Nathan F.

Experience

• Expressway

  Fractional CTO

  Apr 2026 - Present

  Expressway Tech is the backoffice toolkit that restaurants need. Inventory planning, scheduling, and analytics are all the tools needed for a restaurant after they close a ticket, to be ready for the next one.

  • Planned out a full stack rewrite of the system
  • Executed the foundation layers to ensure we are setup for success
  • Worked strategically on integrating ML and AI into future product roadmaps
  • Coach internal devs, and proposed a new team organization in an agentic software world.

• Smart Tag

  Fractional CTO

  Apr 2026 - Jul 2026

  Smart Tag helps students safely get to and from school. This involves a custom driver app, a parent app, routing software as well as the infrastructure to help with bus and fleet management

  • Leading security and SDLC efforts to get the team a SOC Audit
  • Lead recruitment efforts of a full RTO team
  • Transitioned ownership of 20 year tech leadership to myself in < 4 weeks
  • Onboarded as a developer myself to respond to production incidents due to team attrition
  • Leading agentic coding practices to help level up the engineering team.
• 

  FranklinCovey

  Head Of Engineering

  Apr 2022 - Nov 2025

  FranklinCovey is a leadership development company undergoing a strategic shift toward becoming more technology-driven.

  • Scaled engineering from 9 to 25 across the U.S., Canada, Dominican Republic, Brazil, and other regions
  • Led technical due diligence for an acquisition and integrated developers with 0% attrition while achieving >10% budget savings and increasing velocity
  • Guided AI transformation through vendor evaluation, internal enablement, and delivery improvements without sacrificing quality
  • Improved roadmap execution, delivery cadence, and cross-team operating consistency
  • Balanced leadership with hands-on contributions in prototyping, build systems, and developer productivity work
• 

  PowerSchool (via acquisition of Schoology)

  Senior Director / Director / Engineering Manager

  Nov 2015 - May 2022

  Schoology is a mission-critical Learning Management System used daily by millions of teachers and students.

  • Led engineering organizations from team level through senior director scope, culminating in a ~50-person org across mobile, backend, frontend, data, architecture, and cloud operations
  • Owned uptime, roadmap predictability, retention, and a roughly $10M annual budget across people, vendors, and cloud hosting
  • Built and optimized distributed teams across North and South America and India
  • Mentored and promoted 5 ICs into management through structured coaching and career development
  • Stayed close to the work through architecture oversight, technical reviews, and support for major platform efforts including Kubernetes migration
  • Improved development productivity, accelerated feature delivery, and helped launch product work that materially increased adoption

• Spredfast, Allen Technologies, eBay, Works, rightshop.net

  Ranged from IC to Team Lead

  Jan 1999 - Jan 2015

  Built the technical foundation for my current work through software architecture, platform engineering, performance and reliability improvements, integrations, data systems, and early team leadership across consumer, healthcare, finance, and enterprise software environments.

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  University of Pittsburgh

  Undergraduate Teaching Assistant

  Jan 1998 - May 1999

  The University of Pittsburgh is a prestigious research university dedicated to academic excellence and innovation.