Ryan Redmond

Evaluator
DISC Type : csd

Co-Founder at Digital Talk AI

Greater Richmond Region, United States

Overview

Ryan Redmond is the Founder of Cold Outreach Systems, a pay-per-meeting agency specializing in B2B lead generation. Drawing on his MBA from the University at Albany and extensive sales management experience at GEICO, he helps e-commerce agencies scale by booking over 500 meetings for clients each month.

After a 737-day hiatus from LinkedIn, Ryan revealed he had scaled his appointment setting business from $10K to over $130K per month during his time away from the platform.

Personality Overview

Quality Focused

Fast But Analytical

Thorough Evaluator

They focus on the results, but can still be quite procedural and analytical about how to get there  They are not very likely to become strong advocates of your product or service They have a unique set of diverse traits where they are decisive and methodical but can sometimes be extra cautious and skeptical

Topics They Care About

Appointment Setting
His company, Cold Outreach Systems, is a pay-per-meeting service that he states books over 500 meetings for clients every month.
Sales Coaching
He shares specific advice for coaching sales reps and has a background as a Sales Training and Operations Manager at GEICO.
B2B Agency Growth
His LinkedIn headline specifically states he helps e-commerce agencies book more than 50 meetings in under 90 days, focusing on their growth.

Media Appearances

Ryan has no verified media appearances

Work History

8-2025
Co-Founder at Digital Talk AI
3-2022
Founder at Cold Outreach Systems
10-2019 - 5-2022
Marketing and Sales Consultant at GEICO
3-2018 - 10-2019
Sales Operations Manager at GEICO
1-2014 - 4-2018
Sales Training Manager at GEICO

Education

2013 - 2019
Master of Business Administration - MBA from University at Albany
2005 - 2009
Bachelor's degree from University at Albany

More Information

Social Presence :

Prographics :

Exp : 16 Location : Greater Richmond Region, United States Job Level : Leadership Designation : Co-Founder at Digital Talk AI
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Insights For Selling To Ryan

During A Call Or A Meeting

DO's

  • Help them weigh the risks by sharing objective proof points instead of anecdotes and examples
  • Showcase your competitive superiority clearly when possible or address it at the minimum
  • Help them see both - the ‘big picture’ impact and the ROI of the investment

DONT's

  • Avoid inviting them for any social interactions until you have built some rapport with them
  • Avoid too much small talk, just a few formal pleasantries should be fine
  • Avoid self-deprecating references or general informality, it could decrease their trust in you

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Ryan is

  • ROI matters the most to them, followed by process and finally proof of results
  • Will you ever get a clear answer from Ryan

  • They might hesitate a little, but will go ahead and say no when necessary (or asked)

Insights For Deal Planning

    How fast (or slow) will Ryan move?

  • They are unlikely to move very fast, especially when it comes to new products or services
  • Can Ryan take some risk or not?

  • They have relatively low risk-appetite and are not very likely to go for something unproven and risky

You And Ryan

Personality Compatibility


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