Barry O'Leary

About

Over the past decade, I've helped B2B SaaS companies translate market complexity into growth by connecting product strategy, customer insight, competitive intelligence, and go-to-market execution.My career has been built around solving strategic business problems—understanding why customers buy, why they leave, where markets are moving, and how organizations can align product, marketing, sales, and customer success around a shared go-to-market strategy. Increasingly, I'm focused on how AI is reshaping the way modern GTM teams operate, enabling faster decision-making, greater efficiency, and more impactful customer experiences.Today, I lead Product Marketing at Robin, partnering across Product, Sales, Customer Success, and Executive Leadership to define positioning, bring new products to market, enable revenue teams, and drive product adoption. My role extends beyond launches and messaging to helping shape GTM strategy, aligning cross-functional teams, and ensuring market insights influence product direction.Previously, at Rippling, one of the fastest-growing SaaS companies in the world, I established the competitive intelligence function for the IT product suite, building scalable programs that informed product strategy, strengthened sales execution, and improved the organization's ability to compete in a rapidly evolving market.At Tripadvisor, I led global win/loss and customer research initiatives that influenced product strategy, positioning, pricing, and retention across international markets, helping leadership make more informed product and investment decisions.I thrive at the intersection of product, marketing, data, AI, and business strategy. Whether building scalable GTM programs, developing AI-enabled workflows, uncovering market opportunities, or helping organizations align around customer needs, I'm motivated by creating clarity, accelerating execution, and delivering measurable business outcomes.I'm always interested in conversations about product marketing, AI, competitive intelligence, GTM strategy, and building the next generation of high-performing go-to-market organizations.

Company history

1. 
   Dell TechnologiesProduct Marketing Manager2016-07 – 2018-06 · 1y 11mo
2. 
   RobinProduct Marketing 2025-12 – present · 8 mo
3. 
   Trusted LocalGTM Engineer2022-08 – 2025-05 · 2y 9mo
4. 
   Dell TechnologiesProduct Release Program Manager2014-08 – 2016-06 · 1y 10mo
5. 
   TripadvisorSenior Manager, GTM Strategy2021 – 2022-09 · 1y 8mo
6. 
   RipplingProduct Marketing2025-05 – 2025-11 · 6 mo
7. 
   Dell TechnologiesTeam Lead, Product Marketing and Competitive Intelligence2019-07 – 2020-08 · 1y 1mo
8. 
   Dell TechnologiesSenior Product Marketing Manager2018-07 – 2019-07 · 1y

Skills

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