Zach Cusimano

Captain
DISC Type : SD

Advisor - COO Office at ClickUp

United States

Overview

Zach Cusimano is a leader in SaaS operations and people strategy, known for scaling companies and building high-performance teams. He co-founded and scaled Bizness Apps to a successful acquisition and held key roles at People. ai. He currently advises high-growth companies like ClickUp. People who have worked with him describe him as knowledgeable, organized, and a tremendous leader.

Outside of work, Zach has had an eventful year, having gotten married to his partner, Sarah, and welcoming a new baby. He is an avid traveler and snowboarder, having recently enjoyed an "all-time" snowboarding season across multiple states and countries.

He drove Bizness Apps from its inception to over $10M in annual recurring revenue and 30 million monthly active users, leading to its acquisition.

Personality Overview

Dynamic But Sincere

Long-Term Thinker

Output-Driven

They might take some time to make their mind up but once they do, they don't change it easily.  Reading between the lines and seeing beyond your words comes naturally to them. They are very professional in their approach and can weigh multiple perspectives together.

Topics They Care About

Company Scaling
He has extensive experience scaling companies, notably taking Bizness Apps from inception to a successful exit and advising other high-growth startups like ClickUp and acquire. com.
People Operations
His career focus is on creating exceptional teams and world-class companies, holding roles like SVP of People at People. ai and advising ClickUp's People Team on culture and strategy.
Startup Fundraising
In his advisory roles at acquire. com and BluePallet, he directly counsels CEOs on strategy and capital fundraising, leveraging his experience from People. ai.

Media Appearances

Zach has no verified media appearances

Work History

1-2025
Advisor - COO Office at ClickUp
1-2024 - 2-2025
Advisor - People Team at ClickUp
9-2020 - 9-2024
Advisor at acquire.com
9-2021 - 10-2023
Advisor at BluePallet
6-2020 - 12-2022
SVP People at People.ai

Education

BS from California State University, Chico
Full Stack Web Development from General Assembly

More Information

Social Presence :

Prographics :

Exp : 8 Location : United States Job Level : Leadership Designation : Advisor - COO Office at ClickUp
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Insights For Selling To Zach

During A Call Or A Meeting

DO's

  • Come across as a trustworthy professional and be respectful, they usually know their game
  • During followups, use phone or text if needed, they should be fine
  • You can spend time on BANT (or other qualification methodology) but keep it to the point

DONT's

  • Don't get into pricing discussions early on, steer conversation towards proven results
  • Avoid putting conscious effort into relationship-building
  • Don't shy away from asking hard questions, but be extra polite

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Zach is

  • Strong proof of impact and their conviction will matter the most, but they wouldn't want to act unilaterally either
  • Will you ever get a clear answer from Zach

  • They will say no if they are not convinced but you will have to prompt them.

Insights For Deal Planning

    How fast (or slow) will Zach move?

  • They will want to understand things well but can move fast once they have a clear picture.
  • Can Zach take some risk or not?

  • They have good risk tolerance but are likely to think it through once or twice.

You And Zach

Personality Compatibility


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