Greg Starling

Technology Executive | AI Strategy & Implementation · Oklahoma City, OK
gstarling@gmail.com

About

20+ years building and scaling technology organizations across SaaS, managed services, federal contracting, and tribal government sectors. Track record of creating platforms that generate tens of millions in revenue, leading teams through successful acquisitions, and turning AI strategy into production-grade capability. Two-time Innovator of the Year. Contributing author featured in Wired, Inc., Forbes, and Entrepreneur.

Experience

Head of Innovation and Growth - Doyon Technology Group (Fairbanks, AK)

2023 – Present

  • Designed and executed DTG’s first unified AI strategy, converting isolated experiments into production capabilities serving multiple business units and customer sectors.
  • Deployed generative AI, predictive analytics, and intelligent automation that reduced manual effort by 30%+ in targeted workflows while preserving service quality.
  • Partnered with executive leadership and sales to package AI capabilities into commercial offerings, supporting retention, expansion, and new market entry.
  • Established governance patterns appropriate for regulated environments.

Head of Innovation & Strategic Partnerships - Tailwind (Oklahoma City, OK)

2019 – 2023

  • Built and executed technology roadmaps centered on generative AI and advanced analytics to strengthen adoption and competitive position.
  • Identified, negotiated, and integrated multiple acquisitions in NLP, machine learning, and neural-network capabilities to accelerate the roadmap.
  • Led global product and engineering teams and shortened the innovation cycle from idea to shipped capability.

Chief Technology Officer - Monscierge (Oklahoma City, OK)

2018 – 2019

  • Rebuilt the technology organization, restoring delivery effectiveness and morale within two quarters.
  • Developed product roadmaps and go-to-market plans that improved time-to-market and positioned the company for acquisition.
  • Repaired and strengthened strategic partnerships with Apple and Airbnb, converting strained relationships into active advocacy.

Chief Information Officer - Victory Family Church (Norman, OK)

2016 – 2018

  • Designed scalable infrastructure that absorbed rapid growth without service disruption.
  • Built analytics-driven systems to forecast growth, inform real-estate decisions, and improve resource allocation across campuses.
  • Delivered technology improvements that increased responsiveness for hospital visits and crisis situations.

Chief Technology Officer - WeGoLook (Oklahoma City, OK)

2014 – 2016

  • Built the technology division from scratch (team, platform, and infrastructure), creating the foundation that contributed to a $40M acquisition.
  • Architected a flexible stack blending custom software with best-in-class commercial tools across finance, logistics, communications, and HR.
  • Translated executive business priorities into technology roadmaps that expanded operational capacity and reach.

Vice President of Technology - MTM Recognition (Oklahoma City, OK)

2002 – 2014

  • Conceived and launched an employee engagement platform generating $35M+ in annual revenue, over 35% of total company earnings.
  • Built and mentored teams spanning software development, business analysis, network operations, and technical support.
  • Founded an internal R&D division whose initiatives drove a 14% increase in organizational efficiency.

Skills

Category Skills
Executive Leadership Strategy and operating model design, org design, team building, executive alignment, portfolio prioritization, budgeting, stakeholder management, mentorship
AI Leadership Enterprise AI strategy, AI governance in regulated environments, use-case discovery and value sizing, adoption planning, human-in-the-loop workflow design, AI productization, impact measurement
Applied AI Generative AI solution design, NLP capability integration, predictive analytics, intelligent automation, fit-for-purpose evaluation, workflow redesign with quality preservation
Product & Platform Product strategy and roadmaps, platform modernization direction, delivery cadence and quality systems, time-to-market improvement, build vs buy decisions, vendor strategy
M&A Technical diligence support, capability mapping, integration planning and execution, post-merger platform and team consolidation
Operations Process optimization, metrics-driven execution, continuous improvement, Lean practices

Domains

  • Government and federal contracting
  • Tribal government and tribal enterprises
  • SaaS for small business marketing
  • Managed services and technology services delivery
  • Hospitality technology and guest experience
  • Healthcare experience enablement
  • Nonprofit operations and multi-campus growth environments
  • Crowd-sourced inspections for insurance, investment, and consumer services
  • Employee engagement, recognition, and retention platforms
  • Strategic partnerships and ecosystems (including Apple and Airbnb)
  • M&A-driven capability expansion in AI/ML and NLP

Education

Coursework in Civil Engineering - University of Oklahoma (Norman, OK)
Lean Six Sigma Black Belt - Management and Strategy Institute (Downingtown, PA)

Recognition & Publications

  • Innovator of the Year, Journal Record (2013, 2015), only two-time recipient in award history
  • Contributing author, The AI Advantage: Thriving Within Civilization’s Next Big Disruption (2025); work featured in Wired, Inc., Forbes, and Entrepreneur
  • Conference speaker across North America and Europe on AI implementation, employee engagement, and technology strategy
  • Inc. 500 Fastest Growing Companies (WeGoLook)
  • Most Influential People, 405 Business Magazine; Leadership Oklahoma City, Class XXXIII
  • Distinguished Guest Lecturer, University of Oklahoma