Head of AI & Digital Transformation

Chartwell is a closely-knit professional financial advisory firm where a high degree of intellectual curiosity, dedication to continuous improvement, and the ability to work in a team environment are critical for success. We conduct business in an honest, ethical manner, and treat everyone with the highest level of respect, integrity, and professional courtesy. We believe providing quality service to our clients will develop enduring relationships and ensure our long-term success. We support an environment where every team member is empowered to attain their professional goals.

The Head of AI & Digital Transformation will serve as Chartwell’s senior leader responsible for defining and executing the firm’s AI, data, and digital enablement strategy. This individual will act as a business-driven product owner, translating Chartwell’s strategic priorities and client needs into a practical roadmap for AI adoption, data modernization, and workflow transformation across advisory services and internal operations.

This role is not about building complex models in isolation or experimenting with tools for their own sake. It is about identifying where AI and digital capabilities can meaningfully improve advisory quality, consistency, speed, and scalability—while maintaining independence, auditability, and regulatory discipline critical to the financial advisory ecosystem.

The role will partner closely with Chartwell’s senior leadership, practice leaders, and client-facing teams to embed AI-enabled tools into valuation, capital structure analysis, compensation consulting, transaction advisory, and capital markets workflows. The leader will also help Chartwell evolve from ad hoc experimentation to a repeatable, firmwide digital operating model.

Essential Role Activities

Strategic

Develop and maintain Chartwell’s enterprise AI and digital strategy, aligned with the firm’s growth objectives, service offerings, and client expectations.
Translate firm and practice-level priorities into clear, sequenced digital and AI initiatives with defined ROI, adoption metrics, and governance standards.
Serve as the internal product owner for AI, data, and digital initiatives—balancing innovation with independence, compliance, and explainability.
Establish firmwide standards for data management, model governance, documentation, and quality control, particularly for valuation and fairness-related analyses.
Advise leadership on how AI and advanced analytics can enhance existing offerings and enable new services across advisory, valuation, M&A, and capital raising.
Partner with the growth and marketing functions to optimize workflows and automations associated with client acquisition, CRM enablement, and marketing automation.

Tactical / Operational

Map and redesign core workflows across valuation, financial modeling, compensation analysis, diligence, reporting, and client deliverables to identify high-impact AI and automation use cases.
Partner with practice leaders to deploy AI-enabled tools for data ingestion, modeling support, scenario analysis, document review, benchmarking, and reporting.
Lead selection and implementation of technology vendors and platforms in partnership with IT, compliance, and risk management resources.
Build and maintain a centralized repository of AI-enabled tools, templates, datasets, and best practices accessible to advisory teams.
Support change management, training, and adoption to raise firmwide AI literacy while maintaining professional judgment and accountability.

Basic Qualifications

10–15+ years of experience in digital transformation, product strategy, analytics, or technology enablement within financial services, professional services, consulting, or a data-driven advisory environment.
Demonstrated experience deploying AI, advanced analytics, or automation into client-facing, analytically rigorous workflows.
Ability to translate complex technical concepts into clear business value for senior advisors and clients.
Understanding of financial modeling, valuation, transaction advisory, or capital markets processes preferred, but not required
Excellent verbal and written communication skills, including the ability to communicate effectively with clients and develop compelling business presentations in PowerPoint
Acute attention to detail and dedication to providing high-quality work products
Highly motivated with the ability to learn and solve problems in a fast-paced environment
Strong work ethic, organizational skills, and ability to multitask