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.

What You'll Own

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.

What Success Looks Like

3 months in:

You've built strong trust with the CEO and Operating Committee, clarified role expectations across leadership, and are actively leading recruiting for priority senior hires. A clear onboarding and performance framework is in motion.

6 months in:

Key Operating Committee and management roles are filled with high-caliber leaders. Hiring velocity is strong, onboarding is driving early retention, and managers are operating with clearer accountability and feedback.

12 months in:

Wellist has a cohesive, high-performing Operating Committee and management team. The people systems you've built—hiring, onboarding, performance, and development—are scalable, effective, and tightly aligned with company goals.

What You Bring

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

Why Work at Wellist

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

At this time, Wellist is unable to sponsor a new applicant for employment authorization, or offer any immigration-related support for this position.

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