Madison Leonard ☀️

CEO

United States11 yrs 3 mos experience
Highly Stable

Key Highlights

  • Transformed sales-led motion into hybrid GTM approach.
  • Architected product-led growth strategy increasing retention by 3.4x.
  • Launched products achieving 186% adoption growth within 8 weeks.
Stackforce AI infers this person is a SaaS Product Marketing expert with a strong focus on growth strategies and market positioning.

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Skills

Other Skills

AdvertisingComputer ProficiencyCustomer ServiceEagerness to LearnEntertainment IndustryEvent PlanningEvent ProducingFacebookGoal-oriented individual with strong leadership capabilitiesLeadershipMarketingMicrosoft ExcelMicrosoft OfficeMicrosoft WordPress Releases

About

I'm an end-to-end GTM architect who specializes in uncovering strategic market positioning. My superpower? Spotting patterns across buyer behavior, competitive landscapes, and product adoption. I merge data with intuition to craft compelling narratives that drive technical understanding, articulate business value, and highlight competitive differentiation. Over the last 10 years, I've built 0-to-1 GTM strategies that drive meaningful business results: - Transformed a traditional sales-led motion into a hybrid GTM approach, reducing sales cycles by 25% and increasing qualified pipeline by 15% - Architected a complete product-led growth strategy that increased platform retention by 3.4x through targeted segmentation and optimized user journeys - Built high-performing product marketing functions from scratch at multiple startups, establishing processes that scaled with 100%+ YoY growth - Developed positioning frameworks that successfully differentiated products in crowded markets, leading to $9M+ in influenced revenue - Launched new products that achieved 186% adoption growth within 8 weeks through strategic narrative development and cross-functional alignment I'm passionate about the intersection of data, storytelling, and customer experience -- transforming technical capabilities into compelling value propositions that inspire action. Recently, I've become deeply curious about how AI is reshaping the GTM landscape -- from how we uncover market insights to how we personalize customer journeys. I'm actively exploring how these emerging technologies can amplify strategic positioning and create even more differentiated market narratives while staying grounded in human-centered storytelling. --- On a personal note, I'm a big personality framework nerd. I love everything from Enneagram to CliftonStrengths to Big Five and more. I believe the more we can harness our unique strengths, the more efficient we can be towards accomplishing our goals and working together as a team.

Experience

Theskimm

Interim, Head of Product & Brand Marketing

Dec 2024Present · 1 yr 3 mos · Remote

  • The Skimm is a digital media company that delivers skimmable news and tips to millions of millennial women worldwide. I was brought on to define positioning, packaging, and product/brand roadmap for their new premium subscription.

Stensul

Interim, Director of Product Marketing

Mar 2024Mar 2025 · 1 yr · Remote

  • Stensul is a marketing creation platform that helps enterprises democratize campaign creation at scale, without risking brand compliance. I was brought on to build product marketing foundations such as launch tiering and processes, workflow transformation positioning, and consistent messaging across customer touch points.

Gtm happy

Fractional Product Marketer & GTM Consultant

Jan 2023Present · 3 yrs 2 mos · Orange County, California, United States · Remote

  • GTMHappy is a strategic consulting firm that helps high-growth B2B and DTC companies go-to-market with a smile on their face. I provide strategic consulting, advising, and hands-on fractional work - my specialties include PLG, product growth, brand marketing, and product marketing.
  • I'm a big nerd for all things workflow, AI, and automation so when I build product marketing foundations I don't just mean positioning and messaging docs. I mean building processes that scale, cross-functional workflows that span across your entire organization, and frameworks that set the strategic direction across your product and marketing roadmaps.
  • And when I say fractional, I don't just mean 'tell you what to do' fractional. Once we align on the foundations, I roll my sleeves up and dive in myself. I've optimized the execution process after a decade of trial and error across various size teams, so I know quickly what to prioritize and what to move to the backlog.
  • DM me for a free intro call to see if it's a good mutual fit! :)

Vanta

PLG Product Marketing Lead

Sep 2022Feb 2023 · 5 mos · San Francisco Bay Area

  • Vanta is an automated security and compliance platform, with a focus on trust management for mid-market/enterprise. I was responsible for crafting new positioning and GTM strategy centered around PLG - resulting in a new free trial offering launched into the existing sales cycle.

Clickup

2 roles

Platform Product Marketing Lead

Oct 2021Sep 2022 · 11 mos · San Diego, California, United States

  • I led platform positioning, product GTM, and new product launches (including a new product SKU) and lead GTM strategy for the Core Platform (responsible for all 16 products within the platform).

Founding Product Marketer

Oct 2020Sep 2021 · 11 mos · San Diego, California, United States

  • ClickUp is a work management platform with over 16 products in the portfolio. I founded the team as the first PMM hire after our Series A funding, joining when there was less than 100 employees and growing with the team to a nearly ~1,000 person global organization, $200M ARR, and $4B valuation. 🦄 As the founding PMM, I set up frameworks, processes, and foundations for all things messaging, product launches, and more.

Bred ventures inc.

Head of Product Marketing and User Engagement

Jan 2016Jan 2020 · 4 yrs

  • Led content, product marketing, social, and creative for investment & incubation firm, Bred Ventures Inc. Launched over 20+ DTC mobile apps and B2B products during my tenure.

Buyerly

Senior Product Marketing Manager

Jan 2015Jan 2016 · 1 yr

  • Led marketing and growth for SaaS startup Buyerly, which helped connect product owners with retail buyers.

City of thousand oaks

Product Marketing Manager

Jan 2014Jan 2015 · 1 yr

  • Won 1st place in a “growth hacking” competition for the City of Thousand Oaks. Produced and launched a creative ad in local movie theaters and increased sales by 125% in 6 months.

Florence university of the arts

Event Producer

Jan 2013Jan 2014 · 1 yr · Florence, Tuscany, Italy

  • Planned, produced, and hosted 6-course dinners and an art exhibit at a restaurant in Florence, Italy.

Evolutionary media group (emg pr)

Event & Marketing Associate

Jan 2012Jan 2013 · 1 yr

  • Spearheaded an advertising campaign for a mobile application while assisting in the marketing and PR for Billabong’s 6th Annual Design for Humanity event hosted at Paramount backlot.

Dreamworks animation

Product Research Assistant

Jan 2011Jan 2012 · 1 yr

  • Conducted user research for Ptch, a social video-sharing mobile app that was acquired by Yahoo! in 2013.

Education

California Lutheran University

Bachelor of Arts (B.A.)

Stanford University

Continued Education — AI & Entreprenuership

Florence University of the Arts

Special Events Management focus

General Assembly

Marketing

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