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Win M.

Win Maddox

I build agents & automations that give you back 10+ hrs a week

2,480 min coached

65 followers

McIntire School of Commerce - University of Virginia Logo

Studied at McIntire School of Commerce - University of Virginia

LinkedIn Logo

Admissions Committee at LinkedIn

Successful clients at

LinkedIn
CoStar Group
Northrop Grumman
Bain & Company
Georgetown University
+7

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

LinkedIn Logo

Product BizOps

LinkedIn

April 2022 - Present

Admissions Committee

Stakeholder Management, SQL and +4 skills

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

22 Reviews

Overall Rating

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Knowledge

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Value

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Responsiveness

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Win has helped clients get into these companies:

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Win M.

Win M.

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