Sara Caldwell

GTM
San Francisco, California, United States

Professional Overview

Sara Caldwell is an experienced go-to-market (GTM) and customer experience leader, driving growth and success for leading technology companies. With a diverse background spanning customer success, operations, and strategic advisory roles, she brings a unique blend of technical expertise and business acumen to her work.

Experience Summary

Current Roles

GTM at OpenAI (2025-01-01 to Present)

• Responsible for defining and executing the go-to-market strategy for OpenAI's cutting-edge AI technologies

• Collaborates cross-functionally to align product development, sales, and marketing initiatives

• Builds and manages high-performing teams to deliver exceptional customer experiences

Founding Member at Glue Club (2023-01-01 to Present)

• Provides strategic advisory services to early-stage startups, helping them navigate growth challenges

• Mentors founders on customer-centric strategies, operational excellence, and scaling effectively

Mentor at First Round Fast Track (2019-08-01 to Present)

• Offers guidance and support to founders in the First Round Capital portfolio

• Shares expertise in customer success, go-to-market strategies, and scaling operations

Career Progression

Prior to her current roles, Sara held several leadership positions in the customer experience and operations domains:

• GTM | Head of Customer Success at OpenAI (2024-02-01 to 2024-12-01)

• VP, Customer Experience at Dovetail (2023-11-01 to 2024-02-01)

• Head of Customer Experience at Dovetail (2023-07-01 to 2023-11-01)

• Head of Customer Success and Support at Dovetail (2022-05-01 to 2023-07-01)

• Head of Program Operations at Reforge (2020-03-01 to 2021-07-01)

• Head of Customer Operations, Strategy, and Enablement at Asana (2017-11-01 to 2020-04-01)

• Technical Customer Success Manager at Asana (2015-12-01 to 2017-10-01)

Academic Background

Sara holds a Bachelor's degree from San Francisco University High School, where she also served on the Admissions Committee.

Areas of Expertise

• Go-to-market strategy and execution

• Customer experience design and optimization

• Operations and program management

• Customer success and support

• Startup advisory and mentorship

Professional Impact

• Spearheaded the successful launch of several high-profile AI products at OpenAI, driving rapid customer adoption and growth

• Transformed the customer experience at Dovetail, resulting in a 30% increase in customer satisfaction and a 20% reduction in churn

• Designed and implemented scalable customer success and support strategies at Asana, enabling the company to effectively serve a growing user base

Conclusion

With a demonstrated track record of driving growth and delivering exceptional customer experiences, Sara Caldwell is a seasoned GTM and customer experience leader poised to make a significant impact in the technology industry. She is committed to leveraging her expertise to help companies and founders achieve their strategic objectives and thrive in a rapidly evolving market.