Nova Chat: EA to Chief of Staff: Stay, Grow, or Pivot?
Whether you're an EA considering the Chief of Staff path, a CoS looking to refine your role, or an executive wanting to better leverage these positions, this conversation is for you!
Join our amazing panel of strategic leaders, Maggie Olson, Kristina Willis, and Becky Kaapuni, for an open, honest discussion about career growth in executive back office roles. Should you stay and deepen your expertise, grow in your current role, or pivot into something new?
What you’ll take away from this session:
✅ Understanding the real differences between an EA and a CoS—beyond just the title.
✅ Insights into why some EAs stay, why some transition, and what that pivot can look like.
✅ Practical advice on navigating career growth and advocating for yourself.
✅ The power of authenticity: how to thrive in the role that fits you best.
✅ How EAs and Chiefs of Staff create an unstoppable partnership in a CEO’s back office.
You’ll hear perspectives from:
💡 Becky Kaapuni, a career EA who has intentionally stayed in the role and mastered it.
💡 Kristina Willis, a former EA who transitioned into a Chief of Staff role.
💡 Maggie Olson, a seasoned Chief of Staff and entrepreneur who has deep experience in the role.
This live panel discussion, moderated by Nova Founder Maggie Olson, will wrap with Q&A, giving you the chance to ask your own career questions.
Who should attend?
✔ Executive Assistants considering their next career move
✔ Chiefs of Staff refining their role and responsibilities
✔ Executives looking to maximize their support team
Can’t make it live? Register anyway, and we’ll send you the recording afterward!
This is going to be a great discussion you won't want to miss!
This Nova Chat is Presented by Offsite
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Becky Kaapuni's Bio
A fierce advocate for Executive Assistants and leader of the EA Revolution, Becky has spent over two decades masterfully navigating the C-suite at powerhouse companies including Salesforce, Twitter, and Goldman Sachs. Her mission: to unlock the vast untapped potential within every EA, empowering them to rise up, claim their worth, and become the CEOs of their own lives.
Through the EA Social Club and her book "The Unstoppable EA," she's transforming how EAs see themselves. With her dynamic community, mentoring, and advocacy, Becky ignites Executive Assistants to reshape not just their own futures, but the entire profession.
Kristina Willis' Bio
Kristina is a versatile leadership partner who has worked across various roles and industries, and now serves as Head of Customer Success at ShareCal, a software company revolutionizing the art of time management and scheduling for Assistants.
Prior to joining ShareCal, Kristina spent the last four years at a company by the name of We Are Rosie where she successfully transitioned from EA to Chief of Staff.
With experience supporting Founders and C-suite Executives, Kristina is an advocate and mentor of the Admin profession with an overarching message that there’s no such thing as being “just” an EA.
She is also the 2022 Award Recipient of The Adweek 50: Honoring Media, Marketing, and Tech's Indispensable Behind-the-Scenes Stars.
Maggie Olson's Bio
Maggie Olson is the Founder of Nova Chief of Staff, the premier destination for Chief of Staff education and development. As the first Chief of Staff to a president at a Fortune 40 company — who led a multibillion-dollar business with 5,000+ employees — Maggie built the president’s Chief of Staff model from the ground up. Maggie has 20 years’ experience leading large teams and has spent her career focused on both customer and employee experience at companies including T-Mobile, Nordstrom, and Starbucks.
In addition to operating the Nova Chief of Staff Certification course, Maggie is a fractional Chief of Staff focused on helping mission-driven, for-profit startup founders scale their businesses quickly. In her spare time, Maggie loves spending time outside with her husband, their dog, and their 2-year-old, Max!