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Win M.

Win Maddox

Career Development Coach - Expert on Interviewing, Networking, and More

  • McIntire School of Commerce - University of Virginia Logo

    McIntire School of Commerce - University of Virginia

  • 2.9k

    Expert mins

  • 70

    Followers

Available tomorrow

Starting at 2:00 PM UTC

Questions?

You can start chatting with Win before you get started.

Work with Win

About

  • Customer favorite

    In the top 10% of Career Coaching experts on Leland

I build AI automations and agent systems, and I coach people to do the same in their own jobs. I run a personal AI agent every day. It’s built on Claude Code, runs on a schedule, keeps its own memory, and does real work for me: triaging email, monitoring data, drafting writing, shipping code. At LinkedIn, I built the Claude Code workflows my team uses. On the side, I’ve shipped six apps to the App Store, including NutriPlan, an AI meal planning app I built solo and grew to 4,000+ organic users. I work with operators, analysts, and managers who want three things: hours back every week, to become the person on their team who actually knows how to use AI, and automations that matter in their job, not demos. Common projects: recurring reports and status updates, inbox and meeting workflows, research and monitoring agents, and connecting AI to the tools you already use (email, Slack, spreadsheets, docs). Sessions are hands-on. We start with your actual week, find the work that’s eating it, and build the automation together. You leave with something running and a plan for the next one.

Win’s Career Coaching Qualifications

Coaches professionally

Experience level: Manager

30+ Career Coaching clients

AI Certified

Completed Level 1 of Leland’s AI Builder Program

Win has helped clients get into these companies:

I coach professionals breaking into and moving up in tech, and my clients have landed roles at Google, Amazon, LinkedIn and Bain. I made the jump myself, from a top-tier finance role to big tech, so I know firsthand what a major career pivot takes. I specialize in resume reviews tailored to tech recruiting, interview preparation from product and strategy cases to behavioral rounds, and salary negotiation strategy. I've guided dozens of clients, from early career planning to mid-career moves, so they reach their goals with confidence and clarity.

Win can help with:

Career Planning

Interview Prep

Personal Branding

Professional Networking

Resume Review

Salary Negotiation

Skill Building

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

25 reviews


Overall rating

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Knowledge

5.0

Value

5.0

Responsiveness

5.0

Supportiveness

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Win has helped clients get into these companies:


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