AI Transformation Lead

AI Transformation Lead

As the AI Transformation Lead, you are responsible for orchestrating and translating AI investments into positive EBITDA impact across the Twin Valley Family of Companies. This role will help move the company from experimentation and reliance on outside consultants, to a company that has proven internal expertise to use AI as a differentiator for the clients we serve. This role will proactively identify, prioritize, and drive AI-enabled opportunities aligned with the business strategy and vision. It supports the business by translating rapidly evolving AI capabilities into practical, business-relevant initiatives that improve processes, decision-making, efficiency, automation, clear outcomes for customers, and customer credibility, while ensuring efforts are tightly coupled with data quality, reporting mechanisms, and clear guardrails for acceptable use, security, access controls, and data freshness. The role has enterprise-wide impact, developing an actionable roadmap, guiding prioritization, informing build-vs-buy and vendor evaluations, and enabling demonstrable progress within defined time horizons. You will create and direct a small ecosystem of resources rather than personally executing every technical task, but you are technical enough to prototype yourself where speed demands it. While this role is not the architect of our long-term AI platform, the early pilots and architectural patterns established under this leader will form the foundation for a future platform we intend to productize. Decisions made now about agent design, data access patterns, tooling selection, and software-enforced guardrails should be made with that long-term strategy in mind. This role will possess the ability to communicate and work with all areas of the business, while partnering internal teams for requirements, leadership, the internal IT team, and external partners to coordinate resources and execute prioritized initiatives.

Key Accountabilities:

1. Develop and maintain AI use cases and deployment roadmap
2. Support the security team in setting organizational security guardrails and governance policies in support of AI strategy and ensure compliance
3. Develop and maintain data strategy in support of AI opportunities
4. Prioritize, project manage, and deliver AI supported outcomes from ideation through practical use
5. Source, develop and lead resources needed to deliver on AI deployments (internal and external partners)
6. Provide structured monthly, quarterly, and annual executive and Board level reporting on AI initiatives and roadmap

Key Measurables:

1. Clearly defined and actionable AI use cases and deployment roadmap documented and approved within 3 months
2. Develop and launch methodology for how we will measure success, failure, and when to pivot for prioritized AI pilots/initiatives within 3 months
3. Support the security team in implementing data protection and acceptable use guardrails for AI within 3 months
4. At least one AI pilot deployed in production with measurable results within 6 months
5. Demonstrated positive impact on EBITDA from deployment of AI initiatives within first 12 months
6. Measurable increase in organizational capability and confidence in using AI tools through structured enablement/training within 12 months

What You Bring To The Position:

• You are a team first leader who leads by example and knows how to have fun in a professional environment. You embrace change and have the resiliency required to continually improve yourself and the team around you. As part of a values-led organization, not only do you embody and align with our core values, you develop and build teams that do the same, ensuring we have the right people to fuel our growth.
• You embody and align with our core values and appreciate the strength and stability that comes from working with a values-based company. You appreciate the power and efficiency of consistency in the "ways" we operate.
• You embrace change and have the resilience required to continually improve yourself. You can think creatively and can adapt to evolving situations.
• You understand the need to collaborate with your team members and other departments and that synergy comes from everyone rowing in the same direction.
• You have a strong desire to provide customers with optimal technology solutions and exemplary customer service.
• You are a self-starter who is prepared to develop and execute your plan and deliver on quarterly goals on a consistent basis.
• You take what you do seriously, but you do not take yourself seriously and you know how to have fun in a professional environment. You are humbly confident and use your knowledge to build confidence without being arrogant.

Requirements:

You successfully fulfill the following essential duties and responsibilities:

• Evaluate where AI can meaningfully improve business processes, customer service and outcomes, service delivery workflows, decision-making, and efficiency.
• Orchestrate the delivery of AI pilots and for pilots that demonstrate measurable value, determine resourcing needed to go-to-market.
• Personally validate partner-delivered work (architecture reviews, model choices, retrieval performance) rather than relying on partner self-reporting
• Prototyping or piloting use cases directly when speed or learning demands it
• Evaluating AI tooling and platforms hands-on, not just through vendor demos
• Lead a structured, collaborative approach to opportunity identification, including discovery with leaders and teams to surface pain points and requirements.
• Define a consistent methodology for assessing, framing, and prioritizing AI use cases. Clarify what success and failure look like, learn quickly, and "fail fast" where appropriate. Develop clear reporting on AI initiatives measurement criteria.
• Develop and articulate AI strategy that connects business objectives, data strategy, and technology capabilities. Sequence investments across data, security, hardware/software, people, partners, reporting, and automation layers.
• Apply enterprise AI architecture principles to early pilots, including scoped agents with defined tools, governed retrieval, and software-enforced access controls, recognizing that early design choices establish patterns that the long-term AI platform will inherit.
• Guide prioritization of AI and automation initiatives across teams without personally executing all technical work. Prevent scope creep and fragmented experimentation.
• Coordinate across disparate systems and data sources to enable effective internal AI use.
• Support the security team in defining and enforcing governance and security guardrails for internal AI use, including acceptable-use practices and protections against sharing sensitive or competitive data.
• For every AI capability we need, lead the decision on the right path: build it ourselves, buy it off the shelf, leverage AI tooling already available through our partner ecosystem, or bring the capability in-house through hiring.
• Engage and manage external vendors and partners: ask informed questions about product roadmaps, evaluate solutions, and coordinate internal/external resources to accelerate execution.
• Participate in client conversations to understand and identify AI supported solutions to meet client and market needs.
• Educate and communicate AI concepts in practical, digestible terms—meeting leaders and teams where they are—and strengthen organizational capability and confidence in using AI tools.
• Enable all levels of employees to develop AI as a core competency with a structured, scalable plan.
• Continuously scan the external landscape for disruptive threats and emerging opportunities, helping leadership think like a startup or new market entrant.
• Support the company by completing other duties as assigned.

As a successful employee, you will demonstrate the following professional skills as you carry out your position:

• Oral Communications – Speak clearly and persuasively in positive and negative situations; respond well to questions; demonstrate group presentation skills and participate in meetings.
• Written Communications – Write clearly and informatively, edit work for spelling and grammar; present numerical and statistical data effectively and read and interpret written information.
• Customer Service – Respond promptly and courteously to customers' requests for service and assistance; manage difficult or emotional customer situations.
• Presentation – Deliver business, non-technical, and limited-technical presentations to audiences of 20-500 individuals. This includes presentations to internal employees, prospective or existing customers, and industry events/conferences.
• Leadership – Lead people and get results through others in a positive and inspiring manner.
• Ethics – Treat people with respect; keep commitments; inspire the trust of others; work with integrity and ethically; uphold company values.
• Organizational Support – Follow company policies and procedures and complete other duties as assigned.
• Judgment – Include appropriate people in decision-making process.
• Interpersonal Skills – Maintain confidentiality; keep emotions under control; listen well.
• Strategic Thinking – Develop strategies to achieve organizational goals; analyze market and competition; identify external threats and opportunities and adapt strategy to changing conditions.
• Planning and organization – Organize and manage multiple priorities; plan work activities; use time efficiently; plan for additional resources; set goals and objectives; meet