Paul Oliver

Commander
DISC Type : D

Chief Revenue Officer (CRO) at Caregility

Annapolis, Maryland, United States

Overview

Paul Oliver is a seasoned sales leader with over 25 years of experience, currently serving in a senior leadership capacity within the healthcare industry. He was previously the Chief Revenue Officer at Caregility and held director-level roles at Cisco, specializing in building high-performing teams that apply technology to clinical and enterprise workflows. He holds a first-class honors BSc from Staffordshire University.

His professional focus extends to improving healthcare delivery through technology. He cares about fostering teamwork to streamline patient care and is passionate about expanding virtual services to underserved and rural communities. People who have worked with him describe him as pragmatic, tactful, ethical, and a strong leader.

As CRO at Caregility, he led the revenue organization to grow the companys fiscal year 2024 revenue by over 30%.

Personality Overview

Very Quick

Impact-Driven

Decisive

They are not always relationship oriented.  More than the product, they care about the impact of the product. They like to move fast and expect the same from others.

Topics They Care About

Healthcare Technology
His career focus is on applying technology to solve challenges in healthcare, from his time at Cisco's Healthcare Practice to his executive role at Caregility.
Virtual Care
As CRO of Caregility, he was dedicated to expanding telehealth operations and supporting new use cases across the continuum of care for major health systems.
Building Sales Teams
His personal philosophy is centered on a specific equation for building effective sales teams: combining talent, technology, and collaboration to drive transformation.

Media Appearances

Caregility Appoints Paul Oliver as Chief Revenue Officer Amid Rapid Growth in Virtual Care Adoption. Featured in Business Wire

See Now

Work History

3-2023 - 2-2026
Chief Revenue Officer (CRO) at Caregility
11-2017 - 3-2023
Operations Director - Global Enterprise Collaboration Platform Team at Cisco
8-2015 - 11-2017
Collaboration Platform Team Leader at Cisco
8-2014 - 8-2015
Workforce Experience Practice Lead at Cisco
12-2009 - 7-2014
Regional Manager at Cisco

Education

BSc - 1st Class Hons from University of Staffordshire

More Information

Social Presence :

Prographics :

Exp : 35 Location : Annapolis, Maryland, United States Job Level : N/A Designation : Chief Revenue Officer (CRO) at Caregility
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Insights For Selling To Paul

During A Call Or A Meeting

DO's

  • Help them weigh the risks by sharing objective proof points without becoming too analytical
  • Make sure that you circle back fast on any action items, it wins their trust
  • Objectively showcase the impact that your product creates

DONT's

  • Do not hesitate from asking counter questions, just avoid challenging their authority
  • Don’t be in a rush to invite them for a social meet and greet
  • Avoid being a storyteller and don’t try to oversell

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Paul is

  • Conviction around the impact matters the most to them, followed by a sense of achievement and ROI.
  • Will you ever get a clear answer from Paul

  • If they decide not to use your product, they will say no clearly.

Insights For Deal Planning

    How fast (or slow) will Paul move?

  • They can reach decisions fairly quickly if they are convinced.
  • Can Paul take some risk or not?

  • They don’t mind risks but can be quite binary about them.

You And Paul

Personality Compatibility


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