Product Ops & Strategy Leader

Stephen
Thiessen

I turn product ambition into execution infrastructure — the operating systems, planning rhythms, and AI-augmented workflows that let product orgs move with precision instead of noise.

See the tools → About me
// Career snapshot
15+
Years operating
5
Industry verticals
$1B+
Org scale navigated
IC→
To strategic lead
PMP — Project Management Professional
Advanced Certified Scrum Master
AI Product Management — Certified
Prompt Engineering & AI Workflow Design
DoubleVerify — Drata — Peloton — Capital One — Oracle — Operating Model Design — Planning Rhythms — Roadmap Facilitation — AI-Augmented Workflows — Cross-Functional Alignment — DoubleVerify — Drata — Peloton — Capital One — Oracle — Operating Model Design — Planning Rhythms — Roadmap Facilitation — AI-Augmented Workflows — Cross-Functional Alignment —
About
Built for the
messy middle
Stephen Thiessen

I'm a strategic product and operations leader with 15+ years operating at the intersection of product, engineering, and go-to-market — across ad tech, security and compliance SaaS, data infrastructure, and AI.

My work lives one level above delivery and one level below strategy: translating complex goals into operating models, planning systems, and cross-functional rhythms that hold up under pressure and scale with the org.

I've built and rebuilt product operating systems inside some of the most demanding environments in tech — joining Peloton pre-IPO and operating through hypergrowth, building compliance infrastructure at Drata during its scale-up, and driving verification platform programs at DoubleVerify.

More recently I've focused on one question: how do AI-native workflows change what product ops looks like? Not AI as a feature, but AI as the backbone of how a product org plans, decides, and executes. That's what the tools on this site are built around.

I'm looking for roles where I can own the operating model — not manage the execution layer, not chase teams for updates, but design and run the system that makes excellent product work possible.

Operating model design
How product teams plan, decide, and run
Planning rhythms
Quarterly cycles that connect to strategy
Roadmap facilitation
Prioritization as a decision process, not a list
AI-augmented workflows
Embedding AI into how orgs actually work
// Previously operated at
DoubleVerify Drata Peloton Capital One Oracle
Product Ops Intelligence
Tools I built.
Use them.

These aren't portfolio pieces. They're working tools built on the frameworks I use to diagnose and fix product operating models. If you run a product org, they'll tell you something real.

// Live now
Product Ops Maturity Assessment
18 questions across six dimensions — strategic direction, planning rhythm, roadmap process, cross-functional alignment, AI adoption, and ops infrastructure. You get a scored diagnosis, not generic advice.
Take the assessment →
6
Dimensions
18
Questions
~5
Minutes
// Live now
AI Workflow Audit
An honest audit of where AI is and isn't embedded in how your product org works — workflow by workflow, with specific recommendations for every gap.
Take the audit →
// Live now
Planning Session Facilitator
Input your team context, tensions, and goals — get a structured agenda, calibrated prioritization framework, and the questions that matter most to ask in the room.
Build your session →
// Live now
AI Ops Playbook
A phase-by-phase framework for building AI-augmented product operations from scratch — foundation, planning infrastructure, AI integration, and scale. Work through it at your own pace with progress tracking built in.
Open the playbook →
4
Phases
27
Moves
6
Dimensions
The Product Intelligence Loop
A five-layer agentic framework

Most product ops failures trace back to five universal problems — ideas that get lost, strategy that doesn't drive decisions, planning driven by politics, execution that goes dark, and lessons that never stick. The PIL is a multi-agent system designed around all five. One layer per problem. Twelve agents. A scoring matrix, a planning lock, and a loop that closes.

// Framework documentation
The PIL Master Framework
The full system — five layers, twelve agents, eight scoring dimensions, the Planning Lock, and the exception process. Built to replace political prioritization with evidence-driven planning.
Layers
5
Agents
12
Dimensions
8
Read the framework →
// Live demo · Layer 1 · Capture
PRD Intake Agent
A live demonstration of the PIL's Layer 1 Capture agent in action. Describe a product idea — the agent guides you through structured intake, maps it to OKRs, generates a PRD outline, and routes it to the right PM. Real AI, real output.
Mode
Live AI
Fallback
Scripted
Try the demo →
Writing
Latest thinking
All articles on LinkedIn ↗
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Let's talk about
your operating model

I'm selectively exploring roles where I can own the operating model for a product org — planning systems, roadmap infrastructure, AI-augmented workflows, and the rhythm that makes strategy executable.

Connect on LinkedIn → Explore the tools