Jumbo Enterprise Account Executive

Spring Health; New York (NY); Remote; USD 180,000 - 280,000; Full time

Benefits offered by this job

Health insurance

Job summary

Spring Health is seeking an experienced enterprise sales professional to lead complex, multi-stakeholder deals with large employers. You will own the full sales cycle from discovery to close, self-generate pipeline, and build ROI-based business cases for CFOs and CHROs.

You will collaborate with BDRs, brokers, and alliances teams, and use AI tools for account research, outreach, and strategy. This is a fully remote role with ~20% travel to client sites.

Qualifications

• 8+ years of quota-carrying enterprise sales experience.
• Able to close 6- and 7-figure deals with large employers.
• Sharp, resourceful, and able to build compelling business cases for executives.

Responsibilities

• Run the full sales cycle into HR, Benefits, and People leaders at large enterprises from discovery to close.
• Self-generate pipeline through brokers, consultants, referrals, and dormant accounts.
• Engage target accounts before formal RFPs and build multi-thread relationships across the buying committee.
• Prioritize accounts aligned to GTM strategy and map stakeholders for procurement and legal objections.
• Develop ROI-backed business cases for VP/C-level buyers and tailor to each buyer’s problem.
• Negotiate pricing, proposals, and contracts through to close.
• Own your book with deep knowledge of org structure and incentives to navigate without a map.
• Grow relationships with brokers and benefits consultants, driving SQOs from those relationships.
• Collaborate with BDRs and alliances teams; travel ~20% for closing and events.
• Represent Spring Health at industry events as needed.

Skills

Enterprise sales

Quota-carrying

Negotiation

Account strategy

Job description

Our mission: eliminating every barrier to mental health.

Spring Health is a global mental health company on a mission to eliminate every barrier to mental health. We're building a world where getting support is simple, personal, and built around the person, so care can continue through every job, move, health plan, and life stage.

Our AI-native platform helps us deliver personalized support across self-guided tools, coaching, therapy, medication management, and specialty care. With outcomes independently validated by JAMA Network Open and the Validation Institute, Spring Health reaches more than 170 million people worldwide through leading employers, health plans, and partners.

As an AI-native company, we believe technology should expand the reach, quality, and humanity of care. Every Spring Health team member is expected to use AI tools thoughtfully, apply human judgment to AI outputs, and keep building AI fluency in ways that support their role and our mission.

Spring Health is reimagining mental healthcare for the workforce. We work with the country's largest employers to give every employee and their family access to fast, personalized mental health support, and we're still early in capturing a massive market. We're competing for share in a category we helped define, against well-funded incumbents, this is a seat to help shape what winning looks like, not just execute in an established motion. 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, escrow 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. 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.

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.