• Skip to primary navigation
  • Skip to main content
  • Skip to footer

Side Hustles

Side Hustles

Side Hustles For All

  • Best Side Hustles
    • Woman sitting on a pile of coins and working on a laptop surrounded by icons representing different side hustle ideas

      31 Best Side Hustles to Earn Extra Money in 2026

    • Bicycle courier delivering food for their side hustle.

      What Is a Side Hustle?

    • Remote worker sitting at his desk making money from home

      18 Ways to Make Money from Home (Online and Offline Jobs)

    • By Category
      • Arts & Crafts
      • Business Services
      • Caregiving
      • Creative Services
      • Digital Freelance Services
      • View All
    • By Lifestyle
      • I’m introverted
      • I’m a man
      • I’m a woman
      • I’m a stay-at-home mom
      • I’m unique
      • View All
    • By Profession
      • Artists & Creatives
      • Musicians
      • Nurses
      • Physicians
      • Teachers
      • View All
    • By Age Group
      • College Students
      • Teens
      • Age 50+
      • Seniors
      • View All
    • By Skills & Interests
      • Get Paid to Lose Weight
      • Get Paid to Play Games
      • Get Paid to Read
      • Get Paid to Sleep
      • Get Paid to Travel
      • View All
  • Best Gig Apps
    • Freelance worker popping out of a phone screen and considering gig apps on the App Store and Google Play

      Top 6 Gig Apps to Make Real Cash in 2026

    • Smartphone surrounded by the icons of different money-making apps

      Top 10 Best Money-Making Apps to Try in 2026

    • two teenagers using job apps on a phone and laptop

      19 Job Apps for Teens to Find Jobs and Make Money

    • By Gig Type
      • Cashback
      • Data Entry
      • Delivery
      • Games
      • Product Testing
      • View All
    • By Payment Method
      • Bingo Games that Pay to Cash App
      • Games that Pay Real Money
      • Games that Pay to Cash App
      • Games that Pay via PayPal
      • Surveys that Pay to Cash App
      • View All
    • By Benefits
      • $20 Signup Bonuses
      • $25 Signup Bonuses
      • $50 Signup Bonuses
      • Best Signup Bonuses
      • Instant Signup Bonuses
      • View All
    • By Skills & Interests
      • Driving
      • Losing Weight
      • Playing Games
      • Product Testing
      • Watching Ads
      • View All
  • Job Hunting
    • Freelance worker browsing a job post on a freelance job board.

      23 Job Boards You Can Use to Find Remote Work

    • Freelance writer sitting at her laptop working on a project

      15 Best Remote Jobs That Require No Paid Work Experience

    • Teenager sitting at laptop working an online job

      14 Online Jobs for Teens (With No Experience)

    • Freelancing
      • Freelance Writing Sites
      • Freelance Writing Job Boards
      • Freelance Writing Platforms
      • View More
    • Gig & Shift Work
      • Gig Work Apps
      • On-Demand Work Apps
      • Shift Work Apps
      • View More
    • GPT (Get Paid To)
      • Microtasking
      • Product Testing
      • Survey Taking
      • View More
    • Remote Working
      • Best Remote Job Boards
      • Top 15 Remote Jobs
      • View More
  • Job Board
    • Work Schedule
      • Part-Time Jobs
      • Per-Diem Jobs
      • Go Search
    • Work Environment
      • Hybrid Jobs
      • Remote Jobs
      • Go Search
    • Employment Type
      • Contractor Jobs
      • Internship Jobs
      • Temporary Jobs
      • Go Search
    • Job Title
      • Accounting Jobs
      • Data Entry Jobs
      • Nursing Jobs
      • Online Teaching Jobs
      • Software Engineer Jobs
      • Go Search
    • State
      • California Jobs
      • Florida Jobs
      • New York Jobs
      • Pennsylvania Jobs
      • Texas Jobs
      • Go Search
    • City
      • Chicago, IL
      • Houston, TX
      • Los Angeles, CA
      • New York City, NY
      • Phoenix, AZ
      • Go Search

Home Flexible Job Board Sales and Marketing Expert

$60–70/hr 39d ago

Sales and Marketing Expert

Boost your chances before you apply.

  • ✨ Apply 10x Faster Free

    It takes 30+ tailored applications to land jobs like this one. We'll help you get that done in 1 hour.

    No Credit Card Required

  • Proceed to Application Go directly to the company's job page to apply.
Logo

Weekday AI

US

Contractor Remote

✨ Apply 10x Faster

Analyze your resume for missing keywords, then one-click optimize it. Don't be anything less than a 100% match candidate.

Free

No Credit Card Required

Summary

Contributors will create realistic enterprise go-to-market scenarios and develop high-quality reference outputs for AI evaluation. They will also build evaluation rubrics that capture the decision-making processes of experienced sales and marketing leaders.

Job Description

This role is for one of our clients

Compensation: $60-$70 per hour

We are seeking experienced senior sales and marketing professionals to contribute to an AI evaluation initiative focused on real-world Fortune 500 go-to-market environments.

The work is designed around the deal complexity, stakeholder dynamics, commercial processes, and brand considerations found within Fortune 500 and large public companies. Contributors will create realistic enterprise GTM scenarios, develop high-quality reference outputs, and build evaluation rubrics that capture how experienced sales and marketing leaders make decisions.

