Director of Enterprise Sales

About Vagaro

At Vagaro, we believe in fostering a collaborative and inclusive work environment where every team member can thrive. Our culture is built on innovation, continuous learning, and a passion for making a positive impact. We support our employees' growth and vision for themselves, offering opportunities for professional development and career advancement. Join us and be part of a team that values creativity, teamwork, and a commitment to excellence. Plus, we know how to have fun while getting the job done!

What You'll Be Doing

Vagaro is seeking a Director of Enterprise to lead and scale our Mid-Market and Enterprise revenue motion across the health, beauty, and wellness ecosystem. This role owns the Enterprise initiative end-to-end, driving revenue outcomes while orchestrating cross-functional execution across Sales, Customer Success, Solutions Consulting, Product, Engineering, Marketing, Legal, and Operations.

This role is hybrid with the onsite requirement in Pleasanton, CA.

Compensation

Base Annual Salary: $150,000 - $192,500

Annual On Target Earnings (OTE): $215,000 - $275,000

Your Impact

• Own Enterprise revenue strategy and execution across Mid-Market and Enterprise segments.
• Lead, coach, and scale a high-performing team across revenue, customer engagement, and technical solution design and implementation.
• Drive pipeline creation, deal progression, forecasting accuracy, and closed-won revenue for complex deals.
• Serve as senior deal leader on large, strategic, and multi-stakeholder Enterprise opportunities.
• Provide strong commercial leadership with deep technical fluency throughout the sales cycle.
• Partner closely with Product and Engineering to translate Enterprise requirements into scalable solutions.
• Influence product roadmap priorities based on Enterprise customer needs and market feedback.
• Collaborate cross-functionally with Marketing, Legal, Finance, and Operations to execute deals end-to-end.
• Own Enterprise sales processes including qualification, solution design, pricing, and contract structure.
• Lead complex commercial negotiations including multi-year agreements and custom terms.
• Establish and manage Enterprise KPIs including pipeline coverage, win rates, ACV, and forecast accuracy.
• Ensure tight alignment between Sales and Customer Success to drive retention and expansion.
• Act as executive sponsor and trusted advisor for Enterprise customers and strategic partners.

What You Bring

• 8–12+ years of experience in Enterprise or Mid-Market SaaS sales with 3–5+ years in leadership roles.
• Proven track record of closing large, complex, and multi-stakeholder Enterprise deals.
• Strong technical aptitude with experience selling platform-based or workflow-driven SaaS solutions.
• Demonstrated ability to lead and influence cross-functional teams without direct authority.
• Experience managing and scaling teams across go-to-market execution, pipeline creation, and technical implementation and enablement.
• Highly revenue-driven with strong operational discipline and data-driven decision making.
• Exceptional executive presence, communication, and negotiation skills.
• Comfortable operating in fast-growing environments where structure is still being built.
• Experience using Salesforce or similar CRM platforms.
• Background in vertical SaaS, marketplace, fintech, or workflow-centric platforms is a strong plus.

Why You'll Love Working Here

• Attractive Compensation & Performance Bonuses: Enjoy a competitive salary paired with performance-based bonuses.
• Generous PTO: 15 accrued days, plus 10 company holidays annually.
• Health & Wellness: Comprehensive healthcare, dental, and vision plans for you and your family.
• Exclusive Perks: Discounts on attractions, theme parks, shows, sports events, movies, hotels, and more through TicketsAtWork.
• Beauty Perks: $30/month reimbursement for any Vagaro service, including health, beauty, or wellness treatments.
• Food Perks: $50 monthly stipend for our onsite microkitchen and a complimentary DoorDash DashPass subscription.
• Growth Opportunities: College Assistance Reimbursement, access to EAP & Work/Life Programs, and a LinkedIn Learning account.
• Financial Security: 401k program with 4% matching and optional life/supplemental insurance.
• Stay Active: Access to our on-site gym, flavored water dispenser, and basketball court to keep you fit and energized!