Harry Wilson

Questioner
DISC Type : c

Jr SDR at Outbound OS

United Kingdom

Overview

Harry Wilson is an 18-year-old Junior Sales Development Representative at Outbound OS, focusing on helping SaaS companies book more meetings through cold outbound strategies. A graduate of Monmouth Comprehensive, he is actively and publicly documenting his professional journey as he begins his career in sales.

His daily updates reveal a highly motivated and disciplined individual who is passionate about learning and self-improvement. He sets specific professional goals, such as booking a target number of meetings per week, showcasing a drive for success and a transparent approach to his development.

At just 18, he is publicly sharing his daily learnings and progress in his first sales role.

Personality Overview

Not Easily Convinced

Value Seeker

Cautious & Analytical

They are more likely than others to negotiate on pricing and terms.  They generally do not appreciate an overfriendly approach and prefer to stay to-the-point. While they don't hesitate to ask questions, they are generally risk-averse and tend to be late adopters.

Topics They Care About

Cold Outbound
His role at Outbound OS is entirely focused on helping SaaS sellers book more meetings through cold outreach, a process he documents in detail daily.
Sales Development
As a new Junior SDR, he is deeply immersed in the fundamentals of sales development, from prospecting and messaging to booking his first meetings.
Building in Public
He transparently shares his daily progress, challenges, and successes in his new role, actively building his professional brand online from day one.

Media Appearances

Harry has no verified media appearances

Work History

10-2025
Jr SDR at Outbound OS
8-2024 - 6-2025
Supermarket Assistant at Co-op

Education

9-2023 - 6-2025
A-level from Monmouth Comprehensive
9-2023 - 6-2025
A levels from Monmouth Comprehensive

More Information

Social Presence :

Prographics :

Exp : 1 Location : United Kingdom Job Level : Junior Designation : Jr SDR at Outbound OS
URL has been copied!

Insights For Selling To Harry

During A Call Or A Meeting

DO's

  • Keep some extra margin in hand as they will likely negotiate the pricing
  • If you have a lower priced product compared to the competition, call out the same
  • Emphasize on objective proof of ROI, help them do a thorough evaluation

DONT's

  • Avoid phrases like ‘do not worry about’, ‘no one compares to’ etc.
  • Don’t depend too much on anecdotal evidence, it reduces their confidence
  • Don’t overhype the product/pitch, keep it measured

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Harry 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 Harry

  • 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 Harry move?

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

  • Can Harry take some risk or not?

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

You And Harry

Personality Compatibility


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