Expert Mode: Lessons in Growth to Acquisition from Boots-on-the-Ground Expertise
This article was based on the interview with Chris Tilkov, Director at Docusketch by Greg Kihlström, AI and Marketing Technology keynote speaker for the B2B Agility with Greg Kihlström podcast. Listen to the original episode here:
The prevailing narrative of the tech founder is a well-worn path. It usually involves a prestigious university, a brilliant idea conceived in a dorm room, a whirlwind of venture capital, and a relentless race to “disrupt” an industry, often from the outside looking in. This story, while compelling, overlooks a more common—and arguably more instructive—path to success. It’s the path forged not by external disruption, but by deep, internal expertise; the kind of knowledge earned through years of hands-on work, calloused hands, and an intimate understanding of a specific industry’s friction points.
This is the story of building a business from the ground up, not with a pitch deck full of jargon, but with a solution to a problem you’ve personally experienced hundreds of times. Chris Tilkov’s journey from a flood technician and carpet cleaner to the founder of a successfully acquired tech platform, AskAime, is a masterclass in this approach. His experience offers invaluable, grounded lessons for any marketing leader looking to build something of lasting value, whether it’s a product, a campaign, or a brand. It’s a reminder that the most powerful market insights don’t always come from big data reports, but from walking a mile in your customer’s steel-toed boots.
The Foundation: Building on Lived Experience, Not Market Research
In a world awash with customer personas and journey maps, it’s easy to create a polished, but ultimately superficial, understanding of a target audience. True innovation, however, often springs from a place of genuine empathy born from shared experience. Before founding AskAime, a platform to automate the review of insurance-based estimates, Tilkov wasn’t a SaaS entrepreneur looking for a market to enter. He was a practitioner who lived the very inefficiency he would later solve. He understood the nuances, the frustrations, and the operational drag of the manual review process because it was his day-to-day reality.
This deep domain expertise became his strategic advantage. He wasn’t guessing at a pain point; he was building a solution for a problem he knew intimately. For marketing leaders, this is a crucial lesson. How close is your team to the actual, unvarnished experience of your customer? While we can’t all be flood technicians, we can and should relentlessly pursue a deeper, more authentic understanding of the worlds our customers inhabit. This is the difference between marketing to someone and building for them.
“I was confident from my experience and having becoming an expert, traveling, being a trainer, really knowing these systems inside and out that… I could design a system that could parse these out and help in the process… I saw a pretty significant need to improve efficiencies across the industry.”
This isn’t the language of a founder chasing a trend. It’s the confident assertion of an expert who has identified a clear, tangible need. Tilkov didn’t need to conduct extensive focus groups to validate his idea; his entire career had been a focus group. This allowed him to build a product that wasn’t just technically sound, but contextually brilliant. It addressed the real-world complexities that a purely theoretical solution would have missed. The lesson for us is clear: the most defensible moats are often built not with code or capital, but with expertise.
The Brand: When Your Reputation is the Product
In the early stages of any venture, brand building can feel like an abstract exercise. We talk about mission, vision, and values, but translating those into tangible trust is a long game. For Tilkov, especially in a niche, relationship-driven industry like insurance and restoration, his personal reputation wasn’t just a part of the brand—it was the brand. His years spent training contractors and insurers, speaking at conferences, and fairly negotiating complex claims created a foundation of credibility that no marketing budget could replicate.
When AskAime launched, potential clients weren’t just buying a piece of software; they were buying a digitized version of Chris Tilkov’s expertise and integrity. This concept of the “founder brand” or the “expert brand” is profoundly relevant for enterprise marketing leaders. In a B2B landscape saturated with feature-to-feature comparisons, trust and authority are often the ultimate differentiators. Customers, especially those making significant purchasing decisions, are looking for partners they can rely on.
“The brand at first, at least stood on the shoulders of my reputation… I was told by competitors in the industry… when we’re trying to figure out if they’re looking at any other products, they’ll hear my name as often as they’ll hear the product, they’ll say, ‘you’re working with Tilkov’ versus, ‘we’re working with Aime.’ So it was very apparent that it was kind of one in the same.”
This is a powerful illustration of authentic marketing. The brand wasn’t built through clever taglines or ad campaigns, but through years of consistent, reliable, and expert work. It’s a challenge to every marketing leader: who are the “Tilkovs” in your organization? How are you identifying, elevating, and leveraging the deep subject matter expertise that resides within your teams? Empowering these experts to be the face of your brand—through content, speaking engagements, and direct customer interaction—builds a level of trust that is nearly impossible for competitors to erode.
The Exit: Strategy and Synergy Over a Simple Sale
The decision to sell a company is rarely just about the financials. For a founder who has poured their identity and expertise into a product, the question of legacy and fit is paramount. Tilkov’s approach to the acquisition of AskAime was guided by a clear strategic principle: the product’s integrity must be preserved. He had opportunities along the way, including early investors he ultimately had to buy out, that would have compromised the platform’s core value proposition of being an unbiased arbiter.
He understood that AskAime’s power was in its neutrality—its ability to bring contractors and carriers to a fair agreement faster. Selling to a single party who would use it for their own biased purposes would have destroyed the very thing that made it valuable. This strategic patience is a lesson in long-term brand management. Short-term gains that compromise your core mission are rarely worth the long-term cost.
“Aime’s a very unbiased attempts to be unbiased down the middle… I didn’t want it to land with a group that just wanted to use it for one purpose… When DocuSketch came along and I understood their product, 360 images, it’s kind of the source of truth for a claim and documentation around that. That’s where Aime fits as well. We just want to get to the right number, be truthful, honest, put it all right in front of everybody and help speed up the cycle time.”
The eventual acquisition by DocuSketch wasn’t just an exit; it was an integration. It was a “1+1=3” scenario where two complementary products, both built on the principle of establishing a “source of truth,” came together to create a more powerful, end-to-end solution. For marketing leaders involved in partnerships, M&A due diligence, or co-branding initiatives, this is the gold standard. A successful partnership isn’t just about overlapping customer lists; it’s about synergistic missions and a shared vision for the market. The result was not the end of AskAime, but an evolution that allowed it to achieve a scale and impact it couldn’t have reached on its own.
Chris Tilkov’s story is a refreshing antidote to the hype-fueled narratives that dominate the tech landscape. It’s a testament to the enduring power of deep expertise, the slow and steady work of building a reputation, and the wisdom of strategic patience. His journey reminds us that the most impactful solutions often come from those closest to the problem, and the most resonant brands are built on a foundation of genuine authority and trust. These are not just lessons for aspiring entrepreneurs; they are fundamental principles for any marketing leader aiming to cut through the noise and build something meaningful.
In our roles, we are often pressured to move faster, to chase the latest trend, to find the next “hack.” But perhaps the most agile and sustainable strategy is the one that prioritizes depth over breadth. It’s about fostering an environment where expertise is cultivated and celebrated, where teams are encouraged to “just do” and experiment, and where we never lose sight of the real-world problems we are here to solve. By embracing this boots-on-the-ground mindset, we can ensure that our own work, like Tilkov’s, is built not on shifting sands, but on a bedrock of authentic value.
