From Boots-on-the-Ground Inspections to 459 Milliseconds

David Tobias grew up inside the exact problem Betterview now solves. His father started a property inspection company over 50 years ago, sending boots-on-the-ground inspectors across the country to assess properties for insurance carriers — a business David eventually took over and later sold. Roof condition was a constant pain point in that business, for good reason: roof-related claims account for a little under 40% of all property claims dollars paid out in the US. Getting consistent, cost-effective, fast data on roof condition at national scale, using human inspectors, was never going to work.

That’s the problem David set out to solve when he connected with his co-founder, David Lyman — the two Davids, married to two women both named Catherine, a coincidence David flagged as a fun bit of company trivia. Lyman had previously built and sold a venture-backed social media aggregation startup to Constant Contact. A mutual friend, aware both men were independently exploring drone technology, introduced them roughly seven years before this recording, and Betterview was born.

About David Tobias

David Tobias is Co-Founder of Betterview, a property intelligence platform that processes aerial imagery into risk data for insurance carriers, covering the full policy lifecycle from quoting through claims and reinsurance.

From Drones to Scalable Imagery

Betterview started with drones — high-resolution imagery, captured close to the building, with real advantages over other data sources at the time. The problem was scale: every flight required sending a person out with the drone, which made the model too slow and expensive to deploy broadly. After running tens of thousands of drone flights for insurance customers, David and his team heard the same request repeatedly — do this faster, cheaper, at scale — and pivoted to applying the same computer vision models to other aerial imagery sources instead of drone-captured imagery alone.

David credits that pivot directly to having grown up inside the problem rather than falling in love with a particular technology. He pointed to Airware, a drone company that raised hundreds of millions of dollars and later shut down, as a cautionary example of falling in love with the tool instead of the problem it was meant to solve.

From Selecting Risk to Mitigating It

David drew a sharp distinction between two very different uses of property data: using it to select better risk (the industry’s dominant use case today) versus using it to actually mitigate risk before a loss occurs. His example: if Betterview detects overgrown vegetation near a property in a wildfire zone, a carrier could proactively tell the insured to clear it back — preventing a loss rather than just pricing around the likelihood of one.

He pushed back gently on the idea that most insureds are trying to game their carrier for a free new roof. In his view, a loss is disruptive for almost everyone — homeowners and businesses alike — which means insurers and insureds are far more aligned on preventing losses than the industry’s current posture usually reflects. He also pointed out a specific, present-day gap: carriers already hold data (from Betterview and similar providers) showing, for example, that a policyholder’s roof will likely need replacement within four or five years — but rarely act on that insight by reaching out proactively, the way an Amazon or an Uber would use equivalent data about a customer relationship. He noted Hippo as one of the few carriers he sees genuinely leaning into a proactive, maintenance-first model.

Underwriting First, Then Claims

Underwriting is typically Betterview’s entry point with a new carrier, with claims teams often discovering and requesting access to the same data once they see what’s available — David noted this is sometimes the first real bridge between departments that don’t otherwise talk to each other regularly. Betterview’s imagery reports are also increasingly used in agent conversations — showing an agent the actual image of a damaged roof, rather than asserting a non-renewal decision without evidence, turns a contentious conversation into a data-driven one.

Building With Strategic and Traditional Capital

Betterview has raised roughly $15-16 million, from a mix of traditional venture firms — Compound (New York) and Manchester Story (Des Moines) — and a substantial group of strategic investors, including EMC Insurance, Nationwide (through Nationwide Ventures, where Brian Anderson was David’s contact), Guidewire, and Manulife. David described the strategic investors as a genuine advantage beyond capital — giving Betterview visibility into how large carriers are thinking not just about today’s roadmap, but five to ten years out.

Customer success stories he pointed to include EMC Insurance, Nationwide, and Frederick Mutual, alongside newer entrants in the space building with Betterview from day one, including a startup staffed in part by alumni of Blackboard Insurance, AIG’s insurtech-focused unit.

Building a Partner Ecosystem, Not Trying to Own All the Data

Betterview doesn’t claim to be the source of every data point a carrier needs. At the time of this recording, the company was preparing to launch “Partner Hub” at ITC — a marketplace bringing in third-party data providers like HazardHub, layered on top of Betterview’s own geospatial and imagery data through a rules engine built into the platform. A carrier could, for example, flag any property with high vegetation overhang that also falls inside a HazardHub-scored wildfire zone, automatically, inside Betterview’s interface, inside Guidewire, or via API.

On the technical side, Betterview offers full core-system integrations (with a particularly deep Guidewire accelerator), a standalone API that returns pre-processed property data in 459 milliseconds for a given address or lat/long, and a purpose-built user interface designed to make complex risk data legible to non-specialists — led by Michael Zimmer, formerly Credit Karma’s lead designer, whom David credited with the platform’s emphasis on visualizing exactly what’s wrong with a property, not just scoring it.

Scaling From Pilot to National Rollout

Asked how Betterview scaled from an early pilot to a nationwide, cross-carrier platform, David resisted the “build cool tech and hope people find a use for it” model. Betterview’s approach, instead, centers on consolidating around specific, validated use cases and going deeper on those rather than broadening horizontally — reinforced by a customer council of carriers who directly shape the product roadmap. Scaling, in his framing, was never primarily a technology problem; it was a matter of building out sales, customer success, and technical support in step with moving from top-50 carriers to top-10 to full national rollouts, while staying anchored to a clear, defensible value proposition.

Advice: Strong Beliefs, Loosely Held

For his closing recommendation, David pointed to Jason Lemkin’s SaaStr content as a resource he’s been leaning on heavily while scaling Betterview’s sales organization. His more personal guiding principle, which he credited to himself and co-founder David Lyman living by it together: have strong beliefs, loosely held — conviction about the product and the market, paired with genuine openness to being persuaded otherwise by people closer to a given problem.

Key Takeaways

• Roof-related claims account for nearly 40% of all US property claims dollars — the specific, quantifiable pain point that shaped Betterview’s founding and its pivot from drone-only imagery to broader aerial data sources
• David’s central argument: most of the industry still uses property data to select better risk, not to mitigate risk before a loss occurs — carriers already hold data (roof condition, vegetation) that could support proactive outreach to policyholders, and mostly aren’t using it that way yet
• Underwriting is typically Betterview’s entry point at a new carrier, with claims teams often becoming a second internal champion once they see what data is already available — sometimes bridging departments that don’t otherwise coordinate closely
• Betterview built a mixed cap table of traditional VCs (Compound, Manchester Story) and strategic insurance investors (EMC, Nationwide, Guidewire, Manulife) specifically to combine capital with long-range visibility into how large carriers are actually planning their technology roadmaps
• Rather than trying to be the source of every data point a carrier needs, Betterview built “Partner Hub,” layering third-party providers like HazardHub on top of its own imagery data through a built-in rules engine
• David’s scaling philosophy: consolidate around a small number of validated use cases and go deeper, rather than building broad technology and hoping customers find applications for it — reinforced by a standing customer council shaping the roadmap directly