Harry Bilotto

Trailblazer
DISC Type : DI

Director, Client Success at Affirm

New York, New York, United States

Overview

Harry Bilotto is a Global Customer Success leader at Affirm with over 11 years of experience in Enterprise SaaS. He specializes in building high-performing teams and scalable operating rhythms to drive retention and product adoption for portfolios up to $100M ARR. He holds a Bachelors degree from Rutgers University.

Colleagues consistently describe him as a natural-born leader, a fantastic mentor, and a strategic manager with an ability to de-escalate tough situations. He is known for his transparency and for fostering a culture of collaboration and continuous improvement within his teams.

He once won a "Do or Do not (There is no try)" award for his perseverance in getting the job done with a particularly difficult client.

Personality Overview

Assertive

Persuasive

Achievement-Oriented

They do not mind taking risks and can make hard decisions, if necessary.  They like to keep things under control. They will fight for you if they come to believe in you.

Topics They Care About

Customer Success Leadership
He has over a decade of experience building and leading high-performing, global Customer Success teams at companies like Vimeo and Wunderkind, managing portfolios up to $100M ARR.
AI Product Adoption
At Vimeo, he led a successful initiative that increased AI product adoption by 43% across the customer base through strategic campaigns and training programs.
Client Retention & Growth
He has a strong track record of delivering over 90% renewal rates and developing playbooks that have increased product adoption by 30% to reduce churn.

Media Appearances

Harry has no verified media appearances

Work History

3-2026
Director, Client Success at Affirm
1-2025 - 3-2026
Global Director of Customer Success at Vimeo
5-2024 - 1-2025
Senior Manager, Strategic Customer Success at Vimeo
7-2021 - 5-2024
Director of Customer Success, Strategic Accounts at Wunderkind
4-2020 - 7-2021
Associate Director of Customer Success at Wunderkind

Education

Bachelor's degree from Rutgers University

More Information

Social Presence :

Prographics :

Exp : 14 Location : New York, New York, United States Job Level : Mid-senior Designation : Director, Client Success at Affirm
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Insights For Selling To Harry

During A Call Or A Meeting

DO's

  • Showcase existing customers and use case-studies to grab their attention
  • Keep your pitch focused on the impact but nurture the relationship too
  • Ask them for a lunch or coffee once some rapport has been established

DONT's

  • Don’t hesitate from asking them how they truly feel about your product
  • Do not look like someone who doesn’t know what they are talking about
  • Don’t force involvement of other stakeholders unless it is critical

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Harry is

  • Relationship and product conviction matter equally, followed by a sense of achievement.
  • Will you ever get a clear answer from Harry

  • If they are not convinced, they will say no albeit in a friendly manner.


Insights For Deal Planning

    How fast (or slow) will Harry move?

  • They can reach decisions quickly if they develop trust and confidence in the product.
  • Can Harry take some risk or not?

  • They can take risks if necessary.

You And Harry

Personality Compatibility


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