Craig Macfarlane in

Craig Macfarlane

Wildcard · DISC type isc
CTO at Transitional Data Services
📍 Natick, Massachusetts, United States

Craig Macfarlane is the CTO and Co-Founder of Transitional Data Services (TDS), a company he established in 2002. He spearheads the development of TransitionManager, the companys proprietary IT transformation software. His career includes roles as CTO for iCAST and Student Advantage, and as VP at Digitas, where he built systems for brands like IBM and AT&T.

He is passionate about achieving positive outcomes for clients, expressing excitement when his team helps customers overcome challenging projects on schedule and when government entities complete large-scale migrations efficiently. Craig is actively interested in emerging technologies and is attending a 2025 conference on Agentic AI.

As a co-founder of TDS, he has been developing and refining its core software platform for over two decades to help modernize enterprise IT.

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Experience
30 Years
Current Role
CTO
Job Level
Leadership
Location
Natick, Massachusetts, United States
Personality Overview

How Craig shows up

Requires Proof
ROI Driven
Curious But Skeptical

They are unlikely to ever become strong champions even when the conversations are going well; you should focus on cultivating other champions They are often friendly and nice, but can sometimes suprise you with their piercing questions They typically tend to be late adopters even when they seem friendly and excited about what you have to sell

Priorities

Topics Craig cares about

IT Transformation
As co-founder and CTO of TDS, his primary professional focus is on developing software and services to accelerate complex IT transformations for large enterprises.
Cloud & Data Migration
His company is a leader in cloud and data center migrations, and he has personally presented on strategies for overcoming common migration obstacles.
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Career

Work history

4-2002
CTO
Transitional Data Services
8-2000 - 4-2002
CTO
Student Advantage
CTO
Student Advantage
2-1999 - 7-2000
CTO
iCast
4-1996 - 3-1999
VP, Dir of New Media Development
Digitas
In the press

Media appearances

No media yetWe could not find public media appearances for this person.
Education
1979 - 1981
Education details unavailable
NHTI, Concord's Community College
Education details unavailable
Northeastern University
Social presence
in
Behavioral profile

DISC profile (public)

i

Influence (I)

Influence (I) reflects the degree to which a person prefers to work by influencing or persuading others. Those scoring high tend to be people oriented, motivated by social recognition and building relationships.

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