AI Transformation Lead - Group Benefits

Software Guidance & Assistance, Inc., (SGA) is searching for an AI Transformation Lead - Group Benefits for a direct placement assignment with one of our premier Insurance clients in NYC (preferred), Holmdel, NJ or Bethlehem, PA. NYC preferred. Hybrid schedule: 3 days onsite per week.

Overview

The AI Transformation Lead for Group Benefits drives strategy and execution for high-impact AI initiatives across claims, underwriting, customer service, and core Group Benefits operations. This role combines structured problem-solving, product strategy, analytical rigor, and strong execution leadership.
The ideal candidate turns ambiguous business challenges into clear AI use cases, develops actionable product roadmaps, and leads cross-functional teams to deliver measurable business outcomes. The role is approximately 30% strategy and roadmap development, 70% execution, delivery, and stakeholder alignment.

This is a business-facing, product-and-execution role that requires polished communication skills, executive presence, and the ability to influence senior leaders in regulated, complex environments. While not a technical role, the candidate must be able to speak credibly about AI concepts (LLMs, retrieval, guardrails, feasibility) when partnering with data science and engineering leaders.

The position carries significant enterprise visibility.

Responsibilities

Strategic Framing & Use Case Definition

• Identify, shape, and prioritize AI opportunities across claims, underwriting, and service operations.
• Convert loosely defined problems into structured use cases with clear business value, feasibility, KPIs, and risks.
• Build and maintain multi-phase product roadmaps aligned to enterprise AI strategy.

Execution & Delivery

• Drive end-to-end delivery of AI-enabled products from discovery through launch, business readiness, adoption, and measurable impact.
• Set program structure, milestones, governance, and decision frameworks across complex, multi-stakeholder initiatives.
• Partner closely with data science, engineering, legal, finance, and operations to ensure quality, speed, and compliance.

Cross-Functional Influence & Communication

• Communicate complex concepts simply and persuasively to senior leaders across Group Benefits.
• Influence executives (Claims, Service, Operations) by providing clarity, framing trade-offs, and enabling informed decisions.
• Represent Group Benefits in technical discussions with data science, cloud, applications, and platform engineering leads.

Analytical Rigor & Business Value

• Develop business cases grounded in quantitative analysis, statistical reasoning, and operational impact.
• Evaluate pilot results, model performance, and value realization; refine product direction based on data.

Change Leadership & Adoption

• Lead change management, business readiness planning, training, communications, and operational rollout.
• Drive adoption and ensure AI products are embedded successfully into business workflows.

Required Skills

• 8+ years in product management, management consulting, digital transformation, strategy execution, or relevant hybrid roles.
• Strong ability to structure ambiguous business problems and translate them into actionable roadmaps.
• Proven track record delivering enterprise products or transformation initiatives (not just ideation).
• Exceptional communication and executive presence - must influence senior business leaders with clarity and confidence.
• Comfort engaging with data science and engineering teams; able to understand LLM concepts, retrieval patterns, guardrails, and AI solution patterns at a conceptual level.
• Strong analytical and quantitative orientation; familiar with statistical reasoning, back-testing concepts, and KPI frameworks.
• Experience working in regulated environments (insurance, healthcare, financial services), with insurance being a major plus.
• High EQ and professionalism - listens well, communicates succinctly, handles pressure, and builds trust.
• Background in mid-size tech, high-growth product organizations, or top-tier consulting (Bain, BCG, Deloitte, McKinsey) preferred.
• Passion for AI and a demonstrated ability to ramp up quickly in new domains.

SGA is a technology and resource solutions provider driven to stand out. We are a women-owned business. Our mission: to solve big IT problems with a more personal, boutique approach. Each year, we match consultants like you to more than 1,000 engagements. When we say let's work better together, we mean it. You'll join a diverse team built on these core values: customer service, employee development, and quality and integrity in everything we do. Be yourself, love what you do and find your passion at work. Please find us at .

SGA is an Equal Opportunity Employer and does not discriminate on the basis of Race, Color, Sex, Sexual Orientation, Gender Identity, Religion, National Origin, Disability, Veteran Status, Age, Marital Status, Pregnancy, Genetic Information, or Other Legally Protected Status. We are committed to providing access, equal opportunity, and reasonable accommodation for individuals with disabilities in employment, and our services, programs, and activities. Please visit our company to request an accommodation or assistance regarding our policy.

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