Dr. Oliver Degnan

CEO

Greater Milwaukee28 yrs 3 mos experience
Most Likely To SwitchAI Enabled

Key Highlights

  • Expert in AI product innovation and digital transformation.
  • Top-rated burnout coach with proven systems.
  • Extensive leadership experience in healthcare technology.
Stackforce AI infers this person is a healthcare technology leader specializing in AI-driven solutions and executive coaching.

Contact

Skills

Core Skills

Artificial IntelligenceIt StrategyExecutive CoachingBusiness LeadershipProduct InnovationProduct DevelopmentProduct ManagementMedicare AdvantageElectronic Medical Record (emr)Electronic Health Records (ehr)Saas

Other Skills

Primary CareAgentic AI DevelopmentUniversity LecturingLecturerBusiness IntelligenceBusiness DevelopmentStrategic PlanningBusiness StrategyBusiness Process ImprovementProject ManagementCloud ComputingStrategyEnterprise ArchitectureManagementCross-functional Team Leadership

About

I'm a CIO with a passion for developing the next wave of executive leaders with ultra-resilience. View more for...EXCLUSIVE OFFER šŸ‘‡ Burnout almost ended my career as a C-Suite executive. Now, I’m on a mission to ensure it doesn’t happen to you. I’m Dr. Oliver Degnan, and aside from my work as a fractional CIO in AI product Innovation, I empower professionals to reverse burnout in under 20 days with my Never Burnout AgainĀ® course, then help them unlock new career heights with my LevelUP SystemĀ®. These proven systems are your roadmap to: 1ļøāƒ£ Staying relevant in an ultra-competitive job market. 2ļøāƒ£ Creating clarity on your identity and professional brand, and what to do next. 3ļøāƒ£ Attracting more career growth opportunities (be found by AI recruiters). 4ļøāƒ£ Never burnout again! When you’re ready to escape burnout and fast-track your career growth, let’s create your leadership blueprint. EXCLUSIVE OFFER Book a 25-minute call with me ($280 value) and get my premium Burnout Field Guide ($149 value), with scientific systems to escape burnout forever, for FREE. šŸ‘‰ Go to https://book.drdegnan.com today!

Experience

Aspen hr

Chief Information Officer

May 2023 – Present Ā· 2 yrs 11 mos

  • Aspen HR is the premier provider of professional employer organization (PEO) services. As a fractional CIO via Fortium Partners, I led the company-wide rollout of AI automations and cost-sustainability measures to enhance the customer experience and staff performance. Company was successfully acquired by Engage PEO in 2025.
Artificial IntelligenceIT Strategy

Fortium partners

Partner

Jan 2021 – Present Ā· 5 yrs 3 mos

  • Fortium is a leading provider of board-level fractional executives, connecting organizations with proven C-suite leaders who deliver immediate, high-impact results. As part of this elite network, I help clients navigate digital disruption, implement AI-driven solutions, and achieve transformational outcomes, particularly in high-stakes private equity (PE) and mergers and acquisitions (M&A) contexts.
IT StrategyArtificial Intelligence

Experity

Chief Information Officer

Jan 2021 – Jan 2023 Ā· 2 yrs

  • Performed as product strategy advisor to CEO via Fortium Partners. Then transitioned into CIO role via private equity acquisition to lead the merger of Experity EMR and DocuTab EMR as the largest provider of an urgent care specialized electronic medical record SaaS platform.
Electronic Medical Record (EMR)Product InnovationIT Strategy

Drdegnan.com

Never Burnout AgainĀ® Course

Jan 2018 – Present Ā· 8 yrs 3 mos Ā· United States

  • Join 84k professionals worldwide and reverse burnout in 20 days (or sooner) with the scientific Never Burnout AgainĀ® course. Register for free at https://NeverBurnoutAgain.com!
Executive CoachingBusiness Leadership

Ibm

Chief Technology Officer and SVP | IBM Watson Health - Phytel

Jan 2016 – Jan 2021 Ā· 5 yrs

  • Led IBM Watson Health Phytel ($4.5B historic healthcare merger) companywide SaaS platform consolidation program and unification of all services and data assets and the creation of new product solutions, bootstrapping next-generation revenue streams for patient engagement and PopHealth for 88k clinical staff supporting 160M patients worldwide.
  • Consistent career achievement >98% for retention of critical employees while going through massive restructures and organizational capability overhauls (see my LinkedIn Recommendations Section for more detail).
Product DevelopmentProduct Management

Chenmed

Chief Information Officer

Jan 2013 – Jan 2016 Ā· 3 yrs

  • Led ChenMed ($1.2B PE leader in Medicare Advantage) design and delivery of certified SaaS EMR, data center infrastructure and network, telephony, end-user support, and cybersecurity program. Delivered sustainable solutions to optimize provider efficiency and membership growth.
Medicare AdvantageElectronic Medical Record (EMR)

Marshfield clinic

Chief Technology Officer

Jan 2009 – Jan 2013 Ā· 4 yrs

  • Contracted as Chief Architect and then hired as CTO to lead R&D for homegrown Electronic Health Record (EHR) system (including 83 specialties), and business intelligence reporting for 8K providers across 35 locations. Directed 350-member team and directed technology spend in access of $24M.
  • Featured in LeadIT magazine as innovative healthcare CTO transforming Marshfield Clinic Health System’s digital assets to meet the challenges of value-based and accountable care.
IT StrategyPrimary CareElectronic Health Records (EHR)

Intuit

Chief Architect

Jan 2005 – Jan 2009 Ā· 4 yrs

  • Led product innovation for Quicken Health resulting in new product launch to 1.2M healthcare consumers. Partnered with insurance payers (Mutual of Ohio, United Healthcare, Cigna, Aetna) to establish Open Medical Standard (precursor to the CCD standard) for secure and interoperable data exchange.
  • Received U.S. Technology Patent (US8306255B1) for breakthrough invention on advanced character-image recognition.
Product DevelopmentSaaS

Greenbrier & russel

Microsoft Solutions Architect

Jan 1998 – Jan 2005 Ā· 7 yrs

  • Spearheaded the Microsoft Solutions practice, guiding 150 technology consultants across 4 states in the US. Delivered countless product SAAS solutions to PE and Fortune 100 companies.
  • I wrote more software code than I will ever be able to remember.

Education

University of Wisconsin-Whitewater

Doctor of Business Administration — Technology Innovation Performance

Lubar College of Business

Master of Business Administration

University of Wisconsin-Milwaukee

Bachelor of Arts — German Language and Literature

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