Matthew Gay

Captain
DISC Type : SD

Head of Sales, Technology & Business Services US Commercial Group at First Advantage

New York, New York, United States

Overview

Matthew Gay is a tenacious executive with over 20 years of leadership in the Human Capital Management SaaS sector, currently serving as Head of Sales for First Advantages Technology & Business Services US Commercial Group. He holds a BS from Syracuse University and is described by colleagues as a compassionate, visionary, and energetic leader.

He is a multi-time Presidents Club award winner, recognized for leading his teams to significantly exceed sales quotas.

Personality Overview

Output-Driven

Dynamic But Sincere

Consummate Professional

They are very professional in their approach and can weigh multiple perspectives together.  They exhibit a rare combination of being result-oriented but patient at the same time. They might take some time to make their mind up but once they do, they don't change it easily.

Topics They Care About

Sales Leadership
An executive with 20+ years of experience leading and building sales teams, with certifications in Strategic Selling and Coaching.
Client Collaboration
Actively attends user conferences like #FACollaborate and Workday Rising to engage directly with clients and partners on product enhancements and strategy.
Go-to-Market Strategy
Previously conceptualized and executed the enterprise go-to-market strategy for Greenhouse Software, focusing on up-market business growth.

Media Appearances

Problem‑solving requires trusted partnerships – previous episode of Falive MA (featuring Matthew Gay). Featured in Facebook (First Advantage)

See Now

Work History

11-2024
Head of Sales, Technology & Business Services US Commercial Group at First Advantage
12-2022
Head of Sales, Technology & Business Services US Commercial Group at Sterling
9-2020 - 12-2022
Head of Sales, Financial Services & GM, Diligence at Sterling
1-2020 - 9-2020
General Manager, Small and Mid-Sized Business Group at Sterling
1-2018 - 7-2018
Director of Enterprise Sales at Greenhouse Software

Education

BS from Syracuse University

More Information

Social Presence :

Prographics :

Exp : 21 Location : New York, New York, United States Job Level : Mid-senior Designation : Head of Sales, Technology & Business Services US Commercial Group at First Advantage

Interested in

Sports

Rugby Football

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Insights For Selling To Matthew

During A Call Or A Meeting

DO's

  • You can spend time on BANT (or other qualification methodology) but keep it to the point
  • Suggest clear next steps with confidence, don't be vague or hesitant
  • Come across as a trustworthy professional and be respectful, they usually know their game

DONT's

  • Don't shy away from asking hard questions, but be extra polite
  • Don't get into pricing discussions early on, steer conversation towards proven results
  • Don't take their patience for granted, avoid long-winding sermons

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Matthew is

  • Strong proof of impact and their conviction will matter the most, but they wouldn't want to act unilaterally either
  • Will you ever get a clear answer from Matthew

  • They will say no if they are not convinced but you will have to prompt them.

Insights For Deal Planning

    How fast (or slow) will Matthew move?

  • They will want to understand things well but can move fast once they have a clear picture.
  • Can Matthew take some risk or not?

  • They have good risk tolerance but are likely to think it through once or twice.

You And Matthew

Personality Compatibility


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