Willie Osborn

Energizer
DISC Type : I

GTM Leadership at Watershed

San Francisco Bay Area, United States

Overview

Willie leads Go-to-Market strategy at Watershed, focusing on accelerating the climate economy. He previously built and scaled global sales teams at Confluent as the Global Head of Inside Sales, leading over 100 representatives. People who have worked with him often describe him as an empowering, intelligent, and inspiring leader.

His academic background includes an MSc from SOAS University of London, where his studies culminated in a detailed publication on the political economy of Sierra Leone, reflecting a strong interest in global affairs. He also co-founded a network for sales development leaders in London to foster community and peer-to-peer learning.

He authored a publication on the role of diamonds in Sierra Leones transition from peace to war, examining the "Greed vs. Grievance" argument.

Personality Overview

Informal

Relationship Oriented

Full Of Energy

They are not always early adopters but can be pursuaded by leveraging strong relationships.  Unlike C or D types, they are vocal with their opinions but not so much with their questions. They excel at seeing the bigger picture, and the long-term impact of their decisions.

Topics They Care About

Climate Economy
His current role at Watershed is centered on empowering companies to take measurable action on climate change and accelerate the global climate economy.
Sales Leadership
He has extensive experience building and leading large global sales development and inside sales organizations at high-growth tech companies like Confluent.
Team Development
Praised as a great coach and mentor, he focuses on hiring and developing talent, creating growth opportunities, and fostering career progression for his team members.

Media Appearances

Willie has no verified media appearances

Work History

1-2025
GTM Leadership at Watershed
10-2023 - 1-2025
Global Head of Inside Sales at Confluent
5-2022 - 10-2023
Senior Director, Head of Global Sales Development at Confluent
9-2019 - 4-2022
Director, International Sales Development at Confluent
1-2019 - 1-2023
Co-Founder at Sales Development Leaders (SDL)

Education

MA (Hons) from University of St Andrews
MSc from SOAS University of London

More Information

Social Presence :

Prographics :

Exp : 11 Location : San Francisco Bay Area, United States Job Level : N/A Designation : GTM Leadership at Watershed
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Insights For Selling To Willie

During A Call Or A Meeting

DO's

  • Do some small talk, ask them how things are going on their side
  • Be friendly and entertaining in your conversation
  • Use phrases like ‘people will love’, ‘massive impact’ etc.

DONT's

  • Avoid ifs and buts, don’t talk too much about the risks etc.
  • Don’t be excessively objective, be a storyteller
  • Don’t be too formal, focus on building comfort and trust

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Willie is

  • Relationship and trust can be vital with them, sometimes more than anything else.
  • Will you ever get a clear answer from Willie

  • They are unlikely to say no directly, you have to make that decision yourself.

Insights For Deal Planning

    How fast (or slow) will Willie move?

  • They are not the fastest decision makers, their friendly approach can give false positive signals.
  • Can Willie take some risk or not?

  • They may take certain risks that they deem unlikely of personal repercussions.

You And Willie

Personality Compatibility


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