
Win Maddox
5.0
(20)
Finance to Tech. AI Product Strategy @ LinkedIn. Land Your First AI Role
2,000 min coached
43 followers
Studied at McIntire School of Commerce - University of Virginia
Admissions Committee at LinkedIn
Successful clients at
Available tomorrow at 12:00 AM UTC
Questions? Start chatting with this coach before you get started.
Win's Coaching Offerings
Custom hourly · $129/hr
Get help with AI Fundamentals, Resume, and .
Win also coaches for Business Operations & Strategy, Business Analytics & Intelligence, Career Coaching, Communication & Public Speaking, and AI for Data & Analytics. View all.
Win’s Break Into AI Careers Qualifications
Coaches professionally
Experience level: Manager
10+ people coached for Break Into AI Careers
Win has helped clients get into these companies:
My background isn't what you'd expect. I spent my early career in investment analysis and strategic finance before making the jump into AI and tech. Along the way I built a solo AI app from scratch that grew to 2,000+ users, picked up enough technical skills to ship real products, and found ways to contribute to AI initiatives at LinkedIn without having a CS degree or a traditional tech pedigree. The reason I coach in this space is simple: I figured it out the hard way, and I think I can help others skip some of the confusion. Breaking into AI from a non-traditional background means translating your existing skills into a language the industry understands, building the right kind of proof points, and knowing where to focus your energy. I'm still on this journey myself, which means I'm close to the same questions my clients are wrestling with. If you're coming from finance, consulting, operations, or anywhere outside the traditional tech pipeline, I'd love to help you find your way in.
Win can help with:
AI Fundamentals
Resume
Skill Building
AI Agents
Networking Strategy
Job Search Strategies
Interview Prep
LinkedIn Review
Win also coaches for Business Operations & Strategy, Business Analytics & Intelligence, Career Coaching, Communication & Public Speaking, and AI for Data & Analytics. 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
20 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: