Your Job Search, But Toastier: Meet Rollie
Job searching is exhausting, confusing, and often lonely. That’s exactly why we built Rollie to support you like a smart career assistant in your corner.
In this hands-on workshop, we’ll walk you through Rollie, Toast’s AI career assistant designed specifically to help women in tech think through decisions, get unstuck faster, and navigate both their job search and the Toast community with more clarity and confidence.
You’ll learn how to use Rollie to:
💗 Talk through what roles actually fit your experience and goals
💗 Get guidance on how to tailor your resume for specific jobs
💗 Workshop outreach messages to recruiters and hiring managers
💗 Practice interview questions and refine your answers
Explore negotiation approaches and scripts so you can advocate for yourself
Rollie doesn’t apply to jobs or make decisions for you. Instead, it helps you think, prepare, and move forward with better information and support.
And Rollie’s help goes beyond applications.
We’ll also show you how Rollie can guide you to the right support inside the Toast community, including:
🍞 Suggesting relevant career coaches based on what you’re working on
🍞 Pointing you to the right community manager or city lead for local support
🍞 Recommending past workshop recordings that match your current challenges
🍞 Helping you discover programs and resources you might not know exist
You’ll also hear how Rollie was built using real insights from Toast members and recruiters who work with women in tech every day, so you understand not just what it does, but why it supports your career in a more thoughtful, human-centered way than generic AI tools.
This session is part demo, part guided walkthrough, and part open Q&A. You’ll leave knowing how to use Rollie as a behind-the-scenes career co-pilot, someone to brainstorm with, prepare with, and navigate your next steps alongside.
Bring a job you’re interested in if you have one — you’ll be able to follow along live.
🍞 Help us build a more equitable tech industry
Before attending this event, we ask all guests to complete our Gender Equity Survey. The survey captures real lived experiences in tech and helps shape Toast programs, research, and advocacy. Responses are anonymous, and patterns matter more than individual stories.
Complete the survey here: Toast Gender Equity Report
If you’ve filled this out for a previous Toast event, you don’t need to do it again.
This event is for any women or non-binary person in tech! Sometimes we run member-only events. Curious about becoming a Toast member? Learn more here