Key Responsibilities

  • Develop enterprise sales scenarios involving $1M+ ACV opportunities, complex buying committees, multiple stakeholders, and lengthy procurement cycles within Fortune 500 accounts.
  • Create marketing scenarios covering enterprise brand strategy, account-based marketing (ABM), demand generation, lifecycle marketing, and category positioning.
  • Develop Revenue Operations and GTM scenarios using enterprise platforms such as Salesforce, Marketo, 6sense, Gong, and Outreach.
  • Apply established enterprise sales methodologies, including MEDDIC, Challenger, and Force Management, to develop realistic deal strategies and account plans.
  • Create executive-level sales narratives, customer engagement strategies, and go-to-market recommendations.
  • Develop detailed evaluation rubrics that distinguish genuine enterprise GTM expertise from generic sales or marketing playbook knowledge.
  • Review and refine scenarios and reference outputs to ensure they accurately reflect real-world enterprise practices.
  • Incorporate reviewer feedback and continuously improve the quality, consistency, and relevance of evaluation criteria.

Ideal Qualifications

  • 5+ years of professional experience in enterprise sales, marketing, or Revenue Operations.
  • Experience working for a Fortune 500 enterprise technology company, major SaaS organization, or large public-company sales or marketing organization.
  • Direct experience managing Fortune 500 accounts, enterprise sales cycles, major brand initiatives, or large-scale demand-generation programs.
  • Strong understanding of enterprise buying processes, procurement, budgeting, legal review, stakeholder management, and complex commercial negotiations.
  • Hands-on familiarity with enterprise GTM technologies and platforms, including CRM, marketing automation, sales engagement, conversation intelligence, and account-intelligence tools.
  • Strong knowledge of enterprise sales methodologies such as MEDDIC, Challenger, or Force Management.
  • Excellent written communication and analytical skills, with the ability to clearly explain strategic decisions and commercial reasoning.
  • Experience creating sales enablement materials, evaluation frameworks, training content, or professional development programs is a plus.
  • Prior experience with AI training, evaluation, rubric development, or human-data projects is advantageous.

Application Process

  • Submit your resume or relevant professional background to get started.
  • Qualified applicants may be asked to complete a brief assessment or provide additional information about their enterprise sales or marketing experience.
  • Selected contributors may receive onboarding and calibration guidance before beginning project work.

Engagement Details

  • Remote, flexible engagement.
  • Work is structured around project-based AI evaluation and research initiatives.
  • Project scope and duration may vary based on business and research requirements.
  • Strong contributors may have opportunities to participate in additional evaluation, reviewer, or subject-matter-expert projects.

Equal Opportunity

We consider all qualified applicants without regard to legally protected characteristics and provide reasonable accommodations upon request.

Contract and Payment Terms

  • You will be engaged as an independent contractor.
  • This is a fully remote role that can be completed on your own schedule.
  • Projects may be extended, shortened, or concluded early depending on project requirements and performance.
  • Your work will not involve access to confidential or proprietary information from any current or former employer, client, or institution.
  • Payments are made weekly through Stripe or Wise based on services rendered.
  • H-1B and STEM OPT candidates are not currently supported for this opportunity.

About the company

Weekday AI

Recruitment agency

Finding a great startup job should not feel like a second job.

Weekday AI brings the most exciting roles from premium YC and VC-backed startups into one place. Our team hand-picks every listing, so you skip the agency spam and the dead links and go straight to companies building things that matter.

Why people use Weekday AI?

Curated roles from premium YC and VC-backed startups
Fresh jobs every week, picked by humans
AI that helps you apply in minutes
Free to join

Your next role should come from a company you are proud to work at. We help you find it.
Browse live roles at jobs.weekday.works

Founded

2022

Company size

11-50 employees

Industry

Technology, Information and Internet

Org type

Privately Held

Apply Now

About the company

Weekday AI

Recruitment agency

Finding a great startup job should not feel like a second job.

Weekday AI brings the most exciting roles from premium YC and VC-backed startups into one place. Our team hand-picks every listing, so you skip the agency spam and the dead links and go straight to companies building things that matter.

Why people use Weekday AI?

Curated roles from premium YC and VC-backed startups
Fresh jobs every week, picked by humans
AI that helps you apply in minutes
Free to join

Your next role should come from a company you are proud to work at. We help you find it.
Browse live roles at jobs.weekday.works

Founded

2022

Company size

11-50 employees

Industry

Technology, Information and Internet

Org type

Privately Held

Footer

sidehustles.com
Facebook Twitter Instagram LinkedIn Reddit TikTok YouTube

Show Me The Money

  • Side Hustle Basics
  • Side Hustle Job Board (Remote & Part-Time Jobs)
  • Gig App Reviews
  • Job Hunting
  • Manage Your Money
  • The Gig Apple: News & Events

Company

  • About Us
  • Contact Us
  • Become a Contributor
  • Advertising & Sponsorships
  • Partner With Us
  • Editorial Guidelines

Side Hustles © All rights reserved

  • Privacy Policy
  • Terms of Service

Thanks for using our free job board

Your review would mean a lot to us.

If you love that we're just giving away remote jobs for free with no paywall, please spread the word. (You will need to create an account on Trustpilot, for which we'll be eternally grateful.) Good luck out there!

Leave a Review Not yet. Send me to the job post.