Chief Commercial Officer — Remote-First Enterprise Growth Leader

About Journey

Journey is redefining mental health care for modern companies. Our mission is to help all people live happier, healthier, less stressed lives. Traditional EAPs are reactive. Digital EAPs improved access, but still wait until someone is in crisis. Journey’s proactive approach is redefining mental health care for modern companies.

We are a rapidly growing tech startup, and we work with care and intention to create a high-performance company. We recently raised our Series A and are entering a focused growth phase.

About The Role

Member of: Executive Leadership Team

Stage: Series A | ~$8M ARR | Enterprise B2B

We’re seeking a strategic and results-driven Chief Commercial Officer to lead Sales and Marketing as Journey enters its next phase of growth.

As CCO, you’ll own Journey’s net-new revenue engine and build a unified commercial system that drives enterprise pipeline, consultant influence, market awareness, and closed revenue. This is a highly cross-functional leadership role focused on scaling Journey’s enterprise growth motion while helping sharpen and operationalize our category narrative in the market.

This is not a layer-management role. While leading and scaling the commercial organization, you’ll also stay personally involved in closing high-value enterprise opportunities. The right person is both a strategic operator and hands-on builder who’s excited to create structure, improve systems, and help win important deals.

If you thrive in fast-moving startup environments, know how to build repeatable enterprise growth systems, and want to help define the future of proactive mental health care, this is the opportunity for you.

In this job, you will:

• 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 across commercial channels
• 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. This is not a “step into a well-oiled machine” role.
• Operate with a builder mentality in a fast-moving startup environment where no task is too small and no challenge is too big

Requirements (What makes you a great fit for this role):

• Significant experience at a B2B digital health technology company selling into HR and Benefits leaders
• 10+ years of commercial leadership experience, including 4+ years leading enterprise sales or commercial organizations
• Proven success experience 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

• Culture Focused. We prioritize building a high-performance culture of top talent. At Journey, you’ll work with a team of smart, motivated, and supportive people who bring energy, care, and pride to the work every day.
• Remote First. We are a remote company. Where…