Chief of Staff (Office of the CEO)

Chief of Staff (Office of the CEO) ANNA Autism Care | (Remote) About ANNA Autism Care ANNA Autism Care is a fast-growing autism services organization committed to clinical excellence and family-centered care. We operate in a complex, regulated healthcare environment and are scaling across markets. Our vision is to create a future where every autistic child has access to comprehensive, evidence-based, and neuroaffirming care. The Opportunity This is a high-trust role sitting in the Office of the CEO. The Chief of Staff will serve as the CEO’s strategic and execution partner - a force multiplier responsible for advancing CEO-level priorities from idea to outcome. You’ll own high-priority, cross-functional initiatives, bring structure to ambiguity, and ensure follow-through across the company. The scope will evolve based on the needs of the business, but will consistently include work like: AI-enabled operational and clinical improvement, corporate development and M&A support, new market evaluation and launches, strategic procurement and vendor optimization, performance insights, and special projects requiring senior judgment and fast execution. This role is ideal for someone who wants to operate as a “mini-CEO” with long-term goals of building or running a fast-growing missional company. What You’ll Do 1) CEO Partnership & Strategic Execution Act as the CEO’s right hand to scope, drive, and close strategic priorities. Pick up initiatives directly from the CEO and own them end-to-end: framing the problem, building the plan, driving execution, and delivering a finished outcome.

Run the initiative lifecycle yourself:

define the objective and success metrics map stakeholders and dependencies design the plan + timeline drive execution across teams/vendors measure impact and lock in the new way of operating Operate as the “single threaded leader” for each initiative, working cross-functionally across the entire organization

• Hand off initiatives after they’re stable. Your job is to get the thing working in the business, then transition ownership to the right function with SOPs, metrics, and a clean operating rhythm.

2) Cross-Functional Special Projects (CEO-Level)

Lead critical projects that don’t sit cleanly in one function, such as:

clinical/operational infrastructure and tooling systems implementations/integrations (e.g., Salesforce EMR + adjacent stack) strategic initiatives to improve scale, quality, or unit economics performance improvement programs tied to CEO priorities

• Step in as “owner of last resort” when work is important, ambiguous, or stalled.

3) AI Strategy + Productization Into Operations & Clinical Work

• Identify high-impact AI use cases across operations and clinical support (e.g., scheduling/capacity, documentation assist, RCM workflows, QA, clinical enablement, training, internal knowledge).
• Lead the end-to-end lifecycle from ideation → feasibility → pilot → rollout → measurement.
• Partner with clinical leadership, ops, RCM, and technology vendors to design workflows that improve quality, speed, and consistency.
• Own vendor evaluation or build-vs-buy analysis for AI tools; manage pilots and implementation.

Establish clear KPIs to measure AI impact (clinical quality, clinician time saved, conversion/retention, RCM velocity, margin or throughput gains). 4) Corporate Development, M&A & Deal Execution Support

Build and manage the inorganic growth funnel in partnership with the CEO:

sourcing and tracking targets maintaining a live deal pipeline and prioritization logic market mapping and competitive landscape work

Support end-to-end deal execution:

diligence coordination across clinical, ops, finance, legal, HR, and RCM analysis of fit, synergies, risks, and integration needs materials for IC/board/investors timeline management and closure discipline

• Help plan early integration roadmaps and coordinate post-close execution where needed.

5) New Market Evaluation & Expansion Launches

• Evaluate and prioritize new market opportunities using structured frameworks (payer landscape, labor availability, competition, regulatory complexity, site economics).

Drive market launch planning in partnership with Ops, Clinical, and RCM:

hiring plans and clinical leadership build-out licensing, contracting, credentialing, and payer enrollment site selection / readiness (as relevant) go-live sequencing and early performance monitoring

• Ensure expansion work moves fast without sacrificing quality or compliance.

6) Strategic Procurement & Vendor/Advisor Management

Lead sourcing, evaluation, and management of high-impact vendors and advisors on behalf of the CEO:

technology/AI partners external consultants insurance brokers legal counsel (expansion + M&A) IT and operational vendors

• Run competitive processes, negotiate terms, maintain a contract calendar, and ensure renewals reflect current needs.
• Drive vendor performance accountability and cost optimization without disrupting care delivery.

