Job Details

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 strategiesas 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.