When Justin Levine tells people that Shepherd has reached double-digit millions in revenue without any dedicated sales team members, the reaction is usually disbelief. In a world where construction technology companies often have armies of SDRs, account executives, and sales engineers, how does an insurance startup scale to eight figures using underwriters as their primary sales force?

The answer reveals something fascinating about go-to-market strategy: sometimes the most counterintuitive approach creates the biggest competitive advantage.


TL;DR: Breaking the Traditional Sales Playbook

How Shepherd built a $10M+ insurance business without dedicated sales teams:

  • Underwriters as Salespeople: Technical experts own the entire customer journey from initial outreach to policy binding
  • Channel Partner Focus: 50%+ business comes through broker relationships, creating efficient one-to-many distribution
  • Fast No Philosophy: 60% of opportunities get declined quickly, building trust through rapid, transparent responses
  • Founder-Led Approach: Underwriters have deep stake in outcomes, similar to founder-led sales but at scale
  • Territory-Based Organization: East/West teams with geographic assignments mirror traditional SaaS sales structure
  • 24-Hour Response Times: Technology-enabled speed creates massive competitive advantage over traditional insurers

 

In this episode, Justin Levine shares how he’s revolutionizing construction insurance by rewarding tech adoption, scaling to double-digit millions in revenue, and why reality capture tools reduce claims by 40-50%.

 

The Anti-Sales Team Philosophy

“We have no specific people within our team that are titled as sales members,” Levine explains. Instead, Shepherd has organized their underwriting team to function like an enterprise SaaS sales organization—but with a crucial difference. The people making the sales calls are the same people who will underwrite the risk and manage the account long-term.

This isn’t just a quirky organizational choice. It’s a strategic decision that addresses one of the biggest problems in traditional insurance sales: the handoff between sales and underwriting often creates friction, miscommunication, and unrealistic expectations.

At Shepherd, when an underwriter calls a potential customer, they’re not just trying to get a deal in the door. They’re evaluating whether this is actually a risk they want to take on, what the pricing should be, and how to structure the coverage appropriately. It’s what Levine calls “founder-led sales” mentality, but scaled across an entire team.


The Power of Channel Distribution

Perhaps the most crucial element of Shepherd’s go-to-market strategy is their focus on retail broker partnerships. Unlike most insurtech companies that work through wholesale channels, Shepherd goes directly to retail brokers—the agents who actually represent the construction companies buying insurance.

“Every broker that we work with potentially represents a one to many type of relationship where they’re going to represent multiple customers,” Levine notes. “Our best broker partners have sent us dozens, if not 100 plus submissions across their portfolio.”

This creates incredible efficiency. Instead of hunting individual customers one by one, Shepherd can land a strong broker relationship and access their entire portfolio of construction clients. It’s channel sales at its most effective—but it requires a completely different approach to relationship building.


The Fast No Advantage

Here’s where Shepherd’s strategy gets really interesting: they reject 60% of the opportunities they receive. That’s not a bug in their system—it’s a feature.

“A fast no is incredibly more valuable than a long maybe,” Levine explains. “We’ve gotten really good at the fast no.” When Shepherd can’t write a piece of business, they tell the broker immediately, often within 24 hours. This creates trust and actually drives more business their way.

Traditional insurance companies often string brokers along for weeks before declining an opportunity. Shepherd’s rapid, honest responses mean brokers know exactly where they stand and are more likely to bring future opportunities. It’s counterintuitive, but being helpful when you can’t do business often leads to more business you can do.


Technology as the Sales Enabler

The reason Shepherd can operate this way is technology. While traditional insurance companies use “anywhere from five to 10 different systems just to get from a submission to a price,” Shepherd has built an integrated platform that makes their underwriters dramatically more efficient.

“We are just faster and more responsive and easier to work with than most of our competitors, simply because our team has better tools,” Levine says. This speed advantage—responding to most submissions within 24 hours versus competitors who take weeks—becomes a massive differentiator in a relationship-driven industry.

The technology also enables Shepherd’s unique value proposition: using construction technology adoption data to offer better insurance rates. This isn’t just about efficiency; it’s about having capabilities that traditional competitors simply can’t match.


Building Relationships at Scale

One of the most impressive aspects of Shepherd’s approach is how they’ve systematized relationship building. Levine has written a monthly update to all broker partners for four years straight, sharing company progress, celebrating wins, and maintaining engagement.

“I was expecting we would have a lot of people say, ‘Don’t need your update, please leave me alone.’ But I get a lot of people who come back and say, ‘Thanks for sharing, this is really interesting.'”

They’ve also created partner advisory boards, leaderboards showing broker performance, and even brought broker partners into their office for hackathons. These aren’t traditional sales tactics—they’re community building at scale.


The Underwriter Advantage

Why does having underwriters handle sales work so well? It comes down to credibility and alignment. When a construction company talks to a Shepherd underwriter, they’re speaking with someone who actually understands insurance, not just someone trying to hit a quota.

The underwriter can make real commitments about coverage and pricing because they’re the ones who will ultimately make those decisions. There’s no game of telephone between sales promises and underwriting reality. This alignment creates trust faster and reduces the friction that kills deals in traditional insurance sales.

Moreover, because underwriters own the entire relationship, they’re incentivized to bring in good business, not just any business. They know they’ll be responsible for managing the account long-term, so they’re naturally selective about what they pursue.


Scaling Through Structure

Despite not having traditional sales roles, Shepherd has organized like a SaaS company. They have East and West teams with territory-based assignments. They track funnel metrics, conversion rates, and all the standard enterprise sales KPIs.

“It looks and feels like a SaaS sales team in a lot of ways,” Levine explains. “The funnel honestly is not very different in terms of conversion and how things go through initial outreach through what we call bind order, which is a win.”

This structure allows them to scale systematically while maintaining the relationship-focused approach that makes their model work. As they’ve grown to a 20-person underwriting team, they’ve been able to increase capacity without losing the personal touch that differentiates them.


The Product-Market Fit Signal

Shepherd’s unconventional approach has created strong product-market fit signals. About 50% of their business now comes inbound, driven by word-of-mouth from satisfied customers and broker partners. They’ve had seven straight quarters of growth in submission volume.

“More than 50% of the time, we don’t quote the business,” Levine notes, “but for the 60% of the time that we’re not even quoting the business, it still really matters how we respond and how we show up.”

This disciplined approach—focusing on the right customers and saying no to the wrong ones—has created a sustainable growth engine that doesn’t require increasingly expensive customer acquisition.


Lessons for Other Startups

Shepherd’s success offers several lessons for construction technology companies and other B2B startups:

  • Expertise Sells: Having technical experts handle sales conversations creates immediate credibility and trust.
  • Channel Strategy Matters: Finding the right distribution partners can be more effective than building large direct sales teams.
  • Speed Wins: In industries where competitors are slow, being fast becomes a major differentiator.
  • Saying No Builds Trust: Being selective about customers and transparent about fit creates stronger relationships.
  • Relationship Building Scales: Systematic approaches to nurturing partnerships can create sustainable competitive advantages.


The Future of Sales

As Shepherd considers adding dedicated sales roles, they’re being thoughtful about preserving what makes their current model work. The goal isn’t to replace the underwriter-led approach but to augment it in areas where pure sales skills might add value.

“What we liked about having underwriters own the sales motion is that it feels a little bit like founder-led sales where they have this deep stake in the outcome,” Levine reflects.

In an industry where most competitors are stuck with legacy processes and siloed organizations, Shepherd’s integrated approach—enabled by modern technology and a willingness to challenge conventional wisdom—has created a genuinely differentiated go-to-market strategy.