AI Adoption and Enterprise Transformation Advisory

Turning enterprise investment into measurable adoption.

Trestle Advisory Group helps enterprises turn AI and technology investment into workforce outcomes. We design the adoption strategy, operating model, and change discipline that close the gap between what a system can do and what people actually use. Deep roots in healthcare, with work spanning financial services and manufacturing.

Managing Partner
Tom Dann
15+ years leading enterprise transformation and change in Fortune 500 and high-growth organizations across healthcare, financial services, and manufacturing. Creator of the 8-Pillar OCM Capability Model.
01Approach

AI-enabled change is a business discipline.

Most AI and digital investments fail at the adoption gap: the distance between what a system can do and what an organization actually uses. That gap is where ROI is lost, and it is the discipline Trestle Advisory is built around.

Our method is the 8-Pillar OCM Capability Model, a framework for building adoption capability into the enterprise rather than bolting it onto a project. We measure it with The Human ROI: adoption, proficiency, utilization, and trust. Not license counts. Not training hours.

We work with executives and private equity backed leadership teams wherever the technology investment is real and the workforce shift is the limiting factor. AI adoption, platform and ERP modernization, operating model redesign, and integration.

02Capabilities
01

AI Adoption and Workforce Readiness

Turn AI investment into workforce outcomes. Adoption playbooks, persona-based readiness assessments, maturity models, and dashboards that show leaders who is using what, and how well.

02

Organizational Change Management

Change strategy, stakeholder alignment, communications, training, and measurement built on the 8-Pillar OCM Capability Model. Certified CCMP and Prosci practitioner, proven in regulated, complex enterprises.

03

Enterprise Transformation and Operating Model Design

Stand up transformation offices, redesign operating models for product and platform delivery, and install the governance that holds change in place after the consultants leave.

04

ERP, Data Platform, and Systems Implementation

Implementation strategy and change leadership for ERP modernization, data migration, and platform programs, including the process redesign required to make the technology pay off.

05

M&A Integration and Carve-Outs

The people, process, and operating model side of integration and divestiture, with business continuity through the transition window as the priority.

06

PE Portfolio and Value Creation Advisory

Transformation roadmaps that unlock value at the operating model and workforce layer. Direct CEO and board level engagement on scope, sequencing, and signal.

03Outcomes

Programs that measured. Not just delivered.

85%
Reduction in development cycle time at a major pharmacy benefit management organization through product centric delivery redesign.
25%
Lift in customer satisfaction following the project to product DevOps transition at the same organization.
$1.2M
Annual cost reduction realized through agile and operating model implementation at a healthcare financial services firm.
21%
Customer satisfaction lift at a national health insurer driven by agile maturity and delivery cadence alignment.
04Selected Engagements

A track record built in complex, regulated enterprises.

Senior delivery across healthcare payers, providers, life sciences, and medtech, plus financial services and other enterprise environments. Across both Trestle Advisory and prior practice and in-house leadership roles.

Payer
Pharmacy Benefit Management
Led the Transformation and Change Management Office for a $113B PBM organization. Managed a $3.6M annual budget and an eight person delivery team.
Payer
National Health Insurer
Agile transformation and change leadership reporting to client CTO. Value stream mapping and SAFe based KPI reporting drove measurable adoption and delivery improvements.
Insurance and Digital
Life Insurance Carrier
Designed enterprise operating and maturity models for the new digital division. Transformation roadmap covered legacy data migration and platform modernization.
Medtech
Global Medical Device Manufacturer
Agile transformation, portfolio planning alignment, and change leadership across product delivery teams. Reporting to CIO.
Healthcare Consulting
Healthcare Technology Services Firm
Built and led the OCM and Transformation practice across payer, provider, life sciences, and medtech. Authored the firm's institutional position on AI adoption.
Public Sector Health
State Health and Human Services Agency
Operating model design and transformation advisory through Trestle Advisory Group.
05Contact

Let's talk about the adoption gap.

For consulting engagements, executive advisory conversations, or speaking and panel inquiries, direct outreach is welcome.

Based In
Minneapolis, Minnesota