Ben Winter

Observer
DISC Type : ci

COO & Co-founder at Stuut

New York, New York, United States

Overview

Ben Winter is the COO and Co-founder of Stuut, a venture-backed company simplifying account receivables. An alumnus of Middlebury College and Boston Universitys Questrom School of Business, he has a strong background in scaling Go-to-Market and Growth functions for startups like Fairmarkit and Waldo.

Outside of his primary role, Ben has served as a mentor for First Round Fast Track, guiding other entrepreneurs. He demonstrates a keen interest in effective leadership and continuous learning, emphasizing the importance of reading for founders to maintain a long-term strategic perspective.

Unique fact: His company, Stuut, successfully acquired a new customer just 48 hours after running a creative ad in The Wall Street Journal featuring an animated bug.

Personality Overview

Value Driven

Example Seeker

Curious

They are likely to ask many questions and look heavily for supporting information.  They are generally good communicators and can be hard to convince. They can sound friendly and charming but can quickly change gears to become inquisitive and probing.

Topics They Care About

AR Automation
As the co-founder of Stuut, his core focus is on solving accounts receivable challenges, improving cash flow, and reducing Days Sales Outstanding (DSO) for businesses.
Creative B2B Marketing
He champions unconventional advertising, citing a successful Wall Street Journal ad with an animated bug that drove immediate customer acquisition for his company.
Go-to-Market Strategy
He has a proven track record of scaling GTM and Growth functions for multiple venture-backed companies and has also worked as a fractional GTM advisor for various startups.

Media Appearances

Ben Winter – COO & Cofounder at Stuut - Reforge. Featured in Reforge

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Ben Winter - COO & Co‑founder at Stuut - The Org. Featured in The Org

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Work History

2024
COO & Co-founder at Stuut
2023 - 2024
Fractional GTM Leader & Advisor at Various Startups
2022 - 2023
VP, Growth & Marketing at Waldo
2021 - 2023
Mentor at First Round Fast Track
2019 - 2022
VP, Growth & Marketing at Fairmarkit

Education

2007 - 2010
Bachelor of the Arts from Middlebury College
2016 - 2018
Master of Business Administration (MBA) and Master of Science in Digital Innovation (MSDi) from Questrom School of Business, Boston University

More Information

Social Presence :

Prographics :

Exp : 16 Location : New York, New York, United States Job Level : Leadership Designation : COO & Co-founder at Stuut

Interested in

Sports

Middlebury College Rugby Club

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Insights For Selling To Ben

During A Call Or A Meeting

DO's

  • Help them realize that there is no personal risk in making this decision
  • Be prepared for a lot of questions, answer them objectively
  • Help them understand the risk aspect fully while inspiring confidence

DONT's

  • Don’t rely excessively on your relationship with them to win the deal
  • Avoid making offhand commitments
  • Don’t brush off any concerns, take all questions seriously

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Ben is

  • Proven value, strong testimonials are important to them, relationships will have some weightage.
  • Will you ever get a clear answer from Ben

  • They are practical and friendly, don't expect a clear-cut response often.

Insights For Deal Planning

    How fast (or slow) will Ben move?

  • They like to be detailed and take their time to arrive at decisions.
  • Can Ben take some risk or not?

  • They evaluate their decisions systematically and are less likely to take risks.

You And Ben

Personality Compatibility


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