Gemma Cipriani-Espineira

Head of Digital Success

Gemma is a digital customer success executive with over a decade of experience scaling post-sales organizations in high-growth SaaS. She currently leads Digital Success at Atlassian and previously served as VP of Digital CS & Experience at Twilio, where she built digital-led CS programs and improved experiences for long-tail customers. As Chief Customer Officer at Chili Piper, Gemma led the company through 7x ARR growth and built a CS organization that consistently delivered >90% GRR and >120% NRR. She is also the founder of CS Angel, a syndicate investing in technology that powers customer-led growth.

Gemma is a digital customer success executive with over a decade of experience scaling post-sales organizations in high-growth SaaS. She currently leads Digital Success at Atlassian and previously served as VP of Digital CS & Experience at Twilio, where she built digital-led CS programs and improved experiences for long-tail customers. As Chief Customer Officer at Chili Piper, Gemma led the company through 7x ARR growth and built a CS organization that consistently delivered >90% GRR and >120% NRR. She is also the founder of CS Angel, a syndicate investing in technology that powers customer-led growth.

Gemma is a digital customer success executive with over a decade of experience scaling post-sales organizations in high-growth SaaS. She currently leads Digital Success at Atlassian and previously served as VP of Digital CS & Experience at Twilio, where she built digital-led CS programs and improved experiences for long-tail customers. As Chief Customer Officer at Chili Piper, Gemma led the company through 7x ARR growth and built a CS organization that consistently delivered >90% GRR and >120% NRR. She is also the founder of CS Angel, a syndicate investing in technology that powers customer-led growth.

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