Senior Director of Sales

The Opportunity:

This is not a role where you build from zero. You are joining a company with an established market position, active relationships, and a qualified book of pipeline opportunities across health plan, Blues, and TPA accounts. Your mandate is to take ownership of those opportunities — bring the closing discipline, the executive relationship depth, and the business case rigor required to advance them through complex procurement environments and get them to signature.

Deals in this market run 9 to 18 months. Budget cycles, procurement committees, legal reviews, and clinical sign-offs are not obstacles — they are the process, and you know how to navigate all of them without losing momentum. You are comfortable sustaining a deal across multiple stakeholder touch points over an extended arc, using tools like Mutual Action Plans to keep both sides accountable and the deal moving.

If you have spent years closing complex enterprise deals with health plans or payers, understand how these organizations buy, and want to bring that expertise to a company with differentiated solutions and real market traction, this is the role.

What You Will Own:

• A named book of pipeline opportunities across health plan, Blues, and TPA accounts at various stages from Solution Design through Contracting
• Full ownership of deal strategy, stakeholder mapping, and close planning on every opportunity in your book
• Mutual Action Plans developed and maintained with every active opportunity — used as the client-facing project management and accountability vehicle throughout the cycle
• ROI and business case development and facilitation at the VP and C-suite level — building the financial model, pressure-testing assumptions, and presenting a boardable case for investment
• Multi-stakeholder consensus building across clinical, financial, operational, legal, and IT buying committee members
• Champion identification, development, and validation — you know the difference between a sponsor and a champion, and you build the latter deliberately
• MEDDPICC deal records that reflect real discovery — content that documents genuine customer intelligence, not field compliance
• Salesforce pipeline hygiene maintained to stage expectations on a bi-weekly sprint cadence
• Participation in deal inspection and 1:1 coaching reviews with sales leadership
• Partnership with Solutions Engineering, Clinical SMEs, and Health Market Partner teams to build tailored solution architectures and value propositions

What You Bring:

• 8+ years. 8+ years of enterprise B2B sales experience, with at least 5 years selling directly to health plans, Blues plans, TPAs, or self-funded employers in a closing capacity
• Proven closer. Demonstrated track record closing $1M+ ACV deals with 9–18 month sales cycles involving procurement committees, budget approvals, and legal negotiation
• Payer expertise. Deep command of health plan procurement dynamics — you know who the economic buyer is, how budget gets approved, which stakeholders have veto power, and how to navigate the process without losing momentum between touch points
• Financial fluency. Fluency in healthcare payer economics — PMPM, MLR, trend, network performance, and how cost optimization solutions move the needle on each; you can hold a substantive conversation with a VP Medical Management or CFO without a product deck
• MEDDPICC mastery. MEDDPICC practitioner with real depth — you use it as a discovery discipline and deal management system, not a CRM hygiene exercise; you can demonstrate qualification rigor in a coaching conversation or deal inspection
• MAP execution. Mutual Action Plan experience — you have built and run MAPs with enterprise clients as a joint accountability and deal acceleration tool, and you know how to hold a client to commitments without the relationship becoming adversarial
• Business case builder. ROI and business case facilitation skills — you can build a healthcare cost savings model, pressure-test assumptions with a skeptical CFO, and translate it into a business case that survives committee review
• Consensus driver. Multi-stakeholder consensus experience — you have successfully navigated 6+ member buying committees across functions and driven them to a decision, including where stakeholder interests were not initially aligned
• Experience with network optimization, pharmacy, cost transparency, or adjacent healthcare technology solutions strongly preferred
• Proficiency with Salesforce CRM; familiarity with ZoomInfo, LinkedIn Sales Navigator a plus

What Separates the Right Candidate:

• You can hold a client accountable to a Mutual Action Plan commitment without the relationship feeling transactional
• You understand that a 12-month deal can go dark for 90 days during a client’s budget cycle — and you have a deliberate system for maintaining momentum and relationship warmth across that gap
• You have enough command of payer economics to build a savings model from scratch and present it credibly to a health plan CFO
• You bring intellectual honesty to your pipeline — you would rather disqualify at Solution Design than advance a deal to Solution Optimization without a real economic buyer engaged
• You operate with urgency and structure simultaneously — you are not a freestyler, and you do not mistake activity for progress
• You have navigated a legal and IT security review with a health plan or Blues plan and know how to keep a contract from dying in redlines

The Sales Environment:

MacroHealth operates a structured 2-week sprint cadence for pipeline management. Every deal is inspected against MEDDPICC stage expectations and an AI quality model that evaluates the content of discovery notes — not just whether fields are populated. You will participate in bi-weekly sprint reviews and deal inspections with sales leadership. The commission plan includes a process compliance component tied to MEDDPICC and sales process adherence.

This environment rewards sellers who are disciplined, coachable, and data-driven about their pipeline. If you thrive in a structured, high-accountability selling environment and want to operate against a clear process with strong leadership support, this will feel like home. If you prefer a hands-off environment with minimal structure, this is not the right fit.

Compensation:

• $350,000-4450,000 OTE plus equity, 401k match, flexible PTO and medical/dental/vision insurance.