Account Executive — Voice and Video Contributor

HeyMilo AI; United States; Remote; USD 55,000 - 138,000; Part time

Job summary

HeyMilo Labs is seeking experienced account executives for paid, recorded conversations with other sales professionals. This remote, independent contractor role involves discussing sales strategy, debating how to approach difficult deals, and explaining the reasoning behind decisions.

Conversations help train AI systems; compensation is $40-$100 per hour. Applicants should have B2B sales experience, be fluent in the session language, and comfortable with unscripted, video-based dialogue.

Qualifications

• Professional account executive or equivalent B2B sales experience.
• Experience guiding buyer conversations and advancing deals.
• Fluent spoken communication in the session language.
• Ability to articulate reasoning, defend perspectives, and disagree constructively.
• Comfort with unscripted, interactive dialogue and idea exchange.

Responsibilities

• Discuss discovery, qualification, stakeholder management, pricing, negotiation, and closing.
• Debate approaches to stalled deals, competitive evaluations, or large discount requests.
• Defend a recommended strategy using clear reasoning and experience.
• Question assumptions, ask probing questions, and respond to objections.
• Explore alternative approaches as new information emerges with anonymized examples.

Skills

Account executive

B2B sales

Buyer conversations

Deal progression

Fluent English

Explain thinking

Unscripted discussion

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.