Tobias Cummins

Observer
DISC Type : ic

Chief Operations Officer at Pencil

Amsterdam, North Holland, Netherlands

Overview

Tobias Cummins is the Chief Operations Officer at Pencil, leveraging extensive experience from senior leadership roles at DEPT®, including Head of DACH. He is also a Board Member at GovTech Barbados Ltd. and holds a BA from Tilburg University.

Tobias has strong connections to Barbados, having attended Harrison College and now serving on the board of its government technology initiative. His international experience is further highlighted by his university studies in the Netherlands.

He was a recipient of the prestigious and highly competitive Huygens Scholarship, which supports talented international students.

Personality Overview

Value Driven

Assertive

Example Seeker

They are generally good communicators and can be hard to convince.  They can sound friendly and charming but can quickly change gears to become inquisitive and probing. They ask a lot of questions and rely heavily on information and collaterals.

Topics They Care About

Generative AI Marketing
Leads a company recognized by Gartner as a 'Cool Vendor' for AI in Marketing and is focused on creating high-quality, 'airworthy' brand work using GenAI.
Enterprise Data Security
He recently announced Pencil's SOC 2 Type II attestation, emphasizing the company's commitment to the 'gold standard' for data security, reliability, and trust.
Public Sector Innovation
As a board member for GovTech Barbados, he is involved in modernizing public sector services and promoting citizen engagement through technology.

Media Appearances

Tobias has no verified media appearances

Work History

2-2025
Chief Operations Officer at Pencil
7-2025
Board Member at GovTech Barbados Ltd.
4-2024 - 12-2024
Head of DACH at DEPT®
10-2022 - 12-2024
SVP, Clients at DEPT®
3-2023 - 4-2024
Managing Director at DEPT®

Education

BA from Tilburg University
Education details unavailable from Harrison College Barbados

More Information

Social Presence :

Prographics :

Exp : 10 Location : Amsterdam, North Holland, Netherlands Job Level : Leadership Designation : Chief Operations Officer at Pencil
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Insights For Selling To Tobias

During A Call Or A Meeting

DO's

  • Invite them for a social do but don’t rely solely on the relationship
  • Focus on immediate action-items rather than the larger goals
  • Help them understand the risk aspect fully while inspiring confidence

DONT's

  • Don’t try to rush them into a decision, provide all necessary information first
  • Avoid making offhand commitments
  • Don’t brush off any concerns, take all questions seriously

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Tobias is

  • Proven value, strong testimonials are important for them, rapport can impact decisions a little.
  • Will you ever get a clear answer from Tobias

  • They are practical and friendly, don't expect a clear-cut response often.

Insights For Deal Planning

    How fast (or slow) will Tobias move?

  • They like to perform full analysis and can take time to make any decision.
  • Can Tobias take some risk or not?

  • They weigh all decisions systematically and are unlikely to take many risks.

You And Tobias

Personality Compatibility


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