Chief Commercial Officer

About the role

Reports to: CEO
Member of: Executive Leadership Team
Stage: Series A | ~$8M ARR | Enterprise B2B

Stage

Series A | ~$8M ARR | Enterprise B2B

What makes you a great fit for this role

• Significant experience selling B2B digital health technology to HR, Benefits and enterprise people leaders
• 10+ years of commercial leadership experience, including 4+ years leading enterprise sales or commercial organizations
• Proven success helping a founder-led or early-growth company build and scale a repeatable enterprise sales motion, ideally from $5-10M ARR to $25M+ ARR
• Strong track record of closing large enterprise accounts and successfully navigating complex, multi-stakeholder sales cycles
• Experience leading enterprise Marketing, Demand Generation, and Sales Enablement functions in a complex B2B environment, including working through consultant, broker, channel, or strategic advisor relationships
• Operationally disciplined with deep expertise in forecasting, pipeline management, revenue planning, and metrics-driven decision-making
• Hands-on builder with strong executive presence, able to move seamlessly between strategy and execution while coaching teams and collaborating cross-functionally
• Deep belief in Journey’s mission and desire to make a meaningful, lasting impact on mental health in the workplace

Responsibilities

• Lead and scale Journey’s commercial organization across Sales, Consultant Relations, and Marketing
• Own Journey’s enterprise growth engine, including pipeline generation, consultant influence, market awareness, and closed revenue
• Personally lead and help close high-value enterprise opportunities as an active player-coach leader
• Develop and execute a unified go-to-market strategy that aligns Sales and Marketing around clear commercial priorities
• Oversee the Marketing team, ensuring demand generation, thought leadership, category creation, and sales enablement are tightly aligned with the commercial strategy
• Collaborate closely with the CEO and leadership team on commercial strategy, growth planning, and market positioning
• Build a repeatable commercial operating system, including pipeline management, account prioritization, cross-functional execution, and scalable processes

Benefits

• Culture Focused
• Remote First
• Stock Options
• Medical, Dental & Vision Insurance
• Unlimited PTO
• Parental Leave
• Productivity Stipend
• Learning and Development
• Journey’s Proactive Employee Assistance Program
• Compensation

Pay

$200k-$350k base and a target bonus of $200k-$350k ($500k-$700k OTE) plus equity. Compensation may vary based on skills, experience, and location.

Schedule

Full-time