Director / VP of Product · Seattle, WA

Building products that move fast, own outcomes, and actually ship.

After more than a decade leading product at Amazon, I know exactly what kind of environment brings out my best work — and it's not defined by headcount. It's defined by velocity, accountability, and the ability to connect product decisions directly to business outcomes.

At Amazon, I built products used by tens of millions of people and led teams responsible for hundreds of millions in incremental revenue. But the work I'm proudest of shares a common thread: full ownership. At Amazon Teen, I held end-to-end accountability for a new customer segment — identity model, commerce platform, regulatory strategy, and revenue outcome. At 1&1 Ionos, I carried direct P&L responsibility for a $110M market. That combination of strategic scope and outcome accountability is what I'm looking to carry forward.

I thrive where product decisions are visible, iteration cycles are short, and there's no bureaucratic buffer between a good idea and its execution. I've spent my career building at the intersection of AI, personalization, identity, and commerce — and I'm most energized when I can bring that depth to a team that's genuinely trying to move fast and build something that matters.

What I bring to a Director or VP role isn't just a track record of shipping — it's a demonstrated ability to set product vision, build and develop high-performing PM teams, and translate that into measurable business outcomes. I've led teams through zero-to-one launches, multi-year platform builds, and the kind of organizational complexity that comes with operating at scale. I'm ready to bring that full range of experience somewhere it can make a concentrated difference.

Open to
Director of Product VP of Product Head of AI/ML Product
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Experience

A decade at Amazon. A career built on shipping things that matter — and owning what happens next.

Amazon

Seattle, WA · 2015 to Present

Head of Product, AWS Marketing

2025 to Present

Led a cross-functional team owning digital experiences for AWS Global Events, including the AWS Events Mobile App, microsites, and content publishing infrastructure. Also consulted across AWS Marketing on personalization strategy.

  • Launched a mobile, multi-agent AI search and chat experience adopted by more than half of key event attendees
  • Built an ML-driven session recommendation engine responsible for driving roughly a third of total session attendance
  • Delivered BLE-enabled, location-aware in-app navigation used by nearly half of global attendees
  • Launched in-app event livestreaming, meaningfully increasing viewership of flagship content

Head of Product, Amazon Devices — Alexa Identity and Personalization

2022 to 2025

Recruited to lead a high-impact product team responsible for identity and personalization across Alexa's LLM-driven conversational assistants. Defined and executed a multi-year strategy to scale profile enrollment and customer knowledge inference using NLP and AI. Led a team of cross-functional directs defining the work of a large global engineering organization.

  • Defined the personalization product strategy for Alexa+, leveraging LLM-based architectures to deliver context-aware, user-centric experiences
  • Enriched tens of millions of Alexa profiles with billions of interest signals via ML and explicit inputs, enabling downstream personalization at scale
  • Grew active profile adoption and engagement significantly year over year by adding tens of millions of incremental profiles
  • Led a high-visibility special project to unify consumer personalization data across Amazon experiences, with CEO-level visibility

Principal Product Manager, Amazon Retail — Consumer Electronics Tech

2020 to 2022

Owned the end-to-end shopping experience for PC and Office, and led all search efforts across Consumer Electronics, Wireless, and Video Game Trade-In.

  • Launched the first AI and live chat sales support experience on Amazon.com, generating significant annual incremental revenue
  • Built an ML-driven ink and toner compatibility search feature with measurable annual sales impact
  • Scaled wireless and video game trade-in programs to meaningful annual revenue

Sr. Product Manager, Amazon Retail — Identity

2017 to 2020

Led the end-to-end launch of the Amazon Teen program — a new identity and commerce experience enabling teenagers to have their own Amazon login with shared payment access and parental controls.

  • Drove a more than tripling of weekly orders and multi-thousand-percent revenue growth within 18 months through iterative A/B testing and optimization
  • Managed a complex regulatory, public relations, and public policy launch involving federal agency engagement and hundreds of press mentions
  • Designed the underlying platform for payment sharing, purchase approval, and order management — later expanded to serve additional customer segments
  • Held full end-to-end accountability for customer outcomes and revenue performance, not just feature delivery

Sr. Product Manager, Amazon Retail — Merchant Fulfillment

2015 to 2016

Guided development of Amazon Buy Shipping Service within Seller Central, a critical component enabling Seller Fulfilled Prime.

  • Reduced shipping label purchase time by 80% through API and UI redesign, enabling Seller Fulfilled Prime to grow revenue by more than 200% year over year
  • Developed and launched initial Seller-facing pricing for Amazon Logistics in the U.K.

1&1 Ionos

Chesterbrook, PA · 2011 to 2015

Director, Product Marketing

2011 to 2015

Held direct P&L responsibility for the U.S. and Canadian markets — full ownership of a $110M/year business across product marketing, pricing, commercial modeling, and revenue outcomes. Led a team across four countries managing a portfolio of SaaS products serving independent content creators and SMBs.

