Fast Facts

Timely is seeking an Account Executive to drive sales directly to K–12 school districts, focusing on high-level decision-makers to showcase their AI optimization tool for academic and operational goals.

Responsibilities: Manage outbound sales efforts within an assigned territory, engage with decision-makers, conduct product demos, and oversee the full sales cycle, ensuring smooth implementation through collaboration with the School Success team.

Skills: 2–4 years of EdTech sales experience, strong outbound sales capabilities, excellent communication skills, and familiarity with CRM tools like HubSpot.

Qualifications: Proven success in driving complex sales, ability to sell to executive-level leaders, and a background in education or empathy for educators' challenges.

Location: Boston, MA, United States, with travel required approximately one week per month.

Compensation: Not provided by employer. Typical compensation ranges for this position are between $65,000 - $100,000.

Who we are

We founded Timely to build the tool we wish we'd had when we were in schools -- hoping to save hundreds of hours of wasted time while helping schools develop better schedules that 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.

The school schedule reflects values and priorities. With 75 to 90% of a district budget dedicated to personnel, there are few questions more paramount than how your staff and students spend their time every day, what positions you need, how many teachers you will hire, and how students will interact with them. Strategic resource allocation across schools, proper access to core courses and electives, and dedicated support to sub-groups begins with the development of a school schedule.

Timely is your home for secondary scheduling featuring AI optimization and support from a team of former 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 aligns with their vision.

About the Role

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.

Roles and Responsibilities

• Own and drive outbound sales efforts within an assigned territory
• Identify and engage key decision-makers (Superintendents, CTOs, CIOs)
• Conduct discovery conversations and deliver compelling product demos
• Manage the full sales cycle from first touch to close
• Maintain accurate pipeline data and forecasting in HubSpot
• Collaborate with School Success Managers to ensure smooth implementation
• Build and maintain deep relationships with prospective district partners
• Attend industry conferences and district meetings (travel ~1 week/month)
• Contribute feedback to the product and marketing teams based on field insights

What We Look For in a Candidate

• 2–4 years of experience in EdTech sales, preferably to K–12 school districts
• Proven ability to drive outbound sales and close complex deals
• Strong communication, storytelling, and relationship-building skills
• Comfort selling to executive-level district leaders and navigating long sales cycles
• Self-starter mindset with the ability to manage a pipeline independently
• Experience using HubSpot (or similar CRM) to manage and track outreach
• Deep empathy for educators and an understanding of the challenges in public education
• Willingness to travel 1 week per month for conferences, demos, and relationship-building

Benefits we offer

• Health: medical, dental, vision, and an employee contribution-only 401(k) plan
• Personal growth: at our current early stage there will be many professional development opportunities as the company grows and evolves requiring our founding staff to grow with it
• Flexible PTO

Start date

• July 15 2025