Senior Product Manager · Dublin
I’m Ryan. I lead product work on platforms, trust and AI.
I started in support. In more than 10 years in B2B SaaS, I’ve worked on the systems behind customer experience: developer platforms, trust products and AI support quality. I turn customer conversations, incidents and operational data into clear priorities, then work with teams to deliver them.
How I work with a team→On this page
What guides me
How I make decisions
Start with what people are telling you
Customer conversations, awkward workarounds and incidents help me see what needs attention. I read the support issue, look at the data and ask what someone was trying to do before deciding what we should build.
Make knowledge part of the product
I came into product through support and Knowledge-Centered Service. If people keep needing the same explanation, I look for a gap in the product or its documentation. The answer should be something the next person can find and use.
Give teams room to get on with it
Clear ownership, shared language and sensible system boundaries help teams make decisions. I work through the dependencies with people, make the trade-offs explicit and help agree what we’re aiming for.
Track Record
Engineering teams
40+
Owned a contribution model used by 40+ engineering teams at Zendesk.
Trust workflows
Shared ownership
Aligned legal, security, sales and engineering around clear agreement states, ownership and review paths.
AI conversations reviewed
10,000+
Reviewed Intercom Fin conversations for a B2B SaaS client and defined failure categories, quality criteria and human-handoff rules.
Cross-team pull requests
+135%
Improved contribution tooling, ownership and developer documentation for a React micro-frontend platform.
How I Got Here
My work, most recent first. Download my CV.
Nov 2025 - present
Product Consultant, AI Quality & Data Systems
Ryan Winkler Strategy Ltd · Selected B2B SaaS client
I lead discovery and technical analysis for B2B client work. For a B2B SaaS client, I reviewed 10,000+ live Intercom Fin conversations and defined failure categories, quality criteria and rules for human handoff.
Sep 2021 - Apr 2025
Product Manager, Internal Platforms & Trust Workflows
Zendesk
I owned product work on a contribution model used by 40+ engineering teams. Better tooling, ownership and developer documentation increased cross-team pull requests by 135%. I also owned Access Logs and Audit Logs and improved agreement review workflows.
2018 - 2021
Senior Abuse Analyst, Trust & Safety
Zendesk
I investigated API misuse, account compromise and coordinated abuse using SQL, BigQuery and Datadog. I moved to Dublin as the first EMEA Trust & Safety team member, establishing regional playbooks and escalation paths.
2015 - 2018
Senior Customer Advocate
Zendesk
I diagnosed email infrastructure, integration and API issues for enterprise customers. I wrote Knowledge-Centered Service runbooks and coached frontline teams on technical troubleshooting.
I build and maintain neighbourhood websites and product experiments, including Coolock Village, BulkheadOS and Meitheal. This work runs alongside my consultancy. What I’m working on.
Outside work
A bit of life outside the job
Around Coolock
In my free time, I work on a neighbourhood advocacy group and its website. I built and maintain Coolock Village’s site, bringing together local businesses, services and community events.
Visit Coolock Village →Open source, Linux and a very connected home
I’m an open-source enthusiast, a Linux hobbyist and a huge Home Assistant fan. Home Assistant has become our household’s intranet, with our calendar, home controls and self-hosted tools in one place.
See what I use →Olio volunteering
I volunteer with Olio to collect and redistribute surplus food locally.
About volunteering with Olio →How I Work
From the first question to the release
Work through the problem together
I’m comfortable getting into logs, SQL and API behaviour with engineers, then explaining the decision to people who don’t need that level of detail. I want us to agree on the problem before committing to a solution.
Write down the decision
I use short briefs and decision logs to capture what we chose, why and what would make us reconsider. People should be able to question the plan without having to reconstruct the conversation.
Stay involved through rollout
I work with the team on release criteria, documentation and what happens if something goes wrong. Then I look at how people actually use it and what still needs fixing.
More on collaboration, feedback and decisions in How I Work.
Bookshelf
A few books I keep coming back to. There are notes on what I took from each one on my bookshelf.
Ask Iwata · Thinking in Systems · The Mom TestBrowse my bookshelf →
What colleagues say
People I’ve worked with
He doesn't just execute — he digs deep into the details, challenges assumptions, and ensures that what gets built truly serves the customer. He's equally comfortable rolling up his sleeves with engineers as he is presenting a vision to senior leadership. Ryan never lets silos or red tape stand in the way of doing what's right, and he's the kind of teammate who makes everyone around him better.
Ryan showed that he could balance security risk, business progress and technical constraints very well. Ryan can clearly articulate what decisions are being made. Even when he made decisions that did not prioritise security I always felt understood by Ryan, and he made sure we understood his priorities.
Ryan's ability to form solid relationships with people across the organization is legendary, as is his willingness to go above and beyond to help others. He takes ownership quickly, willingly, and isn't afraid to seek out solutions on his own.
Let’s talk
Looking for a product manager? Let’s talk.
I’m looking for Product Manager and Senior Product Manager roles in developer tools, customer experience, AI and trust. I’m particularly interested in open-source and privacy-conscious products.