Craig Macfarlane

Wildcard
DISC Type : isc

CTO at Transitional Data Services

Natick, Massachusetts, United States

Overview

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.

Personality Overview

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

Topics They Care 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.
Agentic AI
Shows a strong interest in the future of artificial intelligence by planning to attend the Agentic AI Conference in September 2025.

Media Appearances

Craig has no verified media appearances

Work History

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

Education

1979 - 1981
Education details unavailable from NHTI, Concord's Community College
Education details unavailable from Northeastern University

More Information

Social Presence :

Prographics :

Exp : 30 Location : Natick, Massachusetts, United States Job Level : Leadership Designation : CTO at Transitional Data Services
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Insights For Selling To Craig

During A Call Or A Meeting

DO's

  • Use phrases like ‘clear proof that’, ‘data shows’ etc.
  • Be prepared for a lot of questions, answer them objectively
  • Ask them questions to understand their needs better while staying affable

DONT's

  • Avoid phrases like ‘trust me’, ‘you will just love it’ etc.
  • Avoid winging it with them particularly, answer a question only if you know the answer well
  • Don't ask them to move fast, let them take their time and digest all the information

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Craig is

  • Clear proof of product value matters to them, followed by others' testimonials and rapport.
  • Will you ever get a clear answer from Craig

  • They are likely to give you a clear answer without taking you around in circles. However, if you share a good relationship, they might not be so forthcoming.

Insights For Deal Planning

    How fast (or slow) will Craig move?

  • They like to perform full analysis and can take time to make any decision.
  • Can Craig take some risk or not?

  • They weigh all decisions systematically and are unlikely to take many risks.

You And Craig

Personality Compatibility


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