Kaila F.

Energizer
DISC Type : I

Head of Sales Engineering at Sierra

San Francisco, California, United States

Overview

Kaila Fleisig is the Head of Sales Engineering at Sierra, where she leads Go-to-Market strategy. Described as a "force multiplier, " she excels at building and scaling high-performing teams, with previous experience as a Principal Solution Engineer at Salesforce. She holds a BS from Northeastern Universitys DAmore-McKim School of Business.

As the founding Sales Engineer at Sierra, Kaila built the sales engineering team from a solo act to a powerhouse squad of 20 people.

Personality Overview

Relationship Oriented

Imaginative

Informal

They are really good at seeing what the long-term impacts of their decisions could be.  Unlike C or D types, they are vocal with their opinions but not so much with their questions. They are not always early adopters but can be pursuaded by leveraging strong relationships.

Topics They Care About

AI in Customer Experience
Her company, Sierra, is dedicated to transforming customer experiences for major brands using conversational AI agents.
Technical Sales Leadership
She has a track record of building and scaling sales engineering teams from the ground up, focusing on deep technical partnerships and customer education.
Go-to-Market Strategy
Her role and public profile identify her as a GTM Leader, focused on bringing new technology products to market effectively.

Media Appearances

Kaila has no verified media appearances

Work History

8-2025
Head of Sales Engineering at Sierra
4-2025 - 8-2025
Sales Engineering Lead at Sierra
5-2024 - 4-2025
Enterprise Sales Engineering at Sierra
2-2024 - 5-2024
Principal Solution Engineer, Enterprise Core Products at Salesforce
8-2022 - 2-2024
Lead Solution Engineer, Enterprise Service Cloud Specialist at Salesforce

Education

Bachelor of Science - BS from D'Amore-McKim School of Business at Northeastern University
Business Administration and Management from Dublin Business School

More Information

Social Presence :

Prographics :

Exp : 8 Location : San Francisco, California, United States Job Level : Mid-senior Designation : Head of Sales Engineering at Sierra
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Insights For Selling To Kaila

During A Call Or A Meeting

DO's

  • Talk about their team and how your product will help them do things better and easier
  • Use phrases like ‘people will love’, ‘massive impact’ etc.
  • Do some small talk, ask them how things are going on their side

DONT's

  • Don’t be excessively objective, be a storyteller
  • Don’t push them to make a decision too fast, let them get comfortable first
  • Avoid ifs and buts, don’t talk too much about the risks etc.

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Kaila is

  • Relationship and rapport can play an important role, sometimes more than the other factors.
  • Will you ever get a clear answer from Kaila

  • They will probably never say no directly, you have to make that decision yourself.

Insights For Deal Planning

    How fast (or slow) will Kaila move?

  • They are not the quickest decision makers, their friendly attitude could be misleading.
  • Can Kaila take some risk or not?

  • They can take certain risks that are unlikely to have personal consequences.

You And Kaila

Personality Compatibility


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