How do you decide when it’s time to pivot from an existing product strategy, and what criteria do you use to evaluate potential new directions?

Time to pivot when the product feels stuck: users aren’t excited, growth is flat, or the market’s moved on.
Listen for pain: real problems users care about signal where to go next.
Chase energy, not just size: go where there’s momentum and unmet need.
Stay grounded: make sure it fits your team’s strengths and the mission you believe in.

Internal metrics like sales, churn, lead flow, and feedback would be my canary in the coal mine. If those metrics are moving in wrong direction it can indicate time a market shift or poor PMF. If you eliminate PMF as the issue that would be an indicator its time to consider a pivot.

Macro external factors like user expectations changing or disruptive tech entering market (hello AI!) would be indicators of a market level shift, and again indicate time to pivot. 

I use the same criteria to evaluate new directions. Start with the current and prospective users and blend with macro market factors. Has always given me a decent starting place to work with the team from. 

I tend to focus on market signals, user adoption, and strategic alignment first. Example questions to ask & answer: Is our market share declining or stagnant? Are new market opportunities emerging? Do we see poor user engagement or requests for different capabilities or use cases? Does our product strategy no longer align with the business strategy? Has our competitive positioning changed?

Primarily from the user/customer feedback!