Alpesh Patel

Visionary
DISC Type : Ds

Advisor at Outmarket AI

Barrington, Illinois, United States

Overview

Alpesh Patel is a GTM advisor with over 20 years of experience scaling enterprise software and AI companies. A former CRO at H1 and VP at DocuSign, he specializes in building go-to-market motions for regulated industries. He holds an MBA from the University of Chicago and is described by peers as prepared, thoughtful, and knowledgeable.

Unique Fact: While at Salesforce, Alpesh closed the largest deal in the companys history in 2012, showcasing his expertise in complex enterprise sales.

Personality Overview

Direct & Assertive

Early Adopter

Big Vision Person

They exhibit a rare combination of being result-oriented but patient at the same time.  They are very professional in their approach and can weigh multiple perspectives together. Reading between the lines and seeing beyond your words comes naturally to them.

Topics They Care About

Vertical GTM Strategy
Advises companies on expanding into regulated industries like Financial Services, Insurance, and Healthcare, a core theme throughout his career at Salesforce, DocuSign, and H1.
Enterprise AI
Writes frequently about "Agentic Enterprise Architecture" and applying AI to scale GTM motions. He holds a certification in AI for Business.
Scaling Sales Engines
Focuses on helping companies move from product-market fit to predictable growth, often discussing topics like SDR and AE alignment and pipeline conversion.

Media Appearances

Alpesh has no verified media appearances

Work History

9-2025
Advisor at Outmarket AI
4-2025
Advisory Board Member at Simplify Healthcare
7-2023 - 9-2023
GTM advisor at H1
11-2022 - 7-2023
Chief Revenue Officer (CRO) at H1
2-2017 - 6-2022
Vice President, Enterprise Strategic Verticals at DocuSign

Education

1998 - 2001
MBA from University of Chicago
1994 - 1996
MS from Illinois Institute of Technology

More Information

Social Presence :

Prographics :

Exp : 28 Location : Barrington, Illinois, United States Job Level : N/A Designation : Advisor at Outmarket AI
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Insights For Selling To Alpesh

During A Call Or A Meeting

DO's

  • Suggest clear next steps with confidence, don't be vague or hesitant
  • You can spend time on BANT (or other qualification methodology) but keep it to the point
  • Stick to your standard pitch and qualifying script, don't try to wing it

DONT's

  • Don't go over them unless you are left with no other option
  • Don't shy away from asking hard questions, but be extra polite
  • 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 Alpesh 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 Alpesh

  • 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 Alpesh move?

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

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

You And Alpesh

Personality Compatibility


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