Why product and GTM initiatives fail at insurance carriers

Most product and Go-to-Market (GTM) initiatives at insurance carriers do not fail because the ideas are bad or ill-intentioned. They fail because leaders underestimate the decision-making journey inside their own organization.

Insurance carriers have no shortage of opportunities to re-think pricing and packaging structures, launch new products or digitize distribution. What they often lack is the internal alignment and consensus building needed to get these initiatives over the finish line. In practice, transformation is as much about navigating internal dynamics as it is about deploying new capabilities in the market.

The hidden stakeholders

Every initiative touches multiple decision-makers, each with different lenses:

• The CFO wants proof that the investment will show up quickly in the combined ratio or topline. Digital core platforms, AI-driven underwriting, or dynamic rating engines are compelling, but without a clear ROI story, they stall in the budget cycle.
• The COO and operations teams focus on execution. Can existing platforms manage new pricing tiers? Will new digital platforms integrate without adding risk? Many "innovative" programs die here when technology limitations outweigh the promised upside.
• The distribution team is often the gatekeeper to customer adoption. Brokers and agents are quick to push back if pricing or packaging creates confusion or threatens margins. In digital GTM shifts, like embedding products into partner platforms, distribution skepticism can derail an otherwise strong strategy.
• The product team worries about balancing risk against customer experience. They want pricing and packaging to be simple enough to understand but flexible enough to differentiate in-market. Digital channels add new complexity: how do you balance self-service level of clarity with the sophistication of multi-line or usage-based products?

These stakeholders rarely sit in the same room at the same time, which means projects can die from misalignment before they even launch.

Why transformation raises the stakes

Digital tools do not just change how carriers deliver products, they also change the expectations of each stakeholder group.

• For finance: Real-time analytics and scenario modeling mean ROI questions are more pointed. If you can model pricing elasticity and renewal retention in minutes, why haven't you already?
• For operations: Cloud-native architectures and API-driven integrations remove some excuses but introduce new governance and security concerns. The "can we execute?" question shifts from legacy limitations to risk management in digital ecosystems.
• For distribution: Digital platforms create new channels, from embedded insurance to direct-to-consumer digital brokers & aggregators. Packaging decisions need to anticipate how products will flow across these ecosystems, not just through traditional agencies.
• For product: Digital opens the door to micro-packaging and un-bundling with modular coverages, usage-based models, and add-ons that can be sold and serviced online. The challenge remains to avoid choice overload while enabling personalization aligned with risk appetite.

Said differently, transformation does not simplify product and GTM, it only multiplies both the opportunities and the risks.

What successful carriers do differently

The carriers that succeed in digital product and GTM initiatives approach them less as "projects" and more as "products" and "jobs-to-be-done," mirroring the approach of Silicon Valley tech natives. A few common patterns stand out:

1. Anticipate the CFO's questions early. Before investing in technology or design, build the ROI case. Use quantitative and qualitative data to quantify customer willingness-to-pay, distribution impacts, and operational efficiencies.
2. Frame the initiative in terms of growth and efficiency. Technology & digital are often pitched as a growth lever, but operations leaders need to see cost and efficiency gains as well. Anchoring both stories reduces resistance and sets expectations with transparency.
3. Bring distribution into the process early. When brokers or partners help shape packaging and digital enablement, adoption hurdles fall away. Digital tools should empower them, not threaten them. Focus groups and interviews with producers can yield qualitative market insights that drive innovation internally among product and underwriting teams.
4. Translate strategy into executional detail. A growth strategy is only as good as its integration into policy admin systems, digital quoting engines, and enterprise workflows. Carriers that "design strategy for execution" see time-to-market faster.

A different way to think about product & GTM

If there is a lesson in all of this, it is that digital transformation in pricing, packaging, and GTM is less about technology and more about organizational alignment. Digital can be the catalyst that makes bold initiatives possible, but without consensus across finance, operations, distribution, and product, even the best ideas will struggle to launch.

Insurance has always been in the business of managing risk. The promise of transformation is that it can help carriers manage risk better with smarter pricing, more tailored coverage packaging, and more efficient go-to-market strategies. But to get there, leaders need to manage not just market risks, but also the organizational risks of change.

The carriers that win will be those who recognize that the hardest part of any transformation is not building the technology. It is building consensus.