
Win Maddox
I build agents & automations that give you back 10+ hrs a week
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
Questions? Start chatting with this coach before you get started.
Win's Offerings
Custom hourly · $275/hr
Get help with AI Agents, AI Automation, and .
Win also coaches for Build with AI, Break Into AI Careers, AI for Data & Analytics, AI for Product Development, Business Operations & Strategy, Business Analytics & Intelligence, Career Coaching, and Communication & Public Speaking. View all.
Win’s AI Services Qualifications
Coaches professionally
Experience level: Director
AI Certified
Completed Level 1 of Leland’s AI Builder Program
Win has helped clients get into these companies:
WHO I AM AI Product Strategist at LinkedIn, where I routinely built AI automations to help our business perform better at scale and give the team hours back. Outside of that role I build and ship independently: six apps published to the App Store, multiple autonomous agent systems, and a set of production automations I run every day. I've done this work for my own team at LinkedIn and for 50+ clients on the side. WHAT I BUILD -Email and inbox agents that draft, sort, and route based on your rules -Research and reporting agents that replace a recurring manual pull (competitor monitoring, weekly status, market scans) -Internal workflow rebuilds — the process your team does by hand every week, running on its own -Custom internal tools and apps when off-the-shelf doesn't fit HOW I WORK Engagements are scoped as projects with a fixed deliverable, not open-ended hourly sessions. We start with a 30-minute scoping call to define the workflow and the target hours saved. I build it, we test it together in your environment, and I hand off documentation so you can run and modify it without me. Hourly is available, but most people get more out of a package. TOOLS Claude Code, N8N, Microsoft Copilot, ChatGPT Enterprise, Gemini. I'll work inside your existing stack and security constraints rather than asking you to adopt something new. WHAT SUCCESS LOOKS LIKE You finish with something running, not notes from a lesson. Every engagement is measured in hours returned per week. If you can tell me the thing you do every week that you wish you didn't, that's usually the first project.
Win can help with:
AI Agents
AI Automation
AI Insights Dashboard
AI Product Innovation
AI Roadmap Development
AI Strategy
AI Tools & Integration
Freelancing
Team AI Upskilling
Win also coaches for Build with AI, Break Into AI Careers, AI for Data & Analytics, AI for Product Development, 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: