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Location: Remote, with preference for Toronto (EST only). Occasional in-person collaboration in Toronto, Canada, and Tampa, Florida ROLE OVERVIEW Eastwood & Cleef is seeking a Consultant / Sr Consultant (AI & Strategy | Healthcare) to support AI enablement, strategy, and program execution across our healthcare portfolio. You'll work at the intersection of AI, Value Based Care (VBC) strategy, and operational transformation — designing AI-enabled workflows, supporting diligence and growth initiatives, and partnering with clinical, operational, and investment stakeholders to drive measurable impact. High ownership, real scope, day one. KEY RESPONSIBILITIES - Partner with managerial, clinical, and operational teams to identify AI and workflow transformation opportunities - Support the development of AI and technology strategies tied to measurable business outcomes - Analyze processes, data, and systems to identify performance improvement opportunities - Translate business needs into requirements and support solution implementation with technical teams - Help design AI-enabled workflows, operating models, and transformation roadmaps - Support the evaluation and adoption of AI, automation, and data platform tools - Manage assigned workstreams and track deliverables, risks, and timelines - Build clear, executive-ready presentations and analyses - Stay current on AI and healthcare technology trends YOUR EXPERIENCE - Consultant: 0-3 years in consulting, healthcare strategy, healthcare operations, health tech, or a related field - Sr Consultant: 3-6 years in consulting, healthcare strategy, healthcare operations, health tech, or a related field - Strong business problem-solving and structured thinking skills - Familiarity with workflow design, process improvement, or program management - Demonstrated ability to operate in ambiguous, fast-moving environments - Strong interest in applied AI workflow automation - Experience using AI tools in professional or academic settings - Strong Excel / Google Sheets proficiency - Familiarity with SQL, BI tools, or Python is helpful but not required - Bachelor’s degree (Business, Health Administration, Economics, Engineering, Information Systems, or related) - MBA or graduate degree is a plus but not required Our Shared Ethos - Commitment to improving the American healthcare system - Continuous improvement mindset - High attention to detail - Extreme ownership (no task too big or small) - High impact, low ego - Collaboration and communication as the roots of problem-solving - Responsible use of tools and good judgment with sensitive information ABOUT EASTWOOD & CLEEF - Eastwood & Cleef is the management consulting arm of a US-based private equity family office, focused on data-driven problem solving and producing measurable impact. - Our Healthcare practice partners with MSOs, providers, and investors to accelerate VBC transformation.