7) Operating Cadence, Alignment & Organizational Feedback Loops

• Run CEO/leadership rhythm: agendas, operating reviews, all-company updates, and action tracking.
• Maintain a lightweight system so priorities don’t drop (project trackers, check-ins, escalation).

Serve as connective tissue across leadership and the broader org:

gather structured feedback from teams synthesize patterns and risks disseminate decisions and context back to the organization clearly

• Surface misalignment early and help resolve it quickly.

8) Finance, Analytics & Value-Creation Support

• You will provide the financial and analytical horsepower behind CEO initiatives, AI rollout decisions, corporate development, and market expansion.
• Build and maintain core business models tied to CEO priorities (capacity/utilization, churn, market economics, expansion ROI, deal profitability).
• Create decision-grade financial cases for major initiatives (AI pilots, vendor choices, market launches, M&A), including upside/downside scenarios and sensitivity analysis.

Own or co-own deal financial diligence and modeling, including:

quality of earnings / margin normalization revenue durability and payer-rate risk synergy modeling and integration cost curves valuation support and returns analysis (IRR/MOIC/payback)

• Develop and package investor/board reporting with a clear narrative: what changed, why it matters, and what we’re doing next.

Maintain a “single source of truth” for performance insights:

recurring dashboards variance explanations forward-looking forecasts

• Build scenario-planning tools for scaling decisions (hiring pace, geographic sequencing, AI scaling cost, RCM lag impact, pipeline conversion).
• Track realized value post-implementation for CEO initiatives, AI rollouts, market launches, and deals.

Who You Are You’re a rare blend of strategic thinker, deal-minded operator, and execution driver. Comfortable in ambiguity, you quickly get smart, form a view, and push toward outcomes. You thrive as a trusted extension of a CEO — and you want to build the future of autism care at scale. Essential Traits

• High ownership / high initiative. You take responsibility and run with goals.
• Strategic + practical. You can zoom out to direction and zoom in to execution.

Fast, structured, and reliable. You move quickly and keep details clean. Analytical and business-literate. You’re comfortable with models, diligence, and performance drivers. Systems thinker. You turn chaos into durable process where it matters. Executive communicator. Clear writing and calm, credible presence. Cross-functional airflow. You naturally build trust and momentum across teams. Qualifications 6–10+ years in Chief of Staff, BizOps, corporate development, consulting + operating roles, program leadership, or senior generalist roles or investment banking, private equity, growth equity, or corporate development backgrounds, especially with healthcare/services exposure. Strong preference for experience in healthcare services, multi-site operations, and/or regulated environments. Proven record leading complex, cross-functional initiatives end-to-end. Financial fluency: models, KPIs, diligence analysis, and investor/board materials. Strong vendor/procurement and negotiation experience. Demonstrated ability to ideate, pilot, and scale technology/AI workflow improvements. Location & Working Style Remote: Some travel required for key meetings, leadership rapport, and local market/site work. What Success Looks Like (First 6–12 Months) CEO is consistently focused on the highest-leverage strategic priorities. AI is ideated, piloted, and implemented across operations and clinical support, with measurable impact on quality, speed, and clinician experience. A clean inorganic deal funnel exists, with active target tracking, regular CEO review, and disciplined diligence/execution on priority opportunities.

New markets are evaluated and launched efficiently, including:

hiring and clinical leadership build-out licensing and regulatory readiness contracting, credentialing, and payer enrollment in partnership with RCM early-stage monitoring and stabilization

• Vendor and procurement decisions are more rigorous, cost-effective, and aligned with scaling needs.
• The organization feels more aligned: feedback flows up, decisions flow down, and cross-functional work moves faster with fewer dropped balls.
• Compensation & Benefits
• Competitive salary + performance bonus + equity
• Health insurance and 401(k) match
• Unlimited PTO
• High-impact seat with exposure to strategy, AI/product, finance, and market expansion

This is a high-intensity, high-impact role in the Office of the CEO. The pace is fast and the work is time-sensitive; candidates should be excited by periods of high commitment, including evenings / weekends during major deals, launches, or pilots. ANNA is an equal opportunity employer. We’re committed to creating a diverse, inclusive, and supportive workplace. If you’re passionate about our mission but don’t meet every qualification listed, we still encourage you to apply. Your unique perspective might be exactly what we need.