Phil Yennaco

Commander
DISC Type : D

Chief of Staff, Office of the CEO at Showpad

Greater Boston, United States

Overview

Phil Yennaco is the Chief of Staff at Showpad, with extensive experience in business transformation and corporate operations from his 11+ years at Mimecast. He specializes in connecting strategy to execution using Lean Six Sigma and PMO governance. Colleagues describe him as strategic, instrumental, and a versatile team-player.

Outside of his core roles, Phil is actively upskilling in artificial intelligence, having recently completed multiple AI masterclass certifications. He has shown deep loyalty and career evolution within a single company and maintains an interest in his alma mater, the University of Massachusetts Lowell.

He was featured in a Smartsheet case study for driving strategic enterprise initiatives at Mimecast.

Personality Overview

Strong-Willed

Candid & Clear

Decisive

They like to stay in control of the negotiation or defining of the terms.  They respond better to strong and respectful interactions. They prefer to move quickly, and expect the same from others.

Topics They Care About

Strategic Execution
His entire career focuses on aligning high-level company strategy with cross-functional execution, transformation, and delivering key corporate initiatives.
Operational Efficiency
He leverages Lean Six Sigma and PMO principles to optimize business processes, drive scalability, and foster sustainable growth.
Applying AI
Recently completed multiple "Hands-on AI Masterclass" certifications, showing a proactive interest in applying artificial intelligence to solve business challenges.

Media Appearances

Phil has no verified media appearances

Work History

3-2026
Chief of Staff, Office of the CEO at Showpad
6-2025 - 3-2026
Senior Director, Finance Operations at Mimecast
4-2022 - 10-2025
Senior Director, Business Transformation & Corporate Operations at Mimecast
4-2020 - 4-2022
Director, Enterprise Project Management Office at Mimecast
4-2017 - 3-2020
Senior Project Manager, Global Go-To-Market at Mimecast

Education

2005 - 2009
Bachelors Degree from University of Massachusetts Lowell

More Information

Social Presence :

Prographics :

Exp : 16 Location : Greater Boston, United States Job Level : Leadership Designation : Chief of Staff, Office of the CEO at Showpad
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Insights For Selling To Phil

During A Call Or A Meeting

DO's

  • Objectively showcase the impact that your product creates
  • Speak about competitive differentiation that your product offers
  • Be respectful but crisp

DONT's

  • Do not hesitate from asking counter questions, just avoid challenging their authority
  • Don’t take too much time in sending them information if they ask for any
  • Avoid being too verbose

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Phil is

  • Conviction around the impact matters the most to them, followed by a sense of achievement and ROI.
  • Will you ever get a clear answer from Phil

  • If they are not convinced, they will say no without any hesitation.

Insights For Deal Planning

    How fast (or slow) will Phil move?

  • If convinced, they can reach decisions quite fast.
  • Can Phil take some risk or not?

  • They do not shy away from taking risks, but can be quite binary about them.

You And Phil

Personality Compatibility


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