Jumbo Enterprise Account Executive

Our Enterprise team owns the biggest, highest-visibility relationships in the business, deals that range from $2.5M to $20M in annual value with organizations of 10,000 to 100,000+ employees. Top performers on this team are exceeding quota. This is not a role for someone who wants a pipeline mostly handed to them or a script. We're looking for a builder: someone who generates their own opportunities, owns a complex sale end to end, and thinks like a founder inside their territory. You'll work closely with BDRs and our Strategic Alliances team, and report to the Sales Leader overseeing the segment. This is a full time, fully remote position with the expectation of approximately 20% travel.

What you'll do

• 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).

What success looks like in this role

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: 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: draft outreach with AI tailored to the person, so a CHRO, a CFO, and a broker get different messages, never a generic one.
• AI-driven account strategy: 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: 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: 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.

What you'll bring

• 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.

Nice to Have

• Benefits, health insurance, or healthcare sales experience.
• Existing relationships with brokers or benefits consultants.
• Experience selling into HR or People leadership specifically.