  • Grew revenue year over year and exceeded monthly sales plan consistently
  • Increased average revenue per user by more than a quarter through pricing and discount restructuring
  • Reduced customer attrition meaningfully by introducing a new commercial model
  • Launched the product portfolio in seven new countries, growing international sales year over year

Earlier: Sr. Internet Marketing Manager, IQVIA (2009 to 2011) — Founded the Global Interactive Center of Excellence; modernized the company's marketing model under the CMO · Director, Online Product Management, Victory Media (2007 to 2009) — Launched eight revenue-generating online properties in 24 months; led the company's transition from print-only to majority digital revenue

Education

University of Pittsburgh, Katz Graduate School of Business MBA, Strategy and Marketing
University of Pittsburgh B.A., Communications and Media

Selected Work

Three problems. Three bets. Three outcomes worth examining.

Identity Commerce Zero-to-One
Amazon · 2017–2020

Reimagining Identity for the Next Generation of Amazon Shoppers

Amazon had tens of millions of teenage users with no identity of their own. I built the program that changed that — and owned the business outcome end to end, from identity architecture to revenue.

>3× weekly orders
Multi-K% revenue growth
40+ teams coordinated

Problem

Teenagers represented a significant and largely invisible commerce segment on Amazon. They were transacting through their parents' accounts with no distinct identity, no tailored experience, and no way for Amazon to serve them or understand them. Parents, meanwhile, had no visibility or control. The status quo was a trust problem and a business problem simultaneously.

Insight

The barrier wasn't appetite — teenagers wanted to shop, and parents wanted their kids to have access. The barrier was the absence of a safe, controlled structure for doing it. If we could build an identity layer that gave teens autonomy while giving parents meaningful oversight, we could unlock a segment that had been quietly transacting on the platform for years without being properly served.

Decision

I led the full end-to-end launch across more than 40 internal teams: the identity and enrollment model, a payment sharing and purchase approval system, the regulatory and public policy strategy, and a PR launch plan that involved engagement with Congressional staff and federal agencies. I held full end-to-end accountability — not just for the product, but for the revenue outcome, the regulatory posture, and the platform decisions that would determine whether this could scale beyond its original scope. Every decision involved a real tradeoff between conversion, safety, compliance, and parent trust, and I had to hold all of those simultaneously.

Outcome

Within 18 months of launch, weekly orders more than tripled and revenue grew by multiples of thousands of percent through iterative A/B testing and optimization. The underlying platform was designed for reusability and later expanded to serve additional customer segments.

AI/ML Personalization LLM
Amazon · 2022–2025

Personalizing Alexa at Scale Using LLMs

Alexa was transitioning to a large language model architecture. My job was to make sure it actually knew who it was talking to.

Tens of M profiles enriched
Billions interest signals added
~40% YoY adoption growth

Problem

As Alexa moved from rule-based responses to LLM-driven conversation, personalization became both more important and more complex. The system could generate more natural, contextual responses — but only if it had rich, accurate knowledge of the individual user. Tens of millions of profiles existed, but most were sparse. Without a robust identity and interest layer, Alexa's new capabilities would feel generic at best and irrelevant at worst.

Insight

The problem wasn't data — Amazon had abundant signals across its ecosystem. The problem was inference and architecture. Most users would never manually tell Alexa what they cared about. We needed ML to surface interest and preference signals implicitly, and we needed the system to be flexible enough to feed those signals into multiple downstream AI models without creating brittle dependencies.

Decision

I defined and executed the personalization product strategy for Alexa+, including the approach to enriching user profiles at scale using both ML-inferred and explicitly provided signals. I led a high-visibility initiative to unify consumer personalization data across Amazon experiences — a cross-org effort with CEO-level attention that required navigating complex stakeholder dynamics and competing data ownership models. A key part of my role was ensuring the PMs on my team had clear ownership of distinct problem spaces — not just feature tracks — so that the team could move in parallel without constant re-alignment.

Outcome

We enriched tens of millions of Alexa profiles with billions of interest signals, and grew active profile adoption and engagement by roughly 40% year over year, adding tens of millions of incremental active profiles. Those enriched profiles became the foundational layer for personalized, context-aware experiences in Alexa's LLM-driven assistant.

Agentic AI Mobile Events
Amazon · 2025

Building a Multi-Agent AI Experience for 50,000+ Event Attendees

At AWS re:Invent, the challenge isn't getting people there — it's helping them navigate thousands of sessions and make the most of five days. I built the AI product that solved that.

>50% used AI experience
~33% sessions from AI recs
~50% used navigation

Problem

AWS re:Invent is one of the largest technology conferences in the world. Attendees face an overwhelming volume of sessions, content, and logistics — and historically, the event app was little more than a digital brochure. Attendees were making poor session choices, missing relevant content, and struggling to navigate a multi-venue campus. The opportunity was to turn a passive utility into an intelligent guide.

Insight

Attendees didn't need more information — they needed the right information, surfaced at the right moment. That distinction shaped the entire product direction: rather than building better search, we needed to build a system that understood intent, context, and relevance simultaneously. That meant agentic AI, not just keyword matching.

