Available for new opportunities

David O'Brien

Product Leader · Builder · Operator

10+ years delivering digital, SaaS, and enterprise platforms across retail, eCommerce, mobility, and consumer experiences. I build teams that ship and products that stick.

David O'Brien
10+ Years Experience
30% Delivery Efficiency Gain
$500K+ Monthly Conversion Driven
400K Daily Active Users
$1M+ New Business Influenced

I turn complexity
into clarity — and
clarity into shipped product.

I'm a product leader with deep roots in building and modernizing digital products — retail, eCommerce, mobility, SaaS, and enterprise platforms. I've worked everywhere from Fortune 500s to venture-backed startups and know how to calibrate my approach to what the team and business actually need.

I'm most effective close to the problem: working alongside engineering and design, sharpening scope, and building operating systems that make delivery repeatable. I lead with outcomes, not output.

Increasingly, that means leading with AI. I've shipped AI-integrated products — from mobile demand forecasting tools to SageMaker-backed workflows — and spent dedicated time upskilling in generative AI, LLM applications, and AI-enabled product practices. I'm focused on bringing that fluency to teams building the next wave of intelligent products.

Product Leadership Digital Transformation Agile / SAFe / Scrum Roadmaps & MVP Delivery Stakeholder Management Backlog & Requirements Vendor & RFP Management eCommerce & POS Payments & FinTech AI Product Strategy Generative AI AI / Forecasting Integrations LLM Applications AI-Enabled Workflows Mobile & Web Platforms Data & Systems Integration Analytics & Experimentation Team Building

Case Studies

Built with Claude AI

During my career break I didn't just study AI — I built with it. Using Claude AI and Anthropic's Cowork tool, I've been prototyping and shipping real products. This portfolio site itself was built with Claude.

Where I've Shipped

Career Break · Independent

Professional Development & AI Upskilling

Aug 2024 – Jul 2025

Chicago, IL

  • Dedicated planned break to family travel and targeted upskilling in AI concepts and practical applications for SaaS and enterprise platforms
  • Reinforced modern discovery-to-delivery workflows and outcome-based planning practices
  • Returned with clearer prioritization, stronger AI product fluency, and sharper leadership focus

US Foods (CHEF'STORE)

Product Lead

Apr 2023 – Jul 2024

Rosemont, IL

  • Improved delivery efficiency by 30% by establishing structured agile framework across product, development, and business partners
  • Increased online sales conversion to $500K+/month via SaaS integration of Instacart
  • Increased in-store productivity by 20% via Relex Pro mobile AI integration and adoption
  • Scaled execution across blended team of 4 direct reports + 8 consultants

Bounteous

Product Lead (Contract)

Oct 2022 – Apr 2023

Chicago, IL

  • Increased online ordering ROI by 28% via DoorDash + Olo SaaS integrations
  • Unlocked $250K in additional investment by shaping enhancement proposals and aligning stakeholders
  • Conducted eCommerce audit translating findings into prioritized, actionable roadmap recommendations

Codal

Senior Product Manager

Oct 2021 – Oct 2022

Chicago, IL

  • Delivered MVP eCommerce site, POS, and WMS in 10 months from discovery to release
  • Contributed to $1M+ in new business via pitch strategy and roadmap exercises
  • Managed vendor ecosystem: BigCommerce, Teamwork Commerce, Adyen

Cognizant

Senior Product Manager

Oct 2020 – Oct 2021

Chicago, IL

  • Led waterfall-to-agile transformation for CU Direct, establishing sprint rituals and backlog standards
  • Guided front-end and portal design in Figma, tied to measurable user outcomes
  • Consulted on story requirements supporting AWS CloudFront + SageMaker integration work

Southeastern Grocers

Senior Product Manager

Mar 2019 – Feb 2020

Jacksonville, FL

  • Delivered 3-brand mobile app MVP in 6 months; launched 3-brand loyalty program in 7 months
  • Improved cross-team delivery efficiency by 25% via agile best practices
  • Built middleware across AWS, Sitecore, and native frameworks for 6 mobile apps across 3 brands

Humbolt

Product & Business Development

Jan 2016 – May 2019

New York, NY

  • Grew to 50,000 monthly active users in 3 months by launching a B2C music streaming app
  • Achieved venture capital acquisition within 3 years through product traction and licensing
  • Led platform build across iOS, Android, and web; secured music licensing across multiple regions

Avis Budget Group

Director of Product, Mobile & Global Services

Jun 2014 – Jan 2016

New York, NY

  • Delivered improved mobile app + connected car initiative in under 12 months
  • Produced 1/3/5-year roadmap for connected car scalability and global rollout
  • Managed RFP submissions, vendor procurement, and legal review for third-party partners

From.Digital

Director of Product Management

Jan 2014 – Jun 2014

New York, NY

  • Earned acquisition of services within 6 months via high-impact mobile assessment and roadmap for Avis/Budget
  • Delivered industry-first voice reservation capability using Google Voice APIs

What I Work With

Product / Delivery

Roadmaps MVP Definition Agile / Scrum SAFe Epics / Features / Stories Backlog Prioritization Discovery Stakeholder Alignment Vendor Management RFPs

Domains

Digital Transformation SaaS ERP / CRM eCommerce POS Payments Mobility / IoT Dining / Hospitality Retail

ERP / Payments / POS

Dynamics 365 SAP Adyen Stripe FreedomPay Avalara NCR Teamwork Commerce Olo

AI / Forecasting

Relex Demand Forecasting Relex Pro AWS SageMaker AI Product Strategy Prompt Engineering

Tools

Jira Confluence Azure DevOps Figma Mixpanel Optimizely Google Analytics Power BI Tableau

Cloud / Tech

AWS Google Cloud Microsoft Azure Python SQL GraphQL MongoDB iOS Android HTML / CSS / JS

Ready to build
something great?

Whether you're hiring a product leader or looking for a fractional PM to drive delivery — I'd love to talk.

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