Brad Gessler
Owner at Rocketship
San Francisco, California
Overview
Work Experience
Board Member
2022 - Current
- Set goals with executive team on product and GTM strategy, with a focus on deepening enterprise expansion while maintaining strength in higher education. - Advise on org issues as the company evolves from founder-led growth to scalable operational maturity. - Guide long-term roadmap alignment across sales, product, and marketing to ensure focus on enterprise customer needs and sustainable margin.
Co-founder & CTO
2008 - 2022
- Co-founded and led all technical and product operations for Poll Everywhere, scaling the company from idea to $10M+ ARR with no outside funding. - Built and managed a 35-person cross-functional team (engineering, product, design, data) to deliver live polling tools used by 75% of the Fortune 1000 and 100k+ educators. - Owned and operated a $10M+ P&L, making strategic tradeoffs across infrastructure, customer acquisition, pricing, and platform expansion. - Led key partnerships including Microsoft (Office 365 integration), growing enterprise reach and platform extensibility. - Presented at RailsConf and other industry events on real-time systems, stream processing, and scaling Rails APIs. - Transitioned company to new leadership after 14 years of sustainable growth, product-market fit, and team development. - Wrote first lines of code and completed Y Combinator (Summer 2008 batch) during the early growth of Poll Everywhere.
Poll Everywhere is a web, SMS, and Twitter polling service that allows users to submit votes or comments to a PowerPoint or Keynote slide.
Raised $20,000.00 from Y Combinator.
Founder, Technical Operator
2022
- Built and launched Terminalwire, a developer platform that streams STDIO over WebSockets — enabling instant CLI deployment without API servers or binary distribution. - Designed and implemented platform architecture, packaging, and distribution model for zero-install developer kits across macOS and Linux. - Created content and onboarding experience to grow early adopter base and validate market demand. - Operating as a solo founder responsible for product, engineering, GTM strategy, and customer support. - Focused on solving developer workflow pain with a principled, product-led approach to technical distribution.
Angel Investor – Early Stage Companies
2013
- Advise early-stage technical founders on scaling product, platform, and go-to-market operations. - Invested in and supported companies including Clearbit, Replicated, Convox, and Zenefits. - Focus on helping high-potential teams build real businesses, not just raise rounds.
Developer Relations
2022 - 2024
- Led developer adoption efforts for Rails on Fly.io, with a focus on replacing Heroku as the go-to platform after their free tier shutdown. - Drove onboarding volume by publishing docs, fixing broken CLI paths, coordinating with internal teams, and simplifying full-stack deployment flows. - Created content and gave talks that positioned Fly as the modern app host for Rails — converting thousands of devs during a critical inflection point. - Actively managed community presence across Twitter, Discord, and support threads — translating real developer needs into product improvements. - Exited after achieving adoption and onboarding goals for the Rails ecosystem, and looking to return to roles with broader product and P&L ownership.
Solutions Architect
2007 - 2008
Project manager for marketing automation & workflow software. Introduced Rails and Agile processes into organization.
You can either adapt to change, ignore it or lead it. Publicis Worldwide, North America is a full service advertising agency
Consultant
2004 - 2007
Lead various IT projects within the healthcare, telecommunications, and public sector industries.
Deloitte Tax is an advisory firm that provides tax preparation and advisory services.