Vice President of Sales

About the role

BrightBee is an educational technology startup revolutionizing how K-12 schools recruit and engage with support staff, and the Vice President of Sales will be central to executing this mission by building and leading a high-performing sales organization. The hire will own the end-to-end sales strategy and execution, driving go-to-market efforts during a period of massive expansion while maintaining a player-coach role that blends team leadership with personal enterprise business generation. This position requires fostering a culture of ownership, collaboration, and customer obsession, where consistent quota attainment and operational excellence are expected. The Vice President will directly manage a portfolio of accounts, coach sales teams, and represent BrightBee at major industry events to position the company as a leader in the education support staffing market.

Key facts

Location: USA

Engagement: Full-time

Compensation: 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

What you'll do

Establish performance expectations, structured methodologies, and a clear culture of accountability across the sales organization.

Lead, coach, mentor, and direct front-line sales managers and direct reports across sales, SDR, and RevOps functions to ensure alignment with company objectives.

Conduct regular pipeline reviews, deal coaching, and performance management to optimize team productivity and individual growth.

Recruit and hire additional sales talent as the organization scales to meet evolving market demands and revenue targets.

Foster a culture of ownership, collaboration, continuous learning, and customer obsession within the sales team.

Personally manage key relationships with large school districts, childcare providers and strategic partners to secure enterprise business.

Consistently meet or exceed team and individual revenue quotas through disciplined execution and strategic planning.

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 to ensure successful deal closure.

Support team members on high-value opportunities and executive-level negotiations to drive collective success.

Carry an individual quota focused on strategic and enterprise opportunities to maintain a player-coach perspective.

Develop and execute the company's sales strategy in partnership with the CEO to align with broader business goals.

Build predictable pipeline generation and forecasting processes to maintain visibility into sales performance.

Optimize CRM hygiene, sales metrics, and reporting to provide actionable insights for decision-making.

Define KPIs for pipeline health, conversion rates, sales velocity, and customer acquisition to measure and improve performance.

Improve sales playbooks, messaging, pricing strategies, and competitive positioning to strengthen market position.

Identify new market opportunities and expansion strategies that unlock additional revenue streams.

Partner closely with Operations to ensure smooth and successful fulfillment of new contracts sold to maintain client satisfaction.

Collaborate with Customer Success to maximize renewals, expansion, and customer advocacy to drive long-term value.

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 to elevate brand awareness and thought leadership.

Requirements

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.

Nice to have

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.

Practical notes

Willingness to undertake heavy domestic travel for regional conferences, client visits, and industry gatherings.

Compensation includes Target On-Target Earnings (OTE) of $250,000-300,000 with a pay structure of 60 percent base salary and 40 percent uncapped variable incentive.

Comprehensive health, vision, dental, and other insurance benefits are provided.

The role offers a generous vacation policy.

Remote work is available.

Candidates must hold at least a bachelor's degree or equivalent experience.

Required experience includes at least five years of B2B sales experience in education technology and at least three years of management experience, preferably within sales.

Candidates must be willing to travel domestically for regional conferences, client visits, and industry gatherings.

A proven track record of consistently meeting or exceeding individual and team revenue quotas is mandatory.

Experience managing people in either direct territory or sales management roles or related operational management roles is required.

Demonstrated success as a player-coach who can carry an individual quota while managing others is essential.

Fluency in using and building CRM systems, with HubSpot as the current platform, is required.

The ability to thrive in a fast-paced startup environment with evolving priorities is necessary.