Grayden Holubar

Observer
DISC Type : ic

Head of People at Artsy

Detroit Metropolitan Area, United States

Overview

Grayden Holubar is the Head of People at Artsy, where he leads all People functions, including recruitment, talent management, and employee experience. A Princeton University graduate, he is described by colleagues as a strategic and empathetic partner who excels at translating complexity into action. People who have worked with him describe him as committed, strategic, and empathetic.

Outside of work, Grayden has a keen interest in design and architecture, enjoys baking, and has trained professionally in ballet and modern dance. He lives in Manhattan with his partner, and they enjoy making their home a colorful and comfortable sanctuary, with a terrace for entertaining friends and relaxing.

He won a prize at Princeton for his senior thesis on the design of contemporary corporate campuses in Silicon Valley.

Personality Overview

Example Seeker

Value Driven

Assertive

They are generally strong communicators and are not easy 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

Talent Management
Oversees the entire employee lifecycle at Artsy, with a focus on talent development, performance, and compensation management to build a world-class team.
Mentoring Diverse Talent
Volunteers as a mentor for Factor, an organization that connects top talent from diverse backgrounds with careers in NYC startups.
Home Design
Featured in an Apartment Therapy tour of his 650-square-foot NYC apartment, showcasing a bold, colorful style and clever solutions for small-space living.

Media Appearances

Grayden has no verified media appearances

Work History

7-2025
Head of People at Artsy
10-2024 - 7-2025
Director of People Operations at Artsy
7-2021 - 10-2024
Director of People Business Partnership at Artsy
7-2019 - 6-2021
Associate Director of People Operations at Artsy
9-2016 - 7-2019
People Strategy Lead at Artsy

Education

2009 - 2013
Bachelor of Arts (B.A.) from Princeton University
2002 - 2009
High school diploma from Crystal Springs Uplands School

More Information

Social Presence :

Prographics :

Exp : 13 Location : Detroit Metropolitan Area, United States Job Level : Mid-senior Designation : Head of People at Artsy
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Insights For Selling To Grayden

During A Call Or A Meeting

DO's

  • Invite them for a social do but don’t rely solely on the relationship
  • Persuade objectively how your product will help them achieve their goals
  • Build rapport, it will come handy to handle hard questions later

DONT's

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

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Grayden is

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

  • They are practical yet friendly, don’t expect a clear no very often.

Insights For Deal Planning

    How fast (or slow) will Grayden move?

  • They like to analyze well and then make their decisions.
  • Can Grayden take some risk or not?

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

You And Grayden

Personality Compatibility


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