Gillian O'Brien

CEO

San Francisco, California, United States8 yrs 2 mos experience

AI Enabled

Key Highlights

Successfully launched Cherry with $1M funding.
Drove $20M Series A at Dover as Chief of Staff.
Built talent business unit at Remote.

Stackforce AI infers this person is a SaaS and FinTech expert with strong leadership in product marketing and startup growth.

Contact

Skills

Core Skills

Product MarketingMarketing StrategyProduct ManagementBusiness StrategyVenture CapitalPartnershipsDemand GenerationStrategyEntrepreneurship

Other Skills

Strategic CommunicationsPositioning (Marketing)Product LaunchRemote WorkArtificial Intelligence (AI)Product DevelopmentAsyncInvestmentsSpecial EventsSalesDigital MarketingPublic SpeakingInterpersonal SkillsCommunicationTeamwork

About

✖️ follow me on X: https://twitter.com/gillianxobrien 📧 gillian.r.obrien@gmail.com about me: ⭐ Startup Founder: Launched Cherry after graduating from NYU. Cherry let startups (Snackpass, Front, Flatfile) offer personalized employee benefits. YC W19, raised ~$1M. ⚡️ Chief of Staff: Joined Dover as hire #5 / CoS. Led sales as the first non-founder AE, managed internal recruiting ops, handled customer success escalations, grew to 70+ team members & $20M series A 💡 Head of Startup Community: Moved to Series C Pilot: bookkeeping/accounting/tax services for startups and SMBs. Developed our relationships in founder ecosystem, brand evangelism, sales efficiency and customer experience. ☀️ Product GM / Business Unit Leader: joined Remote to build the talent business unit. Acted as a 'founder' within a 2k person global company, focusing on product vision and GTM. 📍 Current - Remote - Director of Product Marketing. Managing a team of 8 to deliver PMM excellence across product launches, sales motions, and the platform messaging & positioning of Remote 🏹 Side Projects: Fellow @ Leaders In Tech, Startup advisor + angel investor. Drummer, guitarist & dog mom :)

Experience

Remote

3 roles

Director of Product Marketing

Promoted

Nov 2025 – Present · 4 mos · Remote

Leading a team of 8 (Product Marketing & Customer Marketing); reporting to Chief Business Officer
Remote isn’t just a remote work company anymore. It’s infrastructure that helps businesses build and scale anywhere in the world. It powers modern teams, keeps them compliant, and makes the experience fast, seamless, and beautifully designed.

Marketing StrategyStrategic CommunicationsProduct MarketingPositioning (Marketing)Product Launch

General Manager, Recruit Product

Oct 2024 – Present · 1 yr 5 mos · Remote

Recruit by Remote is an AI-powered hiring platform that helps companies find, engage, and onboard top global talent with ease.
With advanced sourcing, AI-driven matching, and real-time talent insights, Recruit streamlines hiring while ensuring compliance across 800 million candidate profiles worldwide.

Remote WorkArtificial Intelligence (AI)Product ManagementProduct DevelopmentBusiness Strategy

General Manager, Remote Talent Product

Oct 2023 – Mar 2026 · 2 yrs 5 mos · Remote

Remote Talent is a new BU within Remote. It's the ultimate connection hub for job seekers and top employers worldwide, showcased on our remote-first job board (remote.com/jobs)
Reporting to CEO

AsyncRemote Work

Leaders in tech

Fellow

Jan 2025 – Present · 1 yr 2 mos

500 global

Startup Mentor

Jan 2023 – Jan 2025 · 2 yrs

Crv

Venture Scout

Jan 2023 – Jan 2025 · 2 yrs · San Francisco Bay Area

Venture CapitalInvestments

Pilot.com

Founder in Residence

Jan 2022 – Oct 2023 · 1 yr 9 mos

Led the startup and accelerator ecosystem, driving significant growth and partnerships that contributed to 15% of Pilot’s customer base. Spearheaded a 1.8X increase in customer adoption within startup channels, developed a high-impact sales playbook, and achieved an 80%+ win rate. Worked with Sales, Marketing, CS and orchestrated field events across major cities.

PartnershipsDemand GenerationStrategySpecial EventsSalesDigital Marketing

Dover

Chief Of Staff

Jan 2020 – Jan 2022 · 2 yrs · San Francisco, California, United States

As the first non-founder salesperson, secured 100 customers and added $1.2M in ARR within 10 months. Led initiatives that doubled candidate response rates and increased female applicants from 33% to 62%. Built and managed a 24-member operations team with a 92% retention rate and 38% promotions. Spearheaded recruiting strategy sessions that significantly improved account retention. Contributed to scaling the company from 10 to 120 employees, raising $23M in funding, and driving a 6X increase in revenue.

Strategy

Cherry (yc 19)

Co-Founder, CEO

Jan 2018 – Jan 2020 · 2 yrs · San Francisco Bay Area

www.startcherry.com 🍒⚡ / YC W19
Cherry let employers offer personalized benefits via a smart corporate card and virtual marketplace
Designed with remote, distributed teams in mind 🚀
Our customers included Front, Giphy, Flatfile, Snackpass and 40+ other startups

StrategyEntrepreneurship