Account Executive

Timely is your home for secondary master scheduling featuring AI optimization and support from a team of educators who know and have lived scheduling. Not only does Timely save time and headache, it unlocks resources so district and charter leaders can build a schedule that drives staffing and budget efficiencies.

We founded Timely to build the tool we wish we'd had when we were in schools -- hoping to save school leaders hundreds of hours of wasted time while allowing district leaders to enable their academic, budget and staffing priorities. Our solution addresses the needs of school-based employees who toil away building schedules and central office employees who need visibility into them.

After completing a successful pilot during the 2022-23 school year, we have scaled our impact across the country. Through a lean approach, we've achieved impressive growth - 8.0x and 3.6x ARR increases in consecutive years - with extraordinary renewal rates (95% logo retention, 96% gross revenue retention). Today, Timely is serving schools across 14 states and Washington D.C. This growth has been driven by our strong product-market fit, deep understanding of education, and commitment to customer success.

We’re hiring a territory-based Account Executive to drive new business growth by selling directly to K–12 school districts at the C-suite level. You’ll identify and connect with decision-makers—Superintendents, CTOs, CIOs—to position Timely as an essential solution for their academic and operational goals.

This role is primarily outbound: you’ll be responsible for building pipeline, conducting discovery, delivering demos, nurturing relationships, and closing deals. You’ll collaborate closely with our School Success (implementation) team to ensure a smooth handoff and long-term success for every new partner.

This is a high-impact role within a fast-growing, mission-driven company. You’ll play a pivotal part in shaping our go-to-market strategy and bringing transformational change to schools across your assigned region.

• Prospecting & Pipeline Creation - Source 75-100 net-new District Leadership conversations per quarter, maintain 3× quota coverage aligned to pipeline pacing

• Discovery & Solution Mapping - Run deep-dive calls that uncover critical academic, staffing, and budget pain points. Translate findings into quantified ROI stories

• Product Demonstrations - Deliver tailored demos that tie scheduling scenarios to district metrics (e.g., FTE savings, elective access)

• Deal Strategy & Closing - Build mutual action plans; drive multi-threaded buys and consistently beat a ≥ $800K annual quota with 4-6 month sales cycles

• Forecasting & Reporting - Pipeline hygiene in HubSpot with stage, amount, next step, and close date while maintaining ±10 % forecast accuracy, quarter over quarter

• Cross-Functional Handoff - Brief School Success on goals, stakeholders, and timeline within 48 hours of signature

• Documented Wins - 3+ years exceeding new-business quotas in EdTech or SaaS; provide deal sheets or leaderboard rankings.

• “Hunter’s” Discipline - Proven ability to self-source 70%+ of pipeline through phone, email, LinkedIn, conferences and events

• Metrics-Driven Mindset - Examples of pipeline coverage ratios, win rates, and forecast accuracy you’ve achieved.

• Executive Gravitas - Comfortable challenging Supers and CTOs with data and strategic insights.

• CRM Mastery - HubSpot (preferred) or similar; show us how you track pipe health.

• Education Empathy - Understand the stakes of staffing, scheduling, and student equity in public schools.

• Road-Ready - Willing to travel ~1 week/month for onsite demos, board meetings, and industry events.