Thomas Mailloux
I help enterprises get real operating value out of AI. Not just AI pilots.
About
My work spans AI strategy and commercial execution, translating AI capabilities into measurable business outcomes and building the operating model to sustain them. More recently, my focus has shifted to the commercial mechanics of retention and expansion, designing the sales processes, incentive structures, and account management systems that turn AI solutions into durable revenue.
I live on the North Shore of Massachusetts with my wife and 2 daughters. Outside work I cook, make furniture, and ride gravel. I'm also designing a house in rural Vermont, where I grew up — part workshop, part home base for being outdoors.
Selected Impact
- 2025–2026Drove 30% improvement in gross dollar retention across a 600+ account renewal portfolio
- 2024–2025Delivered $100M+ in annual value across global top 5 investment bank
- 2021–2022Achieved 125% net dollar retention and zero churn across a $10M ARR strategic portfolio
Apps
Meeting Agent
Automates call prep, follow-up drafting, and deal risk flagging, so account managers can spend more time on actual accounts.
Portfolio Risk Analyzer
Shows you which accounts are heading toward a bad renewal before it's too late to do anything about it.
ROI Calculator
Provides a framework to quantify value from AI. Useful for renewals where the value story needs to hold up in front of executives.
Renewal Risk System
A scoring system that gives distributed renewal teams a shared language for risk and early remediation.
Case Studies
$100M+ Annual Business Impact
Drove AI transformation across a $20M+ enterprise portfolio, connecting platform capability to measurable business outcomes across financial services, healthcare, CPG, and TMT.
$85M Media Reallocation
Delivered a Marketing Mix Modeling engagement for a top 3 U.S. auto insurer, quantifying channel-level ROAS across a $1B media portfolio and identifying major reallocation opportunities.
Fraud Detection Platform
Closed and led delivery of a $6M AI services engagement, building a fraud detection platform monitoring billions of transactions annually for a top U.S. credit card issuer.
BCG Joint Solution Motion
Built the DataRobot–BCG partnership from scratch — engagement model, delivery playbook, and early client pipeline.
Experience
Senior Director, Global Renewals Strategy & Commercial Operations
↑ PromotedSenior Director, Strategic Accounts – AMER
DataRobot — Boston, MA
Led enterprise AI transformation across a $20M+ portfolio spanning financial services, healthcare, CPG, and TMT. Delivered $100M+ in annual business impact and $2M+ in GenAI pipeline. Now leading global retention strategy and operating model transformation during the platform transition to agentic and consumption-aligned AI offerings.
Head of Customer Success – AMER
↑ PromotedStrategic Accounts Director
Pecan AI — Boston, MA
Led enterprise customer adoption strategy and co-developed vertical GTM motions for a predictive analytics platform. Co-engineered Supply Chain GTM strategy driving 250% YoY revenue growth.
AI Success Director
↑ PromotedAI Success Manager
DataRobot — Boston, MA
Managed $10M ARR strategic portfolio with 125% Net Dollar Retention and zero churn in FY21. Built the BCG–DataRobot partnership and designed a 400-person enablement program improving modeling efficiency by 40%.
Account Executive, Majors
↑ PromotedEngagement Manager
Soroco — Boston, MA
Led AI solution sales and delivery across large-scale financial services transformation programs. Closed $6M AI services engagement with a top credit card issuer.
Senior Business Analyst
↑ PromotedBusiness Analyst
Boston Consulting Group — Boston, MA
Supported enterprise transformation projects at large global companies, working across analytics, process redesign, and change management.
Systems Analyst II
Beth Israel Deaconess Hospital — Milton, MA
Delivered analytics-driven clinical and operational modernization across a hospital network, including EHR integration, regulatory reporting dashboards, and an early-detection sepsis algorithm.
Implementation Specialist
Meditech — Canton, MA
Coordinated nine multi-million-dollar hospital EHR deployments across complex clinical environments.
Skills
AI value creation
AI strategy, adoption scaling, use-case prioritization, ROI modeling, workflow transformation.
Commercial leadership
Renewal strategy, retention systems, forecasting excellence, consumption transition, expansion playbooks.
Analytics & technology
Hands-on builder across the commercial stack — internal agents, risk dashboards, forecasting tools, and AI workflows. Comfortable going from business problem to working prototype.
GTM & Partnerships
Sales play design, offer packaging, and retention and expansion playbooks built on customer usage and engagement data. Built and operationalized a joint GTM motion with BCG from scratch.
People leadership
Player-coach approach to building commercial teams — focused on professional growth, accountability, and doing the work. Experience leading distributed CSM and strategic account organizations.
Executive communication
Experienced presenting to C-suite and board-level audiences — translating AI complexity into clear investment narratives and driving alignment across executive stakeholder groups.
Education
B.A. Economics & Philosophy
CFA Levels I–III
Passed all three levels (not a charterholder)
Let's Connect