Chris Cunningham

VP of Engineering

Denver, Colorado, United States20 yrs 9 mos experience
AI EnabledHighly Stable

Key Highlights

  • Increased delivery velocity by 33% at Recurly.
  • Delivered $32.7M in new revenue through cloud-based solutions.
  • Scaled engineering teams from 2 to 20 at Galvanize.
Stackforce AI infers this person is a SaaS engineering leader with expertise in AI integration and agile transformations.

Contact

Skills

Core Skills

Agile LeadershipTechnical Product ManagementCloud ServicesSaasAi IntegrationCompliance ManagementAgile PracticesSoftware Quality AssuranceTeam LeadershipWeb DevelopmentAgile Development

Other Skills

Managing Technical PersonnelEngineering ManagementPCI ComplianceHIPAA ComplianceVertex AIGemini LLMsSOC 2 ComplianceSecrets ManagementAutomated TestingCI/CD WorkflowsRuby on RailsJavaScriptSoftware EngineeringSoftware DevelopmentSQL

About

I build high-performing engineering teams that outperform groups of individual 'ninja coders.' I do this by combining a culture of ownership, collaboration, and innovation with intelligent agile processes—I know exactly which practices accelerate teams without becoming burdensome. People work together without ego to solve complex problems efficiently and with agility. Throughout my career, from Lockheed Martin to leading 24 engineers and managers at Recurly, I've consistently transformed delivery performance. At Galvanize, I scaled engineering from 2 to 20 people. At Storyvine and Intelivideo, I dramatically improved delivery velocity in turnaround situations. And at Recurly, my teams delivered $32M in new contracts, on a system that handles $15B annually, while adapting to shifting priorities and learning new technologies like AI integration. What sets me apart is bridging the gap between technology and business needs—I build teams that unite technical excellence with measurable business outcomes. Career Highlights: • Increased delivery velocity by 33% at Recurly through agile adoption, metrics-driven SDLC, and automation modernization, while leading three high-performing teams across multiple time zones. • Delivered $32.7M in new revenue by architecting, deploying, and operating cloud-based SaaS products, ensuring PCI and HIPAA compliance and timely enterprise launches. • Providing technical training and guidance to support the integration of Vertex AI and Gemini LLMs, enabling merchant-specific insights and interactive intelligence features for over 15 enterprise clients. • Led engineering transformations at early-stage SaaS firms, improving delivery velocity by up to 50% and securing $3M in new contracts through HIPAA/SOC 2 compliance and platform modernization. These experiences have proven valuable in driving organizational change, fostering innovation, and turning complex architectures into tangible business outcomes. From high-impact product delivery to enterprise-scale integrations, I bring a blend of strategic leadership and technical depth that connects innovation to positive business outcomes. What I Bring to the Table: • Proven leadership competence in SaaS engineering, AI integration, and cloud platform architecture • Extensive experience managing distributed teams and scaling agile delivery systems • Expertise in secure SDLC, compliance-driven design, and CI/CD modernization • Solid track record of driving revenue growth through innovation and cross-functional collaboration

Experience

20 yrs 9 mos
Total Experience
2 yrs 6 mos
Average Tenure
3 mos
Current Experience

