Enterprise Program Lead: AI, Security & Ops

Booster; Northern (KY); Hybrid; USD 170,000 - 230,000; Full time

Benefits offered by this job

Stock options

Health insurance

Paid vacation

401K

Job summary

Skydio is seeking a strategic operator to manage Enterprise site security programs, evaluating technologies, building ROI models, and driving adoption from pilots to scalable operations across a distributed enterprise.

The role partners with Product, Engineering, Security, and Operations to determine value, readiness, and execution plans, guiding multi-functional teams and executive stakeholders toward measurable business outcomes.

Qualifications

• 8+ years of experience leading enterprise operational programs, technology operations, business transformation, or security operations.
• Experience evaluating emerging technologies for operational adoption in large enterprises or tech companies.
• Proven ability to transition technologies from evaluation/pilot phases into enterprise-scale deployment.
• Experience building business cases, ROI analyses, and metrics that influence executive decisions.
• Strong understanding of enterprise processes, change management, and technology implementation.
• Leadership of cross-functional initiatives involving Product, Engineering, Operations and executives.
• Excellent executive communication and stakeholder management skills.

Responsibilities

• Lead evaluation of emerging technologies and operational capabilities to improve efficiency, safety, and security across commercial operations.
• Develop evaluation frameworks assessing feasibility, impact, complexity, and long-term value.
• Build ROI and financial models to support investment decisions and executive recommendations.
• Partner with Product, Engineering, Security, and Operations to develop customer-specific solutions ready for deployment.
• Own the transition of pilots into repeatable, scalable operational processes.
• Design operating models that enable new technologies as standard business operations.
• Establish governance, documentation, training, and success metrics for sustainable adoption.
• Measure performance and optimize processes based on outcomes.
• Track benefits post-deployment and quantify efficiency, cost savings, risk reduction, and adoption.

Skills

Strategic leadership

Executive communication

Cross-functional leadership

ROI modeling

Enterprise operations

Program management

Operational excellence

Stakeholder management

Job description

Skydio is seeking a strategic operator to manage Enterprise site security programs, evaluating technologies, building ROI models, and driving adoption from pilots to scalable operations across a distributed enterprise.

The role partners with Product, Engineering, Security, and Operations to determine value, readiness, and execution plans, guiding multi-functional teams and executive stakeholders toward measurable business outcomes.