Chris Calkin

Inspirer
DISC Type : id

Head of Revenue at PointFive

Denver, Colorado, United States

Overview

Chris Calkin is the Head of Revenue at PointFive, where he leads global enterprise adoption and revenue growth. His career includes senior sales leadership roles at Census, Moov Financial, and CircleCI. Educated at the University of Oxfords Saïd Business School and the University of Washington, he is described by colleagues as a "consummate professional" and "straightforward. "

Outside of his professional life, Chris has a strong interest in business-themed television shows. He has a curated and ranked list of his favorites, including popular dramas and comedies like "Silicon Valley, " "Mad Men, " and "Halt and Catch Fire, " appreciating them for their realistic portrayal of the business world.

Unique fact: Chris has a ranked list of his top nine favorite business dramas and comedies, which he has shared publicly.

Personality Overview

Generous

Fast Adopter

Decisive

They measure a product on its merit but can be influenced by strong testimonials.  They usually prefer to drive the conversation. They respond well to objective pitches but also attach some value to relationships.

Topics They Care About

Cloud Cost Optimization
As Head of Revenue at PointFive, he focuses on helping customers achieve measurable ROI by turning insights on cloud and AI costs into actionable savings.
Modern Data Stack
His time as CRO at Census gave him direct insight into the challenges of data infrastructure and the steep costs associated with platforms like Snowflake and Databricks at scale.
Sales Leadership
He has spoken about his people-first leadership approach and believes in enabling sales teams with deep technical knowledge to be more effective.

Media Appearances

Chris has no verified media appearances

Work History

1-2026
Head of Revenue at PointFive
10-2022 - 12-2025
Chief Revenue Officer (CRO) at Census - a Fivetran company
11-2021 - 8-2022
Vice President of Sales at Moov Financial
2-2020 - 11-2021
Vice President Of Worldwide Sales at CircleCI
8-2018 - 2-2020
Global Director of Sales at CircleCI

Education

Master of Business Administration (MBA) from Saïd Business School, University of Oxford
Bachelor of Arts from UW Foster School of Business

More Information

Social Presence :

Prographics :

Exp : 14 Location : Denver, Colorado, United States Job Level : Mid-senior Designation : Head of Revenue at PointFive
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Insights For Selling To Chris

During A Call Or A Meeting

DO's

  • Focus on the big picture and the strategic value of your product
  • Acknowledge their status and position during the conversation
  • Keep your pitch focused on the impact but insert some anecdotes into it

DONT's

  • Avoid focusing only on the product or its ROI, keep building trust subtly
  • Don’t keep repeating the same information, it could make them impatient
  • Don’t be too verbose or overly friendly; a little bit, however, is fine

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Chris is

  • Belief in the value of the product, relationship and a sense of accomplishment matter the most.
  • Will you ever get a clear answer from Chris

  • They are not shy of saying no if they do not develop trust in your product.

Insights For Deal Planning

    How fast (or slow) will Chris move?

  • They can take fast decisions if they develop conviction in the product and find you trustworthy.
  • Can Chris take some risk or not?

  • They have the capability of taking risky decisions if necessary.

You And Chris

Personality Compatibility


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