Win Maddox
Career and AI careers coach, Product Strategist at LinkedIn
| Hourly rate range | $90 to $175 an hour |
|---|---|
| Focus areas | |
| Works with | Professionals and Students |
| Credentials | Bachelor's degree in Finance and Management, McIntire School of Commerce, University of Virginia |
Win Maddox coaches professionals on career growth, from early-career planning to technical interviews. Win works as a Product Strategist at LinkedIn. Before that, Win spent 3 years on the team that invested a $15 billion university endowment. Win has coached for six years. Clients have landed roles at McKinsey & Co., LinkedIn, DoorDash and Google. Win also offers help with building with AI and breaking into AI careers.
What Win helps with
Win helps professionals plan their careers and prepare for technical interviews. Win also covers AI topics for people who want to work in or build with AI.
- Early-career planning
- Technical interview preparation
- Breaking into AI careers
- Building with AI
- AI for data and analytics
- AI for product development
- Writing cover letters
Who Win works with
Win works with professionals of all types. That includes people at the start of their careers and people preparing for technical interviews. Clients aim for roles at large companies in tech and consulting.
Background and qualifications
Win is a Product Strategist at LinkedIn and has worked in product business operations since April 2022. Before that, Win was an Investment Associate at the University of Virginia from 2019 to 2022. There, Win helped invest a $15 billion endowment across 7 asset classes and reviewed more than 50 existing investments. In summer 2018, Win worked as a Sales and Trading Analyst at Nasdaq. Win holds a bachelor's degree in Finance and Management from the McIntire School of Commerce at the University of Virginia.
Win Maddox pricing
Win Maddox reviews
Win Maddox has a 5.0 out of 5 rating from 23 reviews on Leland, as of September 2026.
The CoachVouch take
Win combines product strategy work at LinkedIn with a past role investing a $15 billion endowment.
Best for professionals aiming for roles at top tech and consulting firms or looking to move into AI.
Common questions
How much does Win Maddox charge?
Coaching with Win runs $90 to $175 an hour. Request an intro for an exact quote.
What does Win Maddox help with?
Win Maddox helps with early-career planning, technical interview preparation, breaking into AI careers and building with AI.
Does Win Maddox have reviews?
Win Maddox has a 5.0 out of 5 rating from 23 reviews on Leland, as of September 2026.
Is Win Maddox certified?
Win Maddox lists: Bachelor's degree in Finance and Management, McIntire School of Commerce, University of Virginia.
Does Win Maddox coach people who want to move into AI?
Yes. Win lists breaking into AI careers, building with AI, AI for data and analytics, and AI for product development as coaching areas.
How do I contact Win Maddox?
Request an intro on this page. It's free, and we'll connect you with Win and, if you want, 2 or 3 similar coaches to compare.
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Last updated September 2026. Request a correction.