Boxwood Strategy Group · AI Success Management™
The AI Investment the Board Will Trust.
AI Success Management is the management practice that turns the AI portfolio into the asset the board, the regulator, and the customer can all trust. Boxwood Strategy Group is the practitioner-led firm that brings the discipline.
AI governance tells you what to do.
AI assurance proves you did it.
AI Success Management™ ensures it keeps delivering value.
The AI Investment Has Outpaced the Discipline.
The AI projects are funded as projects. The board manages them as projects. The result is the same wall the SaaS industry hit twenty years ago. The fix is the same fix. A management practice that ties the people, the process, and the policy into one continuously delivering asset.
25.2%
of Canadian businesses plan to use AI in the next 12 months, up from 10.6% two years earlier.
19.2%
of Canadian businesses had used AI in the previous 12 months by mid-2026, up from 12.2% a year before.
40%+
of agentic AI projects will be cancelled by the end of 2027, Gartner predicts, citing cost, unclear value or weak risk controls.
Sources: Statistics Canada, Analysis on planned use of artificial intelligence by businesses in Canada, third quarter of 2026 (October 2, 2026); Gartner, press release (June 25, 2025).
The Boxwood Approach.
The practice rests on two layers. The G.A.A.R.E. lifecycle defines what to manage and when. The Value-First Method defines how the work gets done.
Layer 1 · G.A.A.R.E. Lifecycle
Govern the foundation. Assess the risks. Assure the controls. Realize the value. Evolve the maturity. The lifecycle never closes. The relationship with the AI asset only deepens.
Layer 2 · Value-First Method™
People, because adoption fails without buy-in. Process, because trust requires repeatability. Policy, because rules without enforcement are wishful thinking.
For federally regulated financial institutions
OSFI Guideline E-23 takes effect May 1, 2027
AI and machine learning models are in scope. Know, Show, Go is a five-day sprint that gives your board a defensible AI inventory baseline, a gap scorecard and a 90-day plan with names on it.
Four Ways To Engage.
The depth scales to the work. Every engagement starts with the AISM lens applied to your portfolio.
Retainer
Success Partner
Quarterly Health Score reviews, regulator updates, on-call advisory.
Specialty
Ethics & Trust Audit
Independent fairness, explainability, and reputation read.
Free Diagnostic
Take the AI Reality Check.
Fifteen minutes. Eight questions. The first read on the AISM Health Score for the AI portfolio. Nothing to install. Nothing to expose. The starting point of the conversation.
Research
Canada Hyperscale Data Centres dashboard
105 hyperscale and large data centre projects across seven provinces, with developer, capacity, power source and provincial grid constraints. Every row carries its public source. Snapshot dated November 3, 2026.
What clients say.
“The AI coaching transformed our business strategies. The work was ethical and effective. The recommendation stands for any leadership team looking to elevate the operation.”
COO, Fortune 500 organization
“Boxwood integrated our CSM practice with the product development team. The result is the competitive advantage we were looking for.”
VP of Customer Success, SaaS startup
Frequently Asked Questions.
AI Success Management is the consulting discipline that applies Customer Success Management thinking to AI systems across the full deployment lifecycle. AI governance tells you what to do. AI assurance proves you did it. AI Success Management ensures it keeps delivering value.
AI governance defines the rules and the responsibilities. AI assurance tests whether the rules hold up. AI Success Management runs the practice continuously across the lifecycle. The three are complementary. AISM is the management layer that ties them together.
Govern the foundation. Assess the risks. Assure the controls. Realize the value. Evolve the maturity. The five pillars define what to manage and when. The lifecycle never closes.
The AISM Charter maps the AI portfolio to the relevant frameworks. The control library translates the framework requirements into the operating practice. The audit trail produces the evidence the regulator expects. In Canada, federally regulated financial institutions work to OSFI Guideline E-23, which takes effect May 1, 2027 and covers AI and machine learning models. For other organizations the work aligns to PIPEDA and the 2023 Voluntary Code on the responsible development and management of advanced generative AI.
The Realize pillar of the G.A.A.R.E. lifecycle defines a value tracking sheet. The composite AISM Health Score rolls usage, cost, business outcome, and risk into a 0-100 number the executive team will read on one page.
The AISM Diagnostic Sprint. Five working days, the board-ready scorecard, the regulator gap analysis, and the 90-day roadmap. The Sprint is a complete deliverable. Most clients move on to the Pilot or the retainer.
The AI Portfolio Is the Asset. The Discipline Is the Difference.
Thirty minutes is the right starting point. The discovery call confirms fit, the right entry point, and the timing. Practitioner-led. No sales hand-off.