Fast Facts

Timely is seeking a seasoned Founding Head of Sales to spearhead its sales strategy and team development, driving significant growth in the K-12 education sector. The role involves executing a go-to-market strategy, building relationships with school district leadership, and refining the sales process to scale operations effectively.

Responsibilities: Key responsibilities include leading the sales process, building a high-performing sales team, managing contracts and negotiations, and collaborating with other departments to align company strategy.

Skills: Candidates should have extensive experience in K-12 education sales leadership, strong analytical and communication skills, experience managing sales teams, and a history of closing complex deals with substantial contract values.

Qualifications: Preferred qualifications include a proven record of scaling revenue in early-stage companies, experience in selling educational software, and familiarity with K-12 education environments including teaching or administrative roles.

Location: The position is based in Boston, MA, United States, with no additional travel specified.

Compensation: Not provided by employer. Typical compensation ranges for this position are between $150,000 - $250,000.

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

As Founding Head of Sales at Timely, you'll join us at a critical inflection point in our company's trajectory. Through an efficient, founder-led sales motion supported by our School Success team, we've achieved remarkable growth - with 8x and 4x ARR increases in consecutive years. Today, Timely is serving schools across 12 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 now seeking an exceptional sales leader to build upon this foundation and accelerate our impact. You'll be responsible for developing and executing our go-to-market strategy, building our first dedicated sales team, and personally driving strategic enterprise sales opportunities with major school districts. 

As a member of our executive team, you'll work directly with the CEO to translate our early success into a scalable sales organization. You'll leverage our existing momentum and learning while implementing the systems, processes, and team structure needed for our next phase of growth. This is a role for someone who thrives on both strategic leadership and hands-on execution, who understands the complexities of K-12 decision-making, and who is energized by the opportunity to build something meaningful from the ground up.

Role & Responsibilities

The Founding Head of Sales will lead all aspects of Timely’s sales process. 

• Sales Leadership & Team Building
• Build, train, and lead a high-performing sales team
• Partner with the CEO to design and implement a sales compensation system that drives the right behaviors and outcomes
• Refine and position our existing our existing sales process, methodologies, and playbooks for scale
• Create and manage sales forecasting, pipeline management, and reporting systems
• Set and achieve ambitious revenue targets while maintaining our high standards for customer fit and success
• Strategic Sales Execution
• Own a modified quota in order to deeply understand our customers and the nuances of the sales cycle to train and inspire others on the team
• Build and maintain relationships with superintendents, CAOs, CFOs, and other district leadership
• Build and maintain critical channel partnerships which have been very beneficial to Timely
• Structure and manage contract negotiations
• Go-to-Market Strategy
• Work with senior leadership to define and continuously refine our ideal customer profile and target segments
• Partner with the CEO to develop strategic partnerships with education organizations and influencers
• Work with CEO to evolve pricing and packaging strategies, especially if we were to build product adjacencies
• Create compelling sales enablement materials that effectively communicate our value proposition
• Inform establishing and maintaining our competitive positioning in the market
• Identify and pursue new market opportunities
• Cross-functional Leadership
• Collaborate with School Success to ensure productive involvement in sales process, smooth handoffs, and successful implementations 
• Partner with School Success to build a plan for customer renewals and expansions (where relevant) 
• Partner with Product team to ensure our roadmap aligns with market needs and opportunities
• Serve as a senior leader leader at Timely, helping shape company strategy and culture

What we are looking for in candidates

The role requires someone with:

• 5+ years of progressive experience in K-12 education sales leadership
• Experience building and managing high-performing sales teams
• Deep understanding of K-12 district buying cycles and decision-making processes
• History of closing complex, enterprise deals with $100K+ ACV
• Strong analytical skills and data-driven approach to decision making
• Excellence in sales forecasting and pipeline management
• Outstanding presentation and communication skills

The following additional experiences would also be a plus:

• Proven track record of scaling ARR from early stage ($3M+) to growth stage ($20M+)
• Experience selling scheduling, operations, or similar software to K-12 districts
• Direct background in K-12 education (teaching, administration, or district leadership)
• Early-stage startup experience, particularly as a first sales hire

Who you are

• A proven leader and manager: You have a demonstrated ability to build, motivate, and scale high-performing sales teams
• Strategic executor: You can develop comprehensive strategies while maintaining attention to tactical execution
• Results-oriented: You have consistently exceeded targets and know how to build repeatable sales processes
• A compelling communicator: You can articulate complex value propositions to diverse stakeholders
• Data-driven: You rely on data to inform decisions and build scalable systems
• Relationship-oriented: You build lasting relationships and identify strategic opportunities
• Mission-oriented: You're passionate about improving K-12 education and understand the challenges schools face
• Self-starter: You thrive in ambiguous situations and create structure where needed
• Collaborative: You work effectively across functions while maintaining high independence

Benefits we offer

• Health: medical, dental, vision, and a contribution-only 401(k) plan
• Unlimited PTO
• 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