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Christian O'Brien

Senior Product and Strategy Leader

9+ yrsproduct strategy, discovery and delivery
60+discovery-to-ship cycles
$900M+raised by clients in 2025
50+founding and leadership teams

Over nine years partnering with 50+ founding and leadership teams, Fortune 100 to seed stage, shipping products and brands from first idea to launch. Starts every product with a deep understanding of user needs and ties them directly to outcomes. Uses AI to pressure-test the product direction through market research, competitive analysis, prototyping and validation before committing time and budget. Some of the highlights are below. The full story is in the work.

Experience

Off/Menu

2022–Present

Head of Product and Client Experience

Across 50+ engagements spanning brand, web, product and AI-native builds, I lead product strategy and client experience from first call to delivery. Every client wants a different outcome. Some are raising, and their 2025 rounds topped $900M. Some need a cohesive brand, a marketing site and an MVP. Others want growth: better design, better customer experience and AI layered in where it serves their goals. I start with their users and competitive landscape, then build the visual case for the path that gets them there. Grew the agency to $1.3M average ARR across 20–25 retainer clients at 100% client satisfaction. Off/Menu challenges the traditional agency model with a monthly retainer, not a long lock-in contract. The goal is speed: explore the inspiration, the verticals and the concepts, then share new work every couple of business days.

Everest

2019–2022

Senior Product Manager → Principal Product Manager

Clients included Freedom Financial (now Achieve), Medline and SC Johnson. Leading product strategy and delivery, I helped ship a new digital loan experience for Freedom that added $2.3M a month in originations, with loan margins up 110% and TCPA acceptance up 200%. Working with cross-functional teams, we rebuilt the order management behind more than $15B of Medline orders, took the Candor scrub line to market against Figs and drove engagement up 30% on a Rotary International and USAID partnership campaign. I also built the product management practice, mentoring and managing product managers on their growth, their client work and the areas where they could improve.

Solstice now Valtech

2017–2019

Product Analyst → Product Consultant → Product Strategist

Product strategy for Northern Trust and Gallagher. I learned the mechanics early, running Scrum Master and Product Owner ceremonies across three cross-functional agile teams, then moved into the strategy work: growing usership of Northern Trust's Private Passport platform 10% among high-worth members, helping unify Gallagher's regional sites into one global platform that lifted digital applications 7% and leading six executive alignment workshops.

Skills

AI Product Practice

  • AI-native Discovery
  • Market & Competitive Analysis
  • Vertical & Segment Research
  • Opportunity Sizing
  • Rapid Prototyping
  • Agentic Workflow Design
  • Agent & Model Evaluation
  • Prompt Engineering
  • Guardrails
  • Model Selection on Cost-Quality Tradeoffs

Product Management

  • Outcome Definition & Metrics
  • Experimentation & Validation
  • MVP & Prototyping
  • Product Strategy
  • Product Discovery
  • Requirements Definition
  • User Research
  • Roadmap Planning
  • Stakeholder Management
  • Cross-functional Leadership
  • Go-to-Market
  • Agile & Scrum

Design & Research

  • Figma
  • Userlytics
  • Typeform
  • Tally
  • Google Analytics
  • Customer Journey Mapping
  • Design Systems

Project Delivery

  • Linear
  • Jira
  • Asana
  • Trello
  • Notion
  • TFS
  • Loom

AI Tools

  • Claude
  • Claude Code
  • Cursor
  • Replit
  • Lovable
  • v0
  • Bolt
  • Figma Make
  • Zapier
  • Granola
  • Wispr Flow

Education

DePaul University, School of Business

Let's connect See the work →