Executive Assistant, Measure Well — Video Challenge at Measure Well

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

**Executive Support & Rhythm of Business Judgment (25%):** A strong response resolves the scheduling conflict with a clear prioritization principle and anticipates a consequence beyond the immediate ask.**Discretion, Judgment & Confidentiality (20%):** A strong response identifies the real sensitivity in the request and describes a specific, sound boundary for handling it.**Communication & Stakeholder Management (20%):** A strong response is clear, warm, and immediately usable by the stakeholder in the scenario.**Operational & Vendor Coordination (15%):** A strong response proposes a fix that also prevents the problem from recurring, and names who else needs to be looped in.**AI Fluency (10%):** A strong response names a specific moment of redirecting AI output and explains what didn't meet the bar and what changed.**Resume & Background (10%):** Scored separately from your video, based on directly relevant executive-support experience and career trajectory.

What to Submit

Video Response

Video · 10-15 minutesRequired

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).