Enterprise AI Transformation Strategist - Financial Services

We're building an agentic AI platform that helps enterprises transform complex business workflows into AI-powered operations. We work with leading global companies to identify high-value workflows, deploy AI agents into real business environments, and help organizations move from experimentation to measurable enterprise impact. We believe AI adoption inside the enterprise isn't just a technology challenge. It requires business context, workflow understanding, change management, trust, ownership, and a clear path to value. That's where this role comes in. We're a well-funded, early-stage startup, hiring an Enterprise AI Transformation Strategist to bring that transformation discipline to financial services: banking, insurance, payments, and other regulated institutions. This role is ideal for a senior, customer-facing operator who sits at the intersection of strategy consulting and hands-on delivery, and who is as comfortable in a room of C-level executives as in a working session with operators and technology teams. You will own transformation engagements end to end, from executive vision and opportunity discovery through roadmap, implementation, adoption, and value realization. You will also help build the methodology itself: the frameworks, playbooks, and tools that make how we transform customers repeatable. Financial institutions want AI, and most of them are stuck in pilots. You will move them past that point. You will become the advisor their executives trust and turn AI ambition into adopted workflows with value they can measure, and that measured value is the proof you're winning. YOUR IMPACT Executive Strategy & Vision • Partner with CxOs and senior leaders to define how AI reshapes their functions, workflows, operating models, and value chains • Facilitate the executive workshops, discovery sessions, and value realization reviews that align leadership around one clear AI agenda • Build the business cases and value models behind every recommendation, covering productivity, cost, revenue, risk, cycle time, and quality Use Case Discovery & Roadmapping • Translate business ambition into prioritized AI use cases across finance, risk, compliance, customer operations, underwriting, claims, servicing, and back office, each with a clear implementation plan and measurable outcomes • Build adoption roadmaps that connect strategy, workflow redesign, technology readiness, change management, governance, and value tracking Transformation Delivery Lead transformation offices for strategic accounts, owning stakeholders, workstreams, timelines, risks, and executive communication Turn roadmaps into executable plans, and keep milestones, dependencies, and cross-functional teams on track and accountable for outcomes Work with Product, Solutions Engineering, Delivery, and Customer teams to turn customer needs into practical AI agent and workflow automation deployments Adoption & Change • Find what's actually blocking adoption, from regulatory requirements and risk controls to data sensitivity and complex stakeholder environments, and design practical fixes across process, people, governance, incentives, and operating rhythm • Move customers beyond pilots by defining business ownership, human-in-the-loop processes, change management, and success metrics Methodology Building • Create reusable frameworks, playbooks, and workshop formats that strengthen Reindeer's AI transformation methodology • Build the maturity models and value assessment tools that let that methodology scale across customers, functions, and industries WHAT IT TAKES • 5+ years in strategy consulting, enterprise transformation, digital transformation, AI/data strategy, or complex enterprise delivery. (Experience at a top-tier consulting firm, enterprise software company, or AI company is a plus, as is an MBA or advanced degree.) • A track record of leading enterprise-scale transformation programs with senior business and technology stakeholders, ideally at Fortune 1000 or global enterprises. You should be strong across workstream planning, risk management, executive reporting, and delivery governance. • Deep familiarity with financial services: the operational workflows, regulatory realities, stakeholders, and transformation priorities of banks, insurers, and payments companies. • Practical fluency in generative and agentic AI, automation, data, and enterprise systems, and a clear sense of how technology actually gets deployed inside large organizations. • Executive presence: you can lead C-suite conversations, turn ambiguity into a clear path forward, and back it with business cases, roadmaps, and recommendations that hold up. • High ownership, comfort operating in ambiguity, and willingness to travel for customer workshops and executive meetings. COMPENSATION The expected salary for this role is $230,000 to $300,000 OTE. This is a good-faith estimate but does not include equity or other forms of compensation. Pay will be based on experience level, but those outside the salary band are welcome to apply.