Reflections from my first month returning to consulting: Themes and Insights in Insurtech and Employee Benefits

It's been an exciting first month back in the world of consulting, specifically within the Insurtech and employee benefits space. As I dive back into the ecosystem, I've been observing some recurring themes and trends in my conversations that are shaping the landscape. These are themes that companies in this space often struggle with, yet they also present opportunities for growth and success. Let me share with you three key insights I've learned or trends I'm seeing during my first month back in the game.

1. Strategy: The Double-Edged Sword of a Good Plan

One of the most interesting themes I've encountered is the issue of strategy. Everyone either has a strategy, but they’re unaware of its flaws, or they know they need one, but they don’t know where to begin. In the Insurtech and employee benefits world, this is particularly true. Whether it’s refining your go-to-market plan or making sure your partnerships are well-positioned, a strategy that looks great on paper can often fall short in practice due to misaligned priorities, market shifts, or just poor execution.

Companies need a clear vision, but more importantly, they need to be open to evolving that strategy as they learn more about their clients, partners, and the industry. Having a plan is crucial, but knowing when to adapt is just as important.

2. Connection: Breaking Into a Tight-Knit Ecosystem

Another recurring theme I've noticed is the challenge of connection. The Insurtech and employee benefits ecosystem is a small, closely-knit group, and breaking into it can be a daunting task. Relationships matter deeply, and often, companies struggle to figure out how and where to build the right connections.

I spoke with one company recently that had spent several months trying to break into a large organization to discuss a potential partnership — and they had no luck. It’s exhausting. The difficulty is that it’s not just about identifying the right people; it’s about understanding the dynamics, building trust, and knowing where to look. In this ecosystem, getting a foot in the door takes more than just sending an email or picking up the phone. It takes time, persistence, and knowing who’s who in the industry.

3. Timing: Understanding the Long Road to the End Consumer

The third theme I’ve observed is timing — particularly the realization that the path to the end consumer in the employee benefits space is much longer and more complex than many initially realize. A company may have a fantastic product and a go-to-market strategy in place, but they might not fully understand the buying cycle for partnerships.

Here's the process in a nutshell: First, you need to convince a company to say yes to host your product. Then, you must integrate it into their platform. After that, you enter the sales phase, where a sales team needs to sell the product to brokers and employers. Only after the product is customized, built, and set up for enrollment can employees finally purchase it.

That’s a long road to travel, and it requires careful planning and timing to avoid missing the narrow windows of opportunity. The challenge is that if you miss the buying season, you have to wait until the next year. And here’s the kicker: investors often don’t understand the length of this process, which can create tension and frustration.

How RevGem Makes a Difference

This is where we at RevGem come in. We understand the ins and outs of the market, the players, and the timing. We know how to position partnerships strategically to accelerate your product's impact. Having been in the space for years and having gone through this process multiple times, we can step in and make an immediate difference.

We’re not just consultants; we’re partners who dive in when we feel we can help move the needle. We work with you to craft a market-ready, actionable go-to-market plan based on solid research. We open doors and leverage our vast networks — not as salespeople, but as respected industry insiders who keep a pulse on the market.

At RevGem, we don’t waste time. We don’t take on projects that we don't have the expertise for, and we always provide honest and direct feedback. An early "no" is considered a success in our book, as it helps refine your approach.

If you're struggling to navigate this complex, evolving ecosystem or want a second look at your strategy, give us a call. Let’s chat about how we can help you accelerate your path to success.