Learningspring.com

VP of Engineering

Feb 2026Present · 3 mos · Broomfield, CO · Remote

Recurly

Functional Director of Engineering | Sr. Engineering Manager

Apr 2020Jun 2025 · 5 yrs 2 mos · Broomfield, Colorado, United States · Hybrid

  • Led multiple teams at Recurly, delivering major features, payment integrations, and platform improvements. Led cross‑functional teams and shaped a scalable roadmap aligned with business goals. Focused on collaboration, innovation, and process.
  • Subscription management platform that helps leading brands like Twitch, Paramount+, Sling, and the NFL grow recurring revenue through intelligent billing and AI-driven insights.
  • Managed daily engineering operations involving delivery of cloud services, machine learning solutions, and generative AI features that enable merchant-specific business insights and process automation. Provided strategic leadership to multiple teams on secure assimilation of AI technologies into product roadmaps.
  • Increased delivery velocity 33% by building and leading three teams of 24 engineers and managers across time zones, adopting agile and metrics-driven SDLC and modern test automation to enable faster releases.
  • Enabled secure merchant-specific AI insights for over 15 enterprises by guiding an AI team to integrate Vertex AI and Gemini LLMs with prompt engineering and data siloing.
  • Delivered $32.7 million in new revenue by architecting, building, deploying, and operating cloud-based web services and user-facing systems that combine back-end scalability with front-end usability, ensuring on-time PCI and HIPAA-compliant product launches.
  • Boosted innovation pipeline and engagement by launching and chairing a company-wide innovation program with hackathons and prototype-to-production paths, helping accelerate ideation and cross-team collaboration.
  • Accelerated enterprise onboarding of 25 major merchants within four months by integrating an acquired revenue recognition platform and team into the core product, expanding enterprise capabilities and cutting time to value.
  • Improved deployment confidence and cut test runtime 50% by rearchitecting CI/CD and test automation, which reduced release risk and enhanced deployment frequency.
Managing Technical PersonnelAgile LeadershipTeam LeadershipTechnical Product ManagementEngineering Management

Saoi development

Owner/Founder

Oct 2019Apr 2020 · 6 mos · Broomfield

  • Consultant on product definition, agile process implementation, and technical architecture.
Agile LeadershipTechnical Product Management

Colorado community college system

Advisory Board Member

Oct 2018Aug 2020 · 1 yr 10 mos

  • Advised on industry trends and hiring practices

Intelivideo

Vice President Of Engineering; turn-around effort

Aug 2018Sep 2019 · 1 yr 1 mo · Broomfield, Colorado, United States · On-site

  • Brought in as part of executive teams to turnaround early-stage SaaS platforms for growth and potential exit.
  • In this role, I oversaw engineering and compliance initiatives for two SaaS platforms navigating early-stage growth and market expansion. My focus was on rebuilding delivery pipelines, instilling secure development practices, and aligning technology strategy with sales and product goals. In addition, I also worked closely with senior leadership to guide these platforms into regulated markets, where quality, reliability, and compliance were vital to success. This experience refined my ability to balance speed with security, lead teams through transformation, and position technical capabilities as enablers of revenue growth.
  • Significant accomplishments included:
  • Improved release velocity by as much as 50% by revitalizing engineering delivery process with Agile
  • methodologies, full-stack models, and SDLC best practices, which produced the first successful releases in over a year.
  • Secured $3 million in new contracts by leading a core platform re-architecture to achieve HIPAA and
  • SOC 2 compliance with secrets management and access controls, opening new business opportunities
  • for medical and other regulated markets.
  • Doubled engineering headcount to 10 through a mix of contract and full-time hires, helping augment
  • delivery capacity and enabling rapid platform expansion across web, mobile, and Roku.
  • Won three enterprise clients by implementing modern payment solutions such as Apple Pay, Google
  • Pay, and PayPal, as well as ensuring PCI compliance through cross-team collaboration.
Managing Technical PersonnelAgile LeadershipTeam LeadershipTechnical Product ManagementEngineering Management

Storyvine

Vice President Of Engineering; turn around effort

Jan 2017Mar 2018 · 1 yr 2 mos · Denver · On-site

  • Brought in as part of executive teams to turnaround early-stage SaaS platforms for growth and potential exit.
  • In this role, I oversaw engineering and compliance initiatives for two SaaS platforms navigating early-stage growth and market expansion. My focus was on rebuilding delivery pipelines, instilling secure development practices, and aligning technology strategy with sales and product goals. In addition, I also worked closely with senior leadership to guide these platforms into regulated markets, where quality, reliability, and compliance were vital to success. This experience refined my ability to balance speed with security, lead teams through transformation, and position technical capabilities as enablers of revenue
  • Significant accomplishments included:
  • Improved release velocity by as much as 50% by revitalizing engineering delivery process with Agile
  • methodologies, full-stack models, and SDLC best practices, which produced the first successful releases in over a year.
  • Secured $3 million in new contracts by leading a core platform re-architecture to achieve HIPAA and
  • SOC 2 compliance with secrets management and access controls, opening new business opportunities
  • for medical and other regulated markets.
  • Doubled engineering headcount to 10 through a mix of contract and full-time hires, helping augment
  • delivery capacity and enabling rapid platform expansion across web, mobile, and Roku.
  • Won three enterprise clients by implementing modern payment solutions such as Apple Pay, Google
  • Pay, and PayPal, as well as ensuring PCI compliance through cross-team collaboration.
Managing Technical PersonnelAgile LeadershipTeam LeadershipTechnical Product ManagementEngineering Management

