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Dean Carson

Technology Executive & AI Transformation Leader

Transforming financial services through AI strategy, modern workplace innovation, and purpose-driven leadership.

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0+ Years Experience
0M+ Revenue Managed

Executive Summary

Dean Carson

A revenue-driving technology executive with 10+ years at the forefront of enterprise digital transformation, AI integration, and modern workplace strategy across Financial Services.

Responsible for $200M+ in annual Microsoft revenue while serving as a trusted advisor to C-suite leaders at the nation's largest banking institutions — translating complex Cloud and Generative AI capabilities into measurable business outcomes.

A recognized innovator in Microsoft Copilot and AI solution strategy, with a track record of leading high-performing cross-functional teams, accelerating enterprise adoption, and delivering outcomes that redefine how organizations work.

Location Columbus, OH
Industry Technology & Financial Services
Education Gannon University

Leadership Experience

AI Workforce Solutions Leader

Microsoft Corporation

Feb 2021 – Present

Responsible for $200M+ in annual AI Workforce revenue within Microsoft's Financial Services operating unit, leading go-to-market execution for productivity, collaboration, and virtualization solutions across a 20+ account enterprise portfolio.

  • Serve as senior technology advisor to C-suite and IT decision-makers at strategic banking and credit union institutions, translating complex Microsoft Cloud capabilities into measurable business outcomes
  • Spearhead Generative AI integration strategy for enterprise clients, designing and executing Microsoft Copilot and AI solution plays that position clients at the forefront of intelligent work
  • Lead cross-functional virtual teams (v-teams) to align product, sales, and engineering resources — ensuring cohesive account planning and seamless customer experience from discovery through adoption

Microsoft Surface Customer Success Manager

Marketstar (Microsoft Partner)

Sep 2019 – Jan 2021

Managed hardware and software customer success relationships across 25+ large commercial accounts spanning five industry verticals, driving retention, expansion, and executive alignment.

  • Positioned Microsoft Surface, Teams, and Microsoft 365 as integrated business productivity solutions, cultivating trusted advisor status with technology decision-makers
  • Delivered tailored technology roadmaps aligned to clients' unique business environments, resulting in increased Microsoft hardware and software adoption and measurable productivity gains

Branch Technology Leader

Erie Insurance Group

Aug 2015 – Aug 2019

Completed a rigorous IT Apprenticeship Program with rotational assignments across Database Administration, Network Engineering, InfoSec, Strategic Marketing, Change Management, and Customer Engagement — developing a full-spectrum view of enterprise IT operations.

  • Led the branch office technology team through an enterprise-wide migration from Windows 7 to Windows 10, coordinating logistics, user readiness, and technical execution across multiple locations
  • Managed end-to-end break/fix lifecycle for enterprise PCs and drove successful adoption of newly deployed cloud software, establishing change management frameworks that reduced friction and accelerated user onboarding

Founded Ventures

Building solutions to everyday problems from the ground up.

3&aShake Ventures LLC

Founder & Managing Member  ·  Est. March 2026

Active

A holding company born to solve common-day problems with modern solutions — identifying friction in everyday life and engineering purposeful products that make people's routines smarter, easier, and more efficient.

Portfolio Product

PrepStation

Launching in Columbus, OH in 2026

A networked food prep kiosk service that lets meal-prep enthusiasts safely reheat and season their pre-prepared meals at licensed kiosks located in gyms, offices, and apartment buildings. Members access kiosks via mobile app and pay with Apple Pay or card — no meal prep disruptions, no compliance headaches for venue partners.

FoodTech Health & Wellness
Athletes Busy Professionals Moms
Visit PrepStation

Key Achievements

AI & Copilot Strategy

Designed and executed enterprise-wide Microsoft Copilot and Generative AI solution plays, positioning the nation's largest banks at the forefront of intelligent work.

$200M+ Revenue Leadership

Oversees $200M+ in annual AI Workforce revenue within Microsoft's Financial Services unit, consistently driving growth across a 20+ account enterprise portfolio.

Executive Advisory

Trusted C-suite advisor to the nation's largest banking and credit union institutions, translating complex Cloud and AI capabilities into measurable business outcomes.

Modern Workplace Architecture

Led enterprise-scale Microsoft 365, Azure, and Surface deployments across financial services organizations, enabling seamless digital workplace transformation.

Community Leadership

Board Chair of the Youth Leadership Institute of Erie, PA, and co-convener of cross-sector stakeholders around racial equity and community economic development.

Microsoft Certifications

Microsoft 365 Certified and Microsoft Azure Fundamentals (AZ-900) certified, with deep hands-on expertise in the full Microsoft Cloud ecosystem.

Leadership & Community Impact

Former

Youth Leadership Institute

Board Chair

Erie, Pennsylvania

Led strategic direction for a youth development nonprofit serving hundreds of young leaders annually, overseeing organizational governance, fundraising strategy, and community partnerships.

Former

Young Erie Professionals

Chair, Community & Civic Engagement

Erie, Pennsylvania

Facilitated Governor Wolf's visit to Erie to address racial inequality and community economic development, demonstrating ability to convene cross-sector stakeholders around complex social challenges.

Former

Erie Insurance African-American Affinity Network

Co-Chair

Erie Insurance Group

Championed diversity, equity, and inclusion initiatives across the organization, building community, amplifying underrepresented voices, and driving systemic cultural change.

Speaking Engagements

Selected keynotes and panel appearances on AI transformation, modern workplace, and enterprise technology.

Keynote

The Future of Work: Becoming a Frontier Firm

Black Tech Week

Cincinnati, OH

Keynote

The Future of Intelligent Work: Copilot & the AI-Powered Enterprise

Columbus AI Week

Columbus, OH

Panel

Closing the Generational Divide: Technology as a Tool for Equity

Erie Insurance Group

Erie, PA

Publication

Building a Career at the Intersection of Tech & Finance

Career Street

Erie, PA

Panel

DEI in Tech: From Affinity Networks to Systemic Change

Corporate Diversity Leadership Summit

Columbus, OH

Fireside Chat

Governor's Roundtable on Race Relations & Inequality in Erie, PA

Governor Tom Wolf's Roundtable

Erie, PA

Get in Touch

Interested in discussing AI strategy, speaking engagements, or advisory opportunities? I'd love to connect.

Location Columbus, OH