Win Maddox
Ship a Real AI Product with a LinkedIn Builder and Solo Founder
2,480 min coached
65 followers
Studied at McIntire School of Commerce - University of Virginia
Admissions Committee at LinkedIn
Successful clients at
Available today
Starting at 11:30 PM UTC
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Win's Offerings
AI Product Management Recruiting: Start-to-Finish
Starting at $1,16110h+ of coaching
Save up to $3,436
Nail the AI Product Management Interviews
Starting at $6125h+ of coaching
Save up to $1,589
Advance Your AI Product Management Career
Starting at $1,16110h+ of coaching
Save up to $3,436
Become a Vibe Coding Expert
Starting at $1,306.255h+ of coaching
Save up to $110
Custom hourly · $275/hr
Get help with AI Agents, AI Automation, and .
Win also coaches for AI Services, Build with AI, Break Into AI Careers, AI for Data & Analytics, Business Operations & Strategy, Business Analytics & Intelligence, Career Coaching, and Communication & Public Speaking. View all.
Win’s AI for Product Development Qualifications
Coaches professionally
Experience level: Manager
AI Certified
Completed Level 1 of Leland’s AI Builder Program
Win has helped clients get into these companies:
Building an AI product is two different hard problems: knowing what to build and actually shipping it. I've done both. As an AI Product Strategist at LinkedIn I took a GenAI recommendation product from zero to launch for 25 million users, leading a five person pod through opportunity discovery, PRD, UX design, and sprint execution. I co-defined the roadmap for two agentic AI tools with a $50M+ revenue target and got executive buy-in to build them. I know how AI products get scoped, funded, and shipped inside a real company, including the parts that kill most of them: fuzzy success metrics, demos that don't survive real users, and roadmaps built on model capabilities that don't exist yet. I also ship solo. My AI meal planning app reached 4,000+ organic users with 20% premium conversion, I cut its image generation costs by 92% with a custom model, and I build autonomous agents that run multi-step workflows end to end. So whether you're a PM trying to ship your first AI feature, a founder building an AI product, or a builder prototyping with Cursor and Claude Code, I've stood exactly where you are. We'll work on your actual product: sharpen the problem, scope the MVP, pressure test the AI approach, and get it in front of users. You leave with a product plan that survives contact with reality, and usually a working prototype too.
Win can help with:
AI Agents
AI Automation
AI Product Design
AI Roadmap Development
Feature Prioritization
Freelancing
LLM-Optimized Code Base
Product Strategy
Prototyping with AI
QA
Scoping & Requirements
User Research & Insights Automation
Win also coaches for AI Services, Build with AI, Break Into AI Careers, AI for Data & Analytics, Business Operations & Strategy, Business Analytics & Intelligence, Career Coaching, and Communication & Public Speaking. View all.
About Win
As a Product Strategist at LinkedIn, I've supported transformative initiatives that leverage data-driven strategies and robust stakeholder collaboration to significantly boost revenue, product performance, and user engagement. Prior to that, I spent 3 years utilizing my data expertise and financial acumen to invest a $15 billion endowment into various private equity sectors. Over the past six years, I've channeled my expertise from these experiences into coaching professionals of all types — from early-career planning to technical interviewing—helping them achieve their top career goals. My clients have landed roles at top organizations such as McKinsey & Co., LinkedIn, DoorDash, and Google. Let's chat!
Why do I coach?
I coach because it's a way to give back. I was a first generation college student coming from a family of small business owners, and therefore had no connections or help when it came to embarking on my career journey. I understand how difficult career progression can be when you don't have access to these resources, so I want to be able to share my own expertise with others to ease that burden.
Work Experience
Product BizOps
April 2022 - Present
Admissions Committee
Stakeholder Management, SQL and +4 skills
Investment Associate
University of Virginia
July 2019 - April 2022
Admissions Committee
• Invested UVA’s $15 billion endowment across 7 asset classes, performing new investment diligence and refining the existing portfolio • Collaborated with senior team members to craft diligence plans, perform analyses, establish data-driven investment theses, and bring recommendations to committee • Analyzed 50+ existing investments, evaluating underlying positions of each fund, changes in investment approach, and broader macroeconomic shifts affecting them • Performed top-down market research to develop UVIMCO’s strategic plans for new subsector investments
Sales and Trading Analyst
Nasdaq
June 2018 - August 2018
• Crafted Board of Directors strategy materials via collaboration with US and Swiss Heads of Market Services, detailing strategic positioning and shifting market dynamics with a focus on international expansion • Constructed analysis on market trends, competitor positioning, and customer needs within the US and European FICC markets, synthesizing it into formal reports for senior leadership • Partnered with the Options Industry Council to develop an educational options webinar teaching investors how to hedge using financial derivatives; ~2,000 investors streamed in 2018
Win was also given offers to work at
DoorDash
Instacart
Education
McIntire School of Commerce - University of Virginia
Bachelors, Concentrations in Finance and Management, Track in Real Estate
2015 - 2019
Grade: GPA - 3.9
Win was also personally admitted to
College of William and Mary
James Madison University
Virginia Polytechnic Institute and State University
Virginia Commonwealth University
22 Reviews
Overall Rating
5.0
Knowledge
5.0
Value
5.0
Responsiveness
5.0
Supportiveness
5.0
Win has helped clients get into these companies: