Rob Desmond

Wildcard
DISC Type : isc

Operating Advisor at MagicOrange

Boston, Massachusetts, United States

Overview

Rob is a Go-to-Market executive and advisor who specializes in assembling high-performing teams to fuel growth in the enterprise software space. He graduated from Drexel University and has contributed to four company exits exceeding $1. 5 billion in shareholder value. Colleagues describe him as patient, a proven winner, and a creative deal maker.

Outside of his executive roles, Rob is a passionate advocate for mental health awareness, a topic he holds close to his family after losing loved ones to suicide. He actively supports companies with a positive mission, such as those working towards a sustainable future in transportation.

He has helped create over $1. 5 billion in cumulative shareholder value across four different company exits.

Personality Overview

Friendly But Slow

Curious But Skeptical

ROI Driven

They typically tend to be late adopters even when they seem friendly and excited about what you have to sell  They are often friendly and nice, but can sometimes suprise you with their piercing questions  They are unlikely to ever become strong champions even when the conversations are going well; you should focus on cultivating other champions

Topics They Care About

Go-to-Market Strategy
As a GTM Executive and CRO, his career is focused on building and executing strategies for sales, marketing, and customer success, including SaaS and channel models.
High-Growth Teams
States a passion for assembling high-performing teams that fuel growth and fosters collaboration between sales, marketing, and customer success.
Mental Health Advocacy
He has publicly discussed the importance of mental health and suicide awareness, noting the topic is very close to his family.

Media Appearances

Rob has no verified media appearances

Work History

10-2024
Operating Advisor at MagicOrange
5-2019
Core Member at Underscore VC
2-2019
Executive, Founding Member Boston at Revenue Collective
7-2024 - 8-2025
Operating Advisor at Zeelo
8-2019 - 7-2024
GM, North America at Quinyx

Education

BS from Drexel University
BS from Drexel University

More Information

Social Presence :

Prographics :

Exp : 6 Location : Boston, Massachusetts, United States Job Level : Junior Designation : Operating Advisor at MagicOrange
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Insights For Selling To Rob

During A Call Or A Meeting

DO's

  • Ask them questions to understand their needs better while staying affable
  • Persuade objectively how your product will help them achieve their goals
  • Share testimonials from known people and give multiple examples of product value

DONT's

  • Avoid phrases like ‘trust me’, ‘you will just love it’ etc.
  • Don't ask them to move fast, let them take their time and digest all the information
  • Don’t overhype the product/pitch, keep it measured

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Rob is

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

  • They are likely to give you a clear answer without taking you around in circles. However, if you share a good relationship, they might not be so forthcoming.

Insights For Deal Planning

    How fast (or slow) will Rob move?

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

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

You And Rob

Personality Compatibility


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