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Chief of Staff
In Person, New York City
Full Time
Advanced Experience
Reports to the CEO
Operations Strategy
Legal, Finance & Admin
People & Recruiting
Business Development & Partnerships
Implementation & Onboarding
Workforce Management
Risk & Compliance
What is Rima
Rima's mission is to improve population health by building technology that makes using health plans easy. We see a world where it is possible to reduce the economic burden of healthcare on employees and employers while improving the quality of care. This is both a moral imperative and a business opportunity.
Rima is building an agentic navigation platform for self-funded employer health plans. Our agent will meet employees wherever they already are, answers questions about their plan accurately, and help them get to the right care before costly decisions are made. Today we support 25,000+ members, and we’re building toward intercepting and preventing avoidable costs for the employers who pay for their care.
We’re a small, fast-moving team based in NYC and New Orleans. We are all in.
We’re looking for a Chief of Staff who can turn company priorities into completed work, maintain a high standard of excellence across the organization, keep Rima running day to day, and build the systems that enable us to operate at a world-class level.
You’ll work closely with the CEO and leadership team to improve team accountability, run our planning process, create visibility into performance, coordinate timelines, and master the art of follow-through. You'll own the systems behind how the company plans, meets, decides, measures, gathers, and executes. You'll build the processes and systems to make excellence the default. You’ll also own business operations and serve as the CEO’s right hand on the company’s most important projects.
This role is for someone who is extremely organized and is as comfortable facilitating a tense leadership discussion as chasing down a missed commitment. You should enjoy making an organization more effective through first principles thinking, ruthless prioritization, practical processes, and consistent execution.
Minimum Qualifications
Uses AI tools daily and keeps up with how they’re evolving. Fluent in Notion and Slack.
Demonstrated ownership of business operations, cross-functional programs, or an operational executive role.
Experience running a planning or OKR process and the recurring processes that support it.
Experience turning ambiguous priorities into plans and following them through to completion.
Experience defining KPIs and building reporting that leaders actually use.
Ability to hold executives accountable and influence execution without relying on direct reporting authority.
Clear writing, sound judgment, discretion, and close attention to detail.
Willingness to personally handle recurring operational work while improving how it gets done.
4+ years of experience in operations, strategy, or a similar role, including time spent working directly with senior leadership.
Experience facilitating leadership meetings and working through disagreement to a clear decision.
Strong analytical skills and comfort working hands-on with data in spreadsheets or BI tools.
Nice to have
Experience at an early-stage startup, ideally one that grew through a period of rapid scaling.
Familiarity with self-funded health plans, employee benefits, insurance, payroll, or another regulated industry.
Has built AI agents or automated workflows that a team relies on day to day.
Prior experience as a founder, management consultant, or Chief of Staff.
Experience preparing board materials or investor updates.
Experience managing outside advisors, vendors, and contracts, such as legal counsel or accounting firms.
What you'll do
Planning, OKRs, and KPIs
Run quarterly OKR planning, monthly priority setting, and weekly execution reviews.
Help leaders turn company goals into measurable outcomes, clear owners, and realistic deadlines.
Partner with functional leaders to define core KPIs, then own establishing reliable data sources and maintaining a consistent reporting cadence.
Run the leadership team meeting cadence: agendas, pre-reads, a running log of decisions and owners, and regular reviews of where we’re falling short.
Accountability and project management
Make decisions stick: document the decision, owner, deadline, and dependencies, then follow through until implementation is complete.
Set the standards for how projects, sprints, and tasks are run across teams.
Identify slipping work and resolve blockers with the responsible teams.
Bring competing priorities and resource constraints to the CEO with clear options and recommendations.
CEO partnership
Act as the CEO’s right hand: prepare board meetings and investor updates, run special projects, and represent the CEO in meetings when needed.
Turn CEO priorities into delegated work with clear owners, and make sure nothing the CEO commits to falls through the cracks.
Organization, process and operations improvements
Turn process audits into a prioritized improvement plan and drive implementation.
Document recurring workflows as SOPs and reusable AI workflows, then hand each one to an owner with backup coverage.
Build practical automation, including AI agents, that reduces manual work.
Investigate bottlenecks and recurring execution failures, recommend changes, and measure whether those changes worked.
Logistics and events
Own operational readiness for new hires: coordinate onboarding, equipment, access, and documentation so people can contribute quickly.
Own travel, office space, equipment, and internal events such as offsites, onsites, and customer visits. You’ll set the standard, then delegate execution to tools, vendors, or teammates.
What success looks like in your first 90 days
Leadership has a functioning OKR and priorities cadence, with visible progress and early escalation of risks.
Leadership team meetings run on schedule with pre-reads, a maintained decision log, and tracked follow-ups.
Core KPIs have agreed definitions and a dependable reporting cadence.
The highest-priority process gaps have been addressed, and recurring workflows have documented procedures and owners.
The founders spend less time chasing updates and resolving preventable issues.
The company feels organized.
How we work
Love and excellence. We are competing to win at the highest level, and maintain an extremely high bar of performance without losing the humanity that makes us who we are.
Cross-functional collaboration. You work directly with executives and organization leaders to deliver outcomes.
High ownership. You own outcomes end to end, even when you delegate the execution. No “not my problem.”
Crisp communication. You communicate in a way that helps the team act on the right things.
Fast iteration. We ship incrementally, learn from mistakes, and improve rapidly.
Process in service of results. We build process to ship better work faster, and we cut process that doesn’t consistently earn its keep.
Why work at Rima
Real impact, fast. You'll own high-impact work that the company depends on.
Ownership. You own problems end to end, with direct access to the CEO and leadership team and the trust to drive change across the company.
Work with excellent people. Small team, high trust, direct communication. We care about results, not politics.
Learn rapidly. You will wear many hats and be expected to figure things out all the time.
Competitive Comp and Benefits. Base salary range $145,000-$190,000 depending on experience, plus a meaningful equity package, flexible PTO, health insurance, dental, vision, and more.