Head of Commercial

Summary

Join Journey, a leading proactive mental health solution provider, as their SVP, Head of Commercial. This pivotal role involves leading Sales, Consultant Relations, and Partnerships, owning all net-new revenue. You will build and scale the Commercial function, while personally closing high-value enterprise deals. Success requires exceeding revenue goals, strengthening consultant relationships, and executing a unified commercial strategy. Collaboration with other leaders is key to creating a seamless prospect-to-client experience. This is a high-impact role for a results-driven leader who thrives in fast-paced environments.

Requirements

• Significant experience at a B2B digital health tech company selling to HR and Benefits leaders
• Proven track record of scaling revenue from early rapid growth to $50–100M+ in ARR
• Experience closing large enterprise accounts and navigating complex sales cycles
• 10+ years of sales leadership experience across enterprise sales, consultant relations, and partnerships
• Strong background building and leading multi-functional commercial teams
• Ability to shift between executive strategy and tactical execution with ease
• Scrappy, hands-on leader who’s eager to build alongside the team, not just manage from above
• Operational discipline: skilled in forecasting, pipeline management, and metrics-driven decision making
• Excellent communicator, coach, and cross-functional collaborator
• Deep belief in the mission and a desire to make a lasting impact on mental health in the workplace

Responsibilities

• Lead and grow the direct Sales Team to consistently exceed revenue goals
• Oversee the Consultant Relations Team, strengthening relationships with key benefits consultants and strategic advisors
• Develop and execute a unified commercial strategy across Sales, Consultant Relations, and Partnerships
• Personally manage and close high-value enterprise opportunities from first touch through signed contract
• Refine and manage the entire sales process — from lead handoff (SDRs/Marketing) through close and implementation (Customer Success)
• Set performance targets, implement KPIs, and continuously improve sales operations and enablement
• Collaborate with the CEO and senior leadership team on forecasting, planning, and strategic initiatives
• Work cross-functionally with Growth and Customer Success leaders to create a seamless prospect-to-client experience
• Build foundational systems, messaging, and team processes — this isn’t a “step into a well-oiled machine” role

Benefits

• Remote First . We are a remote company. Where you live is where we are located
• Stock Options . We encourage an ownership mindset by giving full-time employees the opportunity to share in the success of Journey
• Medical, Dental & Vision Insurance. Journey contributes 100% of the medical insurance premium for the employee, provided through Aetna
• Unlimited PTO. We trust you to do what is necessary to get your job done while maintaining a healthy work/life harmony. We offer unlimited time off and encourage you to take it
• Parental Leave. 10 weeks of fully paid parental leave for birthing, non-birthing, and adoptive parents is available after one year of employment. Journey also offers paid leave for pregnancy loss as well as travel reimbursement for safe and legal abortion access
• Wisdom Money. Team members receive $1,000 per year to spend on personal development activities, such as meditation classes and retreats, as they see fit
• Productivity Stipend. Team members receive $1,000 to spend on co-working spaces, a new desk chair, or whatever they need to make their work environment more comfortable
• Learning and Development. Journey is invested in your continuous growth. Each year, team members are eligible for up to $500 to spend on professional development opportunities of their choosing
• Journey’s Proactive Employee Assistance Program. Of course, team members and their loved ones have access to Journey Proactive EAP, our proactive mental health solution to stay happy, healthy, and mentally and emotionally fit
• Compensation. The salary range is $200–300K base + $100–300K bonus ($300–600K OTE) + equity. Compensation may vary based on skills, experience, and location