Software Guidance & Assistance, Inc., (SGA), is searching for an AI Transformation Lead – Group Benefits for a direct placement assignment with one of our premierInsurance clients i n NYC, Holmdel, NJ or Bethlehem, PA. NYC is preferred. Hybrid schedule 3x weekly onsite.

The AI Transformation Lead for Group Benefits will drive strategy and execution for high-impact AI initiatives across claims, underwriting, customer service, and core Group Benefits operations. This role requires a structured problem-solver with strong product strategy skills and exceptional execution capabilities. The ideal candidate can turn ambiguous business challenges into well-defined AI use cases, build product roadmaps, and then lead cross-functional teams to deliver measurable business outcomes.

This is a business-facing, product-and-execution role -approximately 30% strategy and roadmap development , and 70% execution, delivery, and stakeholder alignment . The ideal candidate combines product management discipline, consulting-style analytical rigor, and a strong ability to influence senior leaders across large, regulated environments. They must bring a mindset that pushes boundaries ( “an agitator”) while still navigating the realities of insurance and compliance.

The successful candidate will partner closely with data science (model development), engineering (integration and deployment), and operational leaders, including heads of Claims and Service. The role reports to the Head of AI Transformation and, while structured as an individual contributor, carries significant enterprise visibility and influence. This is a central role in the firm’s broader mission to disrupt the industry with AI-driven automation and efficiency.

Responsibilities:

• Drive end-to-end delivery of AI-enabled solutions from opportunity identification through launch, adoption, and impact measurement.
• Convert ambiguous, loosely defined business problems into clear AI use cases, structured problem statements, and actionable roadmaps.
• Develop business cases that quantify value, assess feasibility, and drive prioritization across multiple senior stakeholders.
• Lead and influence cross-functional teams (data science, engineering, claims, underwriting, legal, finance) without direct authority.
• Ensure rapid execution by building structure, establishing clear milestones, and managing interdependencies.
• Partner with data science to understand model behavior, back-testing, statistical considerations, and risk factors (without being hands-on technical).
• Act as a thought leader and “agitator,” challenging existing processes and pushing for AI-driven transformation within a regulated environment.
• Drive enterprise change management, stakeholder communication, and adoption of new AI products.
• Communicate complex ideas clearly and concisely to senior leaders, including executives across Group Benefits, Claims, and Service.

Required Skills:

• 8+ years in product management, management consulting, digital transformation, or similar strategy/execution roles.
• Proven ability to structure ambiguous business problems, create strategic clarity, and develop executable roadmaps.
• Strong execution leadership – demonstrated experience building and delivering products, not just ideating.
• Exceptional communication skills and executive presence; able to influence senior leaders and facilitate decision-making.
• Experience working in regulated industries (insurance, healthcare, financial services, or similar) is a strong plus. Insurance is a major plus.
• Strong analytical and quantitative orientation – comfort with statistical reasoning, model back-testing concepts, and data-driven decision-making.
• Experience partnering closely with data science and engineering teams; ability to understand AI/ML at a conceptual level without being a coder.
• High EQ – listens well, communicates calmly, avoids rambling, and builds trust with partners at all levels.
• Background in mid-size tech , high-growth product organizations , or top-tier consulting firms (Bain, BCG, Deloitte, etc.) strongly preferred.
• Passion for AI, emerging technology, and the transformation of core business workflows.

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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