Program Manager, Major Deployments - Site Security

Skydio

1d•$170,000 - $230,000

About The Position

Skydio is seeking a strategic operator to manage Enterprise site security customers through the 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. This role 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 as an internal business leader within a large enterprise or technology company, responsible for deciding what gets operationalized and how it scales.

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.

Nice To Haves

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.

Responsibilities

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.
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.
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.
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.
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.