Remote Head of Sales

Summary

Join our mission-driven team as the Head of Sales at Casebook PBC! This role leads a high-performing sales team to drive growth, generate leads, close deals, and manage relationships across nonprofit, education, and local government sectors. As a key member of the leadership team, you'll collaborate closely with Product and Customer Experience teams to stay aligned with market needs and client demands.

Requirements

• Proven self-starter with a track record of success in sales, especially within nonprofit, education (K-12 and higher ed), and local government markets
• Excellent presentation and communication skills, capable of engaging with senior leadership and decision-makers
• 5+ years of sales experience as an individual contributor
• 1+ year of sales leadership experience, with a demonstrated ability to guide a team to consistently hit its goals
• High level of accountability and urgency to meet and exceed goals
• Strong competitive drive and work ethic
• Proficiency in HubSpot or similar CRM
• Passionate about Casebook PBC’s mission of supporting human services professionals

Responsibilities

• Recruit, motivate, coach, and mentor a talented sales team to achieve and surpass quotas while maintaining a customer-focused, low-friction sales approach
• Provide guidance on key sales opportunities, assist with RFx responses, proposals, contract negotiations, and other critical deal activities
• Build and maintain a strong sales pipeline, ensuring accurate forecasting and long-term growth
• Actively participate in high-value sales opportunities, offering hands-on support and mentorship throughout the sales process
• Ensure the team delivers accurate weekly forecasts to track progress toward goals and identify any gaps
• Work closely with the Marketing and RevOps teams to ensure your sales team has the tools, resources, and materials necessary to excel in their roles. Additionally, engage regularly with Product and CX teams to provide feedback and stay aligned with customer needs

Benefits

Full benefits package including employer funded health insurance for you and a spouse / domestic partner and children, 401k, and three weeks vacation time