Director / Senior Director of Product · Seattle, WA

Identity. AI. Commerce.Built at Amazon scale. Now looking for the next stage.

A decade leading product at Amazon. Currently Head of Product for AWS Marketing's digital experiences. Previously Alexa identity & personalization, Amazon Teen, and a $110M P&L at 1&1 Ionos.

Tenure

10yrs

at Amazon

Revenue growth

52×

Amazon Teen · 19 mo

AI scale

5.5B

interest signals · Alexa

P&L scope

$110M

1&1 Ionos · U.S./Canada

— About

A product leader looking for a stage where every decision counts.

I've spent the last decade leading product at Amazon, most recently as Head of Product for AWS Marketing's digital experiences, and before that for Alexa identity and personalization. Earlier, I led search and shopping experiences across Amazon Retail's Consumer Electronics business, and I built Amazon Teen — a new identity and commerce program from zero, with end-to-end accountability for the launch, the regulatory posture, and the revenue line.

Before Amazon, I held direct P&L responsibility for 1&1 Ionos' U.S. and Canadian markets: a $110M business across pricing, commercial modeling, and revenue. Across roles, the pattern has been the same: end-to-end accountability for a customer segment, a product, a strategy, or a number. The next chapter is a Director or Senior Director role at a mid-size company in consumer or B2B SaaS, where the work compounds and decisions move quickly.

"Three problems. Three bets. Three outcomes worth examining."

— Selected work · 2017 – Present

— Selected work

Three case studies.

No. 01 — 03
Amazon · 2015–Current

01Identity · Commerce · Zero to One — Amazon, 2017–2020

Reimagining identity for the next generation of Amazon shoppers.

Tens of millions of teens were transacting on Amazon through their parents' accounts. They were invisible to the platform, unsafe by default, and a missed segment for the business. I built the program that fixed all three.

IdentityCommerceRegulatoryZero to One

Amazon Teen parent settings — spending limit and controls

Amazon Teen purchase approval via text message

Weekly revenue

52×

over the 19-month STL tenure

Weekly active purchasing

33%

among enrolled teens · +660bps

Returning order share

94%

strong product-market fit

Weekly revenue trajectory · 19 mo

Problem

Teens were a large, invisible segment on Amazon. They transacted through parents' accounts with no identity, no tailored experience, and no oversight tools for parents. A trust problem and a business problem at once.

Insight

The barrier wasn't appetite. It was structure. An identity layer giving teens autonomy and parents meaningful oversight could unlock a segment that had been quietly transacting on the platform for years.

Decision

Led the program as Single Threaded Leader (Amazon's role equivalent to product owner with end-to-end accountability) from October 2018 to April 2020. Drove the end-to-end launch across 40+ internal teams: identity and enrollment, payment sharing, purchase approval, and the regulatory posture. Served as Amazon's product lead in policy discussions with Congressional staff and federal agencies including the Department of Commerce.

Outcome

Weekly revenue grew 52× and weekly orders grew 4× during the 19-month STL tenure. Weekly active purchasing rate reached 33% among enrolled teens, up 660bps. By end of tenure, 94% of order volume came from returning customers — even as the program scaled 52× in revenue — indicating strong product-market fit.

Validation / Post-tenure

The strategic foundation continued to compound after my STL tenure.

In the years following my transition off the program, weekly revenue grew an additional 55× and weekly active purchasing rate grew an additional 2,200bps, with no incremental feature development. The post-tenure arc demonstrates that the underlying strategy, not timing or luck, drove the outcome.

Additional weekly revenue

+55×

post-tenure

Weekly active rate gain

+2,200bps

post-tenure

Incremental feature dev

None

strategy held without me

Press → The Wall Street Journal TechCrunch CNN CBS News MarketWatch + 100s more

02AI / ML · LLM · Personalization — Amazon, 2022–2025

Teaching Alexa who it's talking to, at the scale of tens of millions.

As Alexa transitioned to a large language model architecture, personalization became essential. The system could generate more contextual responses, but only if it knew who was on the other side.

AI / MLLLMPersonalizationPlatform

Profile adoption

+40%

YoY · +30M incremental profiles

Interest signals

5.5B

across tens of M profiles

Team scope

10 / 75+

direct reports / global engineers

Active profile adoption · 3 yrs

Problem

Tens of millions of Alexa profiles existed, but most were sparse. Without an identity and interest layer, Alexa's new LLM-driven capabilities would feel generic at best, irrelevant at worst.

Insight

The problem wasn't data. Amazon had abundant signals. It was inference and architecture. ML had to surface preferences implicitly and feed them into multiple downstream models without brittle dependencies.

Decision

Defined and executed the Alexa+ personalization strategy, including the approach to profile enrichment from ML-inferred and explicit signals. Recruited and grew the product, design, and data science leadership bench, including promoting a Senior PM to Principal.

Outcome

Enriched tens of millions of Alexa profiles with 5.5B interest signals. Grew active profile adoption 40% year over year by adding 30M incremental profiles. Those enriched profiles became the foundational layer for Alexa+'s context-aware experiences.

Cross-org leadership / CEO-sponsored

Transferred ownership of cross-Amazon personalization data from Alexa to Stores.

Beyond the personalization strategy itself, I led a CEO-sponsored initiative that transferred ownership of cross-Amazon personalization data from Alexa to Stores. The work required architectural decisions about where consumer personalization data should live as the consuming experiences shifted, organizational coordination across two large engineering organizations with legitimate competing claims, and executive alignment across multiple senior leaders. The transfer reshaped the foundational data architecture underlying consumer personalization across Amazon's most-visited experiences.