Galvanize inc

Chief Software Engineer

Jul 2015Jan 2017 · 1 yr 6 mos · Denver

  • As the company’s Chief Software Engineer, I led software engineering operations for a multi-product SaaS platform supporting enterprise education programs. I was responsible for guiding teams through modernization initiatives that improved scalability, performance, and software quality. My work centered on empowering engineers to deliver faster and more reliably by introducing agile practices, automated testing, and architectural upgrades. Working with leadership and product teams, I made sure that our systems could support rapid growth and evolving client needs. This role deepened my expertise in building resilient technical organizations that blend innovation with consistent delivery.
  • Significant accomplishments included:
  • Minimized product delivery cycle by 66% by transforming an underperforming team into a high-
  • performing unit through structured planning, estimation, and mentoring, enabling faster and more reliable
  • product launches.
  • Expanded engineering organization from two to 20 members by establishing hiring qualifications and
  • interview processes that identified capable full-stack engineers, boosting scalability across six active
  • product teams.
  • Improved release stability and speed by introducing automated testing practices and CI/CD workflows,
  • which decreased production bugs and significantly accelerated deployment timelines.
  • Increased development efficiency by implementing rotation, pairing, and mentoring programs that
  • reduced single points of failure and improved onboarding time for new engineers.
  • Optimized platform scalability and user experience by orchestrating the migration of the Galvanize ecosystem to microservices with integrated OAuth2 single sign-on, greatly improving reliability and cross-product access.
Managing Technical PersonnelAgile LeadershipTeam LeadershipTechnical Product ManagementEngineering Management

Splick.it

Head Of Engineering

Apr 2014Jul 2015 · 1 yr 3 mos · Boulder

  • At Splick.it, I managed the engineering organization responsible for both back-end APIs and front-end web platforms for a consumer ordering application. My role involved close collaboration with product, design, and leadership to deliver scalable solutions and prepare the platform for acquisition readiness. This period enhanced my ability to lead multidisciplinary teams, streamline delivery, and balance innovation with operational rigor.growth.
  • Significant accomplishments included:
  • Slashed website launch times from several days to just a few hours by redesigning the Ruby on Rails-
  • based web ordering platform to accelerate client onboarding process.
  • Played a key role in advancing company acquisition efforts by preparing architectural review and due
  • diligence materials and supporting executive negotiations.
  • Strengthened cross-functional collaboration by aligning engineering and product roadmaps, enabling
  • timely delivery of new features and better integration between client systems and back-end services.
  • Redesigned the web ordering platform written using Ruby 2/Rails 4, and Javascript.
Managing Technical PersonnelAgile LeadershipTeam LeadershipTechnical Product ManagementEngineering Management

Mapquest

Sr. Software Engineer

Sep 2011Apr 2014 · 2 yrs 7 mos · Denver

  • Led team that built MapQuest's Oauth 2 compliant login in Ruby on Rails, which handled 30 million logins a month. Revamped agile process that became a role model for all of AOL.
  • Led team that built MapQuest Discover in Ruby on Rails, radically redesigning our architecture and implementing new agile processes.
  • Led team that built MapQuest Vibe in Java.
Managing Technical PersonnelAgile LeadershipTeam Leadership

Lockheed martin

software engineer

Jun 2004Sep 2011 · 7 yrs 3 mos

  • Led installation of software in active warzone, finishing early.

Education

University of Colorado Boulder

Bachelor of Science (BS) — Computer Science

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