Chief of Staff & Business Operations Lead

The Role

Pilot is building a first-of-its-kind, hybrid software/service solution to tackle the financial back office (bookkeeping, tax, CFO, etc.) so that founders and business owners can focus on building and running their businesses. We already work with 1,700+ customers in the tech startup and SMB sectors, and we are expanding rapidly. The Customer Operations department is 125+ employees that partner with our customers to manage their accounting back office and support them in their business goals. This is a leadership role that supports the VP Customer Operations as their Chief of Staff as well as managing a small team of Business Operations Managers. The Chief of Staff will play a critical role in supporting the VP of Customer Operations in major decision-making processes and acting as a key conduit for the operations team. This role requires a strategic thinker with excellent organizational and communication skills, capable of handling confidential information with discretion. This is a high impact role that will have a front row seat into how the key decisions are made at Pilot. This role will drive the priorities for the department, work on critical initiatives for the business, set shared goals with cross-functional organizational leaders, develop multi-year roadmaps with specific actions needed to achieve goals across the enterprise, ensure that resources are prioritized and committed to achieve strategic goals and desired outcomes, monitor whether actions achieved intended goals, and revise future strategy and plans accordingly. Customer Operations is based in Nashville, TN. This role is available both remote and in office (flexible on-site schedule).   

Key Responsibilities

• Data-Driven Insights: Leverage analytics to evaluate business performance and make informed decisions. Prepare reports and presentations to support leadership in strategic planning and decision making.
• Resource Management: Oversee company resources, including budget, personnel, and tools, ensuring they are efficiently allocated to meet business needs.
• Project and Change Management: Lead key initiatives and projects to drive business growth, working with various teams to ensure milestones are met on time and within budget and helping drive that change with clear communications and/or training materials
• Process Optimization: Identify and implement improvements in business processes, workflows, and internal systems to maximize operational efficiency.
• Vendor Management: Manage relationships with third-party vendors, ensuring that services meet company standards and contracts are cost-effective.
• Strategic Leadership: Participate in strategic planning sessions and help translate high-level strategies into actionable plans.
• Culture …