Principal AI Enablement

WebTPA•United States,

22h•$180,000 - $292,500•Onsite

About The Position

Guidewell's Transformation Office (TO) converts the company's strategy into a disciplined, resourced, and governed program of work. The Senior Director, AI Enablement, owns the enterprise's capability to identify, build, and scale AI and automation solutions, leading both the AIM function (AI use-case intake, prioritization, and enablement) and the Automate function (process automation and intelligent automation delivery). This role is accountable for the pipeline that turns a business problem into a deployed AI or automation solution with a measurable adoption and value outcome. Reporting directly to the VP of Transformation and Performance, this role sets the enterprise's AI enablement strategy and operating model and builds the training, tooling, and delivery capacity that other TO functions and the business rely on to execute AI and automation initiatives. This role operates as a peer-partner to the other TO leaders, and is directly accountable for the AI-adoption metrics that feed the enterprise transformation scorecard.

Requirements

10+ years’ related work experience. Experience Details: AI/ML enablement, intelligent automation, RPA, or digital/technology transformation, with direct experience leading teams that deliver AI or automation solutions at enterprise scale.
Experience in technology strategy, digital transformation, or AI/data roles, with progressively senior scope
5+ years’ direct supervisory/management experience
Related Bachelor’s degree or additional related equivalent work experience Computer Science, Data Science, Engineering, or a related technical field
A track record owning the full lifecycle of AI initiatives — strategy and business case through delivery, governance, adoption, and realized value
Experience building or scaling an AI portfolio as a managed investment (prioritization, funding decisions, ROI methodology), not just running one-off proofs of concept
People leadership — hiring and developing a technical/analytical team (data scientists, AI product owners, analysts)
Experience building an intake, prioritization, and delivery pipeline for AI or automation use cases in a large, complex, matrixed organization.
Working knowledge of responsible-AI practices (data governance, model risk, human-in-the-loop design) sufficient to set enterprise guardrails, without requiring a hands-on data science or engineering background.
Ability to translate technical AI and automation concepts for senior business stakeholders, and to translate business problems into scoped, deliverable AI or automation use cases.
Comfort setting and enforcing responsible-use guardrails, including saying no to use cases that carry unacceptable risk.
Ability to talk fluently across both technical AI/data teams and executive/business stakeholders
Responsible AI / AI ethics and risk management literacy (bias, privacy, security)
Experience defining and tracking AI-adoption metrics
Portfolio and investment governance instincts (trade-offs, reinvestment logic, value realization). Comfort operating in ambiguity.

Nice To Haves

Master’s degree (MBA, MS in Data Science/AI, or equivalent) frequently preferred, especially in larger enterprises
Experience in health insurance, healthcare, or another regulated industry.
Experience standing up or scaling an enterprise AI Center of Excellence or intelligent automation function.
Familiarity with major automation platforms (e.g., UiPath, Automation Anywhere, Power Automate) and AI/LLM tooling landscape.
AI leadership programs: e.g., MIT Sloan AI for Business Leaders, Wharton AI programs, Columbia's AI executive program
USAII's Certified AI Transformation Leader (CAITL™) or Certified Artificial Intelligence Scientist (CAIS) Prosci, CCMP Fluency in cloud/AI platforms (Azure AI, AWS AI, Google Cloud ML)

Responsibilities

Leads operating-model redesign where AI can create step-change value partnering closely with leaders supporting organizational redesign, process and IT engineering to deliver results.
Creates repeatable mechanisms for moving priority opportunities from concept through pilot, adoption, measurement, and scale, with clear accountability and disciplined follow-through.
Leads the Automate function: builds and scales the enterprise's process automation and intelligent automation capability, prioritizing candidate processes, supporting delivery, and tracking automation ROI.
Leads the AIM function for AI: runs use-case intake and prioritization, builds AI literacy and enablement programs across the business, and matches business problems to the right AI approach and owner.
Owns the organizational enablement strategy for AI-driven transformation, including role-based AI literacy, leadership education, manager enablement, talent and skill implications, change management, communications, and feedback loops that strengthen adoption.
Owns the AI-adoption metrics in the enterprise transformation scorecard, partnering with the Director, Transformation Governance and Performance, to ensure they are accurate, current, and trusted.
Establishes a durable process to evaluate and prioritize potential AI enablement opportunities. This includes establish business cases, value hypotheses, success measures, and stage gates for priority AI initiatives; partner with Finance and business owners to track realized value and inform investment, scaling, or sunset decisions.
Represents AI enablement in steering committee and governance forums, defending priorities, resourcing trade-offs, and scaling decisions to senior and executive leadership
Builds and develops leadership bench strength across the AIM and Automate teams, and manages a multi-team organization spanning both functions.
Partners with the Senior Director of Business Architecture, Process Excellence and Product Management to ensure AI and automation investment is sequenced against the enterprise's target-state capability and process priorities rather than built in isolation.
Collaborates with senior leadership and cross-functional stakeholders to align AI-enabled transformation with GuideWell's broader enterprise strategy, operating model, transformation agenda, and business-unit priorities.

Benefits

Medical, dental, vision, life and global travel health insurance
Income protection benefits: life insurance, short- and long-term disability programs
Leave programs to support personal circumstances
Retirement Savings Plan including employer match
Paid time off, volunteer time off, 10 holidays and 2 well-being days
Additional voluntary benefits available
A comprehensive wellness program
Competitive pay
Opportunities for incentive or commission compensation
Regular annual reviews with pay for performance considerations for base pay increases