Professional Experience

Curriculum Vitae

24+ years of experience in technology leadership, from startups to IPOs, spanning cybersecurity, privacy, and systems architecture.

Summary

Experienced Chief Technology Officer with 24 years of experience in developing, managing, and overseeing all technical aspects of organizations. Proven track record of creating and driving innovative technical vision, developing world-class technology solutions, and maximizing organizational efficiency.

Skills

Hard Skills

Open Source/Free Software, Unix/FreeBSD/Linux, Bash/fish Scripting, Ruby, Julia Lang, SQL, Crystal Lang, MongoDB, Systems Architecture & Development, Cybersecurity, SaaS/PaaS, Forensic Analysis, Network Analysis

Soft Skills

Executive Engineering Management, Board of Directors, Team Building, Mentoring, Research Management, Product Champion, Public Speaking, Press/Media Interactions

Employment Experience

Chief Technology Officer / Founder

Redwoods Research | Aug 2020 – Present

  • Improve engineering team velocity by 20% by reducing testing and deployment time
  • Mentor System Architects and Senior C Developers on 30-year old codebase with 750,000+ lines of code
  • Architect large scale systems with 50,000+ processing cores, 100s of petabytes of clustered storage
  • Achieve 99.9997% annual availability with sub-millisecond performance
  • Integrated locally deployed AI/LLM solutions, enhancing code comprehension by 54%

Chief Technology Officer

Laxdaela Technology | Feb 2016 – Dec 2021

Technology prototyping and consulting.

Vice President / CTO

DarkOwl | Apr 2017 – Aug 2020

  • Expanded darknet collection into three new darknets with hundreds of millions of new content items
  • Grew sales 130% year over year with AICPA SOC 2 and PCI-DSS 3 compliance
  • Revamped marketing to generate 125% more leads

Chief Revenue Officer

Farsight Security, Inc. | Apr 2016 – Apr 2017

  • Grew revenue 187% in 9 months through collaborative selling
  • Developed 3 new products generating new revenue streams
  • Rebooted Marketing and PR to 500% increase in leads

Senior Vice President of Engineering

Norse Corporation (Federal) | Jul 2015 – Feb 2016

  • Deployed on-premises appliance into Top Secret government facility
  • Cut defect rate by 54% in under 7 months
  • Increased sales 350% through product refinement

Co-Founder & CEO

The Tor Project | Jan 2009 – May 2015

  • Co-founded $10M/yr privacy and security organization
  • Grew Tor's daily users from hundreds to millions
  • Conducted 1,000+ interviews across global media
  • Presented as invited keynote speaker to global governments

Vice President of Engineering

TechTarget | 1999 – 2009

  • Led team of 110+ engineers with 99.9% SLA
  • Acquired 10 companies with $35M in revenue
  • Completed successful IPO in 2007 at $1B valuation

Education

Bachelor of Science (B.Sc.)

Framingham State University | 1989 – 1994

Biology, Biochemistry, and Ethology

  • Published research on brooding behavior of Common Loon at Quabbin Reservoir
  • Internship at Mass Fish and Wildlife for Bald Eagle recovery
  • Teaching Assistant for Biology II, Comparative Vertebrate Zoology, Ornithology
  • Founding member of Framingham State Computer Club

Publications

Semantic Scholar → Google Scholar →

Owenson, G., Cortes, S., & Lewman, A. (2018). The darknet's smaller than we thought: The life cycle of Tor Hidden Services. Digit. Investig., 27, 17-22.

Lewman, A. (2013). Tor: Uses and Limitations of Online Anonymity. Fordham University Press.

Multiple EMCDDA reports on internet drug markets (2015-2017)

Honors & Awards

2023

Rookie of the Year

St. Francis Yacht Club Race Committee

2014

Top Leader

Boston Magazine "Power of Ideas"

2013

Best App

World Bank Latin America DV Hackathon

2003

Formula Car Racer

7th place out of 280 in Formula V

Volunteer Work

Board Member and Clerk

F-Droid | Jan 2023 – Apr 2025

Successfully bootstrapped the Board of F-Droid, a Commons Conservancy Programme.

Chairman of the Board and Treasurer

Each One Teach One Tech | Jan 2014 – Present

  • Mentored hundreds of teenagers in coding
  • Evaluated iOS and Android apps for student development
  • Helped raise $100k in funding

Board Member and Treasurer

Emerge DV | May 2015 – Present

  • 10 years of clean, successful audits
  • Strategic guidance for grant writing resulting in 20 new donors

Specialist, Crimes Against Children

Interpol | Nov 2015 – Dec 2020

  • Domain expert in darknet and Internet technologies
  • Helped build next generation case management system
  • Annual meetings in Lyon, France and Singapore

First Vice President, Silicon Valley Chapter

HTCIA | Sep 2017 – Oct 2021

  • Organized monthly meetings for hundreds of members in San Francisco Bay Area
  • Reduced member churn by 25% through strategic guidance
  • Collaborated with local, state, and federal law enforcement on high tech investigations

Co-Founder

IPVTech | Jan 2012 – Present

Winning Application Prototype at World Bank Latin America, Washington DC 2013. Collaborate with Emerge, Transition House, and legal aid/DV organizations on the intersection of domestic violence and technology.

Board Member, Secretary, and Treasurer

The Tor Project | Dec 2006 – May 2015

  • Managed 7 successful years of audits and reviews with audit partners
  • Provided strategic guidance on finances, growing to millions per year
  • Managed international challenges and hostile government interventions
  • Recorded 7 years of quarterly board meetings with public notes and transparent financial statements

Board Member and Treasurer

Privacy Enhancing Technology Symposium (PETS) | May 2009 – May 2015

Top-tier academic conference and publication on privacy technology. petsymposium.org

Lecturer

MIT Co-Design Graduate Class | 2014-2015 Academic Year

Civic Media Collaborative Design Studio focused on surveillance and privacy. Team designed and deployed a research portal for advocates from Transition House to better understand technology abuse in Intimate Partner Violence.

Board Member and Chief of Event Operations

COM Sports Car Club | 2004 – 2005

One of the oldest active sports car clubs in the country, with reputation for excellence in high-speed driving instruction and competitive time trials.

Board Member, Secretary, and Treasurer

NCAHS Parents Network | 2015 – 2017

  • Connect and communicate with parents via meetings, email, web and social media
  • Collaborate with faculty and administration to promote school community
  • Fundraise to enrich learning experience for students