Chief of Staff

About AKASA

At AKASA, our mission is to build the future of healthcare with AI. As the leading provider of generative AI solutions for the healthcare revenue cycle, we help health systems comprehensively capture and communicate the full patient clinical journey. By empowering health systems to streamline their operations, they can focus on what matters most - delivering quality patient care. We have raised over $205M in funding from investors such as Andreessen Horowitz, BOND, and Costanoa Ventures.

This is the most exciting time to join AKASA. Revenue bookings for our new AI-native product suite have grown over 20x since launching in 2024. In this time, we have broken our record for the largest deal in company history three times consecutively. This growth is driven by the massive improvement we are generating for our customers across clinical quality and documentation accuracy, both top priority areas for health system leaders.

Our deployments have been recognized nationally as "one of the most comprehensive real-world uses of GenAI in healthcare finance to date" (link). Our customer base represents more than $120B+ in net patient revenue and includes the most innovative health systems in the country, like Cleveland Clinic, Duke, Stanford, and Johns Hopkins.

Some of our recent recognitions include being named one of America's Top Startup Employers 2026 by Forbes, #1 most promising healthcare RCM startup of 2025 by Black Book Market Research, and one of the fastest-growing GenAI startups to watch by AIM Research. Our CEO was ranked among the “Top 50 Healthcare Technology CEOs” by the Healthcare Technology Report, and we have been certified as a “Great Place to Work” for the past 6 years in a row.

We’re building on this momentum to redefine what’s possible in healthcare. We’re looking for exceptional people to help us accelerate that reality.

AKASA is looking for an exceptional Chief of Staff to report directly to the COO and serve as a strategic partner and force multiplier to the broader executive leadership team. This is a highly visible, high-impact role that sits at the intersection of strategy, operations, and execution. You will work directly alongside the COO and CEO on the company’s most consequential priorities, helping translate vision into aligned action across a fast-moving organization.

We’re looking for someone with serious horsepower — sharp strategic thinking, strong business acumen, and the drive to move mountains. You should be deeply passionate about AI: already using it extensively in your day-to-day work and eager to help drive AKASA’s continued evolution toward truly AI-native operations. The ideal candidate is on a COO or similar strategy leadership trajectory, and wants to accelerate that path by operating at the center of a high-growth AI company transforming one of the largest industries in the world.

This role is based in New York or San Francisco.

• Serve as a thought partner and right hand to the COO and CEO — helping set priorities, structure decisions, and ensure the most important work moves forward with clarity and accountability

• Lead high-priority strategic and operational initiatives from inception through execution, spanning multiple functions across the organization

• Synthesize complex information — from market dynamics to internal performance data — into crisp analyses, decision memos, and executive-ready materials

• Identify and remove organizational roadblocks, process bottlenecks, and cross-functional misalignments before they escalate

• Act as a force multiplier for executive bandwidth: keep leadership focused on the highest-impact areas and ensure nothing critical falls through the cracks

• Drive special projects. For example: competitive strategy, product bundling analysis, partnership evaluation, organizational design, and operational scaling

• Represent the COO’s voice and priorities in meetings and workstreams across the company

• 7+ years of professional experience with a demonstrated track record of exceptional performance and rapid advancement

• Deep strategic and analytical horsepower — ability to structure ambiguous problems, synthesize complexity, and develop crisp recommendations

• Genuine passion for AI, with hands-on experience using AI tools extensively in your work; you’re not just AI-curious, you’re already operating differently because of it

• Strong business acumen with working knowledge of healthcare — ideally healthcare provider operations, health IT, or healthcare AI

• Extraordinary execution orientation: you don’t just advise, you get things done

• Outstanding written and verbal communication; you can turn a half-formed idea into a polished memo without hand-holding

• Proven ability to influence cross-functionally without direct authority and build trust quickly at all levels

We’d love to see one or more of:

• 4–6 years in healthcare-focused investment banking, private equity or consulting, ideally followed by an operating role

• MBA from a top-tier program with 2–5 years of post-MBA operating experience

• Fast progression at a leading technology company (Anthropic, OpenAI, Google, Meta, Amazon, or similar) with ambitions to step into a COO or similar role

• Current or recent COO, CEO, or founder of an early-stage AI or technology company looking for a larger stage

• Flexible paid time off (PTO)

• Expansive coverage for health, dental, and vision

• Employer contribution to Health Savings Accounts (HSA)

• Generous parental leave policy

• Full employee coverage for life insurance

• Home office stipend

• Cell phone/internet reimbursement

• Commuting benefits

• Company-paid holidays

• 401(K) plan

• Based on geo, market data, and other factors, the salary range for this position is $200,000–$240,000 + Equity. However, a salary higher or lower than this range may be appropriate for a candidate whose qualifications differ meaningfully from those listed in the job description.

The above represents the expected salary range for this job requisition. Ultimately, in determining your pay, we’ll consider your location, experience, and other job-related factors.

We’re committed to doing the best work of our lives, together. Come see if we're the right team for you.

AKASA is a proud equal opportunity employer and we believe that a diverse and inclusive workforce is an imperative. We welcome people of different backgrounds, genders, races, ethnicities, abilities, sexual orientations, and perspectives, just to name a few. We do not discriminate based upon any protected class and we encourage candidates of all identities and backgrounds to apply. AKASA considers qualified applicants regardless of criminal histories in accordance with the San Francisco Fair Chance Ordinance.

AKASA is committed to providing reasonable accommodations for candidates with disabilities in our recruiting process. If you need any assistance or accommodations due to a disability, please let us know at [email protected].