Cumberland Trust Adds CAO and CTO to Leadership Team

Cumberland Trust is expanding its executive leadership structure with three appointments covering administration, corporate strategy, and technology. Lori Wilson, formerly Chief Strategy Officer, moves into the Chief Administrative Officer role; Alex Gillott becomes Chief Strategy Officer; and Nathan Stewart joins as the company’s first Chief Technology Officer. The changes reflect the Nashville-based trust company’s efforts to strengthen its organizational infrastructure as it expands nationally, with a particular focus on people operations, technology security, and operational efficiency.

Cumberland Trust Strengthens Leadership for National Growth

Growth in financial services requires more than expanding a customer base. Organizations managing complex financial and fiduciary responsibilities must also strengthen governance, technology infrastructure, workforce capabilities, and operational controls.

Cumberland Trust is addressing those priorities through three executive leadership appointments. The independent corporate trustee has named Lori Wilson Chief Administrative Officer (CAO), promoted Alex Gillott to Chief Strategy Officer (CSO), and appointed Nathan Stewart to the newly established position of Chief Technology Officer (CTO).

The changes create clearer executive ownership across administrative operations, long-term strategy, and technology. They also highlight how established financial-services organizations are adapting their leadership structures to support growth while maintaining service models built around personal relationships.

Chairman, President, and CEO Jennie Menzie said the appointments are intended to strengthen the company’s organizational leadership, strategic direction, and technology capabilities without compromising its client-first approach.

Lori Wilson Takes Responsibility for Administration and People Operations

Wilson moves into the CAO position after previously serving as Cumberland Trust’s Chief Strategy Officer. She joined the company in 2008 and has held responsibilities across corporate strategy and personal trust administration.

In her new role, Wilson will oversee administrative operations, human resources, governance, and organizational support functions. She will also serve as corporate secretary to the Board of Directors.

The appointment gives the company a dedicated executive leader responsible for coordinating several functions that influence organizational effectiveness and workforce performance.

For HR, the expanded remit is particularly relevant. As companies grow across locations and business units, people operations must remain aligned with governance, internal processes, and broader corporate priorities. Workforce planning, employee development, organizational coordination, and administrative consistency become increasingly important as teams expand.

Wilson’s experience in trust administration and financial services also gives her familiarity with the operational environment in which Cumberland Trust works. Her Certified Financial Planner (CFP) and Certified Trust and Fiduciary Advisor (CTFA) credentials add industry-specific expertise to the administrative leadership role.

The appointment illustrates how the CAO position can serve as a coordination point between HR, governance, and companywide operations rather than focusing exclusively on traditional administrative responsibilities.

Alex Gillott Moves Into the Chief Strategy Officer Role

Gillott has been with Cumberland Trust since 2013 and most recently served as Senior Vice President and Managing Director of Personal Trust Administration.

In that position, he led a growing team supporting high-net-worth individuals and families with trust administration and fiduciary services. His experience spans legal work, trust administration, and team development.

As CSO, Gillott will lead long-term growth strategy, market development, and strategic initiatives intended to strengthen Cumberland Trust’s national presence.

His internal experience is relevant to the transition. Having worked directly with trust administration teams and clients, he brings an understanding of the company’s operating model and the needs of families and professional advisors.

The strategy role will involve connecting market opportunities with the company’s operational capacity and service priorities. For a relationship-driven financial-services business, expansion requires maintaining consistency in client service, fiduciary standards, and internal processes as the organization reaches new markets.

Gillott holds a Juris Doctor from Quinnipiac University School of Law and is licensed to practice law in Tennessee.

Nathan Stewart Becomes Cumberland Trust’s First CTO

The creation of a dedicated CTO position is the most significant structural technology change in the announcement.

Stewart joins Cumberland Trust with more than a decade of experience in technology consulting and leadership, specializing in cloud infrastructure, cybersecurity, and enterprise technology solutions.

Previously, he served as Practice Director of Cloud Infrastructure at Provisions Group, where he advised more than 100 clients on technology initiatives. His earlier experience includes strategic consulting roles with Microsoft and KPMG.

At Cumberland Trust, Stewart will lead technology strategy, infrastructure, and digital capabilities. His responsibilities include strengthening systems, improving operational efficiency, and identifying solutions that support employees and enhance the client experience.

His cybersecurity background is particularly relevant to a business that handles sensitive financial and personal information. Trust administration involves managing records, beneficiary communications, reporting, distributions, and complex asset information. These activities depend on secure systems, reliable data, and effective access controls.

Stewart also serves as a Senior Master Sergeant specializing in cybersecurity in the Air National Guard. His military experience brings additional exposure to operational readiness, security, and risk management.

The creation of the CTO position suggests that Cumberland Trust wants technology to have a more explicit place in executive-level decision-making as its business expands.

Technology and People Operations Become Growth Priorities

Cumberland Trust’s leadership changes reflect the relationship between organizational infrastructure and client service.

The company describes itself as an independent corporate trustee that works alongside clients’ chosen financial, legal, and tax advisors. Unlike traditional investment-management businesses, its model focuses on trust and estate administration, allowing clients to retain their existing investment professionals.

That operating structure places considerable importance on coordination, reliable information, regulatory accountability, and continuity of service.

The company’s published corporate information reports more than $11 billion in assets under administration, over 1,300 families served, more than 1,200 collaborating advisors, and a workforce of over 140 professionals across 11 offices. These are company-reported figures that illustrate the scale of its operations.

As that footprint develops, technology infrastructure can support more consistent internal processes and better coordination across locations. At the same time, HR and administrative leadership must help ensure that employees have the capabilities and organizational support needed to maintain service standards.

The three appointments therefore address complementary aspects of the same business challenge: how to grow without weakening the operational discipline and personal attention on which a fiduciary business depends.

A Leadership Structure Designed for the Next Stage

The appointments do not announce a specific HR technology implementation, AI deployment, or new digital platform. Instead, they establish executive responsibility for functions that can shape future modernization efforts.

Wilson’s administrative remit brings HR and governance into a broader organizational leadership role. Gillott’s strategy responsibilities connect expansion plans with the company’s existing trust administration expertise. Stewart’s CTO appointment creates a dedicated executive focus on infrastructure, cybersecurity, and digital capabilities.

For the wider HRTech industry, the development offers a useful example of how financial-services organizations are structuring leadership around growth and operational resilience.

As technology becomes more central to regulated and relationship-led businesses, people strategy and technology strategy are increasingly interconnected. Systems need to support employees, security controls must protect clients, and organizational structures must enable consistent service across an expanding operation.

Cumberland Trust’s leadership changes reflect that broader shift: sustainable growth depends not only on market opportunities, but also on the people, processes, and technology required to deliver on them.

Market Landscape

Cumberland Trust’s appointments reflect a broader organizational priority across financial services: aligning people leadership, business strategy, technology infrastructure, and governance as operations expand.