Enterprise Sales Domain Expert

$60–90/hrrate as listed

Experienced enterprise sellers audit multi-step AI sales workflows, build golden reference examples across prospecting, CRM, and pipeline reporting, and refine the rubrics used to score model output. The role is W-2 employment through Cincinnatus LLC, fully remote in the US, with observed rates of $60–90/hr.

Summary, eligibility guidance and screening preparation are prepared by Sidequest from the platform's posting. Check the source listing before applying.

The work

An AI lab is training models to perform real enterprise sales work — the multi-step, judgment-heavy sequences that only someone who has carried a quota can evaluate credibly. Your job is to be the ground truth. That means working tasks end-to-end inside sandboxes that mirror a live sales stack (CRM, communication, billing tools), producing the expert trajectory the model learns from, then turning around and grading the model's attempts at the same tasks.

A typical week mixes three kinds of work:

Golden trajectories: completing prospecting sequences, pipeline hygiene passes, forecast reporting, and customer-facing documents at the quality a senior sales leader would sign off on.
Workflow audits: reviewing what the AI did across a multi-step task and articulating precisely where its judgment diverged from a strong seller's — not just that the output was weak, but which decision went wrong and why it matters commercially.
Rubric work: pressure-testing the scoring criteria so they capture what actually separates excellent selling from competent selling, and flagging where a rubric rewards surface polish over substance.

What the screen looks for

Mercor's AI-led interview probes for specifics, and follow-ups get concrete fast. Expect to be asked about deal sizes, cycle lengths, quota attainment by year, and the mechanics of how you ran your pipeline — vague summaries of "exceeding targets" don't survive the second question. The bar is roughly a decade of hands-on enterprise selling; ICs, front-line managers, and VPs are all in scope, but the common requirement is that you personally did the work recently enough to reconstruct it. Day-to-day fluency with Salesforce, Google Workspace, Microsoft Office, Jira, and Confluence is assumed, plus the comfort to pick up HubSpot, Zoho, Slack, Notion, Stripe, Intercom, Aircall, or Teams on short notice. Strong writing matters as much as sales instinct — much of the output is prose and slides someone else will be judged on. Experience with two-sided AI-powered B2B SaaS creator marketplaces and outcome-based campaign targets is called out as a differentiator worth mentioning.

Logistics

This is structured W-2 employment with Cincinnatus LLC acting as employer of record, with placement into a lab's extended workforce — not a freelance or task-marketplace engagement. Cincinnatus administers payroll, benefits, and onboarding; Mercor is the discovery channel. Fully remote within the United States, with part-time or full-time commitments depending on the pod, and enough overlap with the client team's hours to participate in calibration and rubric discussions. Rates in the $60–90/hr band reflect what has been observed on comparable postings and are not guaranteed.

What they look for

~10 years hands-on enterprise sales experience across the full cycle
Documented record of quota attainment you can discuss in specifics
Deep working knowledge of Salesforce and CRM administration, pipeline tracking, and sales reporting
Strong business writing — pitches, decks, and executive summaries at senior-leader polish
Fluency with the enterprise stack (Google Workspace, Microsoft Office, Jira, Confluence) and quick pickup of HubSpot, Zoho, Slack, Notion, Stripe, Intercom
US-based and eligible for W-2 employment

Before you apply

Would you pass this screen?

Drawn from what this listing actually requires. Answered in your browser — nothing is sent to us, and we do not store your answers.

Do you have at least 10 years of hands-on quota-carrying experience selling into enterprise customers or accounts?
Enterprise sales experience · required
Can you speak to a consistent track record of meeting or exceeding your sales quota in at least 3 of your last 5 years?
Sales quota achievement · required
Are you authorized to work in the United States and able to accept a W-2 employment position?
US work authorization · required
Do you have hands-on, day-to-day fluency with Salesforce, Jira, or similar enterprise sales platforms?
Salesforce proficiency · preferred
Are you located in, and available to work full-time from, the United States?
Remote work eligibility · required

0 of 5 answered

Included with this listing

Interview prep — 12 questions

Matched to what this platform's screening actually measures. Answer each out loud in 60–90 seconds: claim → concrete example → implication.

What it tests: Verifying the candidate has actual quota-carrying experience with real enterprise sales cycles and can articulate specific seller moves, not just a timeline.
A strong answer: The answer names a concrete deal (size, customer type, industry context), timeline in months, and at least two or three specific actions the candidate personally took—discovery calls, objection handling, stakeholder alignment, proposal strategy—that directly influenced the outcome.
Where people lose it: Candidates often describe the deal passively ('the team closed it,' 'we had a strong product') or skip the deal size and cycle length, which makes it impossible to judge whether this was enterprise selling or transactional, and whether the candidate drove it or rode along.