Founding Chief of Staff

Who we areTimely 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 roleAs 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 & leadershipTeam 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 alignmentStrategic 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 CommitteeStrategic Initiatives & Project Management: Partner with the CEO and Steering Committee to oversee and project manage critical/sensitive cross-functional initiativesCross-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 organizationTalent strategyPerformance Management: Design, build, and implement an annual performance management process with career development frameworks to support our growing teamStrategic support to the CEOData & 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 strategyExternal 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 customersGeneral Support: Provide strategic and operational support to the CEO and Steering Committee across various initiatives to help generate capacity for high-impact workBe part of the brain trust to build a lasting and valuable companyOur 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 futureWhat we are looking for in candidatesWe'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 detailStrategic planning and execution: Experience developing comprehensive strategic plans and translating vision into actionable roadmaps that drive measurable resultsExceptional communication and writing: Outstanding written and verbal communication skills, with experience creating executive-level materials, presentations, and external stakeholder communicationsLeadership and team coordination: Experience managing teams, facilitating meetings, and coordinating across multiple stakeholders and functional areasSystems and process design: Ability to build scalable operational systems and organizational processes from the ground upAnalytical and data proficiency: Strong quantitative skills with experience in data analysis, KPI development, reporting dashboards, financial modeling, and business intelligence analysesEducation sector knowledge: Understanding of K-12 education, ideally with experience in district, school-based, or edtech rolesStartup adaptability: Willingness to roll up sleeves, wear multiple hats, and work in a scrappy, fast-moving environment where priorities can shift quicklyAdditional qualifications that would set you apart:Management consulting experience: Background in strategic planning, organizational development, and/or business transformationStartup or high-growth company experience: Track record of scaling operations and building systems in entrepreneurial environmentsHR and talent development experience: Experience designing performance management systems, hiring processes, and organizational development programsFinancial planning and analysis: Experience with budgeting, forecasting, and capital allocation strategyWho you areA 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 workstreamsA systems thinker: You excel at designing and building systems and processes that enable teams to operate efficiently and effectively at scaleCollaborative: You have experience working across cross-functional teams and are comfortable in an environment requiring constant collaboration with colleagues at all levelsAn 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 meetingsData-driven: You use data and analytics to inform decisions and measure success, with strong skills in creating dashboards and reporting mechanismsEfficient: You are excited to build an impactful company in a lean environment. You can handle multiple priorities, tasks, and requests simultaneously while maintaining high standardsPassionate 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 studentsBenefits we offerHealth: medical, dental, vision, and a contribution-only 401(k) plan, life insurancePersonal 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 itFlexible PTO

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