Skydio

Program Manager, Major Deployments - Site Security

Skydio$170K — $230K *
US-AnywhereRemote in United States
Business Services
8 - 10 years of experience
Job Overview by Ladders

Qualifications

  • 8+ years in enterprise operational programs, business transformation, or security operations.
  • Experience in large enterprises evaluating technologies for operational use.
  • Track record of scaling technologies from pilot to full deployment.
  • Proficient in developing business cases and operational metrics for executives.
  • Strong grasp of enterprise processes and change management principles.
  • Proven leadership in cross-functional settings involving multiple stakeholders.
  • Excellent communication skills with an aptitude for stakeholder management.

Responsibilities

  • Lead the assessment of technologies enhancing operational efficiency and security.
  • Create evaluation frameworks for technical feasibility and business value.
  • Develop ROI models to guide investment decisions and executive proposals.
  • Collaborate with cross-functional teams to tailor solutions for customers.
  • Drive the transition from pilot projects to scalable operations.
  • Design operating models that integrate new technologies into daily business activities.
  • Establish governance and metrics for sustainable technology adoption.

Benefits

  • Comprehensive health insurance plans for full-time employees.
  • Paid vacation and sick leave, plus holiday pay.
  • 401K savings plan for retirement.
  • Equity opportunities through stock options for long-term growth.
Full Job Description
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.

What You'll Do
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.
What We're Looking For
Required Qualifications
  • 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.

Compensation: At Skydio, our compensation packages for regular, full-time employees include competitive base salaries, equity in the form of stock options, and comprehensive benefits packages. Compensation will vary based on factors, including skill level, proficiencies, transferable knowledge, and experience. Relocation assistance may also be provided for eligible roles. The annual base salary range for this position is $170,000 - $230,000*. Fundamentally, we believe that equity is the key to long-term financial growth, and we ensure all regular, full-time employees have the opportunity to significantly benefit from the company's success. Regular, full-time employees are eligible to enroll in the Company's group health insurance plans. Regular, full-time employees are eligible to receive the following benefits: Paid vacation time, sick leave, holiday pay and 401K savings plan. This position and all associated benefits are subject to applicable federal, state, and local laws, as well as the Company's policies and eligibility criteria.

*Compensation for certain positions may vary based on the position's location.

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About Skydio

Skydio is a leading manufacturer of autonomous drones for consumer and commercial use. The company's drones are equipped with advanced computer vision and artificial intelligence technology, allowing them to navigate complex environments and avoid obstacles. Skydio was founded in 2014 by a team of experts in robotics, computer vision, and artificial intelligence. The company is headquartered in Sunnyvale, California.
Learn more about Skydio
Size
200 employees
Industry
Founded
2014

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