What We Heard in Our First InsurTech Open Office Hours

Last week, we tried something new: open office hours.

No formal agenda. No pitch decks required. No filter. First come, first served. Just 20-minute conversations with founders, operators, and people beginning to explore ideas across insurance.

The prompt was simple: what would be useful to you?

That structure, or lack of structure, was the point. We wanted to create space for conversations that did not need to fit neatly into a fundraising process, a diligence call, or a polished pitch. Insurance is a complex market. Sometimes the most valuable conversations happen before the company is fully formed, before the deck is finished, or before the founder has complete clarity on what the next step should be.

First, thank you to everyone who signed up and spent time with us. We appreciated the openness, the questions, the early ideas, and yes, the one or two pitch decks that were pulled up along the way. That was perfectly okay too.

A few themes stood out.

‍

1. There is real energy coming from inside the insurance industry

One of the clearest signals from the conversations was how much builder energy is coming from people who already understand insurance.

That matters.

Insurance is not an easy market to enter from the outside. The workflows are complex, the buying cycles are long, the regulatory environment matters, and the path from product interest to adoption is rarely linear. Founders who have lived inside the industry often bring a more grounded understanding of where the friction actually sits.

They know which processes are inefficient because they have worked inside them. They know where technology can help, but also where technology alone is not enough. They understand that in insurance, the best idea is not always the one that sounds most disruptive. Often, it is the one that fits into the way the industry actually evaluates risk, trust, workflow change, and distribution.

That does not mean every strong InsurTech company needs to be founded by an insurance insider. But it does reinforce something we believe strongly: context matters. The closer a founder is to the real problem, the better their odds of building something that can survive the complexity of the market.

‍

2. Distribution is still the hardest and most interesting problem

Across the conversations, distribution kept coming up.

That was not surprising, but it was important.

In insurance, product quality is only part of the equation. A company still has to answer several harder questions: who is the actual buyer, who influences the decision, how does trust get built, how does the product fit into existing workflows, and what has to be true for adoption to happen?

Distribution in insurance is rarely just a sales motion. Itis a trust-building process. It often involves carriers, brokers, agents, employers, reinsurers, regulators, or other stakeholders depending on the business model. A product may create clear value, but if the path to adoption is unclear, the company can still struggle.

That is why we continue to spend so much time with founders on go-to-market strategy, not just product strategy. The market opportunity may be large, but the route into that market has to be specific.

For early-stage founders, this is often where the most important work begins. Who feels the pain most acutely? Who owns the budget? Who has the authority to change the workflow? Who benefits from the outcome, and are they the same person who has to buy the product?

The answers to those questions can change the entire shape of the company.

‍

3. The best conversations were not always the most polished

Some of the most useful conversations were early, messy, and honest.

That stood out.

There is a natural tendency in venture to wait until everything is polished before starting a conversation: the deck, the narrative, the market map, the financial model, the customer pipeline. There is a time and place for that. But open office hours created a different kind of environment.

People could ask unfinished questions. They could test assumptions. They could talk through an idea that was not yet a company. They could say, “I am seeing this problem in the market, but I am not sure if it is venture-scale,” or “I know this workflow is broken, but I am still trying to understand who would pay to fix it.”

Those conversations are valuable because they get closer to the real thinking process. They also create room for more candid feedback. Sometimes the right next step is not to raise capital. It might be to validate the buyer, narrow the wedge, talk to five more operators, or pressure-test whether the problem is painful enough to support a standalone company.

That kind of feedback is easier to give when the conversation is not overly formal.

‍

4. People value access and candor

Another theme was simple: people value direct access and honest feedback.

That is especially true in a category like insurance, where the market can be difficult to navigate from the outside. Founders are not only looking for capital. They are looking for pattern recognition. They want to understand how carriers evaluate new technology, what brokers actually need, where incumbents are open to change, and where sales cycles can get stuck.

This is also where ManchesterStory’s model is highly relevant. Our work sits at the intersection of entrepreneurs and industry incumbents, with a strategic network across carriers, brokers, and insurance leaders. The firm’s broader platform is built around more than capital: it includes sector expertise, relationships, and insight across the insurance value chain.

Open office hours gave us a simple way to make that access more direct. Not every conversation needs to be a formal fundraising conversation. Sometimes the highest-value thing we can do is help someone think through the market, the buyer, the wedge, or the next proof point.

‍

What we learned from removing structure

The biggest takeaway was this: when you remove some of the structure and expectations, you often get better conversations.

A formal pitch process has a purpose. But it can also shape the conversation around what a founder thinks an investor wants to hear. Open office hours created a different dynamic. The conversations were more exploratory, more direct, and in many cases more useful because they started with the founder’s actual question.

That is something we want to keep making room for.

Insurance is changing quickly. AI, data infrastructure, embedded distribution, claims automation, underwriting intelligence, healthcare-finance intersections, and new broker workflows are all reshaping where opportunities may emerge. But the best ideas do not always arrive fully formed. They often start with someone close to the problem noticing that a workflow, incentive, or customer experience does not work the way it should.

Those are the conversations we want to have earlier.

‍

We’ll do this again

Thank you again to everyone who joined us.

If you are building, exploring, or seriously thinking about where insurance is heading, we would love to connect next time.

No pitch deck required. No formal agenda needed. Just a useful conversation.

‍