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Account Executive — Voice and Video Contributor

🏢 Heymilo · 📍 New York City · 💼 remote · ⏰ Contract
⚡ Direct Talent Broker Referral
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✔ $500 Cash Hiring Bonus: Receive $500 direct cash reward after 30 days of active employment.

Position Summary & Responsibilities

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–$10

🎯 Candidate Preparation Guide For Heymilo Applicants

Key Role Competencies & Evaluation Highlights

Key Role Focus:

Evaluating your ability to build and scale conversational AI workflows and autonomous recruiting agents with extreme user-centric speed.

📋 Preparation Priorities (Key Areas to Clarify):
  • 1. Treating AI agents as static chat scripts rather than dynamic autonomous decision-makers
  • 2. Showing over-reliance on massive theoretical frameworks instead of rapid prototyping
  • 3. Lacking understanding of HR tech compliance, data privacy, and bias mitigation
✨ Recommended Role Alignment Hook:

I've spent my career cutting recruitment friction through intelligent automation, and I want to scale that impact directly with Heymilo's AI agents.

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