Ali Shepherd

Inquirer
DISC Type : cd

Head of People & Talent at Pencil ✏️

United Kingdom

Overview

Ali Shepherd is the Global Head of People & Talent at Pencil, bringing extensive experience from scaling tech companies like Omnipresent and Elliptic. She holds a Bachelors in Economics from The University of Sheffield and a CIPD Diploma in HR Management. Colleagues often describe her as capable, personable, and tenacious, with great integrity.

While at Omnipresent, she designed and led a comprehensive course on international hiring, sharing her expertise with other professionals.

Personality Overview

ROI Conscious

Demanding

Hard To Convince

They respond well to confident salespeople.  They focus on objectivity in a pitch and pay little attention to bells and whistles. They don’t always try to control the conversation but neither do they like yielding it fully.

Topics They Care About

Generative AI in HR
Expressed excitement about the potential of Generative AI in the talent industry, particularly for finding candidates and creating new opportunities.
Global Talent Strategy
Previously led People & Talent teams across more than 50 countries and developed a course to certify professionals in international hiring.
Scaling Company Culture
Has a background in leading people operations for scaling B2B SaaS and software consultancies, with a focus on talent management and development.

Media Appearances

Ali has no verified media appearances

Work History

3-2025
Head of People & Talent at Pencil ✏️
10-2021 - 11-2024
Global Head of People & Talent at Omnipresent
2-2021 - 10-2021
Senior Talent Partner at Elliptic
10-2018 - 12-2020
Head of Talent at BlackCat Technology Solutions Ltd
6-2010 - 9-2018
Senior Account Director at Monarch Recruitment Ltd

Education

2020 - 2021
Level 5 from Avado
2007 - 2010
Bachelor's Degree from The University of Sheffield

More Information

Social Presence :

Prographics :

Exp : 14 Location : United Kingdom Job Level : Mid-senior Designation : Head of People & Talent at Pencil ✏️
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Insights For Selling To Ali

During A Call Or A Meeting

DO's

  • Make sure that they have the necessary authority, they could present false stature sometimes
  • Refer to testimonials from others in similar positions
  • Stress on the business value that your product offers

DONT's

  • Refrain from asking too many questions
  • Do not give up if they are not convinced, try again with a different approach
  • Don’t try to be an alpha salesperson, give them equal space

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Ali is

  • Confidence in the product plays an important role, followed by powerful testimonials.
  • Will you ever get a clear answer from Ali

  • They might hesitate a little, but they will say no if they are not convinced.

Insights For Deal Planning

    How fast (or slow) will Ali move?

  • They are neither the fastest decision makers nor the slowest.
  • Can Ali take some risk or not?

  • Once they have analyzed the pros and cons, they can take some risks.

You And Ali

Personality Compatibility


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