Benjamin Jackson

Benjamin Jackson

Brooklyn, NY

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–Present

Founder · Brooklyn, NY

Currently building an AI-driven career search platform for senior operators.

Independent Consultant & Coach

2019–Present

Independent · 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

2017–2025

Founder & 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

2015–2017

Director 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

2012–2015

iOS 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

2011–2015

Mobile Consultant · Brooklyn, NY

Built iOS apps for clients including Artsy, UNIQLO, Vice, MSNBC, and Betaworks.

The New York Times

2010–2011

Sr. Mobile Software Engineer · New York, NY

Relaunched the NYT news reader for the digital subscription era.

INCOMUM Design & Concept

2004–2010

Cofounder & 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–Present

Director, Strategy & Development

Branding and naming, fundraising, operations, and tech infrastructure at a financial education nonprofit for immigrants.

Wharton Venture Lab

2020–Present

Expert in Residence, Workplace Culture

Mentoring MBA students in Wharton’s tech entrepreneurship program on culture, employee voice, and organizational design.

Swing Left

2017–2020

Senior 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

2015–2024

Guest Lecturer, Design Mentor & Curriculum Advisor

Career readiness coaching and design mentorship for students transitioning from frontline work into tech careers.


Press


Talks & Panels


Education

University of Pennsylvania

1999–2003

B.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