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Anna Wolfston has had a varied work experience since 2011. Anna began their career as a Telemarketer at Allstate in 2011, then volunteered with Foundation Cristosal in 2015. In 2016, they worked as a Designer for Similarly Different. In 2017, they were a Social Media Marketing Intern for ALBA Study Abroad in Barcelona. In 2018, they worked as a Barista at Starbucks and a Volunteer Tutor at Action Tutoring. In 2019, they were a Customer Success Specialist at Bark.com. Anna began working at Second Nature in 2020 as a Customer Support Specialist and Senior Knowledge Lead, and in 2023 they became a Customer Advocate at Mighty Networks.

Anna Wolfston holds a Bachelor of Science in Community Development from Portland State University. Anna has also obtained three certifications from LinkedIn; Social Media Marketing: ROI (November 2019), Winning Back a Lost Customer (November 2019), and Managing Your Career as an Introvert (October 2019).