Director of Sales

Summary

Join SimplePractice as the Director of Sales and spearhead the development and optimization of sales strategies for Inside Sales, Cross-Sell, and Outbound campaigns focused on Group Therapy Practices. Lead the entire sales funnel, from pipeline generation to deal closure, with operational rigor. Conduct data-driven experiments to refine sales motions and collaborate with Marketing, Product, and Customer Success teams. Hire, coach, and manage a growing remote sales team, driving sales forecasting, reporting, and analytics. Champion a culture of agility and continuous learning. This role reports to the Chief Customer Officer.

Requirements

• Proven experience working with Small and Medium Businesses (SMB) to understand their unique challenges and needs
• 7+ years of Sales experience, with at least 3+ years in a Sales leadership role
• Demonstrated success managing and scaling Sales functions such as Inside Sales, Mid-Market, or Cross-Sell
• Proven ability to build and lead Sales teams in fast-paced, rapidly changing startup environments
• Experience owning the full Sales funnel and working closely with GTM functions
• Strong collaborator with a hands-on, roll-up-your-sleeves mentality
• Deep comfort with data: able to define key metrics, set up A/B tests, and leverage analytics to inform decision-making
• Proven ability to collaborate across teams, including marketing, product, and customer success
• Excellent communication and presentation skills, with the ability to engage both internal and external stakeholders
• Openness to developing new Sales strategies leveraging AI to better scale and enhance the function
• Proficiency with ZenDesk, CS Case Management Tools
• Bachelor's degree in Business, STEM field, or a related field (MBA preferred)

Responsibilities

• Design, execute, and iterate on scalable Sales strategies for Inside Sales, Cross-Sell, and targeted outbound campaigns
• Lead the entire Sales funnel—from top-of-funnel pipeline generation through deal close—with strong operational rigor
• Set up and manage data-driven experiments to test, prove, and refine new Sales motions
• Collaborate closely with Marketing, Product, and Customer Success teams to align goals and drive revenue growth
• Hire, coach, and manage a growing Sales team with a focus on performance, accountability, and professional development
• Drive sales forecasting, reporting, and analytics in partnership with the Revenue Operations team
• Champion a culture of agility, experimentation, and continuous learning
• Manage a remote Sales team across multiple regions focused on supporting Cross Sell, Inside Sales and Mid Market

Preferred Qualifications

• SaaS Experience: Preference for candidates with BtoB SaaS experience
• Experience with Hubspot a plus

Benefits

• Medical, dental, vision, life & disability insurance
• 401(k) plan with company match
• Flexible Time Off (FTO), wellbeing days, paid holidays, and summer Fridays
• Mental health resources
• Paid parental leave & Backup Care
• Tuition reimbursement
• Employee Resource Groups (ERGs)