Executive Assistant, Measure Well — Video Challenge
Description This challenge is entirely video-based. You are asked to respond on camera to scenarios you might face in this role. There's no right script to memorize; we want to see how you think through the situation in real time. Measure…
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What You'll Be Doing
Description
This challenge is entirely video-based. You are asked to respond on camera to scenarios you might face in this role. There's no right script to memorize; we want to see how you think through the situation in real time.
Measure Well is an early-stage data, AI, and technology social impact venture that helps place-based organizations advance education and workforce development. Their Executive Assistant is a force multiplier for the CEO — protecting focus and time, building a reliable rhythm of business, and bringing calm and discretion to a complex stakeholder map spanning funders, an Advisory Council, and a fast-moving leadership team.
Constraints to Consider
- You are supporting a CEO at a small, fast-moving nonprofit-adjacent organization — you won't have a large admin team behind you, and most decisions are yours to make in the moment.
- The organization operates in Eastern Standard Time and works with a distributed set of stakeholders (funders, an Advisory Council, leadership team, vendors).
- You do not have unlimited access to the CEO — many judgment calls need to be made with partial information, not a quick check-in.
Communication note: This is an executive-facing, stakeholder-facing role, so how you communicate is part of what we're assessing — clarity, warmth, and professional judgment matter here. Speak naturally and conversationally, as if you were actually talking through the situation with a colleague. We are not scoring for a particular accent or for native-English fluency — we're listening for clarity, warmth, and sound judgment.
On-camera requirement: Please stay visible on camera for the full video. This isn't a formality — part of this role involves representing the CEO and Measure Well in video and virtual settings, so being present and comfortable on camera is part of what we're assessing. If you need a reasonable accommodation related to the video format, let us know before you submit and it won't affect your evaluation.
Submission: Record your responses as a single video file (MP4 or MOV) and upload it directly on the Provn platform.
What You'll Accomplish
Demonstrate sound, real-time judgment when protecting an executive's time and calendar
Show how you handle confidential or sensitive information with discretion
Demonstrate ability to coordinate operational and vendor issues without hand-holding
Show clear, professional, stakeholder-appropriate communication under realistic constraints
Demonstrate thoughtful, critical use of AI tools in real administrative work
How Your Work Will Be Scored
What to Submit
Video Response
Format: .mp4, .mov, .webm
Record as MP4 or MOV and upload directly on the Provn platform. Your video should cover, in order:
- Introduction: Tell us something about yourself that isn't on your resume.
- Executive Support scenario: The CEO calls you in the morning with a personal emergency and you need to reschedule all of today's meetings. An important meeting is scheduled for the afternoon with a board member, before they go on vacation for two weeks, to make a decision that cannot wait until they return. Explain how you'd resolve this scenario and why.
- Discretion & Confidentiality scenario: A member of the Advisory Council reaches out to you directly, outside the regular meeting cycle, asking for an advance copy of the CEO's talking points for an upcoming funder presentation — before the CEO has reviewed or approved the final version. They mention they're on a tight timeline and imply the CEO "wouldn't mind." Explain how you'd handle this request and why.
- Operational & Vendor Coordination scenario: Two weeks before Measure Well's quarterly Advisory Council offsite, the caterer you'd booked for a 35-person in-person session cancels last minute, citing a double-booking. The venue only allows caterers from its approved vendor list, and the other two vendors on that list are already booked for that date. Explain how you'd resolve this and prevent something like it from happening again.
- Mandatory AI question: Walk me through one moment where you disagreed with, pushed back on, or redirected what the AI gave you — and what you did instead. Name the specific moment. Explain what the AI produced that didn't meet the bar, what you did differently, and why.
Stay on camera for the entire video (see On-Camera Requirement above).
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