Director, Strategic Finance & Chief of Staff

About HealthCare Information Management, Inc. (HCIM)

Healthcare Information Management, Inc. (HCIM) is an intelligent robotic process automation (RPA) software company serving health plans, risk-bearing providers and their management services organizations (MSOs), and third-party administrators (TPAs). For nearly 25 years, HCIM has partnered with healthcare organizations to streamline operations, increase efficiency, and improve accuracy — all with proven ROI.

Our flagship product, SymKey, uses intelligent automation to execute complex administrative workflows, processing manual tasks up to 8x faster than staff with 100% accuracy. This allows healthcare teams to focus on higher-value activities while reducing costs and improving service quality. What sets HCIM apart is the deep industry expertise behind our solutions — our products are designed and delivered by professionals who understand the real-world operational challenges healthcare organizations face.

The U.S. healthcare system is at an inflection point. A looming shortage of physicians, increasing regulatory burdens, and rising administrative complexity are putting immense pressure on payers and providers. In this context, HCIM’s mission is more urgent than ever: to empower healthcare organizations with software that drives operational efficiency and streamlines workflows, allowing our clients to focus on what matters most – improving patient care.

Position Overview

We’re seeking an analytical, execution-oriented Director of Strategic Finance & Chief of Staff to serve as the CEO’s right hand and help lead the next chapter of HCIM’s growth. This hybrid role blends corporate strategy, operational leadership, & high-impact financial planning & analysis. You'll play a critical role in shaping our strategy, evaluating growth opportunities (new products & acquisitions), driving cross-functional initiatives, and partnering with the CEO to operate the Company at peak effectiveness.

Key Areas of Responsibility

Strategic Finance

• Partner with the CEO on strategic planning, annual budgeting, and long-range forecasting
• Build and own dynamic financial models, dashboards, and KPIs to support decision-making and board reporting.
• Lead diligence of potential acquisition targets and deal execution (with support from the CEO).
• Analyze operational data to drive efficiency, margin improvement, and revenue growth including, (1) ROI and payback analysis on product, hiring, and commercial initiatives and (2) pricing strategy analysis & design.
• Collaborate with external CPA firms on financial audits, tax filings, and the generation of financial reports.
• Manage company cash flow, bank accounts, and financing sources, ensuring optimal allocation of resources and cost of capital.
  
  

Chief of Staff to the CEO

• Act as a trusted thought partner and sounding board to the CEO.
• Prepare strategic materials for board meetings, investors, and other stakeholders.
• Lead and project manage cross-functional strategic initiatives across product, engineering, sales & marketing, finance, and operations.
• Collaborate with other senior leaders to ensure alignment and execution against company priorities.
• Step into high-impact gaps across the business to unblock key projects and decisions.
  
  

Professional Qualifications

The ideal candidate will have:

• 2–5 years of experience in private equity is preferred
• Similar experience in investment banking, strategy consulting, and/or corporate strategy at a high-growth company will also be considered
• MBA preferred but not required
• Exceptional analytical, communication (verbal and written), and project management skills
• Highly self-motivated with a bias toward action and ownership
• High attention to detail with demonstrated ability to produce high quality results with limited external input.
• Comfortable operating in ambiguity and shifting between strategy and execution
• Experience or interest in SaaS, healthcare, or automation software is a plus
  
  

What We Offer

• A high impact leadership role working directly with the CEO, Board of Directors and senior leadership team
• Opportunity to learn and grow from CEO who is an experienced private equity investor and operator having closed ~17 M&A transactions worth ~$4 billion in enterprise value
• Competitive compensation with performance upside
• Opportunity to shape company strategy and scale operations in a growing software business
• Remote-first culture with flexibility and autonomy
• Mission-driven work improving healthcare efficiency and outcomes
  
  

Work Environment

The Director, Strategic Finance and Chief of Staff will perform duties from a home-based office in collaboration with HCIM colleagues located elsewhere. Travel for occasional face-to-face work sessions with colleagues will be necessary. This role may require up to 20% travel.