The Head of Sales leads a high-performing team focused on driving growth, generating leads, closing deals, and managing ongoing relationships across nonprofit, education (K-12 and higher ed), and local government sectors. As a key member of the leadership team, the Head of Sales collaborates closely with Product and Customer Experience (CX) teams to stay aligned with market needs and client demands. At Casebook PBC, we are mission-driven, and this role requires a deep commitment to improving outcomes through technology, supporting our mission of “helping the helpers.”
This position is responsible for meeting annual revenue targets by guiding, coaching, and developing the sales team, ensuring that the team consistently achieves its goals. Travel expectations are reduced to 15-20%, and the compensation package includes both a base salary and performance-based incentives.
Key Responsibilities
Team Leadership: Recruit, motivate, coach, and mentor a talented sales team to achieve and surpass quotas while maintaining a customer-focused, low-friction sales approach.
Sales Process Management: Provide guidance on key sales opportunities, assist with RFx responses, proposals, contract negotiations, and other critical deal activities.
Pipeline Management: Build and maintain a strong sales pipeline, ensuring accurate forecasting and long-term growth.
Sales Cycle Engagement: Actively participate in high-value sales opportunities, offering hands-on support and mentorship throughout the sales process.
Weekly Forecasting: Ensure the team delivers accurate weekly forecasts to track progress toward goals and identify any gaps.
Collaboration: 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.
Travel: Ability to travel 15-20%.
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.
Compensation: $140,000 - 170,000 Base Salary + Commissions + Equity + Benefits
Demo of Casebook: https://play.goconsensus.com/ac9bc58df
In addition to salary and sales commission, this position includes a full benefits package including employer funded health insurance for you and a spouse / domestic partner and children, 401k, and three weeks vacation time.
