BrightBee is an educational technology startup revolutionizing how K-12 schools recruit and engage with support staff. Our mission is to create a future where schools thrive and workers have the support they need to prosper and grow. We believe in unlocking the potential of every school team member, no matter where they started their career journey.
The Opportunity: BrightBee is seeking an entrepreneurial, high-energy Vice President of Sales to lead our go-to-market organization during a period of massive expansion. This is a player-coach role designed for an exceptional sales leader who excels at both scaling teams and personally closing enterprise business.
The VP of Sales will manage direct reports and territory teams—including Account Executives, Sales Development Representatives (SDRs), and Revenue Operations/Enablement—while maintaining an individual sales quota. You will lead strategic sales execution, coach front-line managers and reps, refine go-to-market strategy, and represent BrightBee at major industry events nationwide.
The ideal candidate brings significant EdTech sales experience, a consistent history of meeting or exceeding quotas, and a deep understanding of selling into the operations side of education.
What You’ll Be Doing- Sales Experience
- Lead, coach, mentor, and direct front-line sales managers and direct reports across sales, SDR, and RevOps functions.
- Foster a culture of ownership, collaboration, continuous learning, and customer obsession.
- Establish performance expectations, structured methodologies, and a clear culture of accountability.
- Conduct regular pipeline reviews, deal coaching, and performance management.
- Recruit and hire additional sales talent as the organization scales.
- Revenue Generation
- Personally manage key relationships with large school districts, childcare providers and strategic partners.
- Consistently meet or exceed team and individual revenue quotas.
- Directly target, negotiate, and close complex enterprise opportunities with large school districts and childcare organizations
- Lead complex, multi-stakeholder sales cycles from prospecting through contract execution.
- Support team members on high-value opportunities and executive-level negotiations.
- Carry an individual quota focused on strategic and enterprise opportunities.
- Sales Strategy & Operations
- Develop and execute the company's sales strategy in partnership with the CEO.
- Build predictable pipeline generation and forecasting processes.
- Optimize CRM hygiene, sales metrics, and reporting.
- Define KPIs for pipeline health, conversion rates, sales velocity, and customer acquisition.
- Improve sales playbooks, messaging, pricing strategies, and competitive positioning.
- Identify new market opportunities and expansion strategies.
- Cross-functional Leadership
- Partner closely with Operations to ensure smooth and successful fulfillment of new contracts sold.
- Collaborate with Customer Success to maximize renewals, expansion, and customer advocacy.
- Channel direct client and market feedback to Product leadership to inform roadmaps and competitive positioning.
- Represent BrightBee at conferences, customer events, webinars, and industry meetings.
- Education: A bachelor’s degree or equivalent experience.
- Required Experience
- At least 5 years of B2B sales experience in education technology.
- At least 3 years of management experience, preferably within sales.
- Willingness to undertake heavy domestic travel for regional conferences, client visits, and industry gatherings
- Proven history of consistently meeting or exceeding individual and team revenue quotas.
- Experience managing people in either direct territory/sales management or related operational management roles.
- Demonstrated success as a player-coach carrying an individual quota while managing others.
- Strong consultative selling and executive relationship-building skills.
- Experience managing complex sales cycles with multiple decision makers.
- Fluency in both using and building out CRM systems (HubSpot is our current CRM).
- Ability to thrive in a fast-paced startup environment with evolving priorities.
- Preferred Experience
- Demonstrated success selling into the operations side of school districts or childcare systems (HR, Finance, Operations, Facilities).
- Significant people management experience outside of direct sales management, backed by exceptional individual EdTech sales performance.
- Experience building and scaling sales organizations from early-stage through growth.
- Experience working within a K-12 school district or childcare provider
- Communication Skills: Excellent communication, presentation, negotiation, and leadership skills.
- Target On-Target Earnings (OTE): $250,000-300,000
- Pay Structure: 60/40 Split (Base Salary / Uncapped Variable Incentive)
- Comprehensive health, vision, dental, and other insurance benefits
- Generous vacation policy
- Remote work
Skills Required
- Bachelor's degree or equivalent experience
- At least 5 years of B2B sales experience in education technology
- At least 3 years of management experience
- Willingness to undertake heavy domestic travel
- Proven history of meeting or exceeding individual and team revenue quotas
- Experience managing people in territory/sales or related operational management roles
- Demonstrated success as a player-coach carrying an individual quota while managing others
- Strong consultative selling and executive relationship-building skills
- Experience managing complex sales cycles with multiple decision makers
- Fluency in using and building out CRM systems (HubSpot current CRM)
- Ability to thrive in a fast-paced startup environment with evolving priorities
- Excellent communication, presentation, negotiation, and leadership skills
- Demonstrated success selling into operations side of school districts or childcare systems (HR, Finance, Operations, Facilities)
- Significant people management experience outside of direct sales management with strong EdTech sales performance
- Experience building and scaling sales organizations from early-stage through growth
- Experience working within a K-12 school district or childcare provider
What We Do
BrightBee is an educational technology startup and staffing partner that connects K-12 schools and nonprofits with vetted support staff. Through an app-based platform, they provide on-demand coverage for roles such as paraprofessionals and custodians, aiming to ensure schools thrive while offering workers flexibility, competitive pay, and opportunities for professional growth and upskilling.
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