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Cayleigh McCarthy has a diverse work experience that spans multiple companies and roles. Cayleigh is currently the Director of Customer Success for the Global Field Team at Discuss, a position they started in February 2023. Prior to that, Cayleigh worked at Criteo as a Sales Enablement and Learning Partner for the Americas from July 2022 to February 2023.

Cayleigh's longest tenure was at HubSpot, where they held various roles from July 2018 to July 2022. Cayleigh started as a Customer Success Manager, where they managed an average install base of $3.5M ARR with 104% retention. Cayleigh also developed and implemented a peer learning program to improve retention and growth strategies for a team of 45 Customer Success Managers. Cayleigh was selected to be part of a CSM/Sales alignment working group and served as a mentor for new hires. Additionally, they created and delivered monthly risk mitigation and forecasting bootcamps for new CSM onboarding.

Before joining HubSpot, Cayleigh worked at Academic Studies Abroad (ASA) from June 2016 to July 2018. Cayleigh held the positions of Senior Programs Advisor and Programs Advisor, where they managed study abroad programs, coordinated program requirements, recruited students, and participated in program development and negotiation.

Throughout their career, Cayleigh has demonstrated expertise in customer success, sales enablement, learning and development, program management, and negotiation.

Cayleigh McCarthy holds a BSBA in Marketing and a BA in Graphic Design from Stonehill College. Cayleigh obtained various certifications from HubSpot Academy, including Inbound Marketing, Inbound Sales, Content Marketing, Inbound, HubSpot Marketing Software, and HubSpot Sales Software.