Head of AI

Job Description

Overview

We are seeking a highly strategic and hands-on Head of Artificial Intelligence to lead the company’s enterprise-wide AI transformation initiatives. This is an executive-level leadership role for someone who combines strong technical expertise, operational insight, exceptional business acumen, and an entrepreneurial mindset to help scale and modernize a rapidly growing organization.

Reporting directly to the COO, this individual will serve as the organization’s primary AI leader and internal subject matter expert, responsible for assessing current operations, identifying opportunities for intelligent automation and operational improvement, and building a long-term roadmap that drives measurable business impact across the organization. This role will play a critical part in helping the business scale operations, improve efficiency, modernize workflows, and optimize customer and borrower experiences through AI-enabled transformation initiatives.

The ideal candidate is both a strategist and builder — someone capable of influencing executive stakeholders while remaining highly hands-on in execution. This individual should be comfortable operating independently, navigating ambiguity, and driving enterprise-wide transformation initiatives within a fast-paced, high-growth environment where AI capabilities and supporting infrastructure are still evolving.

This role requires someone who is energized by solving complex business problems, building scalable operational processes, implementing practical AI-driven solutions, and helping shape the long-term future of a modern AI-enabled organization.

Key Responsibilities

AI Strategy & Business Transformation

 • Develop and execute the company’s enterprise-wide AI and intelligent automation strategy aligned with overall business objectives and operational growth initiatives.

 • Conduct a comprehensive assessment of current business operations, systems, workflows, and inefficiencies during the first 60–90 days to identify opportunities for modernization and process optimization.

 • Identify opportunities to automate processes, improve operational efficiency, enhance borrower and customer interactions, and optimize business decision-making across the organization.

 • Build detailed AI transformation roadmaps, implementation plans, business cases, and ROI-driven proposals for executive leadership.

 • Drive AI adoption and operational modernization initiatives across originations, underwriting, loan servicing, asset management, operations, accounting, and capital raising functions.

 • Serve as a trusted advisor to executive leadership on emerging AI technologies, intelligent automation trends, operational risks, and opportunities for competitive differentiation.

Leadership & Cross-Functional Collaboration

 • Partner closely with leaders across all business functions to deeply understand operational complexities and identify scalable AI-enabled solutions.

 • Collaborate with existing IT and business data analytics teams to integrate AI capabilities into current systems, workflows, and operational processes.

 • Directly manage and mentor the business data analytics function while working collaboratively with internal technology resources and business stakeholders.

 • Act as a change leader within the organization, helping teams adapt to AI-enabled workflows, automation initiatives, and evolving operational processes.

 • Communicate highly technical concepts to non-technical stakeholders in a clear, practical, and business-focused manner.

AI Solutions Architecture & Execution

 • Design, develop, and implement AI-driven solutions that improve productivity, operational scale, workflow efficiency, and customer experience.

 • Evaluate build-versus-buy opportunities for internal AI systems, automation tools, workflow platforms, and operational technologies.

 • Help modernize existing systems and identify opportunities for intelligent automation, workflow orchestration, and data-driven operational improvements across the business.

 • Establish governance standards, AI best practices, and responsible AI frameworks that support scalable and sustainable growth.

 • Maintain a highly hands-on leadership approach while helping define the future structure, scaling, and long-term vision of the AI organization.

We are a company committed to creating diverse and inclusive environments where people can bring their full, authentic selves to work every day. We are an equal opportunity/affirmative action employer that believes everyone matters. Qualified candidates will receive consideration for employment regardless of their race, color, ethnicity, religion, sex (including pregnancy), sexual orientation, gender identity and expression, marital status, national origin, ancestry, genetic factors, age, disability, protected veteran status, military or uniformed service member status, or any other status or characteristic protected by applicable laws, regulations, and ordinances. If you need assistance and/or a reasonable accommodation due to a disability during the application or recruiting process, please send a request to [email protected] learn more about how we collect, keep, and process your private information, please review Insight Global's Workforce Privacy Policy: https://insightglobal.com/workforce-privacy-policy/.

Skills and Requirements

Qualifications:

 • Proven experience leading enterprise AI initiatives from strategy through execution, with measurable impact on business operations, efficiency, and scalability.

 • Ability to operate both strategically and hands-on, building and implementing AI-driven solutions while influencing executive leadership.

 • Demonstrated success applying AI to automate workflows, optimize processes, and drive operational improvements across multiple business functions.

 • Experience working in fast-paced, high-growth environments with limited infrastructure, comfortable building processes and capabilities from the ground up.

 • Strong business acumen with the ability to translate AI capabilities into practical solutions that enhance customer, borrower, and internal team experiences.

 • Background supporting or partnering with operations-heavy or financial services environments (lending, underwriting, servicing, or similar) preferred.

 • Proven ability to work cross-functionally, drive adoption of new technologies, and lead organizational change in evolving technical landscapes. Financial Services, Wealth management, Commercial real Estate, investment banking, etc.