Director of Enterprise Sales

Why 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 based onsite in Pleasanton, CA Monday through Friday

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!

Equal Opportunity Employer:

Vagaro is proud to be an Equal Employment Opportunity and affirmative action employer. We foster an inclusive environment where individuals are evaluated without discrimination based on gender, race, ethnicity, age, disability, religion, sexual orientation, gender identity, veteran status, or any other characteristics protected by law.

Privacy Policy:

Your privacy matters! At Vagaro, we are committed to protecting your personal information. Before proceeding with your application, please review our Employee and Applicant Privacy Notice here ( By submitting your application, you acknowledge that you have read and understood our Privacy Notice, which outlines how we collect, use, disclose, and protect your information during the recruitment and employment process.

Vagaro is an E-Verify employer. Learn more at (

Learn More About Vagaro:

Visit us at vagaro.com/pro ( and vagaro.com ( to learn more.

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