Founding Chief of Staff

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.

About the role

As Founding Chief of Staff at Timely, you'll be a key member of our team responsible for driving cross-functional coordination/leadership, strategic initiatives, talent strategy, and supporting our CEO and team leaders to scale our impact. This is a unique opportunity to shape the future of an education technology company with strong signs of product-market fit and help build the team, culture, systems, tools, and processes that will enable our continued growth.

Role & Responsibilities

The Founding Chief of Staff will lead critical aspects of Timely's strategic operations and organizational development:

• Team coordination & leadership

  • Team Coordination: Manage all-staff agendas and follow-ups; coordinate Steering Committee meetings and follow-ups; oversee retreat planning and logistics; general cross-functional communication and alignment

  • Strategic Planning: Design, build, and implement an annual strategic plan and goal development process for the company, by functional areas, and for individuals in partnership with the CEO, Head of Operations, and Steering Committee

  • Strategic Initiatives & Project Management: Partner with the CEO and Steering Committee to oversee and project manage critical/sensitive cross-functional initiatives

  • Cross-functional collaboration and leadership: Collaborate closely across all teams to ensure alignment on strategic priorities and execution of company-wide initiatives; serve as a liaison between the CEO and various teams, ensuring clear communication and accountability across the organization

• Talent strategy

  • Performance Management: Design, build, and implement an annual performance management process with career development frameworks to support our growing team

• Strategic support to the CEO

  • Data & Analytics: Help support ad hoc analytical needs, such as the development of KPIs, reporting dashboards, and business intelligence; lead analyses to inform sales forecasting, financial planning, budgeting, and capital allocation strategy

  • External Stakeholder Communication: Design and build materials for board meetings, grant applications, and other stakeholder communications such as the authoring of white papers that capture Timely's impact with specific customers

  • General Support: Provide strategic and operational support to the CEO and Steering Committee across various initiatives to help generate capacity for high-impact work

• Be part of the brain trust to build a lasting and valuable company

  • Our small and quick-moving team is committed to both impact and scalable growth, and this role will work hand-in-hand with the CEO, CTO and other senior leaders in making and implementing major decisions that determine Timely’s future

What we are looking for in candidates

We're seeking a versatile, well-rounded individual who can thrive in multiple domains and bring a diverse skillset to our founding team. This role requires someone who can seamlessly move between strategic thinking and tactical execution across various functional areas.

Core competencies we're looking for:

• Project management excellence: Proven ability to manage complex, cross-functional initiatives from conception to completion, with strong organizational skills and attention to detail

• Strategic planning and execution: Experience developing comprehensive strategic plans and translating vision into actionable roadmaps that drive measurable results

• Exceptional communication and writing: Outstanding written and verbal communication skills, with experience creating executive-level materials, presentations, and external stakeholder communications

• Leadership and team coordination: Experience managing teams, facilitating meetings, and coordinating across multiple stakeholders and functional areas

• Systems and process design: Ability to build scalable operational systems and organizational processes from the ground up

• Analytical and data proficiency: Strong quantitative skills with experience in data analysis, KPI development, reporting dashboards, financial modeling, and business intelligence analyses

• Education sector knowledge: Understanding of K-12 education, ideally with experience in district, school-based, or edtech roles

• Startup adaptability: Willingness to roll up sleeves, wear multiple hats, and work in a scrappy, fast-moving environment where priorities can shift quickly

Additional qualifications that would set you apart:

• Management consulting experience: Background in strategic planning, organizational development, and/or business transformation

• Startup or high-growth company experience: Track record of scaling operations and building systems in entrepreneurial environments

• HR and talent development experience: Experience designing performance management systems, hiring processes, and organizational development programs

• Financial planning and analysis: Experience with budgeting, forecasting, and capital allocation strategy

Who you are

• A strategic operator: You can see the big picture and execute on the details. You understand how to translate vision into actionable plans and drive results across multiple workstreams

• A systems thinker: You excel at designing and building systems and processes that enable teams to operate efficiently and effectively at scale

• Collaborative: You have experience working across cross-functional teams and are comfortable in an environment requiring constant collaboration with colleagues at all levels

• An exceptional communicator: You excel at both written and verbal communication, whether you're crafting executive memos, leading strategic discussions, presenting to stakeholders, or facilitating cross-functional meetings

• Data-driven: You use data and analytics to inform decisions and measure success, with strong skills in creating dashboards and reporting mechanisms

• Efficient: You are excited to build an impactful company in a lean environment. You can handle multiple priorities, tasks, and requests simultaneously while maintaining high standards

• Passionate about education: You are driven to improve how schools operate and help them use their most precious resources -- time, money, and talent -- to best serve students

Benefits we offer

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

• 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