Jack Day

Inquirer
DISC Type : cd

Director of Customer Success at Deskpro

London, England, United Kingdom

Overview

Jack Day is a Director of Customer Success with over seven years of SaaS experience. He specializes in driving client adoption, retention, and value for diverse portfolios, from SMBs to Fortune 500 companies. An alumnus of the University of Leicester, he has a proven track record at companies like Freshworks and Workiva.

He has successfully leveraged his background in History to build a thriving career in the technology and SaaS sectors.

Personality Overview

Judgemental

ROI Conscious

Demanding

They can be nudged to make faster decisions by offering what they value.  They respond well to confident salespeople. They focus on objectivity in a pitch and pay little attention to bells and whistles.

Topics They Care About

Customer Value Realization
Focuses on ensuring clients achieve measurable ROI from their solutions, drawing on his experience with global brands and leading media agencies.
SaaS Adoption & Retention
Specializes in developing strategies to help SaaS clients drive product adoption, increase retention rates, and secure long-term value from their investments.
Enterprise Account Management
Experienced in managing and strengthening relationships with a diverse portfolio of clients, including Fortune 500 companies and high-potential accounts.

Media Appearances

Jack has no verified media appearances

Work History

11-2025
Director of Customer Success at Deskpro
5-2022 - 8-2025
Lead - Customer Success at Freshworks
3-2021 - 5-2022
Enterprise Customer Success Manager at Workiva
8-2018 - 3-2021
Customer Success Manager at Mediaocean
2-2016 - 8-2018
Customer Support Team Lead at Mediaocean

Education

Jack has no verified education history

More Information

Social Presence :

Prographics :

Exp : 14 Location : London, England, United Kingdom Job Level : Mid-senior Designation : Director of Customer Success at Deskpro
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Insights For Selling To Jack

During A Call Or A Meeting

DO's

  • Highlight the competitive differentiation of your product
  • Ask them questions confidently while doing discovery, don’t be apologetic
  • Make sure that they have the necessary authority, they could present false stature sometimes

DONT's

  • Avoid repeating yourself or making generalizations
  • Don’t try to be an alpha salesperson, give them equal space
  • Do not give up if they are not convinced, try again with a different approach

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Jack is

  • Belief in the product plays an important role, followed by objective proof and testimonials.
  • Will you ever get a clear answer from Jack

  • They may hesitate slightly, but if they are not convinced, they will say no.

Insights For Deal Planning

    How fast (or slow) will Jack move?

  • Their decision making speed is somewhere in the middle.
  • Can Jack take some risk or not?

  • They can take risks only after they have analyzed the advantages and disadvantages.

You And Jack

Personality Compatibility


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