Program Manager, Major Deployments - Site Security

Skydio is the leading US drone company and the world leader in autonomous flight, the key technology for the future of drones and aerial mobility. The Skydio team combines deep expertise in artificial intelligence, best-in-class hardware and software product development, operational excellence, and customer obsession to empower a broader, more diverse audience of drone users, from utility inspectors to first responders, soldiers in battlefield scenarios, and beyond.

About the Role

We are looking for a strategic operator who thrives at the intersection of emerging technology and enterprise operations. This role is responsible for managing Enterprise site security customers through evaluation of Skydio solutions, building the business case for adoption, and leading the transition from pilot programs into scalable, day-to-day operations across commercial site security. Rather than sitting within an innovation or R&D organization, this leader partners closely with business operations, product, engineering, and security teams to determine which technologies create measurable operational value, establish ROI frameworks, and ensure successful operational deployment across a distributed enterprise. The ideal candidate has experience inside a large enterprise or technology company evaluating emerging technologies—not as a vendor or consultant, but as the internal business leader responsible for deciding what gets operationalized and how it scales.

Responsibilities

• Technology Evaluation & Operational Strategy
  • Lead the evaluation of emerging technologies and operational capabilities that improve efficiency, safety, and security across commercial operations.
  • Develop structured evaluation frameworks that assess technical feasibility, operational impact, implementation complexity, and long-term business value.
  • Build financial and operational ROI models that support investment decisions and executive recommendations.
  • Partner with Product, Engineering, Security, and Operations to develop customer-specific solutions and determine readiness for operational deployment.
  • Own the transition of successful pilot programs into repeatable, scalable operational processes.
• Operational Excellence
  • Design and implement operating models that enable new technologies to become part of standard business operations.
  • Establish governance, documentation, training, and success metrics required for sustainable adoption.
  • Measure operational performance and continuously optimize processes based on business outcomes.
  • Track benefit realization post-deployment and quantify improvements in efficiency, cost savings, risk reduction, and user adoption.
• Program & Portfolio Leadership
  • Lead a portfolio of strategic operational initiatives supporting commercial site security programs.
  • Define program scope, milestones, resource requirements, and execution plans across multiple concurrent initiatives.
  • Manage budgets, forecasts, vendor relationships, and resource allocation to ensure successful delivery.
  • Develop executive-level reporting that communicates progress, risks, dependencies, and business outcomes.
• Cross-Functional Leadership
  • Serve as the operational bridge between Product, Engineering, Security, IT, Manufacturing, and Business Operations.
  • Align cross-functional teams around implementation priorities, timelines, and operational readiness.
  • Resolve complex organizational challenges that impact program execution.
  • Influence executive stakeholders through data-driven recommendations and business case development.
• Team Leadership
  • Build, mentor, and develop a high-performing team of program managers and operational subject matter experts.
  • Establish delivery standards, documentation practices, and operational governance.
  • Foster a culture focused on execution, continuous improvement, and measurable business impact.

Requirements

• 8+ years of experience leading enterprise operational programs, technology operations, business transformation, or security operations.
• Experience within a large enterprise or technology company evaluating emerging technologies for operational adoption.
• Demonstrated success transitioning new technologies from evaluation and pilot phases into enterprise-scale operational deployment.
• Experience developing business cases, ROI analyses, and operational success metrics that influence executive decision making.
• Strong understanding of enterprise operational processes, change management, and technology implementation.
• Experience leading complex cross-functional initiatives involving Product, Engineering, Operations, and executive stakeholders.
• Excellent executive communication and stakeholder management skills.

Preferred Qualifications

• Experience supporting commercial site security, physical security operations, or enterprise security technology.
• Experience evaluating AI, automation, robotics, computer vision, autonomous systems, or other emerging technologies.
• Background in program management, business operations, or operational excellence.
• Experience building operational governance frameworks and post-deployment performance measurement.

Pay

The annual base salary range for this position is $170,000 - $230,000. Relocation assistance may also be provided for eligible roles.

Benefits

• Competitive base salaries and equity in the form of stock options.
• Comprehensive group health insurance plans.
• Paid vacation time, sick leave, holiday pay, and 401K savings plan.