Chief Of Staff Jobs in Ridgefield, CT (NOW HIRING)

About TouchCare

TouchCare is a healthcare concierge service dedicated to simplifying the complexities of health insurance and the healthcare system. By assigning each member a personal assistant, TouchCare helps resolve billing issues, coordinate with providers, and save individuals time and money. Committed to providing a healthier understanding of healthcare, TouchCare makes navigating healthcare more convenient and stress-free for its users.

The Role

We are seeking a highly strategic and execution-oriented Chief of Staff to the CEO to serve as a trusted partner in driving company-wide priorities, operational excellence, and cross-functional alignment.

This role operates at the center of the business—translating vision into action, ensuring key initiatives move forward, and acting as a force multiplier for the CEO and leadership team.

You will work closely with senior leaders across Sales, Marketing, Operations, Finance, and Product to drive execution, improve communication, and scale the business effectively.

What You'll Do

Strategic Execution & Prioritization

• Partner with the CEO to define and drive key company priorities and initiatives
• Translate high-level strategy into actionable plans with clear owners, timelines, and outcomes
• Ensure alignment and accountability across leadership

Cross-Functional Leadership

• Act as a connective tissue across teams (Sales, Marketing, Ops, Finance, Client Success)
• Drive coordination on high-impact initiatives and remove blockers
• Lead special projects from concept through execution

Operational Excellence

• Build and optimize processes that improve scalability and efficiency
• Establish and track KPIs across functions; drive accountability and reporting
• Support annual planning, quarterly priorities, and ongoing business rhythms

Executive Support & Communication

• Prepare the CEO for key meetings, presentations, and decision-making
• Drive internal communications and ensure clarity across the organization
• Help manage and streamline leadership team meetings and follow-ups

0→1 & Growth Initiatives

• Support new verticals, product launches, and strategic growth opportunities
• Help build operational infrastructure for new initiatives from the ground up

Who You Are

• 5–10+ years of experience in consulting, strategy, operations, or high-growth startup environments
• Proven ability to operate in ambiguity and drive execution in fast-paced environments
• Strong business acumen with experience working cross-functionally
• Exceptional communication and stakeholder management skills
• Highly organized with strong attention to detail and follow-through
• Ability to influence without authority and drive alignment across teams
• Experience supporting senior executives or leadership teams preferred

• Experience in healthcare, benefits, HR tech, or broker-driven ecosystems
• Background in high-growth startups
• Experience building processes from scratch (0→1 environments)

What We Offer

• Competitive base salary commensurate with experience
• Opportunity to build and shape company culture from day one
• Direct impact on improving financial wellness for thousands of employees
• Flexible benefits package

Why Join Us?

• Impactful Growth: Lead the expansion of specialized services that provide critical support to members during complex life events.
• Collaborative Environment: Work closely with a supportive team across Sales, Client Success, Product, and Marketing.
• Strategic Leadership: Shape the go-to-market strategy and future evolution of TouchCare's specialized portfolio.

Compensation: The salary range for this role is $125,000–$170,000, based on experience, skills, qualifications, and alignment with the scope of the role.

Benefits: TouchCare offers a competitive benefits package, including medical, dental, vision, paid time off, parental leave, and other company-sponsored benefits.

Location & Work Environment: This role is based at our Stamford, CT headquarters and is expected to be onsite 5 days per week. Candidates must be able to reliably commute to Stamford, CT for the required onsite schedule.

TouchCare is an Equal Opportunity Employer. We are committed to building a diverse and inclusive workplace and consider all qualified applicants without regard to race, color, religion, sex, gender identity or expression, sexual orientation, national origin, age, disability, veteran status, or any other legally protected status.