Justifying Non-Sexy Product Investments
Fund performance, UX and velocity work by making the invisible measurable and the downside of neglect concrete.
- Difficulty
- Advanced
- Time to result
- ~months to results
- Steps
- 4
- Confidence
- 90%
At scale, some of the most impactful projects — user experience, performance, developer velocity — are the hardest to measure and so get chronically underfunded ('what gets measured gets managed'). Winters lays out how to win support: manufacture metrics, run small proof tests, set team principles, and reframe the work as protecting gains you could otherwise lose. The linchpin is aligning your peer leaders before pitching upward.
Origin
Casey Winters' essay on justifying unsexy product work, discussed here; references Scott Belsky's product life cycle and the concept of falling out of product-market fit over time.
Core principles
- 01Hard-to-measure work gets chronically underfunded because what gets measured gets managed
- 02At early stage everything is about upside; at scale you can actually lose what you've built
- 03Protecting existing gains becomes increasingly valuable the more you've built
- 04User expectations and competitors keep rising, so standing still means falling out of product-market fit
- 05This work can't be done alone — it requires team buy-in first
How to run it
- 1
Align your peer leaders first
Before pitching upward, get your engineering manager and design leader bought in that the unsexy work matters. A small team of two or three aligned people makes it far easier to build the game plan.
Watch out You can't do a lot of this work alone; approaching leadership solo without peer alignment weakens the case.
- 2
Build a custom metric that captures the value
Create a metric that makes the otherwise-invisible value of performance, UX, or velocity legible to executives who need something they can understand.
Watch out When you genuinely can't create a metric they understand, lean harder on the loss-framing in step 4.
- 3
Run small tests to prove worthwhileness
Run small experiments that demonstrate the impact of the investment, and structure OKRs to both prioritize the work and surface its impact — building buy-in that can get the whole company excited to invest.
Pro tip Set team principles that make sure these important-but-easy-to-forget elements never fall off the radar.
- 4
Reframe the work as protecting gains you could lose
Help executives and managers see that a high conversion rate or strong engagement can erode if neglected — show concretely what it would look like if that gain went away. At scale, protecting what you've built is as important as adding more.
Watch out Teams built in early-stage 'always add upside' mode often forget that at scale you can lose existing gains.
In the wild
Pinterest was a fast-growing startup that stopped growing due to Facebook-related market changes, and later — after switching to growth primarily through SEO — got hit by a search algorithm change that severely impacted growth.
→ These shocks built company-wide intuition that past gains aren't guaranteed and that deliberate work to protect them is essential.
Common mistakes
Staying in pure upside mode at scale
Continuing to treat every effort as adding growth on top, as in early stage, ignores that at scale you can lose what you've built — a high conversion rate or strong engagement can disappear if the unsexy work is neglected.
Pitching unsexy work without a metric or peer alignment
Without a custom metric executives understand and without peer leaders aligned behind it, the work stays illegible and gets deprioritized regardless of its long-term importance.
Is it for you?
Best for
Product managers at scaled companies fighting to fund performance, UX, reliability, or developer-velocity work that doesn't obviously move headline metrics.
Not ideal for
Early-stage startups still searching for product-market fit, where driving upside legitimately dominates protecting gains.
From the transcript
“some of the most impactful projects that product teams can work on at scale ... are the hardest to measure and because of that they…”
“what gets measured gets managed”
“you have to get a team to buy in to this you can't really do a lot of this work alone”
“when you're at scale you can actually lose what you've built”
“protecting what we've got actually is increasingly important once you build scale”
From the episode
How to sell your ideas and rise within your company
Casey Winters, Eventbrite