Sam Wiskow

I lead complex
product work toward
clearer decisions
and better outcomes.

I bring customer needs into technical strategy and the practical work of delivery and change. That helps teams decide what matters and act on it.

Customer voice
Clearer
decisions
  • Technical
    strategy    Make the hard technical choices explicit.
  • Complex
    delivery    Break risky work into stages people can reason about.
  • Operating
    models    Keep ownership and decisions clear as a team grows.
  • Change
    stewardship    Help people understand a change and make it stick.
Customer valueBetter outcomes
Resource constraints

There is never unlimited time or capacity.

External uncertainty

Markets move and assumptions turn out to be wrong.

Technical complexity

New work has to coexist with old systems.

Adoption friction

People need time and a reason to change.

  • Technical strategy
  • Complex delivery
  • Operating models
  • Change stewardship
How I work
Technical strategy
Make the hard technical choices explicit.
Complex delivery
Break risky work into stages people can reason about.
Operating models
Keep ownership and decisions clear as a team grows.
Change stewardship
Help people understand a change and make it stick.
Resource constraints
There is never unlimited time or capacity.
External uncertainty
Markets move and assumptions turn out to be wrong.
Technical complexity
New work has to coexist with old systems.
Adoption friction
People need time and a reason to change.

Preparing the platform for Agent Scale

I led a small pod of engineers using AI agents to migrate a critical legacy system without lowering the safety bar. This was a new way of working that would become widely adopted at GitLab.

Decisions and sources
Decision
Capcity was constrained, so I pushed us torwards levereging Agentic development whilst people made the rollout calls.
Constraint
We had to make changes to a legacy system that touched every part of GitLab without introducing breaking changes for customers across 4 deployment types. All with limited team capacity.
Sources
Outcome
A more available and reliable platform for our customers. One shared foundation for managing application rate limits, with rollout designed to protect reliability.

Multi-region platform for AI services

How Runway supported GitLab’s first multi-region AI service.

Decisions and sources
Decision
Give service teams one route to deploy and operate software across regions.
Constraint
Regional reliability could not come at the cost of a cumbersome developer experience.
Sources
Outcome
Global users could receive latency-sensitive AI features through regional services, while service teams gained a reusable route to production.

Stewarding disruptive platform change

A program of change internally, driving a different approach to breaking changes and deprecations. Followed up by a set of articles which helped customers prepare for deprecations, breaking changes, and a new release schedule.

Decisions and sources
Decision
Change the way the company approached breaking changes, taking ownership of change and providing a low friction major upgrade experience for customers.
Constraint
The engineering effort required to drive change without customer impact. Additionally, the guidance had to keep up with continuous delivery and give customers enough notice to plan.
Sources
Outcome
Breaking changes decreased 60% following the change program. Customers had one place to find upcoming breaking changes and a release schedule they could plan around.

Writing

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About

The big picture matters. So does the awkward detail that changes the decision.

I became a product manager because I wanted to help teams decide what to do next and show why the work mattered.

More about how I work