Benjamin Jackson
Hands-on AI builder, founder, and product engineer with over 20 years shipping software at scale. Built products and led teams at the New York Times and Vice Media. Currently building an AI platform and teaching Claude Code to values-aligned leaders and teams.
Experience
Offtrail
2025–PresentFounder · Brooklyn, NY
Currently building an AI-driven career search platform for senior operators.
Independent Consultant & Coach
2019–PresentIndependent · Brooklyn, NY
Executive coaching, AI advisory and education for leaders and organizations.
- Teaching Build Your AI Chief of Staff, a cohort-based course on AI-driven productivity.
- Leading Claude Code study halls for organizers and nonprofit leaders with Cooperative Impact Lab.
- Panelist at Netroots Nation 2026, running all-day hackathon and Claude Code study halls.
Hear Me Out
2017–2025Founder & Principal · Brooklyn, NY
Led 6–12 month embedded transformation engagements with startups, nonprofits, and late-stage tech companies.
- Atlassian: Ran qualitative and quantitative research—23 manager interviews and 600+ new-hire surveys—that became the foundation for their revamped global onboarding program in 2019.
- Peloton: Directed mixed-methods research across 5 projects, driving a 40% YoY increase in hires/recruiter and a 20-point increase in Greenhouse candidate NPS.
- SuperHi: Designed and implemented programs across the full employee lifecycle: onboarding, people analytics (Lattice), performance management, growth ladders, and compensation.
- The OTW: Ran a confidential listening tour of the board, chairs, and volunteers at a global nonprofit, along with a 360° engagement survey of 1,000 volunteers, with analysis and visualization in D3.js.
Vice Media
2015–2017Director of Mobile · Brooklyn, NY
Led the company’s first in-house mobile team, reporting to the CTO. Owned iOS, Android, Roku, Apple TV, and Apple News.
- Led a team of 4 mobile engineers to launch Viceland, the company’s first foray into linear cable.
- Built a unified mobile API on Sinatra syncing 12 legacy databases, serving millions of MAUs at launch.
- Developed an in-house CMS for VICE’s Apple News channel; featured in Apple’s outdoor campaign and in user onboarding at launch → 2M subscribers, ~1M pageviews/week.
- Led platform unification of a dozen editorial verticals, raising the floor of ad visibility from 30% to 86%.
Longform
2012–2015iOS Lead · Brooklyn, NY · Contract
Architected the iOS app, backend, and cloud infrastructure for an long-form social reading platform.
- 200k downloads at launch; MAUs up 500% from 10k to 50k; 30M avg sessions, 3M+ views, 500k+ hours of use.
- Launch covered in The New York Times, NY Magazine, and Forbes.
- App featured by Apple at every major update.
90WPM
2011–2015Mobile Consultant · Brooklyn, NY
Built iOS apps for clients including Artsy, UNIQLO, Vice, MSNBC, and Betaworks.
The New York Times
2010–2011Sr. Mobile Software Engineer · New York, NY
Relaunched the NYT news reader for the digital subscription era.
INCOMUM Design & Concept
2004–2010Cofounder & Technical Director · Rio de Janeiro
Cofounded a design agency in Rio de Janeiro. Led development on an award-winning weblog editor and dozens of websites for clients including Petrobras, TV Globo, LG, and Coca-Cola.
Civic & Volunteer Work
Out of the Mattress
2024–PresentDirector, Strategy & Development
Branding and naming, fundraising, operations, and tech infrastructure at a financial education nonprofit for immigrants.
Wharton Venture Lab
2020–PresentExpert in Residence, Workplace Culture
Mentoring MBA students in Wharton’s tech entrepreneurship program on culture, employee voice, and organizational design.
Swing Left
2017–2020Senior Advisor, People & Culture
Advised on operations and workplace culture as Swing Left scaled from founding team to 25+ FTEs and thousands of volunteers, raising $10M and driving 7.5M voter contacts in the 2018 election cycle.
Pursuit
2015–2024Guest Lecturer, Design Mentor & Curriculum Advisor
Career readiness coaching and design mentorship for students transitioning from frontline work into tech careers.
Press
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The Wall Street Journal
March 2023“ChatGPT Can Save You Hours at Work. Why Are Some Companies Banning It?”
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The Atlantic
November 2021 -
TechCrunch
May 2017“Vice’s Director of Mobile Apps Ben Jackson is creating his own startup advisory firm”
Talks & Panels
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Designing with AI 2026
“From tools to staff: What the next generation of agents means for the future of design”
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Netroots Nation 2026
AI Coding Hackathon and Claude Code Study Hall -
SXSW 2017
Education
University of Pennsylvania
1999–2003B.S.E. in Digital Media Design · Minor in Fine Arts
Skills & Expertise
- Engineering
- Ruby, Rails, Sinatra, SQL/Postgres, Redis, REST APIs, Elasticsearch, Docker, AWS, nginx
- AI Engineering
- Claude API, Claude Code, Cursor, DSPy, Exa, Langfuse
- Frontend
- SASS, Tailwind CSS, JavaScript; familiar with TypeScript, React, and Next.js
- Research
- Mixed-methods research, in-depth interviews, usability testing, ethnographic research, survey design, qualitative coding, journey mapping, service blueprinting
- Leadership
- Executive coaching, performance management, structured hiring, DEI, public speaking, organizational change management
Languages
- English
- Native
- Portuguese
- Fluent (20 years)
- Spanish
- Proficient