[Hiring] Senior Director, Enterprise Sales @Spring Health

Role Description

Reporting to the SVP of Sales, you will lead a small team of Enterprise Account Executives selling to employers with 5,000+ employees. You will own the team’s revenue results, pipeline creation, and seller development, helping AEs build and close seven-figure opportunities in a complex employer benefits market. This is a hands-on frontline leadership role. You will coach sellers, help create access to priority accounts, engage customer executives, and bring discipline to deal execution and forecasting. This is a full-time, remote opportunity. Occasional travel is required for in-person customer meetings and team events.

What you’ll do:

• Translate revenue goals into account priorities and pipeline plans for each AE.
• Develop and test creative strategies—including consultant introductions, executive outreach, customer referrals, targeted events, and campaigns tied to employer needs and buying windows.
• Scale what produces 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 conversations while keeping the AE accountable for the opportunity.
• Help sellers work effectively 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.

What success looks like in this role:

• Delivering the team’s annual revenue target and agreed quarterly milestones.
• Broad quota attainment across the team.
• Sufficient qualified pipeline for current and future periods, grounded in actual conversion rates and buying timelines.
• Reliable forecasts and stronger conversion through critical deal stages.

How you’ll use AI in this role:

• 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 Revenue operating model from human-initiated to AI-initiated workflows where appropriate.
• Integrates AI fluency into hiring, career ladders, onboarding, and performance frameworks across Revenue.
• Builds cross-functional AI accountability: Revenue, Product, and Finance share AI impact metrics.

Qualifications

• Minimum of 10 years of experience in sales, with at least 5 years in a senior leadership role.
• A 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 that you have built repeatable pipeline strategies and can explain what generated qualified opportunities, what converted, and what you changed.
• A hands-on approach to coaching, deal strategy, forecasting, and performance management, including practical use of AI to improve how your team works.

Benefits

• Health, Dental, Vision benefits start on your first day at Spring.
• You and your dependents also receive access to One Medical accounts.
• HSA and FSA plans are also available, with Spring contributing up to $1K for HSAs, depending on your plan type.
• Employer sponsored 401(k) match of up to 2% for retirement planning.
• A yearly allotment of no cost visits to the Spring Health network of therapists, coaches, and medication management providers for you and your dependents.
• Competitive paid time off policies including vacation, sick leave, and company holidays.
• At 6 months tenure with Spring, parental leave of 18 weeks for birthing parents and 16 weeks for non-birthing parents.
• Access to Noom, a weight management program tailored to your unique needs and goals.
• Access to fertility care support through Carrot, in addition to $4,000 reimbursement for related fertility expenses.
• Access to Wellhub, which connects employees to the best options for fitness, mindfulness, nutrition, and sleep in one subscription.
• Access to BrightHorizons, which provides sponsored child care, back-up care, and elder care.
• Up to $1,000 Professional Development Reimbursement a year.
• $200 per year donation matching to support your favorite causes.