Breaking into a new industry with zero references is one of the hardest challenges in B2B. Here's how Tenderbolt won its first insurance client — and what it taught us about selling into compliance-heavy sectors.
Every B2B company that has tried to break into a new vertical knows the feeling.
You have a strong product. You have references — good ones. But none of them are in the sector you're now targeting. And the first question in every meeting is the same one: "Have you done this in our industry before?"
For Tenderbolt, that industry was insurance. And the answer, at the time, was no.
This is the story of how we won that first client anyway — what we changed, what we learned, and what it opened up. We're sharing it because the lessons apply to any B2B company navigating the catch-22 of vertical expansion: you can't get the reference without the client, and you can't get the client without the reference.
Insurance is a compliance-heavy, risk-averse sector. Procurement teams in insurance don't take chances on unproven vendors. The RFP process is rigorous by design — IT security questionnaires, GDPR compliance, CSR frameworks, financial stability assessments. The stakes of choosing the wrong vendor are high, and the evaluation process reflects that.
When we started receiving inbound interest from insurance companies, we had a genuine problem: zero sector references. We knew Tenderbolt could handle the complexity — our platform is built specifically for high-volume, compliance-intensive RFP environments. But we hadn't proven it in this sector yet.
The classic response to this situation is to either fabricate proximity ("we've worked with companies that face similar challenges") or to heavily discount to reduce the perceived risk. We did neither. Instead, we changed the conversation entirely.
The first and most important shift we made was in how we opened meetings.
We stopped leading with what Tenderbolt does. Features, integrations, time savings — none of that was the right entry point. Instead, we started every conversation by describing what insurance pre-sales teams experience on a weekly basis:
We weren't pitching our product. We were describing their week — in enough detail that it was clear we'd done our homework.
The shift in room temperature was immediate. Instead of "interesting, but have you worked with insurance companies before?", we started hearing "yes, that's exactly the problem — tell us more."
This is the single most underrated move in vertical expansion: before you talk about your solution, demonstrate that you understand the problem better than anyone else in the room. Sector experience is one way to earn that credibility. Deep problem knowledge is another — and it's available to you even on day one in a new vertical.
Once we had the attention of the room, we still needed to handle the reference objection directly.
Rather than avoiding it, we addressed it head-on with a three-part argument:
First, we acknowledged the gap honestly. We hadn't yet deployed Tenderbolt in an insurance company. We said so directly.
Second, we made the transferability case explicitly. We mapped the compliance questionnaire types that insurance RFPs typically include — IT security, GDPR, CSR, financial stability — and showed, category by category, how Tenderbolt handles each one. We used references from software publishers and B2B service companies who face identical questionnaire structures. The compliance burden isn't unique to insurance — it's common to any regulated B2B environment. We made that case with specifics, not generalities.
Third, we flipped the framing. We argued that a vendor who has worked in insurance for years may have built workarounds to a broken process — whereas we were building the right process from scratch, without legacy habits. Coming in fresh, with a purpose-built platform, was a feature, not a liability.
Was it a risk for them to go first? Yes, and we acknowledged that too. But we also proposed a structured pilot with clear success metrics and a defined exit point if the results didn't meet expectations. That reduced the perceived risk enough to move forward.
Once the first insurance client went live, the learning curve was steep — and valuable in ways we hadn't anticipated.
Insurance RFPs layer security, regulatory and financial validation in ways that most other sectors don't reach. The depth of IT security questionnaires alone — covering everything from encryption standards to incident response protocols to third-party audits — is significantly above what we typically saw in software or services RFPs.
Our knowledge base configuration process got sharper as a direct result. We developed more granular category mapping, better source labelling and a more structured review workflow specifically for compliance-intensive environments. These improvements benefited every client, not just insurance.
In most sectors, a Tenderbolt user generates a response and submits it after an internal review. In insurance, responses typically pass through compliance, legal, and procurement before submission — sometimes with multiple revision rounds.
This meant our workflow and task assignment features became critical, not optional. The ability to assign sections to specific reviewers, track approval status in real time and manage version history went from a nice-to-have to a core requirement. We invested accordingly, and those improvements are now part of the standard platform.
In almost every other sector, the first metric prospects ask about is time savings. "How many hours will we save per RFP?" In insurance, that question comes second. The first question is always: "How reliable are the responses? Can we stand behind what the platform produces?"
This required a fundamental shift in how we demo the product and how we measure success in the first 90 days. We moved from time-savings metrics to accuracy and compliance metrics as the primary KPIs. Response reliability — not response speed — is the value proposition that lands in regulated sectors.
That first insurance client is now one of our most active Tenderbolt users. Their pre-sales team has reduced average response time per RFP by more than 60%. Since going live, they've used Tenderbolt across more than 80 tenders — including some of the most complex compliance questionnaires we've seen on the platform.
More importantly for us strategically: they became the reference that opened three more doors in the sector. The catch-22 resolved itself, the way it always does — by finding one client willing to go first and doing exceptional work for them.
We now have a dedicated insurance use case in our sales process, a refined onboarding playbook for compliance-heavy environments, and a track record in the sector. None of that existed 12 months ago.
If you're facing the same challenge — strong product, strong track record, but no references in the vertical you're targeting — here's what worked for us:
1. Lead with problem knowledge, not product features
Before you earn the right to talk about your solution, demonstrate that you understand their specific situation better than anyone else in the room. Deep sector research, specific pain point mapping and fluency in their operational vocabulary will get you further than any feature list.
2. Make the transferability argument explicitly
Don't hope they'll connect the dots between your existing references and their context. Draw the line for them — show exactly how the problems you've solved elsewhere map to the problems they're facing. Be specific, not vague.
3. Name the gap and address it directly
Pretending you have sector experience you don't have is a bad strategy — experienced procurement teams will find out. Acknowledging the gap honestly, then arguing past it with a structured transferability case and a de-risked pilot proposal, is far more credible.
4. Invest in making the first client a genuine success
The first client in a new vertical isn't just a client — it's your proof of concept, your reference, and your learning lab. Invest disproportionately in their success. The returns compound.
New verticals aren't won with credentials. They're won with relevance, intellectual honesty and exceptional execution on the first opportunity.
Tenderbolt is built for high-volume, compliance-intensive RFP environments. For insurance, financial services and other regulated sectors, that means:
You can also read our guide on how to improve your RFP responses with client references and our overview of writing proposals for tenders for more on building a winning response process.
Visit /contact to book a demo and see how Tenderbolt works in your sector.
