Alex Witherspoon

Profile

Builder, operator, and strategic advisor are the through-lines I keep choosing. I build and scale technology, product, and design organizations from zero to 1,200+ people, from early-stage startups through Fortune 100 platforms. I advise and coach founders and leadership teams on strategy, execution, and culture. I have been involved in many M&A events across buy-side, sell-side, and advisory roles; counting only deals above $100M, the ten largest deals I participated in sum to about $39B in transaction value.

Experience

Going.com

Remote

VP of Engineering

April 2025 - Present

  • Lead engineering and technology for Going.com (23 people across product engineering, SRE, security, and data engineering).
  • Own delivery across web, mobile, APIs, and the full data lifecycle (acquisition, processing, ML, and AI).
  • Building company-wide security and privacy standards and practices, selecting CISA- and NIST-aligned frameworks appropriate to the business.
  • Implementing and operating them across engineering and the company.
  • Partner with leadership to mature operating practices, reliability, and delivery tempo as the organization grows.
  • Technology Leadership
  • Executive Leadership
  • Travel
  • Mobile Apps
  • Mentorship
  • Culture Building

AviationWX.org

Sandy OR, USA

Founder & Maintainer

August 2023 - Present

  • Founder and maintainer of AviationWX.org, with public source in alexwitherspoon/aviationwx.org (platform) and alexwitherspoon/aviationwx.org-bridge (RTSP camera bridge). Free for the community and built to help general aviation pilots verify go or no-go decisions with live cameras, quality-checked weather, multi-source dashboards, and transparent handling of stale or bad data rather than trusting a single automated feed.
  • Partner with airports, government, and businesses to integrate or stand up cameras and community weather stations, then host unified mobile-first dashboards with density altitude, VFR/IFR context, wind visualization, time-lapse history, and cross-checks against METAR and local sensors.
  • Active network includes 35 airports, 65 live webcams, and 42 weather stations, with documented REST APIs and embed tooling for pilots, schools, and airport operators.
  • Open Source Software
  • Aviation Safety
  • Resilience Engineering
  • RTSP(s) Video Streaming
  • Weather Data Systems

Skyfarer Academy

Portland OR, USA

Chief Operating Officer

June 2024 - August 2025

  • Cofounded as COO from zero to initial go-to-market, owning finances, hiring, product and roadmaps, partnerships, fundraising support, and business development through the early operating cadence.
  • Shipped core product work including an interactive map experience, payment flows and pricing design, and reservation systems end to end.
  • Grew fully onboarded, active flight-instructor supply from zero to over 100 CFIs on the platform.
  • Advising
  • Startups
  • Strategy Development
  • Executive Coaching
  • Technology Leadership
  • Aviation
  • Edtech

CompanyCam

Remote

Software Engineering Manager

September 2023 - February 2025

  • Led a team of nine engineers shipping contractor workflow capabilities across web, mobile, and APIs during a hypergrowth phase of the company.
  • Delivered features that move jobs from assignment to verified completion, including configurable forms, checklists, reminders, exception handling, callbacks, invoicing, and handoffs for edge cases so work reaches a reliable done state in the field.
  • Mobile App Development
  • Technology Leadership

AW.Run

Portland OR, USA

Founder

October 2022 - Present

  • Founding practice for executive advising, coaching, and consulting, helping leadership teams build and scale products and organizations through growth and complexity.
  • Hands-on work across technology, product, and design effectiveness, operating cadence, hiring, and strategy, typically alongside founders and key executives in confidential client settings.
  • Advising
  • Consulting
  • Strategy Development
  • Technology Leadership

Edify

Portland OR, USA

Advisor

January 2018 - October 2022

  • ChatOps SaaS platform that speeds employee onboarding and education to improve time-to-value and day-to-day experience.
  • Advised and coached the founding team throughout company growth phases including fundraising.
  • Hired first engineers, and advised growth of technology, product, and design elements of company.
  • Partnered with leadership to review company strategy, performance, technology, and product growth.
  • Onboarding
  • SaaS
  • Artificial Intelligence
  • Machine Learning
  • Natural Language Processing

Smile.io

Remote (Canada)

Head of Engineering, Product and Design

February 2021 - July 2022

  • Grew the company to become the largest international e-commerce loyalty provider with >1 billion users and >300,000 merchants in the Shopify, Wix, and BigCommerce ecosystems.
  • Built a remote company culture with employees in 22 countries and >7 languages.
  • Led a foundational company rebuild to get finances, process, tech, teaming, and the product into a mature growth stage.
  • Increased revenues with value-based pricing and packaging changes and user journey refinements.
  • Improved reliability, performance, and cost efficiency through tech platform improvements for world-scale commerce.
  • e-commerce
  • SaaS
  • Ruby
  • Agile
  • JavaScript
  • HTML
  • CSS

