Jackie Cai

Enthusiast
DISC Type : i

Executive Assistant at Sierra

San Francisco Bay Area, United States

Overview

Jackie Cai is an Executive Assistant at Sierra, where she supports the Go-to-Market teams operations and strategic initiatives. Educated at the University of Southern California and Stanford, she has extensive experience supporting high-level executives at firms like General Catalyst, SoftBank, and Freshworks. Colleagues praise her for her matchless organization and attention to detail.

She has a unique background in the venture capital space, having directly supported the CEO of General Catalyst and three Managing Partners at SoftBank simultaneously.

Personality Overview

Non-Confrontational

Optimistic

Consensus Focused

They prefer to build relationships rather than staying totally transactional.  Unlike D or C types, they are convinced more by stories and testimonials. They agree with others often, so exercise caution when relying on their word.

Topics They Care About

Go-to-Market Operations
Her current role focuses on supporting the GTM team, a responsibility she also held at Freshworks, where she acted as a liaison for the team.
Conversational AI
Expressed excitement about starting a new chapter at Sierra, which she describes as an "AI company at the forefront of innovation. "
Venture Capital Support
Has significant experience supporting top-tier VCs, including the CEO of General Catalyst and Managing Partners at SoftBank Investment Advisers, focusing on tech investments.

Media Appearances

Jackie has no verified media appearances

Work History

11-2024
Executive Assistant at Sierra
11-2023 - 11-2024
Executive Assistant to CEO & Managing Director, Hemant Taneja at General Catalyst
1-2022 - 11-2023
Executive Assistant to Chief Executive Officer at Mixpanel
9-2019 - 1-2022
Executive Assistant to President of North America at Freshworks
7-2018 - 7-2019
Executive Assistant to Managing Partners at SoftBank Investment Advisers

Education

Bachelor’s Degree from University of Southern California
Continuing Studies from Stanford University

More Information

Social Presence :

Prographics :

Exp : 7 Location : San Francisco Bay Area, United States Job Level : Junior Designation : Executive Assistant at Sierra
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Insights For Selling To Jackie

During A Call Or A Meeting

DO's

  • Invite them for a lunch or a drink/coffee
  • Compliment them about their personality if you get a chance
  • Speak from experience about success that the product has seen with other customers

DONT's

  • Don’t be too formal with them, they trust informality more
  • Don't be critical or challenge them openly, they can react defensively
  • Avoid overloading them with too much information

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Jackie is

  • Relationship and rapport are valuable for them, but so is proven product value.
  • Will you ever get a clear answer from Jackie

  • They probably won't say no directly.


Insights For Deal Planning

    How fast (or slow) will Jackie move?

  • They are not the ones to make fast decisions, even while they stay committed.
  • Can Jackie take some risk or not?

  • They can take some low-probability risks if needed.

You And Jackie

Personality Compatibility


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