10 CVS Caremark operations leaders
Senior Vice President, Caremark Operations, Executive Director, CVS/ Caremark Member Operations and Lead Director Client Operations are among the current roles held by these CVS Caremark operations leaders. A reader can learn how operations leaders work at CVS Caremark from people who have held the role.
Professionals to explore
Brian Allanbrook, PharmD
LinkedInExperience: Lead Director - Caremark Data Exchange Operations · CVS Health
Brian Allanbrook, PharmD has been Lead Director - Caremark Data Exchange Operations at CVS Health since June 2026 and was Lead Director - Caremark Member Operations Strategy there from 2025 to 2026. Brian Allanbrook, PharmD was Senior Manager - PBM Operations, Strategy and Product Owner at CVS Health from 2021 to 2025 and Manager - Retail Pharmacy Operations from 2018 to 2021.
David Hummel
LinkedInExperience: Vice President – Enterprise Operations, CVS Caremark · CVS Health
David Hummel is a former Vice President – Enterprise Operations, CVS Caremark at CVS Health, a role held from 2019 to 2024, and was Senior Director – Operational Excellence, CVS Caremark there from 2017 to 2018. David Hummel has been Fractional COO at Eyesnorth LLC since 2025 and was Vice President – Technology Strategy & Operations at ReedGroup in 2017.
Gary Smith
LinkedInExperience: Lead Director Member Experience & Client Operations · CVS Health
Gary Smith is a former Lead Director Member Experience & Client Operations at CVS Health, a role held from 2000 to 2022 that the profile headline lists as retired and with CVS Caremark. Gary Smith was also Sr Manager of Operations at CVS Caremark from 1994 to 2000, based in Dallas, Texas.
Jason Proulx
LinkedInExperience: Senior Director - Enrollment Operations · CVS/Caremark
Jason Proulx is a former Senior Director - Enrollment Operations at CVS/Caremark, a role held from October 2018 to October 2019. Jason Proulx has been Vice President Specialty Pharmacy Operations at CVS Specialty since August 2022, was AVP - Specialty Pharmacy Operations there in 2022 and was Managing Director - PBM Support at CVS Health from 2013 to 2018.
Kali Wooldridge
LinkedInExperience: Lead Director Client Operations · CVS Caremark
Kali Wooldridge has been Lead Director Client Operations at CVS Caremark since November 2025, based in Lafayette, Indiana. Kali Wooldridge was Lead Director Member Experience at CVS Caremark from 2024 to 2025, Operations Manager there from 2021 to 2024 and Operations Supervisor from 2019 to 2021.
Kevin Brabson
LinkedInExperience: Executive Director, CVS/ Caremark Member Operations · CVS Health
Kevin Brabson has been Executive Director, CVS/ Caremark Member Operations at CVS Health since August 2023, based in Knoxville, Tennessee. Kevin Brabson was Director, Customer Care, Knoxville, TN, Nashville, TN, Orlando FL and Cary, NC (Southeast, US) at CVS Health from 2011 to 2023 and Senior Manager, Call Center Operations at Jewelry Television from 2006 to 2011.
Michael H. Taday
LinkedInExperience: Senior Vice President, Caremark Operations · CVS Health
Michael H. Taday has been Senior Vice President, Caremark Operations at CVS Health since April 2025 and was Senior Vice President, Aetna Operations there from 2023 to 2025. Michael H. Taday was Senior Vice President, Prescription Home Delivery, Retail Pharmacy, and OTC at Humana from 2021 to 2023 and Vice President, Pharmacy Clinical Strategies and Operations at Humana from 2019 to 2021.
Scott Jackson
LinkedInExperience: AVP, Caremark Member Ops-Government Programs · CVS Health
Scott Jackson has been AVP, Caremark Member Ops-Government Programs at CVS Health since April 2023, based in Woonsocket, Rhode Island. Scott Jackson was Executive Director, Customer Care Quality at CVS Health from 2022 to 2023, Sr. Director, Medicare Quality & Testing from 2021 to 2022 and Director, Medicare D CD&A (Quality/Audit) from 2017 to 2021.
Trenten Derrick
LinkedInExperience: Lead Director, Caremark Member Operations (Eastern Region) · CVS Health
Trenten Derrick has been Lead Director, Caremark Member Operations (Eastern Region) at CVS Health since November 2023, and the profile headline describes PBM and omnichannel contact center operations leadership. Trenten Derrick was Director, Member Experience | Customer Care Ops at CVS Health from 2022 to 2023 and Senior Manager, Program & Project Mgmt PBM from 2021 to 2022.
Trish Ponczkowski
LinkedInExperience: Director of Operations · CVS Caremark
Trish Ponczkowski has been Director of Operations at CVS Caremark since January 2008, based in Northbrook, Illinois, and the profile headline reads Director at CVS/Caremark. Trish Ponczkowski also lists a current Director role at CVS Health with a start date of November 1993.
Choose the right perspective
Match the person's operations area, such as member operations, client operations or data exchange, to the decision you face. Check when each role started or ended to judge how recent the experience is.
Questions to take into the conversation
- 01What did a typical week look like in your operations role, and which measures did you watch most closely?
- 02How did you work with client, clinical or technology teams when an operational issue affected members?
- 03What did you learn about scaling an operations team while keeping service quality steady?
Reaching CVS Caremark operations leaders
How can I contact one of these CVS Caremark operations leaders?
Pick one of the 10 people on this page and choose "Book a paid call", or describe your project to find others. You offer a fee for a 15-minute call or a written answer, Instant Expert finds the person's work email and sends the invitation, and they decide whether to accept. The list covers 3 companies: CVS Health, CVS/Caremark and CVS Caremark, based on profile data retrieved on October 23, 2026. Being listed here doesn't mean someone has agreed to take calls.
How much does it cost to reach CVS Caremark operations leaders?
You choose the offer, starting at $5 per person. The offer is what the person receives, and Instant Expert's fee is added on top, so a $100 offer costs you $125. The fee is 20% of what you pay. You're charged only when the person books the call or sends the answer.
What if they don't reply?
You pay nothing. Instant Expert sends follow-up reminders, and if the person hasn't booked or answered within 7 days, the request expires and any hold on your card is released. You can invite several of the 10 people on this list at once and cap your total spend, so you pay only for the ones who accept.
Can an AI agent ask one of these CVS Caremark operations leaders a question?
Yes. An agent with a USDC wallet on Base can ask one question without an Instant Expert account. It names the person, for example by the LinkedIn URL on this page, and pays per ask over x402 (HTTP 402). The person answers in writing or by voice note, and if nobody answers within 7 days, the payment goes back to the wallet automatically. Claude and ChatGPT can do the same through the Instant Expert connector: setup is at /docs/mcp for Claude and /docs/chatgpt for ChatGPT. x402 docs
About this directory
This is a professional research starting point based on business profile data retrieved on . Titles and companies reflect that source snapshot; roles marked former had ended by then. Check the linked profiles for current details. Inclusion does not imply Instant Expert membership or availability.
Request a correction or removal