Cuyler Berg

Editor
DISC Type : SC

Director, Platform Engineering at Skyline Technology Solutions

Baltimore, Maryland, United States

Overview

Cuyler Berg is the Director of Platform Engineering at Skyline Technology Solutions and a graduate of the University of Maryland Baltimore County. With a background in DevOps, he has led major initiatives in enterprise application modernization, implementing platforms like ServiceNow and Microsoft Dynamics 365 to streamline organizational processes.

He successfully retired numerous legacy tools and spreadsheets by migrating processes from four separate divisions into a modern application suite.

Personality Overview

Late Adopter

Objective Thinker

Self-Disciplined

Being observant comes to them naturally.  They are thorough and always follow a systematic approach. They do not like taking risks at all and go for proven options in the end.

Topics They Care About

Platform Engineering
As the Director of Platform Engineering, he is focused on building and managing the core technology infrastructure for his company.
Application Modernization
He led a major initiative migrating four divisions to a modern application suite including ServiceNow and Microsoft Dynamics 365, retiring numerous legacy tools.
DevOps & Cloud
He actively recruits for his team with expertise in a modern tech stack that includes GitLab, Terraform, GCP, Azure, Ansible, and Red Hat.

Media Appearances

Cuyler has no verified media appearances

Work History

1-2026
Director, Platform Engineering at Skyline Technology Solutions
2-2021 - 1-2026
Major Initiatives Manager at Skyline Technology Solutions
6-2017 - 2-2021
DevOps Software Engineer at Skyline Technology Solutions

Education

2013 - 2018
Bachelor’s Degree from University of Maryland Baltimore County

More Information

Social Presence :

Prographics :

Exp : 8 Location : Baltimore, Maryland, United States Job Level : Mid-senior Designation : Director, Platform Engineering at Skyline Technology Solutions
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Insights For Selling To Cuyler

During A Call Or A Meeting

DO's

  • Share a one-off customer success story but keeps the focus on highlighting objective, numerical results
  • If they are not asking many questions, nudge them to ask questions rather than just starting to talk yourself
  • Use phrases like 'results based on data', 'measurable proof', 'X% growth' etc.

DONT's

  • Don't ask them to move fast, let them take their time and digest all the information
  • Do not sound overly eager, modulate your energy levels especially if you are generally enthusiastic
  • Avoid winging it with them particularly, answer a question only if you know the answer well

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Cuyler is

  • Low-risk, adoption by others are very important to them, followed by confidence in ROI.
  • Will you ever get a clear answer from Cuyler

  • They are unlikely to say no, it's better to stop yourself once you have exhausted all the options.

Insights For Deal Planning

    How fast (or slow) will Cuyler move?

  • They do not like to rush and therefore can be quite slow in their decision-making.
  • Can Cuyler take some risk or not?

  • They have little risk-appetite and prefer to take measured decisions.

You And Cuyler

Personality Compatibility


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