03AI / ML · AWS Marketing & Sales — Amazon, 2024–Present

Two pillars of AI product work for AWS Marketing & Sales.

As Head of Product for AWS Marketing, I'm leading two distinct AI initiatives: a multi-agent search and chat experience for AWS re:Invent, and a cross-functional propensity scoring platform for Marketing and Sales. Together, they bring the personalization and ML product approaches I developed at Alexa into two new domains — consumer events, and B2B account intelligence.

Agentic AIML RecsPersonalizationB2B Intelligence

Ask AWS chat surfacing reserved Gen AI sessions

AWS Events app calendar with Generate my agenda AI action

Pillar 01 Shipped · re:Invent 2024

A multi-agent AI experience for 50,000+ attendees across five days.

At AWS re:Invent, the challenge isn't getting people there: it's helping them navigate thousands of sessions and a multi-venue campus. The app was a useful but passive utility. I led the work to make it intelligent.

Used AI search & chat

51%

of key event attendees

Sessions from ML recs

33%

of total session attendance

Used in-app navigation

45%

BLE routing

Feature adoption · re:Invent week

Problem

Attendees were making poor session choices, missing relevant content, and struggling to navigate a multi-venue campus. The opportunity: 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 meant agentic AI, not keyword matching.

Decision

Led the launch of a multi-agent AI search and chat experience inside the AWS Events app, plus ML-driven session recommendations and BLE campus navigation. Also led a livestreaming program that drove an 11% increase in flagship content viewership.

Outcome

51% of key attendees used the multi-agent experience. The recommendation engine drove 33% of all session attendance. 45% of attendees used in-app navigation. The features turned a passive app into an active product used throughout the conference.

Pillar 02 In progress · 2026

A cross-functional propensity scoring platform for Marketing & Sales.

In parallel, I'm leading a cross-functional propensity scoring platform spanning AWS Marketing and Sales. The platform applies the personalization and ML product approaches I developed at Alexa to a new domain: B2B account intelligence.

Problem

AWS Marketing and Sales operate against an enormous universe of accounts and leads, but without unified scoring on topic, product, and next-best-action dimensions, prioritization stays manual and competitive insight stays shallow.

Insight

The same personalization-architecture patterns that worked at consumer scale (implicit signal inference, continuous enrichment, multiple downstream consumers) map directly to B2B account intelligence, with very different inputs and outputs.

Decision

Designing and building the platform end-to-end: account-level and lead-level scoring across topic, product, and next-best-action dimensions, continuously updated on customer activity signals. Aligning Marketing and Sales stakeholders with legitimate competing claims on the system's outputs.

Outcome

Targeting general availability across AWS Marketing and Sales surfaces. Early signals indicate strong stakeholder adoption and meaningful lift in lead conversion when scored signals are integrated into existing motions.

— How I work

Five principles I lead by.

Own the outcome, not the output.

End-to-end accountability, at Amazon Teen and 1&1 Ionos, changes how you prioritize. You stop asking "did we ship it?" and start asking "did it work?" I bring that orientation to every team I lead, whether or not the P&L formally sits with me.

Hire for problem ownership, not feature delivery.

My job isn't to be the smartest person in the room. It's to make sure the right people own the right problems with clarity and autonomy. I structure teams around problem spaces, not feature tracks, and hire PMs who can defend a roadmap from first principles.

Strategy is mostly saying no.

The hard part isn't identifying opportunities. It's building the clarity and organizational trust to decline ones that don't belong. I anchor prioritization to a small set of outcome metrics the team can recite, and revisit them often enough to stay honest.

Move before the fog clears.

Most ambiguity isn't missing information. It's missing agreement on what question we're trying to answer. I decompose fast, separate what we know from what we're assuming, and find the smallest experiment that resolves the most uncertainty.

AI products demand a different kind of judgment.

The output is probabilistic, the failure modes are often invisible, and the gap between a demo and a reliable system is enormous. I set clear performance thresholds before launch (not after), involve data science in roadmap conversations rather than treating them as an execution dependency, and stay skeptical of benchmarks that don't map to actual user behavior.

— Experience

A decade at Amazon. A career built on shipping things that matter.

Amazon

Seattle · 2015 — Present

Amazon

Head of Product, AWS MarketingAWS Global Events · digital experiences · personalization

2025 — Now

Amazon

Head of Product, Alexa Identity & PersonalizationAlexa+ personalization strategy · profile enrichment at scale

2022 — 2025

Amazon

Principal PM, Consumer Electronics TechPC & Office shopping · CE/Wireless/Trade-In search

2020 — 2022

Amazon

Sr. PM, Retail IdentityBuilt and launched Amazon Teen end-to-end

2017 — 2020

Amazon

Sr. PM, Merchant FulfillmentBuy Shipping Service · Seller Fulfilled Prime

2015 — 2016

1&1 Ionos

Chesterbrook, PA · 2011 — 2015

1&1 Ionos

Director, Product MarketingDirect P&L · U.S./Canada · $110M · team across 4 countries

2011 — 2015

Education

University of Pittsburgh

Katz

MBA · Strategy & MarketingKatz Graduate School of Business

Pitt

B.A. · Communications & MediaUniversity of Pittsburgh

— Get in touch

Selectively exploring Director and Senior Director roles at mid-size companies.

Looking at consumer and B2B SaaS companies where the work compounds and decisions move quickly. Based in Seattle. Open to remote and hybrid. If your team is solving consumer, identity, AI/ML, personalization, or platform problems, I'd love to hear from you.

ryancieslak@gmail.com LinkedIn →