Senior Director, Enterprise Sales

This is a fully remote position, open to applicants in United States.

📋 Description

• Lead a small team of Enterprise Account Executives focused on selling to employers with over 5,000 employees.

• Take ownership of the team’s revenue outcomes, pipeline development, and sales personnel growth.

• Assist AEs in constructing and closing seven-figure deals within a complex employer benefits landscape.

• Convert revenue objectives into account priorities and pipeline strategies for each AE.

• Create and evaluate strategies, including consultant introductions, executive outreach, customer referrals, targeted events, and campaigns aimed at employers.

• Implement scalable strategies that yield qualified sales opportunities.

• Utilize weekly coaching sessions, call evaluations, and account planning to enhance discovery, prospecting, executive engagement, and negotiation skills.

• Recruit top-tier sales professionals, establish clear expectations, and address any performance deficiencies.

• Mentor sellers in cultivating champions, engaging decision-makers across Benefits, HR, Finance, and Procurement, developing business cases, and executing mutual action plans.

• Participate in crucial customer discussions while ensuring accountability among AEs.

• Assist sellers as they collaborate with brokers and consultants, align with budget and renewal cycles, and navigate existing relationships, competing priorities, and implementation needs.

• Collaborate with Strategic Alliances and Clinical Sales to further sales opportunities.

• Assess pipeline integrity, buyer commitments, potential deal risks, and closing timelines.

• Maintain a reliable sales forecast and address any coverage gaps or stalled deals.

• Integrate approved AI tools into research, prospecting, meeting preparation, and coaching processes.

• Analyze the impact of AI on sales quality and performance outcomes.

• Ensure the team maintains accurate and relevant communication with customers.

• Achieve the team’s annual revenue goals and quarterly targets.

• Propel broad quota achievement, build a qualified sales pipeline, deliver dependable forecasts, and enhance conversion rates through critical deal phases.

• Contribute to a company-wide Revenue AI roadmap linked to pipeline, NRR, and cost-to-serve metrics.

• Navigate an AI-driven ABX outbound strategy to secure account-level agents.

• Facilitate the transition of the Revenue operating model from human-driven to AI-driven workflows where suitable.

• Incorporate AI proficiency into hiring practices, career pathways, onboarding, and performance frameworks throughout the Revenue team.

• Establish cross-functional accountability for AI initiatives across Revenue, Product, and Finance.

⛳️ Requirements

• A minimum of 10 years of sales experience, including at least 5 years in a senior leadership capacity.

• Proven track record of leading a frontline enterprise sales team to meet quotas, with success distributed among multiple sales personnel.

• Experience in coaching and closing seven-figure contracts involving various stakeholders, executive approvals, and complex procurement processes.

• Direct experience in selling employer benefits solutions.

• Solid understanding of the influence of consultants and brokers, employer buying cycles, and decisions regarding benefits funding.

• Evidence of developing repeatable pipeline strategies and articulating how qualified opportunities were generated, converted, and what changes occurred.

• A hands-on approach to coaching, deal strategy, forecasting, and managing performance.

• Practical experience utilizing AI to enhance team workflows.

• Ability to thoughtfully employ AI tools, apply human judgment to AI outcomes, and foster AI fluency.

🏝️ Benefits

• Health, Dental, and Vision benefits commence on your first day.

• One Medical accounts provided.

• HSA and FSA plans available, with Spring contributing up to $1,000 for HSAs, depending on the plan type.

• Employer-sponsored 401(k) matching up to 2%.

• Annual 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 of service.

• Access to Noom for wellness support.

• Fertility care assistance through Carrot, plus reimbursement of up to $4,000 for related fertility expenses.

• Access to Wellhub for fitness, mindfulness, nutrition, and sleep resources.

• Access to BrightHorizons for sponsored childcare, back-up care, and elder care services.

• Up to $1,000 per year for Professional Development Reimbursement.

• $200 per year for donation matching.

• Equity offerings included.

• Commission opportunities available.

• Flexible remote work arrangements.

• Occasional travel required for in-person customer meetings and team events.