Senior Director, Enterprise Sales

Spring Health • New York, NY

11h • Remote

About The Position

Spring Health is seeking a hands-on frontline sales leader to lead a small team of Enterprise Account Executives selling to employers with 5,000 or more employees. Reporting to the SVP of Sales, this role owns the team’s revenue results, pipeline creation, and seller development, including helping account executives build and close seven-figure opportunities in a complex employer benefits market. The position is full-time and remote, with occasional travel for in-person customer meetings and team events.

The leader will translate revenue goals into account priorities and pipeline plans, develop repeatable opportunity-generation strategies, coach and develop sellers, support executive-level customer engagement, and improve deal execution and forecasting. The role also advances the use of approved AI tools in sales workflows and contributes to a function-wide Revenue AI roadmap and cross-functional AI accountability.

Spring Health is a global mental health company whose AI-native platform provides personalized support through self-guided tools, coaching, therapy, medication management, and specialty care. The company expects team members to use AI thoughtfully, apply human judgment to AI outputs, and build AI fluency in support of their roles and the company’s mission.

Requirements

• At least 10 years of sales experience, including at least 5 years in a senior leadership role.
• Demonstrated record of leading a frontline enterprise sales team to quota, with success distributed across multiple sellers.
• Experience coaching and closing seven-figure contracts involving multiple stakeholders, executive approval, and complex procurement.
• Direct experience selling employer benefits solutions, with a working understanding of consultant and broker influence, employer buying cycles, and benefits funding decisions.
• Evidence of building repeatable pipeline strategies and explaining what generated qualified opportunities, what converted, and what was changed.
• Hands-on approach to coaching, deal strategy, forecasting, and performance management, including practical use of AI to improve team workflows.

Responsibilities

• Translate revenue goals into account priorities and pipeline plans for each Enterprise Account Executive.
• Develop and test opportunity-generation strategies, including consultant introductions, executive outreach, customer referrals, targeted events, and campaigns aligned with employer needs and buying windows; scale approaches that produce qualified opportunities.
• Use weekly coaching, call reviews, and account planning to improve discovery, prospecting, executive engagement, and negotiation.
• Hire strong sellers, set clear expectations, and address performance gaps directly.
• Coach sellers to build champions, engage decision-makers across Benefits, HR, Finance, and Procurement, establish a compelling business case, and execute mutual action plans.
• Join critical customer conversations while keeping the account executive accountable for the opportunity.
• Help sellers work with brokers and consultants, align to budget and renewal cycles, and address incumbent relationships, competing priorities, and implementation requirements.
• Partner with Strategic Alliances and Clinical Sales to advance opportunities.
• Inspect pipeline quality, buyer commitments, deal risks, and close timing; maintain a credible forecast and act early on coverage gaps and stalled opportunities.
• Embed approved AI tools into research, prospecting, meeting preparation, and coaching; evaluate their impact on selling quality and results, and hold the team accountable for accurate, relevant customer communication.
• Help drive a function-wide Revenue AI roadmap tied to pipeline, NRR, and cost-to-serve outcomes.
• Navigate AI-led ABX outbound strategy to ensure account-level agents.
• Help shift the Revenue operating model from human-initiated to AI-initiated workflows where appropriate.
• Integrate AI fluency into hiring, career ladders, onboarding, and performance frameworks across Revenue.
• Build cross-functional AI accountability so Revenue, Product, and Finance share AI impact metrics.
• Deliver the team’s annual revenue target and agreed quarterly milestones, support broad quota attainment, maintain sufficient qualified pipeline, and improve forecast reliability and conversion through critical deal stages.

Benefits

• Health, dental, and vision benefits beginning on the first day.
• One Medical accounts for employees and dependents.
• HSA and FSA plans, with Spring contributing up to $1,000 to HSAs depending on plan type.
• Employer-sponsored 401(k) match of up to 2%.
• Yearly allotment of no-cost visits to Spring Health therapists, coaches, and medication management providers for employees and dependents.
• Paid time off policies including vacation, sick leave, and company holidays.
• Parental leave after six months of tenure: 18 weeks for birthing parents and 16 weeks for non-birthing parents.
• Access to Noom, a psychology-based weight management program.
• Fertility care support through Carrot, plus up to $4,000 reimbursement for related fertility expenses.
• Access to Wellhub for fitness, mindfulness, nutrition, and sleep options.
• Access to BrightHorizons sponsored child care, backup care, and elder care.
• Up to $1,000 per year in professional development reimbursement.
• $200 per year in donation matching.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed