Director of Engineering (Product)

School scheduling is a hard problem, one that technology was meant to solve. Yet for decades, the master schedule has been built by hand, consuming educators’ valuable time while delivering a sub-optimal result for students. We started Timely to build the tool we wish we had when we were in schools. And today, we are changing how schools create high quality schedules for teachers and students. Timely combines groundbreaking AI technology with support from a team of expert school schedulers: saving schedulers’ time, and surfacing opportunities for leaders to unlock staff potential. Timely delivers optimized master schedules that are more efficient, accommodate diverse educator needs, and enable student access to courses and pathways that impact their lives.

Our district and school partners agree: scheduling is a key opportunity for educational innovation, and that Timely is the indispensable partner in addressing the challenge. We’re experiencing exciting growth as a company, while doubling down on our mission and people-centered approach to leveraging powerful technology. We serve districts and charter school organizations across 20+ states, growing (and renewing) at rates that lead the education technology industry. This growth has been driven by our strong product-market fit, deep understanding of education, and commitment to customer success.

We are seeking a Director of Engineering (Product) who can take ownership of multiple product squads within our engineering organization. You are expected to provide independent leadership for these squads with key outcomes being:

• Delivery on all goals for squads under your leadership.

• Managing team members across squads and driving both results and retention for them within the context of company and team goals.

• Shepherding key architecture and engineering decisions and development priorities within the context of product and business goals.

• Establishing healthy teams, defined by their ability to deliver value for the company in a sustainable, efficient, and high-quality manner.

In all of the responsibilities below, it’s expected that you are effectively empowering and operating through your team but taking final and direct responsibility for the results.

• Partner with Product and broader cross-functional stakeholders to define squad goals and align engineering priorities against these goals.

• Balance company and squad goals with business constraints to develop a staffing strategy for teams under your leadership.

• Identify and advance key technical decisions impacting the squads’ abilities to efficiently deliver against their goals at high quality.

• Work with your squads to multiply their impact through levers such as culture, process, tooling, and technology.

• Own critical relationships with internal and external stakeholders who are enabling or dependent on the work of your squads.

• Establish practices on each squad and across the engineering organization that bake quality into our development process.

• Encourage and facilitate continuous learning and improvement from production errors or incidents.

• Raise the bar for the team around security, testing, and scaling practices.

• Operate as the escalation point for major production issues while establishing processes and technology improvements that rarely require such escalation

• Directly recruit, hire, and manage team members across multiple squads.

• By default, operate through your team to influence change and improvement in the strategic and tactical delivery of engineering value to the organization.

• Own the retention and growth of team members, aligning growth to value delivered to the business and meeting expectations of roles.

• Own performance management for the squad, delivering regular feedback and guidance for team members to meet and exceed expectations for their roles.

• Ensure teams under your purview are operating at high velocity and with clarity on their goals.

• Unblock the team on cross-team and cross-functional challenges that hinder delivering value. Ensure that each engineering squad member across your teams are collaborating effectively with other functions and teams.

• Monitor and action on learnings from sprint retrospectives, project progress, and overall team reflections to continuously improve how your teams operate.

• Directly take on hands-on ownership of challenging or critical needs when necessary, though biasing to empowering your team where possible.

• Proactively identify and take action on opportunities for the overall engineering organization to improve.

• Support team members through pairing, review, and other activities to accelerate and improve their decision-making.

• Represent the team and organization in various settings internally and externally.

• Prior experience in technical leadership roles driving business, product and technical outcomes: tech lead, manager, director, etc.

• Hands-on development and design experience with demanding architectures (in terms of scale, security, and product considerations).

• Ability to onboard to a variety of tech stacks as needed. Ours consists of React, Python, AWS, MongoDB. We don’t expect exact overlap, but a demonstrated ability to onboard effectively.

• Successfully managed and scaled multiple teams and balanced your own impact in the process.

• Previously shepherded engineering organizations through major technical decisions, changes in scale, and maturation of technology platforms powering mission-critical products.

• Represented your organization and company in internal and external settings in high stakes conversations.

• Comfortable working in ambiguous, fast-paced environments (especially startups); proactive and solutions-oriented.

• Nice to have: prior experience or interest in educational technology products.

• Ownership mentality with a commitment to delivering exceptional results for customers.

• Work with an exceptional team tackling meaningful challenges in education.

• Be part of a growing, financially healthy company with a proven product.

• Enjoy comprehensive benefits, including health insurance, parental leave, 401(k), unlimited PTO, access to coworking, and equity in a fast-growing startup.