Mike Cipolla

Questioner
DISC Type : c

Area Vice President, Enterprise Sales at DocuSign

San Francisco, California, United States

Overview

Mike Cipolla is the Area Vice President of Enterprise Sales at DocuSign, where he has held several leadership positions, including Chief of Staff to the CEO. This prior role provided him deep, cross-functional expertise in operational efficiency and customer success. His career began at Oracle after earning a B. S. E. from Saint Marys College of California.

Outside of his corporate roles, Mike has a history of leadership and community involvement dating back to his college years. He was a two-time captain of the Saint Marys baseball team, where he was recognized for fostering a culture of excellence, commitment, and a winning attitude among his teammates.

His unique experience as Chief of Staff to the CEO gave him a holistic view of the business, focusing on platform virality and people development.

Personality Overview

Value Seeker

Price-Sensitive

Not Easily Convinced

They are more likely than others to negotiate on pricing and terms.  They prefer to fully evaluate every situation. They generally do not appreciate an overfriendly approach and prefer to stay to-the-point.

Topics They Care About

Enterprise Sales
Has built a long-term career in enterprise sales leadership, with progressive roles at both DocuSign and Oracle, managing key and national accounts.
Operational Efficiency
A primary focus during his tenure as Chief of Staff to the CEO at DocuSign, where he worked to streamline processes across the organization.
Team Leadership
Demonstrated early leadership skills as a two-time captain of his college baseball team and now leads large enterprise sales teams at DocuSign.

Media Appearances

Mike has no verified media appearances

Work History

2-2021
Area Vice President, Enterprise Sales at DocuSign
2-2018 - 1-2021
Regional Vice President, Enterprise Sales at DocuSign
3-2016 - 2-2018
Chief of Staff to the CEO at DocuSign
1-2015 - 2-2016
Sales Director Key Accounts at Oracle
3-2013 - 1-2015
Regional Sales Manager, National Accounts at Oracle

Education

B.S.E from Saint Mary's College of California
Education details unavailable from De La Salle High School

More Information

Social Presence :

Prographics :

Exp : 14 Location : San Francisco, California, United States Job Level : Senior Designation : Area Vice President, Enterprise Sales at DocuSign
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Insights For Selling To Mike

During A Call Or A Meeting

DO's

  • Back up any claims with data and numbers
  • Share as much information as possible regarding your product
  • If you have a lower priced product compared to the competition, call out the same

DONT's

  • Don’t depend too much on anecdotal evidence, it reduces their confidence
  • Don’t try to be too friendly or informal with them
  • Avoid phrases like ‘do not worry about’, ‘no one compares to’ etc.

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Mike is

  • Confidence that the product provides ROI, effective pricing and process adherence matter the most to them.

  • Will you ever get a clear answer from Mike

  • It doesn’t come naturally to them but they can say no if they are not convinced.

Insights For Deal Planning

    How fast (or slow) will Mike move?

  • They can move at a reasonable pace while making their decisions if they have the necessary information.

  • Can Mike take some risk or not?

  • If they believe that they have analyzed the situation well, they can take a little risk.

You And Mike

Personality Compatibility


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