Shake Dewan

Track Record

Scaling teams. Driving ROI. Delivering outcomes.

An extensive history of architecting data platforms, optimizing business bottlenecks, and building internal AI capabilities across enterprise and startup environments.

$10M+

New Contracts & ARR Driven

30+

Enterprise AI Engagements

Top 10

Tableau Iron Viz globally

Endorsed by Google's Director of Research

Professional Experience

A track record of scaling teams and architecting high-ROI platforms.

Oct 2022 — Present Toronto, ON

Founder & Chief Executive Officer

AI Forward

Delivering production-grade AI solutions and advanced strategy to small and medium-sized businesses (SMBs). Scaled consultancy from ground up, securing 30+ client engagements.

  • Lead team of 5 practitioners and 4 development partners, overseeing all aspects of solution scoping, architecture, and delivery.
  • Serve as principal architect across the portfolio, delivering AI-powered automations, data pipelines, and custom applications.
  • Manage P&L, client relationships, and strategic direction while maintaining hands-on technical leadership.
Mar 2025 — Present Toronto, ON

Fractional Chief AI Officer

Hexona Systems

Driving AI strategy for a business automation and AI education platform with $1M+ in annual recurring revenue.

  • Serve as senior technology and AI strategist, reporting directly to the CEO.
  • Architect automation playbooks and POC frameworks that accelerate enterprise adoption and improve sales conversion.
  • Define market positioning strategy focused on measurable ROI as competitive differentiator in crowded AI landscape.
Jun 2021 — Oct 2022 Toronto, ON

AI Consultant

Deloitte

National Lead for the NLP Center of Excellence, standardizing reusable solution assets, implementation playbooks, and quality assurance protocols.

  • Scaled NLP Center of Excellence to 20+ practitioners in under 18 months.
  • Developed a flagship deployment accelerator that reduced project delivery timelines by 50% across multiple engagements.
  • Contributed to $10M+ in new NLP contract value through technical pre-sales, solution architecture, and strategic POV demonstrations.
Jun 2021 — Dec 2022 Toronto, ON

Fractional Chief AI Officer

Paperstack

Owned the entire AI function for a Forbes 30 Under 30-founded e-commerce and fintech startup, reporting directly to the CEO.

  • Architected the end-to-end data platform enabling real-time analytics that supported strategic pivot and expansion to $10M ARR.
  • Presented AI innovations to Google's Director of Research, Peter Norvig, earning direct product endorsement.

Technical Expertise

Bridging the gap between engineering and business strategy.

Core Competencies

Driving growth through high-level strategic oversight and product execution.

AI Strategy Product Management Enterprise Sales & Consulting NLP Computer Vision Deep Learning

Technologies

Building production-ready pipelines.

Python TensorFlow Keras AWS GCP Data Engineering

Visualization

Communicating complex data clearly.

Tableau (Global Top 10) Power BI

Education & Certifications

Mount Allison University

BA (Hons) Computer Science & Mathematics
BSc Cognitive Science
Reisman Award ($15K) & President's Scholarship ($20K)

Certifications

Lean Six Sigma Black Belt (SSAA)
Machine Learning (Stanford)
Deep Learning (Deeplearning.ai)