Senior Director, Chief of Staff

Boulder Care

15h • Remote

About The Position

The Senior Director, Chief of Staff is part of Boulder’s senior leadership team. This role is a force multiplier for the executive team—ensuring clarity, alignment, and disciplined execution as Boulder scales its impact. The Chief of Staff is a high-impact and deeply trusted leader, operating across growth, strategy, finance, operations, and culture. You’ll help translate vision into action, serve as connective tissue across the organization, and act as a confidant and thought partner to execute the priorities of the CEO and COO. This is a unique opportunity to shape the growth of a mission-driven healthcare company while amplifying the effectiveness of its leadership.

Requirements

• 8+ years of professional experience, with 3+ in a people leadership role within a startup, ideally in a growth, operations, or strategy role
• Proven ability to lead cross-functional initiatives in dynamic, fast-paced environments
• Exceptional communication skills—written, verbal, and interpersonal
• Trusted advisor mindset, with discretion, judgment, and empathy
• Deep passion for Boulder’s mission and commitment to improving health outcomes
• Applicants must be authorized to work for any employer in the U.S. We are unable to sponsor or take over sponsorship of an employment visa at this time

Nice To Haves

• A Master of Business Administration degree

Responsibilities

• Translate the company vision into clear, actionable plans, supporting leaders in planning, communication, and implementation
• Lead organizational goal-setting and OKR processes, ensuring buy-in and alignment across departments
• Spot gaps, risks, and redundancies early—and drive solutions
• Using data dashboards and senior leadership operating rhythms, ensure disciplined execution against Boulder’s key performance metrics
• Act as a trusted proxy for the CEO and COO in critical internal and external meetings
• Ensure seamless communication across the executive team, board, and broader organization
• Help translate company performance into board and market-facing materials with compelling storytelling and data
• Handle sensitive updates (organizational changes, legal and financial reports, etc.) with discretion, using excellent judgment about how information is cascaded
• Support CEO and COO in preparing for external thought leadership opportunities including media interviews and speaking engagements
• Build alignment and influence across teams without relying on formal authority
• Support executive hiring, onboarding, and leadership development
• Implement systems that improve decision-making, accountability, and collaboration
• Ensure leadership time is focused on the highest-value activities
• Act as an extension to the Office of the CEO where leadership influence is most needed
• Lead, coach, and develop the Office of the CEO team members

Benefits

• Contribution to meaningful, life-saving work!
• Comprehensive medical, dental, vision, and short-term disability benefits designed to take care of our employees and their families
• Mental Health Services via insurance coverage, including Talkspace, and EAP for continuous care
• 4 weeks of vacation accrued per calendar year with a tenured increase to 5 weeks at 2 years of employment
• Sick leave accrued at 1 hr for every 30 hrs paid
• 9 Paid Holidays per year
• 12 weeks of 100% paid parental leave for the birth or adoption of a child (after 6 months of employment)
• 401(k) retirement savings
• Remote-friendly with hardware provided to complete your work duties

What This Job Offers

• Job Type: Full-time
• Career Level: Senior