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 contract value with organizations of 10,000 to 100,000+ employees. Top performers on this team have a strong history of 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 with an entrepreneurial mindset: 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 and be supported by a high-performing BDR team, and our Strategic Alliances team, and report to the Sales Leader overseeing the segment. This is a full time, fully remote position on our team with the expectation of approximately 10% travel.

What you’ll do:

• Run the full sales cycle into HR, Benefits, and People leaders at large enterprises in your assigned 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.
• Prioritize the accounts that matter most in your territory, aligned to the GTM strategy.
• Multi-thread accounts, building relationships across the buying committee.
• Build ROI-backed business cases for VP and C-level buyers, translating outcomes data into numbers a CFO can take to their board.
• Identify the specific business problem(s) each buyer is solving for and tailor the business case accordingly.
• 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 to close.
• Own your book to the point of obsession: understand 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. Drive SQOs from these relationships.
• Read the room. Adjust your language and framing for a CFO, a CHRO, and a consultant, all in the same week, without a different deck for each.
• Partner closely with your BDR on account strategy and execution.
• Escalate risk early, with a recommended path attached, not just the problem.
• Bring market and client feedback back to Product and Marketing.
• Represent Spring Health at industry events and travel as needed to close (~20%).
• Maintain fast response times with prospects, consultants, and internal partners.

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:

• AI-assisted preparation. You leverage tools like Claude and ChatGPT use AI to build account research briefs, map the competition and get ready for every high-stakes call. You come in already knowing the org’s priorities, recent news and likely objections.
• Personalized outreach at scale. You draft outreach with AI that’s tailored to the person: different for a CHRO, a CFO and a benefits consultant, and never generic.
• 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.
• Judgment and data discipline. You know what doesn’t belong in an AI tool. We sell into a sensitive category, so you protect client and prospect confidentiality and check what AI gives you before it reaches a buyer.

What you’ll bring:

• 5+ 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.

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.