Stephen M. Dick

Pioneer
DISC Type : sdi

Member at IDC CIO Executive Council

Portola Valley, California, United States

Overview

Stephen is the VP of Infrastructure & Cloud Engineering at Paylocity, leading a global team of over 150 people. He has a proven track record in scaling teams, reducing infrastructure costs by over 40%, and improving system reliability to 99. 99%. People who have worked with him describe him as a wise strategist and a supportive leader.

Beyond his executive role in tech, Stephen is the founder of Keygen Capital, a real estate investment firm with $10 million in assets under management, focusing on multi-family properties and mobile home parks. He has an active interest in Proptech, using tools like Appfolio and EliseAI.

He is the President of the Silicon Valley Chapter of the DevOps Institute, where he launched the new chapter.

Personality Overview

Friendly But Fast

Driven But Considerate

Decisive But Friendly

If they are convinced, they can become very strong champions for your product  They have the unique ability to win both love and respect from their team (or outsiders) They combine a unique set of diverse traits where they are fast and friendly but can slow down to be thorough when needed

Topics They Care About

FinOps Practices
He is a foundation member and speaker at the FinOps Foundation, co-chairs its sustainability working group, and actively hires FinOps engineers at Paylocity.
Reliability Engineering
His expertise centers on SRE practices, having built reliability teams at Salesforce and SAP and drastically improved mean time to recovery (MTTR) at Paylocity.
DevOps Community
As President of the DevOps Institute's Silicon Valley Chapter, he is deeply involved in organizing events and fostering the local DevOps community.

Media Appearances

Stephen has no verified media appearances

Work History

10-2024
Member at IDC CIO Executive Council
6-2023
VP - Infrastructure, Cloud & Platform Engineering | DevOps | SRE | FinOps at Paylocity
6-2023
VP - Infrastructure, Cloud & Reliability Engineering | SRE | DevOps | FinOps | AIOps at Paylocity
8-2021 - 12-2024
President - Silicon Valley Chapter at DevOps Institute
2-2021 - 6-2023
Vice President - Infrastructure, Cloud & Reliability Engineering (SRE | DevOps | FinOps) at BetterCloud

Education

Bachelor of Science (BSc) from Queen's University Belfast
Stanford Advanced AI Leadership Program from Stanford University

More Information

Social Presence :

Prographics :

Exp : 5 Location : Portola Valley, California, United States Job Level : Senior Designation : Member at IDC CIO Executive Council
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Insights For Selling To Stephen

During A Call Or A Meeting

DO's

  • Build a trustworthy relationship while keeping the product center-stage
  • Use phrases like ‘your decision will’, ‘you will impact’ etc.
  • Showcase existing customers and use case-studies to grab their attention

DONT's

  • Avoid focusing only on the product or its ROI, keep building trust subtly
  • Don’t hesitate from asking questions or pushing them, but take a formal approach
  • Don’t be too verbose or overly friendly; a little bit, however, is fine

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Stephen is

  • Nothing less than a strong combination of proof of results, relationship and high levels of professionalism is effective with them.
  • Will you ever get a clear answer from Stephen

  • They can say no while staying friendly, but can also be pursuaded to reconsider

Insights For Deal Planning

    How fast (or slow) will Stephen move?

  • They are generally fast movers and can take quick decisions
  • Can Stephen take some risk or not?

  • They have high risk-appetite but can get ahead of themselves once in a while. Observe carefully

You And Stephen

Personality Compatibility


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