deaa6ad2-d184-436b-b69e-17f761da1d94 - Jumbo Enterprise Account Executive
Requirements
• 8+ years of quota-carrying enterprise sales experience, with a track record of closing 6- and 7-figure deals against target. • You build your own pipeline. When a deal stalls, you treat it as a problem to solve, not a reason to wait for direction. • You engage with pushback instead of defending your original read. When new information contradicts your plan, you update it. • You seek out feedback proactively. • You can independently build and defend a business case, not just explain product features. • Sharp and resourceful. You bring solutions, not just problems, and you can articulate the counter-argument to your own deal strategy before it's raised. • You use AI tools daily to work more efficiently. • Direct communicator who adjusts to the audience in the room, whether that's a CFO, a CHRO, or a broker. • Comfortable with ambiguity and building structure where none exists yet. • You are always learning, staying close to what the top reps across the team are doing, reviewing lost deals for what to do differently next time, etc. • Willingness to travel ~20% for closing activity and industry events. • Benefits, health insurance, or healthcare sales experience. • Existing relationships with brokers or benefits consultants. • Experience selling into HR or People leadership specifically. • Note: We have even more benefits than listed here https://www.springhealth.com/careers#:~:text=Our%20perks%20%26%20benefits and below, your recruiter will provide more in-depth information as you continue in the interview process. Benefits are subject to individual plan requirements and eligibility criteria. • Health, Dental, Vision benefits start on your first day at Spring. You and your dependents also receive access to One Medical https://www.onemedical.com/membership/ 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. • We offer competitive paid time off policies including vacation, sick leave and company holidays. • At 6 months tenure with Spring, we offer parental leave of 18 weeks for birthing parents and 16 weeks for non-birthing parents. • Access to Noom https://www.noom.com/, a weight management program—based in psychology, that’s tailored to your unique needs and goals. • Access to fertility care support through Carrot https://springhealth.link/jd-2023-07-carrotbenefit, in addition to $4,000 reimbursement for related fertility expenses. • Access to Wellhub https://springhealth.link/jd-2023-07-gympassbenefit, which connects employees to the best options for fitness, mindfulness, nutrition, and sleep in one subscription • Access to BrightHorizons https://www.brighthorizons.com/, 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. • Not sure if you meet every requirement? Research shows https://pubsonline.informs.org/doi/10.1287/mnsc.2023.4907 that women and people from historically underrepresented communities often hesitate to apply for roles unless they meet every qualification compared to other similarly-qualified candidates. At Spring Health, we are committed to fostering a workplace where everyone feels valued, empowered, and supported to Thrive https://www.springhealth.com/careers. If this role excites you, we encourage you to apply. • Our privacy policy: https://springhealth.com/privacy-policy/
Responsibilities
• Run the full sales cycle into HR, Benefits, and People leaders at large enterprises in your territory, from discovery through negotiation to close. • Self-generate pipeline through brokers, consultants, referrals, and dormant accounts, not just BDR handoff. If a deal thread breaks, you build the next one. • Engage target accounts before a formal RFP process begins, and multi-thread relationships across the full buying committee. • Prioritize the accounts that matter most in your territory, aligned to the GTM strategy. • Build ROI-backed business cases for VP and C-level buyers, tailored to each buyer's specific problem, translating outcomes into numbers a CFO can take to their board. • Anticipate procurement and Legal objections before they surface, and reframe a stalled deal into a new business case without being told to. • Run pricing, proposal, and contract negotiations through to close. • Own your book to the point of obsession: know each account's org structure, incentives, and buying process well enough to navigate it without a map. • Develop and grow relationships with health insurance brokers and benefits consultants who influence your territory, and drive SQOs from those relationships. • Partner closely with your BDR on account strategy and execution, escalate risk early with a recommended path attached, and represent Spring Health at industry events as needed to close (~20% travel). • This role is held to clear KPIs including: • Quota attainment • SQOs generated, • Intro meetings booked • How you’ll use AI in this role: We expect AI to be part of how you sell every day, not an afterthought. • AI-assisted prep. You use AI to build account research briefs, map the competition, and walk into every high-stakes call already knowing the org's priorities and likely objections. • Personalized outreach. You draft outreach with AI that's tailored to the person, a CHRO, a CFO, and a broker get different messages, never a generic one. • AI-driven account strategy. You map the buying committee and multi-threaded outreach with AI, so when one thread breaks, you already have the next one mapped. • Objection and business case prep. You use AI to pressure-test your own deal strategy, model CFO and procurement pushback, and prepare the counter-argument before it's raised. • Clean CRM hygiene. You use AI to summarize calls and log notes in Salesforce, so your deal record is complete and leadership can see the real story without asking.
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