Enterprise Sales Expert (AE / Sales Leader)

$50–70/hr

rate as listed

Workload: ~10 hrs/week
Engagement: Project-based
Location: US
Field: Generalist

Review realistic enterprise software deal rooms and write the discovery plans, deal analysis and executive briefs an experienced AE or sales leader would produce. This is a short-pilot expert evaluation role, not a quota-carrying position, and involves no buyer outreach.

The work

You will review self-contained B2B deal scenarios containing materials such as account research, stakeholder notes and sales context. For each scenario, you may prepare a pain hypothesis and discovery plan, distinguish the buyer's current and desired future states, identify required capabilities, or write an executive meeting brief. The goal is to produce concise examples of enterprise deal thinking that can be used as training data for a sales-specialized AI model.

What the platform is likely to screen for

Expect questions about specific enterprise software deals you have worked on, including how you ran discovery, built relationships across a buying group, aligned executives and used mutual action plans. Strong responses will separate known facts from assumptions, connect deal evidence to recommendations and show how you would adjust your approach when stakeholder signals conflict. Experience managing or coaching AEs and working on large, multi-stakeholder deals is preferred.

Scope and logistics

This is not a sales or quota-carrying role, and you will not contact buyers. Individual tasks take roughly 15 to 30 minutes, with an expected commitment of about 10 hours per week during a short pilot. More work may follow if the pilot goes well, but it is not guaranteed. The listing requires candidates to be based in the United States; it describes task-based written work but does not explicitly confirm formal remote status or fully asynchronous scheduling.

Pay band: $50–70/hr

What they look for

Enterprise B2B software sales experience
Enterprise discovery and pain hypothesis development
Multi-threaded stakeholder and executive alignment
Mutual action plan and deal strategy development
Clear, concise written English
Sales coaching or AE management experience

Included with this listing

Interview prep — 10 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: This verifies the required four or more years in an AE or first- or second-line leadership role and whether the candidate's experience involved enterprise software rather than transactional or non-software sales.
A strong answer: Give a chronological, verifiable summary with titles, dates, company context, customer segment and typical deal complexity. Clearly distinguish personal selling experience from work performed as a manager.
Where people lose it: Candidates lose credibility when they cite a senior title without explaining whether they personally ran enterprise deals or led AEs who did.

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