Account Executive — Voice and Video Contributor

HeyMilo • New York City, CA

1d • Remote

About The Position

HeyMilo Labs is seeking experienced account executives or professionals in comparable B2B sales roles to participate in paid, recorded conversations with other sales professionals. Participants discuss sales strategy, debate approaches to difficult deals, and explain the reasoning behind their decisions. The conversations are used to train and evaluate AI systems.

Following an initial screening, selected applicants will be invited to a paid, recorded conversation with another sales professional who has a similar background. Participants will discuss a topic within their shared expertise, debate possible approaches, and challenge each other’s recommendations. The rate, expected time commitment, and recording-use and licensing terms will be shared before an assignment is accepted. Recordings may be licensed to AI developers for training and evaluation under the agreed terms.

Requirements

• Professional experience as an account executive or in a comparable B2B sales role.
• Hands-on experience managing substantive buyer conversations and progressing deals.
• Fluent spoken communication in the language of the session.
• Ability to explain thinking, support a perspective, and constructively disagree.
• Comfort with unscripted exchanges in which both participants ask questions and contribute ideas.
• A quiet environment, reliable internet, a clear microphone, and a webcam.
• Comfort appearing on video with face visible and filters and background blur turned off.

Nice To Haves

• Professional acting experience is optional.

Responsibilities

• Discuss discovery, opportunity qualification, stakeholder management, pricing, negotiation, and closing.
• Debate approaches to realistic sales situations, such as a stalled deal, a competitive evaluation, or a buyer requesting a substantial discount.
• Defend a recommended strategy using experience and clear reasoning.
• Challenge another participant’s assumptions, ask probing questions, and respond to objections.
• Explore alternative approaches as new information emerges, using fictional or anonymized examples.

What This Job Offers

• Career Level: Mid Level
• Education Level: No Education Listed