Director of AI Operations & Enablement

Awardco is seeking a highly capable, results-driven leader to serve as our Director of AI Operations & Enablement. This person will be responsible for helping Awardco adopt and operationalize AI across the business in a way that is practical, secure, measurable, and scalable. This is not a research role. It's not a "tool collector" role. It is a high-impact role focused on turning AI into real workflows, increasing productivity, improving customer experience, and achieving stronger business outcomes.

You will work cross-functionally with leaders in Customer Success, Support, Professional Services, Sales, Marketing, People Ops, Finance, IT, Security, and Product/Engineering to identify the highest value opportunities and drive adoption through pilots, enablement, governance, and change management.

• AI Strategy and Prioritization:
• Build and maintain an Awardco-wide pipeline of AI opportunities across departments
• Lead a structured intake and prioritization process for AI use cases
• Evaluate impact based on ROI, adoption potential, complexity, and risk
• Keep leadership up to date on the AI landscape and what matters for our business
• Cross-Functional Delivery and Implementation:
• Own delivery accountability for AI initiatives, including scope, timeline, adoption, and business impact
• Partner with functional leaders to map workflows and identify automation opportunities
• Lead execution of high-impact AI initiatives from concept to rollout
• Translate business needs into requirements and work with teams to implement solutions (internal build, tools, vendors, integrations)
• Drive operating rhythms to ensure initiatives ship on time and deliver outcomes
• Enablement and Change Management:
• Develop internal enablement materials, playbooks, training, and documentation
• Build an internal community of "AI Champions" across departments
• Improve adoption through communications, training sessions, and role-based enablement
• Track and improve utilization and behavior change over time
• AI Governance and Responsible Use:
• Partner with IT, Legal, and Security to develop and enforce AI policies and guardrails
• Establish an approved vendor stack and usage standards
• Support vendor reviews and procurement processes
• Ensure compliance with privacy, data handling, and security requirements
• Measurement and Operational Excellence:
• Implement success metrics and dashboards to track AI value (time saved, quality improvements, cost reduction, revenue lift)
• Define standards for pilot success and scaling decisions
• Create repeatable systems so AI implementation becomes a capability at Awardco, not a one-off effort

• In your first 90 to 180 days, you will deliver:
• A ranked backlog of the top AI use cases across Awardco
• A structured AI intake, pilot, and rollout process
• 3 to 5 workflows launched into production usage, clear owners, adoption, and measurable impact (not just pilots or proofs of concept)
• An AI enablement program with training, office hours, playbooks, and internal champions
• An AI governance foundation with clear tool standards, policies, and vendor approvals
• A dashboard of AI impact metrics for leadership visibility

You're an operator who thrives at the intersection of business workflows and emerging technology. You can talk to executives, work directly with teams, and drive change without waiting for perfect conditions. You are pragmatic and action-oriented: excited by AI, but grounded in what ships and what drives outcomes.

• Required:
• 6 to 12+ years of experience in operations, strategy, program management, enablement, or digital transformation roles
• Proven experience leading cross-functional initiatives from idea to execution
• Strong working knowledge of modern AI capabilities and use cases (LLMs, automation, copilots, agents, retrieval, summarization, classification)
• Ability to map and redesign workflows across teams to drive efficiency and quality
• Strong communication skills (written, verbal, executive level)
• High judgment and maturity with sensitive data, privacy, and security considerations
• Preferred:
• Experience implementing automation or AI-powered tools in a SaaS environment
• Experience partnering with IT,…