Chief of Staff

About Pear Suite

Pear Suite is a digital health company revolutionizing community-based care. Our care navigation platform equips staff—like community health workers and doulas—with tools to collect, visualize, and act on social determinants of health data. By supporting culturally responsive, person-centered care, we help healthcare organizations close care gaps and improve outcomes.

Job Title: Customer Success Manager

Type: Full-Time

Pay: 90-120K

Location: Remote (pacific/mountain standard timezone preferred)

Reports to: Chief Executive Officer

Essential Functions

As Pear Suite enters its next phase of growth, we’re looking for a strategic and highly organized Chief of Staff to serve as a right hand to the CEO. This high-impact role is ideal for a mission-driven operator who thrives in dynamic environments, brings clarity to ambiguity, and can seamlessly connect strategy to execution. You’ll be embedded across the organization, helping drive priority initiatives, improve internal processes, and extend the CEO’s reach across internal and external stakeholders.

Responsibilities

CEO Enablement

• Serve as a strategic thought partner and sounding board for the CEO, helping prioritize time, decisions, and communication
• Prepare briefings, presentations, memos, and internal updates to support executive decision-making
• Act as a liaison between the CEO and key stakeholders, managing inbound requests and helping triage responses

Strategic Planning & Execution

• Support CEO in defining strategic priorities, OKRs, and KPIs
• Operationalize high-priority initiatives from concept through implementation, ensuring follow-through and accountability
• Lead strategic business development initiatives, including attending and speaking at marketing events, supporting contract negotiations, and securing innovative partnerships
• Facilitate internal alignment and follow-up across leadership, ensuring teams are coordinated and outcomes-focused

Operational Excellence

• Identify opportunities to improve internal workflows, meeting cadences, and decision-making structures
• Partner with department leads to unblock bottlenecks and help scale company operations efficiently
• Own special projects that don’t cleanly sit within one department but are critical to company success
• Help shape a high-performing, mission-driven culture as we grow and scale the team

Advisory Board, Consultant, & Investor Engagement

• Coordinate meeting prep, materials, and follow-ups
• Support communications and reporting with key stakeholders
• Maintain a pulse on the market, competitors, and investor landscape to inform company positioning

Qualifications

• 4–7 years of experience in high-growth startups, management consulting, or similar strategic roles
• Deep interest and expertise in health equity, community-based care, healthcare software, digital health, and healthcare innovation
• Proven ability to lead cross-functional initiatives and manage complex projects end-to-end
• Exceptional written and verbal communication skills, with a sharp eye for detail
• Highly organized, proactive, and able to manage up, down, and across with confidence
• MBA or similar graduate degree is a plus, but not required

Benefits

• Competitive salary and performance-based bonuses.
• Health, dental, and vision insurance.
• Flexible work hours and remote work options.
• Professional development opportunities.
• A vibrant and dynamic work environment with opportunities for growth.
• Tuition reimbursement

We are an Equal Opportunity Employer - We celebrate diversity and believe it is the key to creating vibrant, healthy co