Should We Pivot?

The conversation that founders and investors should be having - but are often afraid to bring up

As we reach the final quarter of 2023, one of the most common conversations we’re having with founders is whether they should pivot or stay the course. This is normal seeds funds in all vintages, but is especially important during a challenging Series A market.

A founder recently responded to feedback I gave saying that he appreciated how direct I was when we had the “should we pivot?” conversation. Other investors (including much larger funds, with many more dollars in the company) had not taken time to give the same feedback.

The founder took my feedback to heart, reduced their team size, and proceeded with an entirely new direction. Aka they pivoted.

This moment made me think about one question for many weeks:

Why do so many founders and investors procrastinate with having this conversation?

The easy answer is that having the “should we pivot?” conversation is not fun for anybody on the cap table.

A founding team often spends years fundraising, recruiting a team, building a product, and introducing an idea to the tech community.

And now you’re questioning everything, and whether you should start from scratch.

This comes with a sense of embarrassment to some founders or the feeling that they are letting down their investors. If you picked the right investors, the opposite is true.

The best investors are eager to have this conversation when the early experiments aren’t working.

And if we normalize the “should we pivot” question as an expected moment of building a startup, it’s a much easier conversation to have.

Roadmap Debt

I’ve come to understand that at the heart of the “should we pivot?” conversation hesitancy is a phenomenon I've come to identify as roadmap debt.

We all know about technical debt in software. This happens when you have legacy code that often breaks, which leads to bugs and business critical outages. Every company with any amount of mainstream success has software debt.

Software debt is a positive sign that your company and user base has grown. If you don’t have software debt, you probably haven’t built a product that people want.

But for products that do not product market fit, the more common issue that I see if the concept of roadmap debt.

Roadmap debt is an accumulation of medium to large features on a product roadmap that teams commit to building. You can make yourself believe that each part of the roadmap will magically unlock product-market fit, but this rarely happens.

More often than not, roadmap debt weighs down a startup’s agility and vision.

The “Next Big Release”

Every founder, especially in the early stages, knows the feeling of convincing your team and investors that everything will be solved with the “next big release.” This is an easier conversation to have than talking about a pivot.

I’ve long seen and been a part of a ritualistic chant within the hallways of struggling startups that goes something like this: "Once we roll out this feature, we'll find product market fit."

This mindset is understandable. But the roadmap, when laden with debt, becomes less of a guiding tool and more of an anchor. Founders feel beholden to it, fearing that deviating from the plan might signal inconsistency or a lack of vision to their team and investors. But at startups, adaptability is not just a trait — it's a survival skill.

Pivoting doesn't mean abandoning a vision; it means refining it. It's an acknowledgment that while the core idea has potential, its current execution isn't resonating with the market. Pivoting provides an opportunity to reassess, to listen to user feedback, and to realign your product with customer needs.

Should We Pivot?

It's crucial for founders to periodically reassess their product roadmaps. Are you adding features based on user demand and genuine market need, or are they vestiges of an old strategy that no longer serves your target audience?

While the roadmap should guide a startup's journey, it shouldn't become a chain that binds it to a sinking ship.

Recognizing roadmap debt and the false security it can provide is the first step. From there, founders can make informed decisions about whether to persevere or pivot.

In 2023, as early-stage startups grapple with tough decisions, founders and investors should prioritize having hard conversations if needed in Q4.

This starts with having the “should we pivot” talk, and not viewing those conversations as a sign of weakness.

It’s okay to pivot.