Open to opportunities

Kenneth Riley

@kennethriley

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Healthcare technology executive driving clinical systems, cybersecurity, and M&A integration.

United States

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What I'm looking for

I seek senior health IT leadership roles where I can drive enterprise strategy, optimize clinical systems, lead secure interoperability initiatives, and manage high-impact M&A integrations in collaborative, growth-oriented organizations.

I am a strategic healthcare technology executive with over 10 years of progressive IT leadership and more than 5 years in senior leadership roles, combining technical engineering expertise with business acumen to deliver measurable value.

I have directed enterprise technology strategy for multi-site health systems, managed EHR/PMS/RCM and patient engagement platforms, and led regional HIE initiatives to improve interoperability for hundreds of thousands of patients.

I have overseen comprehensive cybersecurity and compliance programs (including HIPAA/HITECH and 42CFR.2), administered multi-million dollar IT budgets, and led IT due diligence and post-acquisition integrations to accelerate synergy realization.

I present thought leadership at industry forums, champion data governance and clinical technology optimization, and continuously pursue leadership and process-improvement certifications to drive operational excellence.

Experience

Work history, roles, and key accomplishments

Director, Patient and Population Health

Baystate Health

Jan 2015 - Jan 2025 (10 years)

Directed enterprise patient and population health technology strategy for a $2.1B integrated health system, leading HIE, CRM, IPC, virtual care, and mobile initiatives that served 750,000+ patients and improved interoperability.

EHR Integration HIE Patient Engagement Data Governance Population Health Virtual Care Vendor Management

Chief Information Officer

Wing Memorial Hospital

Jan 2012 - Jan 2015 (3 years)

Directed IT strategy, security, and operations for a $95M hospital subsidiary, managing $5M CAPEX and $1M OPEX budgets and delivering CPOE, eMAR, patient portal, ICD‑10 and VOIP deployments that improved clinical efficiency.

IT strategy Budget Management EMAR Cybersecurity

Director, Information Systems

Wing Memorial Hospital

Managed applications, network, and desktop teams and led system integrations (Payroll, HR, EMR) and disaster recovery, delivering cost savings through open-source adoption and governance improvements.

System Integration IT Governance Disaster Recovery Open Source Network Administration Change Management Cost Optimization

Staff Sergeant, Communications

Air National Guard

Supervised communications team for installation and maintenance of telephony and computer equipment, supported deployments including a 4-week Operation Enduring Freedom mission in Saudi Arabia.

Telecommunications Team Supervision Deployment Equipment Maintenance