SurfaceSEO

Portland OR, USA

Board Member

March 2008 - October 2022

  • Board member for a distributed digital marketing and SEO firm serving international SMB clients on long-term partnerships.
  • Supported governance, strategy reviews, and leadership continuity as the company scaled content, brand, and data-led search programs.
  • SEO
  • Marketing
  • Advising

GitHub

SF CA, USA

Director of Engineering

January 2018 - March 2021

  • Led engineering at GitHub's core code collaboration platform in the era when the company publicly cited more than 98% worldwide developer participation, spanning enterprise and individual adoption at global scale.
  • Joined in the pre-Microsoft era, focused on Enterprise, Privacy, and Security user experiences, and on identity, trust, and permissions that underpin how organizations and developers collaborate safely.
  • Developed and led seven international teams, cultivating four staff engineers and staff managers.
  • Diversified talent outside the Bay Area and created a creative, agile culture with outsized impact.
  • Led through acquisition by Microsoft for 7.8 billion USD.
  • GitHub
  • SaaS
  • Audit Log
  • GitHub Enterprise
  • GitHub Infrastructure
  • Ruby
  • Go

ATWLab Accelerator

Portland OR, USA

Founder & Chief Executive Officer

August 2008 - December 2020

  • An entrepreneur and principal business development consultant working with partnerships focused on technology startups.
  • $48 million USD fund managed for seed stage and series A stages of growth.
  • Mergers and acquisitions experience in buyer, seller, and mediation roles.
  • Global investments with over 80 companies in over nine countries.
  • Portfolio of investments ranges from automated robotics and avionic systems for lightweight aerial vehicles, to educational technology start-ups.
  • Investing
  • Advising
  • M&A
  • Consulting

FlightStats

Portland OR, USA

SVP of Engineering

March 2014 - July 2018

  • Industry leader in international aviation data and analytics, serving travelers, aircraft, routes, airlines, airports, and more with historical, real-time, and predictive services.
  • Hands-on leader for the global aviation data acquisition, processing, and distribution software and cloud data product platforms.
  • Grew a team of ~40 to over 100 local and remote engineers in cross-functional EPD teams to develop software services, software-defined infrastructure, and big data pipelines and analysis systems.
  • Built and grew our services business, processing hundreds of millions of data points in semi-real-time, servicing customers around the globe.
  • Led the company through acquisition by RELX, hitting all strategic targets on time.
  • Aviation
  • SaaS
  • World Scale
  • Data Services
  • M&A

Presidio

Portland OR, USA

C-Suite Consultant & Sales

March 2012 - November 2014

  • High-end technology consulting firm focusing on CXO partnerships to bring technology strategy and execution together.
  • Partnered with a wide portfolio of nearly 400 private, public, and government companies.
  • Built long-term strategy with leadership teams that incorporated advanced technology solutions for Presidio clients.
  • Provided technical expertise and leadership to lead a virtual data center and data science practice within Presidio.
  • Consulting
  • Sales Engineering
  • Software Architecture
  • Security Architecture
  • Networking Architecture

Network & Software Security Architect

March 2012 - November 2014

  • Partnered with Portland General Electric to modernize and secure their technology solutions.
  • Projects focused on smart electrical metering, modern digital industrial control systems, and customer-facing systems.
  • Migrated PGE data center to a newly designed physical site with no customer impact.
  • Created and implemented CyberSecurity design to secure critical US infrastructure.
  • CyberSecurity
  • Datacenter Architecture

ADP Dealer Services

Portland OR, USA

Solutions R&D

February 2008 - March 2012

  • Created new lines of technology business as part of ADP Dealer Services for wide-scale international use for over 10,000 car dealerships and millions of users.
  • Early employee as the company grew from millions in ARR to billions in ARR during a massive growth phase.
  • My work included leading product, design, and engineering efforts to design new product lines and bring them to market at scale.
  • Product Development
  • Networking
  • CyberSecurity

