Job description

HeyMilo Labs | Remote | Independent Contractor | $40–$100 per hour HeyMilo Labs is looking for experienced account executives to participate in paid, recorded conversations with other sales professionals. You’ll discuss sales strategy, debate how to approach difficult deals, and explain the reasoning behind your decisions. These conversations will help train and evaluate AI systems. WHAT YOU’LL DO - 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 your 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 WE’RE LOOKING FOR - 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. - The ability to explain your thinking, support a perspective, and constructively disagree. - Comfort with an unscripted exchange where both participants ask questions and contribute ideas. Professional acting experience is optional. Domain expertise and conversational ability are essential. THE NEXT STEP Following an initial screening, selected applicants will be invited to a paid, recorded conversation with another sales professional who has a similar background. You’ll discuss a topic within your shared expertise, debate possible approaches, and challenge each other’s recommendations. COMPENSATION AND RECORDING Pay is $40–$100 per hour. The rate, expected time commitment, and recording-use and licensing terms will be shared before you accept an assignment. Recordings may be licensed to AI developers for training and evaluation under the agreed terms. You’ll need a quiet environment, reliable internet, a clear microphone, and a webcam. Be comfortable appearing on video with your face visible and filters and background blur turned off. HOW TO APPLY Share your sales background, industries and customer segments served, availability, time zone, and spoken languages.

Requirements

Must-haves

HeyMilo Labs | Remote | Independent Contractor | $40–$100 per hour
These conversations will help train and evaluate AI systems.
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 your 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.
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.
The ability to explain your thinking, support a perspective, and constructively disagree.
Comfort with an unscripted exchange where both participants ask questions and contribute ideas.
Professional acting experience is optional. Domain expertise and conversational ability are essential.
You’ll need a quiet environment, reliable internet, a clear microphone, and a webcam. Be comfortable appearing on video with your face visible and filters and background blur turned off.

Nice-to-haves

None flagged.

Application prep

Use the role’s language and application details while tailoring your materials.

Keywords to mirror

Platform: ashby
Effort: quick