Senior Healthcare IT Project Manager

We are looking for a powerhouse PM to lead Practice Management System vendor selection, RFP process, and subsequent implementation and integrations. If you have a direct, "no-fluff" communication style and a proven track record of driving complex clinical software migrations across multi-site organizations, we want to talk to you.
Location: Remote but must be within driving distance of Chicago, IL.
What You’ll Do
Drive the RFP & Vendor Selection: Lead structured demos, reference checks, scorecard development, and contract negotiations to select our next PMS.
Bridge the Gap: Translate complex technical architecture and integration requirements from vendors into clear, actionable business decisions for executive leadership.
Coordinate Multi-System Integrations: Manage technical workstreams and downstream impacts across PMS (transitioning from Ortho2), EHR, telephony/VOIP, finance/GL, identity management, and MSP relationships.
Own the Adoption: Ensure smooth post-go-live change management and user adoption—not just pre-go-live planning.
Deliver with Executive Presence: Walk into steering committee meetings, align stakeholders across clinical, finance, and IT teams, and present with high impact and zero clutter.
Non-Negotiable Requirements
10+ Years of Enterprise IT Program Management with a PMP certification.
Multi-Site Experience: At least two full PMS or EHR replacement cycles at multi-site healthcare organizations (DSO, physician group, or hospital system). Note: If you have only managed single-site implementations, you will not be a fit for this role.
Direct RFP/Vendor Selection Mastery: Experience running point on scorecarding, coordinating demos
and supporting contract negotiations.
The Technical Stack: Strong integration experience in a Microsoft ecosystem (E5, Entra ID, Intune).
MSP Collaboration: Comfort working with a third-party IT MSP partner.
Preferences
Dental DSO Experience: Hands-on experience implementing Cloud 9, Ortho2, Dolphin, OpenDental, or Denticon
Integration Expert: Past experience integrating clinical systems with VOIP and General Ledger (GL).
Compliance & Structure: HIPAA/HITECH familiarity and experience with multi-brand/multi-entity IT consolidation on shared infrastructure.
Background: Prior consulting, embedded PM, or fractional CIO experience alongside operating experience.

Work arrangement
Yes