Chief of Staff

Rue Four is a generational opportunity to rethink an entire industry thats run on pen and paper: building the agentic backbone of medical practices nationwide

Our Co-founders come from the Medical and Health Economics space. Rue's Head of Engineering built marketplaces from the ground up ie. Uber Eats. We know healthcare and what it takes to build consumer grade software.

Our broader team joins us from Uber, Amazon, Doordash, Amazon, Two Sigma, Toast, Robinhood and Google.

About the Role:

We’re looking for a meticulously detailed oriented, high-impact, Chief of Staff to join our team to serve as a stunt double for the CEO. Everywhere she goes, you go.

Reporting directly to Dr. Ashley Benne, our Co-Founder and CEO, this role will enable operating across a major function or business domain to connect strategy and execution and welcomes someone who loves wearing "many hats", to join our team. This role is tailor-made for someone who thrives in ambiguity, loves solving hard problems, and can seamlessly jump into different teams to lead mission-critical projects and build the organizations strategy alongside the founders.

You’ll serve as an extension of the leadership team, driving mission-critical initiatives, shaping company strategy, and learn what it takes to build a VC-backed quickly scaling company from the ground up.

Key Responsibilities

• Lead strategic initiatives across the largest gaps in the org, learn how to build processes and
• The position blends strategy and operational oversight. Responsibilities span executive communications, driving platform innovation and adoption, and improving deal governance
• with the founders and other executive leaders to define long-term strategic goals and develop clear operational plans to achieve them
• Assist the founders in being higher leverage by accelerating their core responsibilities across sales, marketing, customers, product, engineering, talent, investors, finance, and leadership!
• Be able to zoom in on a tactical level of creating compelling presentations and zoom out into leading an ambiguous, strategic initiative.
• Quickly take on new strategic projects, fill in gaps, and execute end to end.

Why Rue Four:

We're growing at Rue Speed:

• Exponential growth: Strong product-market fit and are scaling 100x. Rue supports hundreds of practitioners, their teams and their people.
• AI-enabled operating system: Building at the forefront of medical practice and AI enablement.
• Top tier investors: We're humbled to be backed by incredible investors including Kleiner Perkins, Abstract VC, and Inspired Capital as well as angels in the longevity wellness and fintech space-to build an exceptional team of engineers and operators. A team of Ruefourians.

Why You:

You are someone with the ability to: pick up and excel at any task at hand, operate at a strategic level and tactically in-the-weeds, and move with speed while continuously defining the bar for excellence.

You bring:

• Experience as a founder or in a strategic role within a high-growth environment or consulting
• Demonstrated strong problem-solving skills
• Fast at execution
• Entrepreneurial and proactive - looking for creative ways to make the team better and improve processes and looking to take on responsibility
• Flexible, adaptable, willing to get hands dirty, collaborative
• Willingness to work in person at our office 5 days a week

Experience: Typically 5-8 years of experience in management consulting, investment banking, or high-growth tech operations.

Analytical Prowess: Ability to synthesize complex, high-level data into clear, actionable narratives for the leadership team.

• Stakeholder Management: Exceptional communication skills and emotional intelligence to act on behalf of the executive, manage confidential information, and build alignment globally.

What does Rue Speed mean

We operate with intensity because our mission demands it. At Rue Four, we bring the same mindset as the world’s top performers: focused, relentless, and always pushing to be in the top 1% of our craft. Think Albert Einsteins mamba mentality, applied to bold ideas, next-gen tech, and flawless execution. This isn’t a 9-to-5. Our team is deeply committed, often putting in 60 hours a week –not because we’re told to, but because we’re invested. We’re here to build fast, push limits, and deliver without compromise. If you thrive under pressure and want to do the most meaningful work of your career, you’ll feel right at home.

Perks & Benefits

At Rue Four, we’re committed to providing our employees with everything they need to do their best work.

Yearly Octoberfest weekend Offsite- Our Co-Founder went to med. school at TU Munich.

🍽️ Doordashed dinners

🚠 Team building events & happy hours

🌴 Annual Summer Offsites

💻 Apple equipment

Token stipend

Working with us

Rue Four is based in New York, with our full team working out of a beautiful and spacious office in Hudson Square, right by the West Side Highway.

170-200k compensation

Competitive equity, backed by top investors.

Please send your CV to jessica@joinrue.com

We're looking to hire Rue Fourians and that means hiring people who take ownership, communicate openly, have an underdog low ego mindset, and are excited to increase the pace of innovation for every Medical practice nationwide with true grit, hunger and curiosity. We encourage all candidates to apply even if your experience doesn't exactly match up to our job description. We are committed to building a diverse and inclusive workspace where everyone (regardless of age, religion, ethnicity, gender, sexual orientation, and more) feels like they belong. We look forward to hearing from you!