Senior Director, Enterprise Sales

Spring Health

. Lead a small team of Enterprise Account Executives selling to employers with 5,000+ employees .

Posted 11/5/2026full-timeRemote • United StatesSenior💰 $188,000 - $216,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates extensive experience in leading enterprise sales teams, driving revenue growth through strategic pipeline management, and leveraging AI tools to enhance sales processes. Proven ability to coach sellers in complex negotiations and build strong relationships with key stakeholders across various departments.

Highest-signal resume keywords

Enterprise Sales LeadershipSeven-Figure Contract NegotiationPipeline Strategy DevelopmentAI Tool IntegrationEmployer Benefits Solutions

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Sales StrategyRevenue ForecastingPerformance ManagementNegotiationAccount PlanningCoachingStakeholder EngagementDeal StrategyPipeline CreationQuota Attainment

Soft Skills

Team LeadershipCommunicationCoachingProblem-SolvingAccountability

Tools & Technologies

AI ToolsCRM SoftwareSales Analytics PlatformsForecasting ToolsPerformance Management Systems

Industry Keywords

Employer BenefitsConsultant InfluenceBroker RelationshipsBuying CyclesBenefits Funding Decisions

About the role

Key responsibilities & impact

Lead a small team of Enterprise Account Executives selling to employers with 5,000+ employees
Own the team’s revenue results, pipeline creation, and seller development
Help AEs build and close seven-figure opportunities in a complex employer benefits market
Translate revenue goals into account priorities and pipeline plans for each AE
Develop and test strategies including consultant introductions, executive outreach, customer referrals, targeted events, and employer-focused campaigns
Scale strategies 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
Coach sellers to build champions, engage decision-makers across Benefits, HR, Finance, and Procurement, establish business cases, and execute mutual action plans
Join critical customer conversations while keeping AEs accountable
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 address coverage gaps and stalled opportunities
Embed approved AI tools into research, prospecting, meeting preparation, and coaching
Evaluate AI impact on selling quality and results
Hold the team accountable for accurate, relevant customer communication
Deliver the team’s annual revenue target and quarterly milestones
Drive broad quota attainment, qualified pipeline, reliable forecasts, and stronger conversion through critical deal stages
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
Integrate AI fluency into hiring, career ladders, onboarding, and performance frameworks across Revenue
Build cross-functional AI accountability across Revenue, Product, and Finance

Requirements

What you’ll need

Minimum of 10 years of experience in sales, with 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
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 changed
Hands-on approach to coaching, deal strategy, forecasting, and performance management
Practical use of AI to improve team workflows
Ability to use AI tools thoughtfully, apply human judgment to AI outputs, and build AI fluency

Benefits

Comp & perks

Health, Dental, Vision benefits start on your first day
One Medical accounts
HSA and FSA plans, with Spring contributing up to $1K for HSAs, depending on plan type
Employer sponsored 401(k) match of up to 2%
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
Parental leave of 18 weeks for birthing parents and 16 weeks for non-birthing parents after 6 months tenure
Access to Noom
Fertility care support through Carrot, in addition to $4,000 reimbursement for related fertility expenses
Access to Wellhub for fitness, mindfulness, nutrition, and sleep
Access to BrightHorizons for sponsored child care, back-up care, and elder care
Up to $1,000 Professional Development Reimbursement a year
$200 per year donation matching
Offers Equity
Offers Commission
Remote work arrangement
Occasional travel for in-person customer meetings and team events