Chief of Staff to the CEO

About Alaffia & Our Mission

Every year, U.S. health plans lose billions to improper payments and administrative waste. That wasted spending ultimately trickles down across the healthcare ecosystem, driving up costs for plans, providers, and patients alike. We’re here to change that paradigm.

Alaffia is a new kind of claims operations partner for health plans. Using expert clinicians and transparent AI, we deliver deeper insights, smarter automation, and consistently better outcomes across the entire lifecycle of claims. With Alaffia, health plans can cut wasted spending more effectively than ever — and provide their members the most affordable care.

We’re a high-growth, venture-backed Series B healthtech startup based in NYC and are actively scaling our company. Join us in helping to build a healthcare system that works better for everyone.

As Chief of Staff to the CEO, you will serve as a strategic partner and force multiplier, ensuring seamless execution of the company's most important priorities while building the operational infrastructure to scale impact. This role offers unparalleled exposure to every facet of the business, from product strategy and customer operations to investor relations and strategic partnerships.

We are looking for someone who is highly driven, resourceful, and low-ego. This is not a role for someone seeking a narrow scope or clear playbook. The ideal candidate embraces ambiguity, moves seamlessly between high-level strategic analysis and tactical execution, and has the humility to do whatever it takes—from driving growth strategy to ensuring flawless execution on the ground.

CEO Partnership & Organizational Leverage

• Manage the CEO's priorities, prepare briefs for board meetings and investor discussions, and ensure systematic follow-through on all commitments

• Serve as trusted sounding board and thought partner to the CEO on critical business decisions

• Represent the CEO in internal and external settings when needed

Strategic Execution & Special Projects

• Lead high-priority projects spanning multiple functions—from customer expansion strategies to new product launches—ensuring execution from inception to completion

• Develop data-driven models and frameworks to support critical decisions around pricing, market entry, and resource allocation

• Perform market research, competitive analysis, and due diligence on strategic opportunities; synthesize complex healthcare data into actionable insights

Operational Infrastructure & Cross-Functional Alignment

• Design and implement scalable processes for quarterly planning, OKRs, and company-wide initiatives that enhance decision-making velocity

• Act as connective tissue across Engineering, Product, Operations, Growth, and Payment Integrity teams, breaking down silos and driving alignment

• Capture key decisions, ensure action items are tracked, and drive accountability across stakeholder commitments

Investor Relations & Communications

• Draft and refine investor updates, board materials, and company-wide announcements

• Prepare the CEO for high-stakes presentations and meetings

Experience

• 5-8+ years total, including:

  • 1-3+ years in management consulting (MBB preferred), investment banking, or venture capital, developing business acumen, analytical rigor, and executive communication

  • 2-4+ years in a startup or high-growth environment (Series A to Series C), operating and executing at a high level

• Healthcare industry experience strongly preferred

Core Competencies

• Self-starter who thrives in fast-paced, unstructured environments with a bias for action

• Exceptional analytical and problem-solving skills; moves fluidly from high-level strategy to data-driven detail

• Proven cross-functional execution—has led complex initiatives across multiple departments and delivered measurable results

• Technical fluency to engage meaningfully with engineering and product teams

• Proficiency in Excel, PowerPoint, SQL, and modern analytics tools

Working Style

• Low-ego, highly adaptable, comfortable with ambiguity—willing to take on both strategic and operational work

• Ability to influence and collaborate across all organizational levels, from entry-level to C-suite and board members

• Unimpeachable integrity with discretion in handling highly confidential information

• Unparalleled learning: Direct exposure to CEO decision-making, board dynamics, and company building at a critical growth stage

• Real impact: Own strategic projects that shape company trajectory, not just staff work

• Career accelerator: Chief of Staff roles are proven springboards to COO, VP, GM, or founder roles

• Mission-driven: Help reduce billions in healthcare waste and improve the system for everyone

• Competitive Compensation

• Medical, Dental, and Vision benefits

• Flexible, paid vacation policy

• Work in a flat organizational structure — direct access to Leadership