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Hiring now · posted today General Contract · Remote

Enterprise Sales Manager – AI Training Specialist

$100–$125/hr

Published pay. The final rate depends on your test, experience and country.

Remote · United States Language: English Posted 14 Nov 2026

Enterprise Sales Manager – AI Training Specialist is remote AI-training work for sales teams, paying $100–$125/hr, open to applicants in United States. Posted 14 Nov 2026, still open on 14 Nov 2026. Zekai lists it for free; the application goes to the employer's platform.

About this role

Preparing for this role? See the best AI tools for sales teams, practise with ready-made prompts for sales teams, read Best Free AI Tools for Sales Teams (2026 Verified Limits) and take the free 30-day AI challenge.

our partner is partnering with a leading AI company to develop advanced AI models designed to support enterprise sales teams. We are seeking experienced Enterprise Sales Managers, Regional Sales Managers, and Frontline Sales Leaders to contribute their expertise in sales coaching, pipeline management, deal strategy, and revenue forecasting. In this role, you will leverage your sales leadership experience to evaluate realistic B2B sales scenarios, assess deal execution, and develop high-quality coaching recommendations that help train and improve AI systems. This is not a traditional sales management position. You will not be responsible for managing employees, carrying a sales quota, or engaging directly with customers. Instead, you will apply your professional judgment to demonstrate how effective frontline sales leaders evaluate opportunities, coach Account Executives, and drive sales performance.

Key Responsibilities

  • Deal Inspection & Qualification: Review enterprise sales opportunities, assess deal health using established methodologies such as MEDDPICC, identify potential risks, and recommend strategies to improve deal progression.

  • Sales Coaching & Development: Provide structured, actionable feedback to Account Executives on discovery, stakeholder engagement, executive alignment, negotiation, and overall sales execution.

  • Pipeline Management & Forecasting: Analyse pipeline snapshots, evaluate forecast categories, assess opportunity quality, and identify areas requiring management attention.

  • Strategic Deal Reviews: Evaluate complex B2B sales scenarios, including deal histories, call notes, stakeholder relationships, and sales execution challenges.

  • Performance Assessment: Analyse individual Account Executive performance, identify coaching opportunities, and recommend practical improvements to sales effectiveness.

  • AI Model Training & Evaluation: Develop detailed written analyses and coaching recommendations that reflect real-world sales leadership practices and contribute to the training and evaluation of sales-specialised AI models.

Required Qualifications

  • Recent experience in a first-line sales management role within the past 12 months, directly managing a team of quota-carrying Account Executives.

  • Experience in such a role at an organisation with 500+ employees and a sales team of more than 25 representatives.

  • Strong understanding of B2B sales processes, pipeline management, deal qualification, forecasting, and sales coaching.

  • Demonstrated ability to evaluate complex sales opportunities and provide actionable guidance to Account Executives.

  • Excellent written communication and analytical skills, with the ability to articulate sophisticated sales strategies clearly.

  • Must not currently be employed by a company selling go-to-market (GTM) or sales technology, including CRM add-ons, sales engagement platforms, conversation intelligence, or sales data solutions.

  • Willingness to complete all project assignments independently, without the use of AI tools.

Preferred Qualifications

  • Previous success in a quota-carrying Account Executive role before transitioning into sales management.

  • Experience leading enterprise or mid-market sales teams selling B2B software solutions.

  • Demonstrated success in improving team performance, sales productivity, pipeline quality, and forecast accuracy.

  • Familiarity with structured sales methodologies such as MEDDPICC, MEDDIC, Challenger, or similar frameworks.

  • Experience coaching Account Executives through complex, multi-stakeholder enterprise deals involving extended sales cycles.

  • Strong understanding of executive engagement, competitive positioning, and enterprise negotiation strategies.

Why Join This Project?

  • Shape the Future of AI: Apply your sales leadership expertise to help develop AI systems capable of understanding sophisticated B2B sales management practices.

  • Leverage Your Leadership Experience: Contribute your expertise in coaching, forecasting, and deal strategy without the responsibilities of directly managing a sales team.

  • Potential for Growth: Access opportunities for increased project involvement as the engagement expands.

This is a 100% remote contract role. Applicants must be located in: United States.

How applying works

  1. Click Apply now and enter your email.
  2. You go straight to the application. We email you a copy of this role and your link.
  3. Most platforms ask for a CV and a short skills test or AI interview in your field.
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What to know before you apply

Pay
At the published rate, 10 hours a week would be about $1,000–$1,250 and 20 hours about $2,000–$2,500 before tax. Hours depend on the project, so treat this as a ceiling, not a promise.
Location
Only applicants located in United States can be paid for this role. Platforms usually verify where you are, so apply only if you are based there.
Timing
This listing is new today. Projects can close once they have enough people, so it is worth applying while it is open.
Test tips for sales teams
  • Expect a short skills test that checks careful reading, reasoning and clear writing.
  • Read the project guidelines fully before your first task. Accuracy matters more than speed.
  • Explain your judgements in plain, complete sentences. Reviewers look for the reason, not just the answer.
  • Keep a steady weekly schedule. Projects usually prefer contributors they can count on.
Prepare free with Zekai

3 steps to stand out as one of the best sales teams

  1. 01

    Know the AI tools sales teams use

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  2. 02

    Practise with real prompts

    Many tests ask you to write or judge prompts in your field. Practise on these first.

    Concession Strategy Brainstorm

    Act as a negotiation coach. We are in the final stages of a deal. The prospect is asking for a [[e.g., 15% discount]]. I cannot give them the full discount, but I can offer other concessions. Brainstorm 5 non-monetary concessions…

    Deal Health Summary

    Analyze the provided CRM data and call notes for the [[Account Name]] opportunity. Provide a concise deal health summary including: • Forecast Category: (Commit, Best Case, Pipeline) • Confidence Score: (1-100%) • Supporting Evid…

    Prompt library for sales teams →
  3. 03

    Take the free 30-day AI challenge

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