Chief of Staff to CTO

Machinify is a leading healthcare intelligence company with expertise across the payment continuum, delivering unmatched value, transparency, and efficiency to health plan clients across the country. Deployed by over 85 health plans, including many of the top 20, and representing more than 270 million lives, Machinify brings together a fully configurable and content-rich, AI-powered platform along with best-in-class expertise. We’re constantly reimagining what’s possible in our industry, creating disruptively simple, powerfully clear ways to maximize financial outcomes and drive down healthcare costs.

We are looking for an exceptional tech-savy Chief of Staff to our CTO. You will act as a force multiplier for the technology organization. You’ll sit at the intersection of strategy, operations, and execution, ensuring the CTO’s vision translates into clear priorities, disciplined follow-through, and measurable outcomes. You'll be the connective tissue that keeps a fast-moving engineering organization aligned and accountable.

We’re looking for someone who has operated in deeply technical environments, ideally as a prior Chief of Staff or other operational leader supporting a CTO or VP of Engineering; who can move seamlessly between a wide range of tasks/roles

What You’ll Do

**Operational Excellence & Planning**

Drive the operating rhythm of the technology organization. Own the cadence of quarterly and annual planning cycles including OKRs, budget development, headcount and workforce planning, and resource allocation. Track progress against goals, surface risks early, and ensure commitments don’t quietly drift. You’ll be the person who makes sure things actually get done; not by doing them all yourself, but by building the systems and accountability structures that keep a large technical org on track.

**Strategic Partnership & Executive Leverage**

Serve as a trusted thought partner to the CTO. Help synthesize complex information into clear recommendations, prepare the CTO for high-stakes meetings with the board, executive peers, and external stakeholders, and represent the CTO’s perspective when they can’t be in the room. You’ll draft key communications, shape narratives around technical strategy, and ensure the CTO’s time is spent on the highest-leverage activities possible.

**Cross-Functional Alignment**

Act as a bridge between engineering and the rest of the business. Coordinate with product, finance, HR, and other functions to ensure the technology organization’s plans are integrated with company-wide priorities. Facilitate decision-making across teams, resolve bottlenecks, and drive alignment on initiatives that span organizational boundaries.

**Financial Stewardship**

Partner with finance to manage the technology budget end-to-end. Build financial models, analyze trade-offs, and ensure the organization is investing wisely and operating within its means.

What You'll Bring

• Technical Fluency*** You’ve worked closely with engineering and infrastructure teams in a prior role, ideally as Chief of Staff or operational leader reporting to a CTO or VP of Engineering. You don’t need to write production code, but you are comfortable and interested in using AI tools (LLM's etc.), you can follow an architecture discussion, understand the implications of technical debt, and earn the respect of senior engineers.
  
  

Operational Rigor: You have a track record of building and running planning processes; OKRs, budgets, headcount plans, executive reviews. You know how to keep a complex organization accountable without micromanaging it.

Strategic Thinking: You can zoom out from the day-to-day and connect operational details to the bigger picture. You’ve helped shape narratives for boards, leadership offsites, or company-wide communications, and you know how to distill ambiguity into a clear point of view.

Executive Presence: You’re comfortable representing leadership in senior forums, facilitating tough conversations, and pushing back respectfully when needed. People trust your judgment and follow your lead, even without direct authority.

Communication Skills: You write clearly, present confidently, and adapt your message for the audience. Whether it’s a Slack thread to an engineering team or a memo to the CEO.

What We Offer

• Work from anywhere in the US! Machinify is digital-first.
• Top Medical/Dental/Vision offerings

Browse our curated collection of remote jobs across all categories and industries, featuring positions from top companies worldwide.

• FSA/HSA
• Tuition reimbursement
• Competitive salary, 401(k) with company match
• Unlimited PTO
• Additional health and wellness benefits and perks
• Flexible and trusting environment where you’ll feel empowered to do your best work
  
  

The salary for this position is based on an array of factors unique to each candidate: Such as years and depth of experience, set skills, certifications, etc. We are hiring for different levels, and our Recruiting team will let you know if you qualify for a different role/range. Salary is one component of the total compensation package, which includes meaningful equity, excellent healthcare, flexible time off, and other benefits and perks.

Equal Employment Opportunity at Machinify

We are committed to equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender, gender identity or expression, or veteran status. We are proud to be an equal opportunity workplace. Machinify is an employment at will employer. We participate in E-Verify as required by applicable law. In accordance with applicable state laws, we do not inquire about salary history during the recruitment process. If you require a reasonable accommodation to complete any part of the application or recruitment process, please let our recruiters know. See our Candidate Privacy Notice at: https://www.machinify.com/candidate-privacy-notice/