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Fractional CAIO & CTO — Toronto

Previously running Deloitte's national NLP practice. Now on retainer to companies that cannot hire that full-time.

Fractional Chief AI Officer and CTO mandates for scaling companies: the architecture, evaluation, vendor and hiring decisions, at an agreed number of days per month.

Shake Dewan
30+AI solutions delivered
25Practitioners scaled
50%Timeline reduction
$10M+Contract value contributed

The record.

Case studies →
Feb 2026 – Present
Canadian FundingChief AI Officer · fractional

Fractional AI leadership: identifying the practical opportunities, setting the technology roadmap, and applying AI responsibly across the business.

Jul 2025 – Present
Multiple CompaniesChief Technology Officer · contract

Fractional technology leadership for Hexona Systems, Sayvo.ai and Biosquares, spanning product roadmaps, architecture decisions and technical delivery.

Sep 2023 – Present
AI ForwardChief Technology Officer

Consultancy delivering production-grade AI for small and mid-sized businesses. Principal architect across 30+ AI and automation solutions.

Jun 2021 – Dec 2022
PaperstackChief AI Officer · fractional

Architected the data and analytics platform during the company's expansion to $10M+ ARR for a Forbes 30 Under 30 fintech team. Work presented to and positively reviewed by Peter Norvig.

Jun 2020 – Jun 2024
DeloitteNational Head, AI Center of Excellence

Led and expanded the NLP Center of Excellence to 25 practitioners. Built a deployment accelerator that cut delivery timelines by 50%, and directly negotiated $500K+ in AI contracts.

In their words.

From engagements led through AI Forward.

“Within a couple of calls we got the concise roadmap we wanted. The whole deliverable was very smooth.”
Suji JohnCEO, Seoul Box
“Brought world-class experience into our startup environment to give us a genuine edge against the competition.”
Eddie AndersonCEO, Biz Focused
“Knowledgeable, versatile, and efficient — they know this space better than most companies we've worked with.”
Christ BeamanCEO, Astronomic

What I take on.

People call at three moments: the roadmap has too many AI ideas and no way to rank them; a pilot works in the demo and dies before production; or a build-versus-buy, platform, hire or vendor call is about to be made and is hard to reverse.

Cadence
An agreed number of days per month, booked in your calendar in advance.
Horizon
Bounded and reviewed on a fixed cycle — not an open-ended retainer.
Access
Leadership meetings, the engineering team, and the real systems.
Own
  • AI and technology strategy tied to a business metric
  • Architecture decisions and build / buy / skip calls
  • Evaluation criteria, guardrails, and failure boundaries
  • Vendor selection and technical due diligence
  • Technical hiring: scorecards, interviews, calibration
  • Translating the technical position for your board
Do not own
  • Daily project management
  • Line management of your engineers
  • Production monitoring, on-call, or incident response
  • An operational SLA
  • Hands-on implementation — scoped separately, with its own delivery team

Four steps. Stop at any of them.

Each step ends in something you can act on, and none of them commits you to the next.

  1. 01 · Free · 30 minutes

    Intro call

    We find the decision or workflow in question, who owns it, and what changes if it goes well. If there is no real problem here, I will tell you.

  2. 02 · 10 business days

    Diagnostic

    A focused engagement that maps the real process, sets the baseline and business case, defines the evaluation plan, and produces a build-ready 90-day path.

  3. 03 · Ongoing · bounded

    Fractional mandate

    Embedded CAIO or CTO at an agreed cadence. Architecture, evaluation, risk, vendor and executive decision reviews while your team executes.

  4. 04 · Scoped separately

    Implementation

    If a build is the right answer, it runs as its own engagement with a dedicated project manager, engineering owner, and support terms.

Thirty minutes. Bring the hardest question on the roadmap.

If there is no mandate worth having, I will say so on the call.