Head of Sales Operations
Sentry
Job Level
JuniorMid-Level
About the role
- Own the full sales cycle from prospecting to close with K-12 districts, schools, and educational organizations
- Identify, engage, and qualify leads through outreach, events, referrals, and inbound opportunities
- Deliver compelling presentations and demos tailored to administrators, principals, and district leaders
- Consistently build and manage a healthy pipeline of opportunities to achieve and exceed quota
- Execute land-and-expand strategies to grow ChessKid adoption within districts
- Partner with leadership on territory planning and account prioritization
- Ensure smooth onboarding of new customers, working with the Sales Coordinator and Customer Success team
- Clearly document customer needs, goals, and implementation details in the CRM
- Collaborate with Customer Success to ensure satisfaction and identify upsell/renewal opportunities
- Own assigned renewal accounts, keeping relationships strong and positioning ChessKid for expansion
- Use Slack, CRM, and other sales tools to stay aligned with cross-functional teams
- Share market insights, competitor intelligence, and customer feedback with leadership to inform GTM strategy
- Contribute to team meetings, trainings, and process improvements
Requirements
- 2–3 years of sales experience, ideally in EdTech, SaaS, or K–12 education markets
- Background in K–12 education (teaching, administration, or related roles) is a plus
- Proven track record of managing full-cycle sales and consistently meeting or exceeding quota
- Excellent presentation, communication, and negotiation skills
- Proficiency with CRM systems (Salesforce, HubSpot, or similar) and modern sales enablement tools
- Familiarity with Slack or other collaboration platforms
- Genuine passion for education, student engagement, and mission-driven sales
- Strong ability to collaborate and communicate effectively in a fully distributed team
- A strong sense of ownership, accountability, and responsibility
- Ability to work in the United States (role is open to candidates who can work in the US)
