Chief People Officer (hybrid)

Wellist • Boston, MA

5d • Hybrid

About The Position

Chief People Officer (Operator CPO – Hands-On Builder) Hybrid | Boston, MA At Wellist, we’re helping employers deliver the right resources at the right time—so employees can feel supported through every life moment, and HR leaders can maximize the value of their investments. As our Chief People Officer, you’ll play a mission-critical role in building the people foundation that enables Wellist’s next phase of growth. This is a hands-on operator role, responsible for personally designing and executing talent, performance, and organizational strategies as we scale to serve large employers and support more than 1 million people over the next three years. You’ll work closely with the CEO and Operating Committee, ensuring Wellist consistently has the right people in the right roles—leaders who can operate with clarity, accountability, and speed in a high-growth environment. We’re looking for a pragmatic, execution-oriented CPO who loves building from the ground up, thrives in resource-lean environments, and is excited to personally own the work—not just oversee it.

Requirements

• 10+ years of progressive people leadership experience, including time as a hands-on CPO or Head of People
• Proven success building and scaling leadership and management teams in high-growth environments
• Deep experience personally leading executive and senior-level hiring
• Comfort operating with lean teams (one direct report) and owning both strategy and execution
• Strong working knowledge of performance management, organizational design, and employee relations
• Experience operating within EOS or similar operating frameworks

Nice To Haves

• Background in HR tech, digital health, or mission-driven technology companies strongly preferred

Responsibilities

• Talent Acquisition & Operating Committee Build-Out (Top 2026 Priority)
• Personally design and execute Wellist’s talent acquisition strategy, with a strong emphasis on building and strengthening the Operating Committee and management layer.
• Partner directly with the CEO and Operating Committee members on all critical senior and management-level hires—from role definition through final offer.
• Personally support or lead direct candidate sourcing for priority roles.
• Deliver a high-velocity hiring process, with:
• ~2-week interview cycles
• Roles filled within ~60 days
• Establish and maintain rigorous hiring standards focused on capability, values alignment, and long-term leadership potential.
• Build lightweight, scalable recruiting systems that support growth without unnecessary complexity
• Onboarding, Performance & Management Effectiveness
• Design and operationalize a robust 90-day onboarding experience that drives:
• Rapid ramp-up
• Early validation of role fit
• Strong 3-month retention
• Partner closely with Operating Committee members and people managers to:
• Clarify role expectations
• Define success metrics
• Strengthen feedback and coaching rhythms
• Lead Wellist’s annual performance and development process, ensuring alignment with company priorities and accelerating leadership effectiveness.
• Ensure consistent application of Entrepreneurial Operating System (EOS) principles, reinforcing accountability, ownership, and cross-functional execution.
• Culture, Engagement & Organizational Health
• Operationalize a high-trust, high-performance culture grounded in competence, sincerity, and reliability.
• Work hands-on with leaders to ensure teams feel empowered, engaged, and supported to deliver ambitious goals.
• Continuously assess organizational health and proactively recommend changes to structure, roles, or processes as the company scales.
• People Operations & Compliance
• Oversee Wellist’s PEO partner (Genesis), ensuring smooth administration of benefits, time off, leaves, and employee lifecycle processes.
• Ensure all people practices remain compliant with local, state, and federal regulations.
• Personally manage employee relations matters with fairness, consistency, and sound judgment.
• Strategic Partnership & External Presence
• Serve as a trusted advisor to the CEO and Operating Committee on people strategy, organizational design, and workforce planning.
• Help shape Wellist’s operating and financial plans to ensure roles, resources, and KPIs align with business priorities.
• Represent Wellist within CPO and CHRO communities, strengthening the company’s people brand and supporting commercial growth as needed.

Benefits

• A meaningful mission – Help build the support system every employee deserves
• Outstanding benefits – Excellent medical, dental, life and disability coverage, generous PTO, and 401(k) contribution
• Rare impact opportunity – Personally shape the people foundation of a scaling HR Tech company
• Award-winning culture – Recognized by Fast Company, MassTLC, Rock Health, and more

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed
• Number of Employees: 11-50 employees