What check size does Maggie Hott write?

Maggie Hott typically writes checks of $500K – $3M.

Where did Maggie Hott go to school?

Maggie Hott studied at UC Santa Barbara (B.A, Global Studies. Technology Management Program); Universidad de Sevilla.

Maggie Hott

Former Investor at Cowboy Ventures

San Francisco, California

Writes $500K – $3M checks · typically $1.8M

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About

Maggie Hott is Head of Americas, Healthcare GTM at OpenAI, where she joined in 2023 to build and scale ChatGPT Enterprise and now leads healthcare go-to-market strategy. Previously, she held leadership positions at Webflow as Director of Sales and at Slack as an early employee and Senior Enterprise Leader during its growth from $12M to over $1B in ARR. She is also a Founding Partner at 20SALES, a venture fund focused on go-to-market strategy in early-stage companies.

Experience

OpenAIHead of Americas, Healthcare GTMcurrent2025 — present
OpenAIHead of Large Enterprise, West2024 — 2025
OpenAIFounding GTM Leader, ChatGPT Enterprise2023 — 2024San Francisco Bay Area
20SALESFounding Partnercurrent2023 — present
Coalition OperatorsFounding Operator & LPcurrent2021 — present
Sequoia CapitalSequoia Capital Builder & LP2022 — 2026
WebflowSenior Director of Sales2021 — 2023San Francisco, California, United States
SlackRVP, Enterprise Sales2021
SlackSr Manager, Enterprise Sales2020 — 2021San Francisco, California, United States
SlackSenior Manager, Mid-Market Sales2020San Francisco, California
SlackManager, Mid-Market Sales2018 — 2020San Francisco Bay Area
SlackSenior Enterprise Account Executive2017 — 2018San Francisco Bay Area
SlackEnterprise Account Executive2015 — 2017San Francisco Bay Area
EventbriteAccount Executive2010 — 2015San Francisco
EventbriteSales Development Representative2010San Francisco Bay Area
International Women's FestivalsFestival Assistant2009 — 2010
Nuclear Age Peace FoundationInternship2009 — 2010Santa Barbara County, California, United States

Skills & more

SaaSSalesforce.comCustomer SatisfactionCustomer RetentionTeam BuildingTechnology Product DevelopmentCold CallingSales ProspectingSocial MediaMarketing StrategyProduct MarketingMarketing

+7 more

Lead GenerationStrategic PartnershipsStart-upsCompetitive AnalysisSalesSales ProcessLeadership

Languages English · Spanish

Advanced Open Water Diver — PADI

From Maggie's professional profile.

Network4

Aileen LeeScout

Founder & Managing Partner of Cowboy Ventures

Amanda RobsonScout

Partner at Cowboy Ventures

Donna BoyerScout

Executive-in-Residence (EIR) at Cowboy Ventures

Ted WangScout

Board Partner at Cowboy Ventures

Investors connected to Maggie in public investor directories — a warm-intro map.

Frequently asked questions

Who is Maggie Hott?: Maggie Hott is Head of Americas, Healthcare GTM at OpenAI, where she joined in 2023 to build and scale ChatGPT Enterprise and now leads healthcare go-to-market strategy. Previously, she held leadership positions at Webflow as Director of Sales and at Slack as an early employee and Senior Enterprise Leader during its growth from $12M to over $1B in ARR. She is also a Founding Partner at 20SALES, a venture fund focused on go-to-market strategy in early-stage companies.
What check size does Maggie Hott write?: Maggie Hott typically writes checks of $500K – $3M.
Where did Maggie Hott go to school?: Maggie Hott studied at UC Santa Barbara (B.A, Global Studies. Technology Management Program); Universidad de Sevilla.