About The Position

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.

Requirements

  • 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

Nice To Haves

  • Experience implementing automation or AI-powered tools in a SaaS environment
  • Experience partnering with IT, Security, Legal, and Engineering on platform rollouts
  • Familiarity with tools like ChatGPT Enterprise, Microsoft Copilot, Gemini, Slack AI, Notion AI, Gong, Zendesk AI, Salesforce Einstein, Zapier, Workato, etc.
  • Experience running enablement programs and change management
  • Experience building internal communities of practice or champion networks

Responsibilities

  • 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
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