CHERRY ASSISTANT JOBS

Talent Operations Specialist

Remote role for Cherry Assistant through Cherry Assistant.

FULL TIMEAmericas (North, Central, South America)45 hrs/weekR32,500 - R57,000 per/month

Job Description

What this role covers

We are hiring an Talent Operations Specialist for a fast-growing AI startup in the Talent Acquisition and HR Technology industry. This is a full-time remote role for a U.S.-based company.

This role is ideal for a “smart hustler”—someone with a high-slope career trajectory who may come from an SDR or operations background and is eager to optimize human-in-the-loop AI processes to revolutionize how top talent is discovered and matched with high-growth companies.

Key Responsibilities:

  • Supervise AI agent pipelines: Monitor live candidate conversations, flag errors, and intervene when the agent needs human judgment.

  • Handle high-stakes moments: Manage senior candidates, tricky objections, and compensation negotiations.

  • Train AI agents: Review outputs, label responses, and create examples that improve AI performance.

  • Quality control at scale: Audit candidate matches, outreach quality, and conversion rates across thousands of weekly touchpoints.

  • Close placements: Guide candidates through final stages, manage offers, and ensure successful hires.

  • Build the playbook: Document processes, create SOPs, and define how humans and AI agents collaborate effectively.

Required Qualifications:

  • 3+ years of experience a in Sales Development Representative (SDR), Operations Associate, or high-volume recruitment roles

  • Comfort working with AI tools like Claude, ChatGPT, or similar platforms.

  • Strong judgment and decision-making skills.

  • Excellent interpersonal skills and ability to read candidates’ needs beyond their words.

  • Ability to manage high-volume operations without sacrificing quality.

  • Adaptability and willingness to define and shape a new type of role.

Preferred Qualifications:

  • Prior recruiting experience (not required).

  • Experience with AI training, labeling, or operational workflows.

  • Exposure to high-growth startup environments.

Required Skills & Tools:

  • AI platforms: Claude, ChatGPT, or equivalent

  • Productivity tools: Google Workspace, Slack

  • Project tracking: Notion, Airtable, or similar

Schedule & Pay:

  • Schedule: Flexible, at least 40–50 hours/week aligned with PST - including occasional evening or weekend calls.

  • This is a fully remote position for a U.S.-based company.

  • Pay ranges from R32,500 - R57,000 per/month / $2,000 - $3,500 USD (dependent on experience and skill) with an additional commission structure.

System Requirements:

  • Internet speed of at least 20 Mbps

  • Computer with a 2.4 GHz processor or higher

  • 8 GB of RAM or higher

  • Windows 10 or newer, or Mac OS X 10.10 or newer

  • HD 720p webcam

  • Headset with a microphone

Benefits:

  • Competitive pay rates.

  • Consistent work with the same clients, fostering long-term professional relationships.

  • Opportunities for career advancement, dependent on the client.

  • Stable work hours and consistent pay.

  • A supportive and inclusive work environment that values diversity and individual growth.


This is your chance to shape a new function, scale innovative operations, and make a direct impact on the way top talent connects with high-growth companies.