Matthew Esposito

Observer
DISC Type : ic

VP of Engineering at Skedda

Greater Boston, United States

Overview

Matthew Esposito is the VP of Engineering for Skedda and AllBooked, where he leads and grows high-performing, diverse teams. A graduate of the Rochester Institute of Technology and a Certified Scrum Master, he focuses on building critical, scalable solutions and spearheading AI development initiatives. He has a passion for Agile development and improving processes.

Outside of his engineering leadership role, Matthew has a creative hobby in MOC (My Own Creation) building with LEGO bricks. He gained attention for his complex model of Godzilla, which was selected by LEGO Ideas to become an official set after receiving 10, 000 fan votes. He rediscovered this hobby during the pandemic.

He successfully scaled his engineering organization by over 200%, growing the team from 12 to more than 35 engineers.

Personality Overview

Example Seeker

Curious

Assertive

They can sound friendly and charming but can quickly change gears to become inquisitive and probing.  They often ask many questions and rely heavily on information and documentation. They are generally good communicators and can be hard to convince.

Topics They Care About

Scaling Engineering Teams
He successfully expanded the engineering team at Skedda from 12 to over 35 people while implementing new best practices to improve quality and velocity.
AI Development
He spearheads AI development initiatives at Skedda and previously was involved in launching "Comply AI for remediation" in a former role at Secureframe.
LEGO MOC Building
He is an avid LEGO builder, and his fan-designed Godzilla model was approved to become an official LEGO set after receiving 10, 000 votes on the Ideas platform.

Media Appearances

Matthew has no verified media appearances

Work History

3-2026
VP of Engineering at Skedda
3-2025
Senior Director of Engineering at Skedda
2-2024
Director of Engineering at Skedda
8-2023 - 2-2024
Senior Software Engineering Manager at Secureframe
10-2022 - 8-2023
Software Engineering Manager at Secureframe

Education

2009 - 2014
Bachelor of Science - BS from Rochester Institute of Technology

More Information

Social Presence :

Prographics :

Exp : 12 Location : Greater Boston, United States Job Level : Senior Designation : VP of Engineering at Skedda
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Insights For Selling To Matthew

During A Call Or A Meeting

DO's

  • Build rapport, it will come handy to handle hard questions later
  • Focus on immediate action-items rather than the larger goals
  • Invite them for a social do but don’t rely solely on the relationship

DONT's

  • Don’t rely excessively on your relationship with them to win the deal
  • Don’t try to rush them into a decision, provide all necessary information first
  • Don’t brush off any concerns, take all questions seriously

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Matthew is

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

  • They are practical and friendly, don't expect a clear-cut response often.

Insights For Deal Planning

    How fast (or slow) will Matthew move?

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

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

You And Matthew

Personality Compatibility


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