Sarah Jackson

Judge
DISC Type : Dc

Senior Director, GTM Operations at Calendly

Encinitas, California, United States

Overview

Alyssa is the Senior Director, GTM Operations at Calendly, with a strong background in revenue and sales operations. She excels at administering Salesforce and other GTM tools to support sales, marketing, and customer success initiatives. Alyssa earned her degree in English Language and Literature from The University of North Carolina at Chapel Hill.

Alyssa is passionate about building effective GTM strategies and operational efficiency. Her posts indicate an interest in team growth and fostering talent within revenue operations roles.

People often call her dedicated and knowledgeable in GTM tools and Salesforce administration.

Personality Overview

Demanding

Quality Focused

Generally Skeptic

They respond better to strong and respectful interactions.  They are less concerned about the product and more about its potential impact. They prefer to move quickly, and expect the same from others.

Topics They Care About

GTM Operations
As Senior Director of GTM Operations at Calendly, Alyssa is deeply involved in optimizing go-to-market functions, demonstrating expertise in supporting sales, marketing, and customer success.
Salesforce Administration
Alyssa holds Salesforce Certified Pardot Specialist and Administrator certifications and is recognized for her strong knowledge in administering Salesforce.
Revenue Operations
Alyssa has a progressive career history in Revenue Operations at Calendly, from Manager to Director, indicating a focus on streamlining revenue-generating processes.

Media Appearances

Sarah has no verified media appearances

Work History

8-2025
Senior Director, GTM Operations at Calendly
8-2023 - 7-2025
Director, Revenue Operations at Calendly
10-2021 - 7-2023
Senior Manager, Revenue Operations at Calendly
4-2020 - 10-2021
Manager, Revenue Operations at Calendly
4-2019 - 4-2020
Manager, Sales Operations and Enablement at Gather

Education

2009 - 2014
English Language and Literature from The University of North Carolina at Chapel Hill

More Information

Social Presence :

Prographics :

Exp : 12 Location : Encinitas, California, United States Job Level : Senior Designation : Senior Director, GTM Operations at Calendly
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Insights For Selling To Sarah

During A Call Or A Meeting

DO's

  • When negotiating terms, help them build an impression that they are the ones calling the shots
  • Get to the point quickly instead of spending time doing small talk
  • Refer to testimonials from well-known industry leaders

DONT's

  • Don’t take too much time in sending them information if they ask for any
  • Avoid being a storyteller and don’t try to oversell
  • Do not back off when challenged, respond with a confident, objective answer instead

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Sarah 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 Sarah

  • If they decide not to use your product, they will say no clearly.

Insights For Deal Planning

    How fast (or slow) will Sarah move?

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

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

You And Sarah

Personality Compatibility


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