Decision

I led the launch of a multi-agent AI search and chat experience within the AWS Events mobile app, alongside an ML-driven session recommendation engine and BLE-enabled campus navigation. This involved designing the agent architecture, aligning engineering and data science teams, and making deliberate product bets about where AI would add genuine value versus where simpler features would serve attendees better. Speed of execution mattered — this was a high-visibility, high-deadline environment with no room for slow cycles.

Outcome

More than half of key event attendees used the multi-agent search and chat experience. The recommendation engine drove roughly a third of all session attendance. Nearly half of attendees used in-app navigation. Livestreaming drove a meaningful increase in viewership of flagship content. Collectively, these features transformed a passive event app into an active product used throughout the conference.

How I Work

A few things I've come to believe — and actually try to operate by.

On ownership and P&L accountability

Some of the most clarifying moments in my career have come from sitting on the wrong side of a revenue miss. At Amazon Teen and at 1&1 Ionos, I had genuine end-to-end accountability — not just for shipping features, but for the business result. That experience fundamentally changes how you prioritize. When you own the outcome, you stop asking "did we ship it?" and start asking "did it work?" I try to bring that same orientation to every team I lead, even when the formal P&L ownership lives somewhere else.

On building and leading PM teams

My job as a product leader isn't to be the smartest person in the room — it's to make sure the right people own the right problems with the clarity and autonomy to solve them. I hire for outcome orientation, not feature-delivery instincts, and I structure teams to reinforce it: clear problem ownership, explicit customer accountability, and PMs who can walk into an executive review and defend their roadmap from first principles because they actually built it — not because I prepped them.

On strategy and prioritization

Good product strategy is mostly about saying no. The hardest part of the job isn't identifying opportunities — it's building the clarity and organizational trust to decline the ones that don't belong on your roadmap. I try to anchor prioritization to a small number of outcome metrics that the whole team can recite, and I revisit them often enough that they stay honest rather than decorative.

On ambiguity

I don't wait for the fog to clear before moving. When a problem is genuinely ambiguous, I try to decompose it fast — separating what we know from what we're assuming, and identifying the smallest experiment that would resolve the most uncertainty. I've found that most ambiguity isn't actually about missing information; it's about missing agreement on what question we're trying to answer.

On working with engineering

I think of engineering partnership as one of the highest-leverage things a PM can get right. The best collaboration I've experienced happens when engineers are brought into the problem before the solution — when they understand the customer constraint and the business stakes well enough to make good tradeoffs without escalating every decision. I try to write tight problem statements, stay close to technical feasibility early, and give engineers a real voice in shaping what we build and how.

On AI and ML products specifically

Building AI products requires a different kind of judgment than traditional feature development. The output is probabilistic, the failure modes are often invisible, and the gap between a demo and a reliable system is enormous. I've learned to set clear performance thresholds before launch rather than after, involve data science teams in roadmap conversations rather than treating them as an execution dependency, and stay skeptical of benchmarks that don't map to actual user behavior.

Skills & Tools

What I bring to the table — and how I actually use it.

PM Skills

  • Product strategy and vision — setting direction from first principles, not inherited roadmaps
  • Roadmap prioritization — outcome-anchored, defended from first principles
  • Zero-to-one product development — customer discovery through launch and scaling
  • P&L ownership — direct revenue accountability at Amazon Teen and 1&1 Ionos
  • Building and developing PM teams — hiring, coaching, and structuring for outcome ownership
  • Cross-functional leadership — coordinating 40+ teams; earned alignment, not just assigned authority
  • Executive communication — written and verbal, including CEO-level visibility
  • A/B testing and experimentation — design, analysis, and iteration at scale
  • Agentic AI and LLM products — multi-agent orchestration, retrieval, and evaluation
  • ML-driven personalization — profile enrichment, interest inference, and signal architecture
  • Identity and access management — consumer identity models, regulatory strategy
  • Platform and API product management — developer surfaces, reusability, and ecosystem design
  • Regulatory and policy navigation — COPPA, Congressional engagement, federal agency coordination
  • Go-to-market strategy — including PR-driven launches at national scale

Technical Fluency

  • SQL — proficient; analytical and exploratory querying
  • Amplitude — behavioral analytics and funnel analysis
  • Looker and BI tooling — dashboard creation, metric definition
  • A/B testing platforms — experimentation design and analysis
  • Jira and Confluence — standard agile workflow tooling
  • Figma — comfortable in design review; not a designer
  • API concepts and design — REST; able to write and review PRDs at the API level
  • LLM and ML fundamentals — able to work directly with data science on model requirements, evaluation criteria, and tradeoff decisions
  • Agentic architecture concepts — multi-agent orchestration, tool use, retrieval-augmented generation

I'm not an engineer, but I've never needed a translator to work with one.

Let's talk

I'm selectively exploring Director and VP of Product opportunities at product-led companies where ownership is real and iteration cycles are short. If that sounds like your team, I'd love to hear from you.

linkedin.com/in/ryancieslak