Holly Roland

Go-getter
DISC Type : d

Strategic Go To Market and Marketing Consultant at Rebel GTM

San Francisco Bay Area, United States

Overview

Holly Roland is a go-to-market executive and the founder of Rebel GTM, with a background at SAP and Oracle. Specializing in B2B tech, she is an instructor at Stanford Continuing Studies and an alumna of Santa Clara University. Colleagues describe her as a creative and cerebral leader.

She was named one of the "100 Most Influential People in Finance" by Treasury & Risk Magazine.

Personality Overview

Direct & Candid

Challenger

Self-Confident

They care equally about the product and its potential impact.  They don’t always try to control the conversation but neither do they like yielding it fully. They can be nudged to make faster decisions by offering what they value.

Topics They Care About

AI Go-to-Market
Teaches "AI for GTM" at Stanford and actively discusses Generative Engine Optimization (GEO) as the next major trend for B2B companies.
B2B Tech Growth
As the founder of Rebel GTM, she has a documented track record of achieving 2-3X growth for her B2B technology clients within 6-12 months.
Creating New Categories
A key part of her stated expertise involves helping B2B technology firms define and lead new market categories to stand out from competitors.

Media Appearances

Holly has no verified media appearances

Work History

1-2018
Strategic Go To Market and Marketing Consultant at Rebel GTM
4-2025
Instructor - AI for GTM at Rebel GTM
7-2025
Instructor, Stanford Continuing Studies at Stanford Continuing Studies
9-2025
Member, Silicon Valley Chapter at Women Presidents Organization
Advisory Partner at Cota Capital

Education

Education details unavailable from Santa Clara University Leavey School of Business
BSC from Santa Clara University

More Information

Social Presence :

Prographics :

Exp : 8 Location : San Francisco Bay Area, United States Job Level : Middle Designation : Strategic Go To Market and Marketing Consultant at Rebel GTM
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Insights For Selling To Holly

During A Call Or A Meeting

DO's

  • Get to the point quickly instead of spending too much time on pleasantries
  • Refer to testimonials from others in similar positions
  • Make sure that you you respond to any queries from them quickly

DONT's

  • Avoid long winding pitches, stay objective
  • Don't try too hard to get friendly, let it happen with time
  • Avoid repeating yourself or making generalizations

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Holly is

  • Conviction in the product matters to them, followed by proof points and strong testimonials.
  • Will you ever get a clear answer from Holly

  • They may not be very forthcoming, but they will say no if needed.

Insights For Deal Planning

    How fast (or slow) will Holly move?

  • They are neither the fastest decision makers nor the slowest.
  • Can Holly take some risk or not?

  • They can take risks but after weighing up the pros and cons.

You And Holly

Personality Compatibility


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