Stephanie D'Souza-Cafiso, CPA

Visionary
DISC Type : Ds

Director, Finance Operations, Finance Transformation at Plusgrade

Toronto, Ontario, Canada

Overview

Stephanie is the Director of Finance Operations at Plusgrade, where she leads finance transformation initiatives. A Chartered Professional Accountant and a graduate of York University, she focuses on building scalable processes to drive growth. Her current projects include a Treasury Management System implementation and assessing e-invoicing solutions.

Stephanie has a demonstrated interest in advancing financial knowledge within the community. She recently moderated a panel discussion about the impact of generational differences on financial literacy in the workplace at the Mastering Money Conference, an experience she clearly enjoyed.

Unique fact: She is passionate about financial literacy and has publicly moderated discussions on the topic.

Personality Overview

Objective Evaluator

Big Vision Person

Direct & Assertive

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 exhibit a rare combination of being result-oriented but patient at the same time.

Topics They Care About

Finance Transformation
Her current role is focused on driving operational excellence and innovation within the finance function at Plusgrade to enable better business growth.
Treasury Management
She is actively leading a Treasury Management System (TMS) implementation for her company, starting from the initial RFP process.
Generative AI
In a prior role as Director of Finance at a venture studio, she was involved with automating complex business processes using generative AI and LLMs.

Media Appearances

Stephanie has no verified media appearances

Work History

8-2024
Director, Finance Operations, Finance Transformation at Plusgrade
6-2023 - 8-2024
Director, Finance at Mind Lab 56
4-2021 - 6-2023
Finance Manager at ACTO
10-2019 - 4-2021
Senior Accountant, Assurance at Grant Thornton LLP (Canada)
10-2017 - 9-2019
Accountant, Assurance at Grant Thornton LLP (Canada)

Education

Chartered Professional Accountant from Chartered Professional Accountants of Canada (CPA Canada)
Bachelor of Commerce - BCom from York University

More Information

Social Presence :

Prographics :

Exp : 8 Location : Toronto, Ontario, Canada Job Level : Mid-senior Designation : Director, Finance Operations, Finance Transformation at Plusgrade
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Insights For Selling To Stephanie

During A Call Or A Meeting

DO's

  • Suggest clear next steps with confidence, don't be vague or hesitant
  • Stick to your standard pitch and qualifying script, don't try to wing it
  • Ask them at the end if they see a strong value prop in your product; expect an honest answer

DONT's

  • Don't go over them unless you are left with no other option
  • Avoid putting conscious effort into relationship-building
  • Don't focus too much on mutual contacts or bother about other stakeholders, focus on them

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Stephanie 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 Stephanie

  • 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 Stephanie move?

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

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

You And Stephanie

Personality Compatibility


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