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10 Chewy legal leaders
These ten current and former Chewy legal leaders hold or held deputy general counsel, associate and assistant general counsel and legal director roles at Chewy, covering compliance, employment law, pharmacy, privacy, commercial agreements and corporate matters. A reader can learn how legal leaders work at Chewy from people who have held the role.
Professionals to explore
01—10Angela Cummings
LinkedInExperience: Director, Associate General Counsel - Employment · Chewy
Director, Associate General Counsel - Employment at Chewy since August 2021, based in Charlotte, with more than 25 years advising companies on employment law, per the profile. Angela Cummings was Office Managing Partner of the Charlotte office at FordHarrison LLP (2016–2021) and a Shareholder at Littler (2003–2016).
Christine Drobot
LinkedInExperience: Associate General Counsel · Chewy
Associate General Counsel at Chewy since April 2026 and Senior Corporate Counsel at Chewy (2024–2026), based in Fort Lauderdale. Christine Drobot was General Counsel, Global Commercial & TechOps (2021–2024), Senior Director, Associate General Counsel (2017–2021) and Assistant General Counsel (2014–2017) at Ferring Pharmaceuticals.
Deirdre Boling-Lewis
LinkedInExperience: Former Director, Assistant General Counsel, Pharmacy · Chewy
Former Director, Assistant General Counsel, Pharmacy at Chewy (March 2020 to June 2024) in Dania Beach, Florida, and now General Counsel at Harvest Medical Systems. Deirdre Boling-Lewis was General Counsel at Sincerus Pharmaceuticals (2017–2020) and Executive Director, National Pharmacy Compliance Office at Kaiser Permanente (2015–2016).
Elaine Keyser
LinkedInExperience: VP, Deputy General Counsel, Chief Compliance Officer · Chewy
VP, Deputy General Counsel, Chief Compliance Officer at Chewy since May 2025, based in Miami. Elaine Keyser was VP, Deputy General Counsel (2022–2025) and Senior Director, Associate General Counsel - Employment Law (2019–2022) at Chewy, and Shareholder (2015–2019) and Associate Attorney (2007–2015) at Littler.
Heidi Oertle
LinkedInExperience: VP, Deputy General Counsel · Chewy
VP, Deputy General Counsel at Chewy since January 2026, based in Seattle. Heidi Oertle was Associate General Counsel for Amazon Pharmacy (2023–2025), for AWS Sales & Marketing (2022–2023) and for Private Brands and Consumables (2021–2022) at Amazon, and Senior Corporate Counsel, Private Brands at Amazon (2017–2021).
Jane Yang
LinkedInExperience: Senior Legal Director · Chewy
Senior Legal Director at Chewy since January 2026, based in the Seattle area. Jane Yang was Director & Associate General Counsel, Multichannel Commerce & Fulfillment at Amazon (2023–2025), Senior Corporate Counsel for Buy with Prime (2020–2023) and International Expansion (2017–2020) at Amazon, and Senior Legal Counsel at Amazon China (2013–2017).
Jennifer Mae Hoberman
LinkedInExperience: Former Associate General Counsel & Vice President of Business Development · Chewy.com
Former Associate General Counsel & Vice President of Business Development at Chewy.com (2015–2018) and General Counsel at Chewy.com (2013–2014). Jennifer Mae Hoberman earlier ran a law and management consulting practice as Managing Partner (2008–2013) and was Vice President of Development at Watt Development, Inc. (2001–2007).
Martin Michalski
LinkedInExperience: Director & Associate General Counsel · Chewy
Director & Associate General Counsel at Chewy since August 2024, based in Fort Lauderdale, with a headline naming enterprise risk, commercial strategy and operational scale. Martin Michalski was Senior Corporate Counsel (2024) and Corporate Counsel (2021–2024) at Amazon, and a Senior Associate at Sidley Austin LLP (2016–2021).
Shahab Ahmed
LinkedInExperience: Former General Counsel (e-commerce business unit) & Chief Privacy Officer (Associate General Counsel Group) · Chewy
Former General Counsel (e-commerce business unit) & Chief Privacy Officer (Associate General Counsel Group) at Chewy (August 2021 to June 2024), now General Counsel and Chief Privacy Officer at The Binary Holdings. Shahab Ahmed was General Counsel of the Hala Division, Head of Legal and Group Head of Privacy at Etihad (2016–2021).
Tony Bernard
LinkedInExperience: Associate General Counsel · Chewy
Associate General Counsel at Chewy since August 2024, based in the Boston area. Tony Bernard was Corporate Counsel at Dyne Therapeutics (2023–2024), Counsel (2019–2023) and Associate (2015–2019) at Ropes & Gray LLP, and an Associate at Paul, Weiss, Rifkind, Wharton & Garrison LLP (2010–2015).
Choose the right perspective
Pick an employment or compliance lawyer for questions about workforce and regulatory programs, a pharmacy lawyer for questions about pet pharmacy rules, and a commercial or privacy lawyer for questions about ecommerce agreements and customer data. Note who is current and who has moved on.
Questions to take into the conversation
- 01How does an online retailer structure legal support for a pet pharmacy business?
- 02What does an in-house employment law team handle at a company with large fulfillment and customer service operations?
- 03How do ecommerce legal teams manage privacy obligations for customer data?
Reaching Chewy legal leaders
How can I contact one of these Chewy legal 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 2 companies: Chewy and Chewy.com, based on profile data retrieved on October 15, 2026. Being listed here doesn't mean someone has agreed to take calls.
How much does it cost to reach Chewy legal 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 Chewy legal 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. 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.
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