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Win M.

Win Maddox

Get Hours Back Every Week. I Build AI Automations for Small Teams.

  • McIntire School of Commerce - University of Virginia Logo

    McIntire School of Commerce - University of Virginia

  • LinkedIn Logo

    LinkedIn

  • 2.9k

    Expert mins

  • 70

    Followers

Questions?

You can start chatting with Win before you get started.

Work with Win

About

I build with AI, and I coach people to do the same. On my own, I built NutriPlan, an AI meal planning app, solo and full-stack. I grew it to 4,000+ organic users with 60% week-2 retention. I also shipped WalkMap, a street-exploration app, to the App Store, and I run a personal AI agent every day for real work. By day, I'm a Product BizOps Manager at LinkedIn. I work on product strategy and operations, and I spend part of my time on hands-on product projects, including a 0-to-1 GenAI product. I also built the Claude Code workflows my team uses. Before LinkedIn, I spent three years on the investment team for UVA's $15B endowment. I've coached for several years, with a 5.0 rating across 23 Leland reviews. Clients have landed at Google, AWS, Bain, Deloitte, and LinkedIn. I work with career switchers, with operators and analysts who want AI to do real work, and with non-technical people who want to ship something. Sessions are hands-on. We work on your actual problem, and you leave with something that works and a plan for what's next.

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:

If your team loses hours every week to the same reports, inbox sorting, data pulls, or follow-ups, I'll build the automation that takes it over. This is for small business owners, solo operators, and team leads who want the work done, not a course. Each engagement is a scoped project with a fixed deliverable. First we find the one workflow costing you the most time. Then I build it with you or for you, and we measure success in hours returned. Examples of what I build: - a monitor that tracks a market and sends you a daily summary - inbox triage that sorts messages and drafts replies - a recurring report that refreshes itself I built versions of these for my own team at LinkedIn, and I run my own AI agent daily. I build with Claude Code and n8n, and I work inside what your team already uses, including Microsoft Copilot, ChatGPT Enterprise, and Gemini. You'll leave with: - a working automation - documentation your team can follow - a short list of the next workflows worth automating

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

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

LinkedIn Logo

Product BizOps Manager

LinkedIn

May 2022 - Present

Product strategy and operations. Part of my time goes to hands-on product projects, including a 0-to-1 GenAI product. I built Claude Code workflows my team uses for monitoring, inbox triage, and refreshing strategy docs.

University of Virginia Logo

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

Nasdaq Logo

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 Logo

    DoorDash

  • Instacart Logo

    Instacart

Education

McIntire School of Commerce - University of Virginia Logo

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 Logo

    College of William and Mary

  • James Madison University Logo

    James Madison University

  • Virginia Polytechnic Institute and State University Logo

    Virginia Polytechnic Institute and State University

  • Virginia Commonwealth University Logo

    Virginia Commonwealth University

5.0 average review

23 reviews


Overall rating

5
4
3
2
1

Knowledge

5.0

Value

5.0

Responsiveness

5.0

Supportiveness

5.0


Win has helped clients get into these companies:


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