Consultant / Sr. Consultant (AI & Strategy | Healthcare)

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.