MindScapes

Wichita KS, USA

Chief Technology Officer & Founder

January 2006 - November 2007

  • Edtech plays with brick-and-mortar locations to augment public school systems and community schools' education with high-tech services, including software development, visual and audio production, music production, clay animation, robotics, and more.
  • Developed & executed a start-up business technology plan, brought together a team, and supported all elements of the business to get it off the ground.
  • Developed infrastructure and E-learning systems for advanced technology instruction for remote and in-class learning.
  • Pioneering new curriculum and business plans for technology-integrated STEM education.
  • Grew to break-even revenue levels in the first year of operation.
  • STEM Education
  • Robotics
  • Software Development

NetApp

Wichita KS, USA

IT Consultant

June 2007 - January 2009

  • Virtualized and emulated storage systems for sales, quality assurance, and training systems with fully automated SAN environments.
  • Developed new pricing tools for competitive pricing analysis and deal-close support.
  • Created internationalized training programs for SAN storage platforms using video education in 12 languages.
  • Consulting
  • Storage
  • Training

WSU College of Education

Wichita KS, USA

NSF M3 Grant Researcher

August 2003 - June 2007

  • Hands-on NSF Grant work with future educators, providing technology consulting, assistance, and support.
  • Co-created the WSU Robotics Challenge to bring technology education to K-12 students and educators with industry funding from Boeing.
  • Developed remote education techniques and worked with technologies like Internet2 for Kansas schools and international teaching communities.
  • Academic Research
  • Remote Learning
  • Curriculum
  • Security
  • Robotics

SSI Sprinkler Systems

Wichita KS, USA

IT Consultant

June 1997 - August 2003

  • Sprinkler system merchant and installation services company in Wichita, Kansas.
  • Designed, deployed, and managed technology elements of the business, including e-commerce presence, inventory, security, workstations, and software systems.
  • Grew the business from 3m USD ARR to 11m USD ARR through digital transformation efforts and e-commerce.
  • e-commerce
  • IT
  • Networking
  • Security
  • Consulting

Website Developer

Wichita KS, USA

Sole Proprietor

October 1995 - January 2006

  • Provided website hosting, design, and management services to a portfolio of ~200 websites.
  • Included static HTML, custom JavaScript, Joomla, Drupal, and fully custom builds.
  • Website
  • Design
  • Consulting
  • Infrastructure
  • Hosting
photo of me

Personality

Skills

    • Business
    • Strategy
    • Culture
    • Tempo
    • Org Design
    • Decision Architecture
    • Investments
    • Planning
    • Risk
    • Continuity
    • Acquisition
    • Negotiation
      Markets
    • Aviation
    • Consulting
    • Developer Tooling & Enablement
    • AgTech
    • Managed Services
    • Manufacturing
    • Power Distribution Markets
    • Power Generation
    • SaaS
    • Data Platforms
    • Telecom
    • Venture Capital
      People
    • Alignment
    • Growth Mindset
    • Recruiting
    • Talent Management
    • Radical Candor
    • Coaching
    • Mentoring
    • Compensation
    • Contracts
    • Mediation
      Process
    • Agile
    • Kanban
    • Scrum
    • Forecasting
    • Risk Management
    • Retrospectives
    • Incident Management
    • On-Call
    • Software Development Lifecycle
    • Iterative Development
    • Prioritization
    • Product Lifecycle
    • Design
    • Research & Development
    • Site Reliability Engineering
    • Automation at Scale
      Technology
    • Git
    • GitHub
    • CI/CD
    • bash
    • JavaScript
    • TypeScript
    • Node.js
    • Go
    • Python
    • Ruby
    • C++
    • SQL
    • Kubernetes
    • Docker
    • Helm
    • AWS
    • Azure
    • Networking
    • Streaming Data Processing
    • Data Warehousing
    • Data Analytics
    • Edge Computing
    • Artificial Intelligence
    • Generative AI
    • LLMs
    • Machine Learning
    • Natural Language Processing
    • Computer Vision
    • GitHub Copilot
    • OpenAI
    • MLOps
    • Infrastructure Automation
    • CyberSecurity
    • Application Security
    • 3D Modeling
    • Additive Manufacturing
    • Prototyping

Interests

  • Gardener
  • Beekeeper
  • Hiker
  • Cook
  • Pilot
  • Forester
  • Traveler
  • Writer
  • Maker
  • Hacker

Education

Portland State University

Bachelor of Science

2008 - 2012

Computer Science & Business Management

Wichita State University

M3 Grant Researcher

1999 - 2003

Technology Integration into the Classroom & Remote Learning.

MIT Media Lab

Robotics Education Researcher

1997 - 1999

LEGO Robotics, AI, and ML Research

Languages

  • English
    Native