightfully old-school: "We would send physical bubble mailers with handwritten cards and letter openers. You know what they do with mail? They open it," Martin shared.
The results? Within 14 months, they'd closed six or seven enterprise deals worth $100,000+ each, creating step-function jumps in revenue. As Martin put it: "We tripped ourselves into a bunch of revenue."
Chapter 3: The Pricing Puzzle
As Levelset began scaling, they experimented constantly with pricing and packaging – "no joke, like 150 different pricing structures over 10 years," according to Martin.
Their early approach was pragmatic rather than scientific: "Sell to people the way they want to buy." When selling to an equipment rental company, they'd ask what they were paying their current provider, then offer to do it for slightly less.
"That's not value-based pricing," Martin admitted. "But you know what it did? It got us in the door and helped us learn more about the value."
This approach aligned perfectly with Scott's philosophy on product adoption: "We weren't coming in telling a bunch of people in the industry to do something brand new. They were already doing it with tablets and chisels and pen and paper, using service providers all over the place. We stepped in as a substitute for something they were already doing."
Chapter 4: The Focus Shift
By $3-4 million in ARR, Levelset faced a critical challenge – they were running two different go-to-market strategies simultaneously: enterprise and SMB. This split focus was preventing them from scaling efficiently.
"Around 2016 or 2017, we said we're going to put our heads down to the exclusion of everything else and focus on SMB," Martin explained.
This laser focus finally unlocked significant growth. The decision allowed them to refine their messaging, sales process, and customer success approach for a specific market segment.
Key lesson: Running multiple go-to-market strategies simultaneously can stunt your growth. Sometimes you need to make hard choices about where to focus.
Chapter 5: The Scaling Engine
After committing to the SMB segment, Levelset built a remarkable sales machine. Their median sales cycle was just four days for a $5,000 average deal size.
They developed a talent pipeline that transformed people with no software sales experience into high-performers by screening for five key traits: grit, resourcefulness, enthusiasm, curiosity, and ambition.
"We had to get really good at manufacturing software salespeople who didn't understand construction, didn't understand lien rights, and probably didn't understand software sales," Martin recalled.
Their culture emphasized a "help first" approach that became central to their sales success. "When you get on the phone, stop trying to angle them towards some pitch. Just try to help," was their mantra.
Scott explained how this became a core company value: "The value was help first. From as far as Levelset was concerned, we had all this angst about the power dynamics in construction and the access that so many people had to justice or legal help or knowledge. We wanted to help people with their cash stress, their payment stress. And when they come to our site, they're in pain. We want to help and just swaddle them with information and tools."
The results were extraordinary. Scott noted, "At scale, when we sold, we probably had north of 750,000 or a million visitors a month coming into Levelset and tens of thousands of leads. Leads were never a problem for Levelset. Ever."
The Full Growth Curve
Levelset's revenue journey wasn't linear:
First $1.5M: 18 months
$1.5M to $10M: 6 years
$10M to $20M: 18 months
This "bulker" growth pattern is common in construction tech, where enterprise sales cycles are long and product adoption takes time. By the time they reached scale, they were adding $1.5-2M in net new ARR every month.
Scott emphasized how different their journey was from typical venture-backed startups: "That's another secret to the Levelset success story - we just had so much time to marinate and grow naturally. We didn't get a bunch of venture capital and an angel round with an idea on paper. We had years to develop our product, develop our point of view, develop our strategy, get customers, get our team saturated to understand this complicated problem."
From 2012 to 2015, they worked without funding at all, growing to about $2 million in revenue while remaining cashflow positive. When they did take venture capital, Scott was turning down acquisition offers to make a bigger bet on their vision.
The ultimate validation came when Procore acquired the company for over $500 million – proving that their battle-tested sales approach had built something of lasting value.
For founders building in construction tech today, Martin's parting advice is refreshingly simple: "If you're trying to get to a million dollars in ARR, start by just putting 100 people on a list and call them. If you do that every week for 52 weeks, I guarantee you're going to get a bunch of meetings."
Scott's advice on building an attractive business is equally straightforward: "Run your race and focus on building value. It's so hard to tell people what to do to prepare the business for an exit because it's kind of the wrong question. Go find your point of view, run your race, build value. The exit will come. And if it doesn't come, you didn't build the value."
Sometimes the oldest playbooks are still the most effective.
🧠 Final Advice for Founders
Martin’s advice:
“Put 100 people on a list. Call them every week for 52 weeks. You’ll book meetings. You’ll close deals.”
Scott’s advice:
“Forget exits. Run your race. Build real value. If you do that, the exit takes care of itself.”
WEEKLY MUSINGS
Startup Update, Capital Shifts, Infrastructure
Huge congrats to Enji and the B&M team
Dogs, bathtubs, and WhatsApp
US infrastructure challenges and opportunities
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