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.
Apps
Meeting Agent
Automates call prep, follow-up drafting, and deal risk flagging, so account managers can spend more time on actual accounts.
SPY/DIA Pattern Trader
A live simulation of a multi-stage technical trading pattern — watches SPY and DIA in real time and fires buy/sell alerts when a four-stage reversal setup completes, with a trade ledger, analytics, and backtesting.
AccountIQ
A unified account workspace that pulls Salesforce, Amplitude, and Kaia into one filterable view — renewal risk, usage trends, and stakeholder history for every account.
Renewal Risk System
A scoring system that gives distributed renewal teams a shared language for risk and early remediation.
Case Studies
Fraud Detection Platform
Originated, closed, and delivered a $6M TCV AI services engagement — building a predictive fraud detection platform that protects billions of annual transactions for a top payments processor.
BCG Joint Solution Motion
Built the DataRobot–BCG partnership from scratch — engagement model, delivery playbook, and early client pipeline.
$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.
Experience
Senior Director, Global Renewals Strategy & Commercial Operations
↑ PromotedSenior Director, Strategic Accounts – AMER
DataRobot — Boston, MA
Leading global retention strategy and operating model transformation across a $130M portfolio of 200+ accounts during the platform transition to agentic and consumption-aligned AI offerings. Previously led enterprise AI transformation across a $20M+ strategic portfolio spanning financial services, healthcare, CPG, and TMT — delivering $100M+ in annual business impact and $2M+ in GenAI pipeline.
Head of Customer Success, Key Accounts
↑ 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%.
Business Development Manager
↑ PromotedEngagement Manager
Soroco — Boston, MA
Originated, closed, and delivered a $6M AI services engagement with a top payments processor, leading a 10-person delivery team. Originated and closed a separate $650K consulting engagement with a Fortune 100 technology client.
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
Origination and closing, expansion and renewal strategy, deal structuring, retention systems, consumption transition 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
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