Director of Enterprise Sales

Key Responsibilities

Lead Enterprise Revenue Performance

• Manage and coach 6 Enterprise Account Executives selling into healthcare organizations
• Improve discovery depth, workflow diagnosis, and economic value articulation
• Standardize deal strategy reviews and win-plan development
• Increase qualified-to-close conversion rates and reduce performance variance

Strengthen Pipeline Health and Discipline

• Establish clear expectations for pipeline coverage and opportunity creation
• Reinforce AE ownership of prospecting and outbound consistency
• Inspect leading indicators across pipeline stages to identify gaps early
• Partner with Sales Development and Marketing to improve meeting quality and early-stage conversion
• Lean into key partnerships to help drive top of funnel and increase win rates

Elevate Strategic Execution

• Join strategic calls and materially improve outcomes
• Diagnose stalled opportunities and define actionable paths to close or disqualify
• Help team connect pain to value and quantify impact to strengthen the business case
• Coach reps in real time and in Gong on executive engagement, urgency creation, and multi-threading
• Run plays to compete and win when there is an identified project, and slow down and educate when creating the project
• Identify opportunities to improve the overall motion and partner with the VP of Sales and Executive team to drive change across the GTM organization

Build Operations Cadence

• Implement disciplined weekly inspection rhythms (pipeline, deal reviews, forecasting)
• Use conversion data to inform coaching priorities and performance management
• Drive accountability while fostering a culture of ownership and continuous improvement

Required Qualifications

• 7+ years of B2B SaaS sales experience, including significant enterprise selling exposure into 6 and ideally 7 figure deals
• 3+ years managing Enterprise Account Executives in complex, multi-stakeholder environments
• Proven ability to coach enterprise deal strategy and executive engagement
• Experience building operating cadence in high-growth environments
• Consistency in meeting and exceeding revenue and pipeline generation targets
• Demonstrated ability to "figure it out"
• Located in the San Francisco Bay Area

Core Competencies

• Strong enterprise qualification and deal strategy expertise (MEDDPICC, Challenger, GAP Selling, Selling through Curiosity)
• Ability to improve diagnostic quality in complex sales conversations
• Data-driven mindset with strong pipeline and conversion analysis skills
• High standards and comfort holding senior sellers accountable
• Action-oriented leadership style with a focus on measurable outcomes
• Ability to thrive in a dynamic start-up environment
• Deep curiosity and a strong Growth Mindset
• Experience with a modern sales tech stack

Preferred Qualifications

• Experience selling into healthcare providers or revenue cycle environments
• Background in early stage venture-backed SaaS companies
• Familiarity with AI-driven or workflow automation solutions

Compensation & Benefits

• Competitive Compensation: $330,000 - $390,000 per year on target earnings, plus equity
• Unlimited PTO
• Comprehensive Health Coverage: Fully paid medical, dental, and vision insurance
• Equity Opportunities with stock options
• 401(k) with generous company match
• Student Loan Support