AI Automation Lead (Grok Bot)

ClearDesk; San Diego (CA); Remote; USD 120,000 - 180,000; Full time

Job summary

ClearDesk is seeking a hands-on automation lead to own Grok Bot end-to-end, partnering with the CEO and Chief of Staff to shape the AI agents that power recruiting, sales, operations, and finance. You will audit, build, tune, and scale bots, connect Gmail, Slack, HubSpot, Calendar, Drive, and project tools, and ensure safe, human-in-the-loop automation with clear ownership.

This is a high-impact, fast-moving role with exposure to multiple incubated companies and a direct line to leadership,

Qualifications

• Hands-on experience building with AI agents or LLM tools.
• Systems thinking with a track record of automating workflows.
• Strong written communication and ownership.
• Experience in fast-moving startups and in staffing/real estate or small services is a plus.
• Experience running bots in HubSpot or Slack at scale.

Responsibilities

• Build, tune, and maintain Grok Bot agents, routines, and skills across departments.
• Connect and manage integrations with Gmail, Calendar, Slack, HubSpot, Drive, Asana and more.
• Identify repetitive work and automate end-to-end with ownership of outcomes.
• Write prompts, test edge cases, and ensure human-in-the-loop approvals.
• Track bot performance and maintain clear documentation of ownership.
• Train teams to work alongside bots and raise automation standards.
• Stand up initial agents for new incubator companies.

Skills

Grok Bot

AI agents

Systems thinking

Prompt engineering

Documentation

Cross-functional collaboration

HubSpot

Gmail/Slack/Calendar integrations

Tools

ChatGPT/GP T builders

Zapier/Make with AI

n8n

APIs and webhooks

Job description

Own the bots that run ClearDesk | Reports to the CEO | [Full-time / Contract]

ClearDesk helps US small and mid-sized businesses hire and manage full-time Remote Team Members (RTMs) based in the Philippines. We place and support roughly 500 team members today across home care, real estate, bookkeeping, and home services, on a simple flat-fee model with a US leadership team and Philippines-based operations managers behind every placement.

We also build companies. In September 2026 we launched three new businesses out of ClearDesk, in healthcare AI, pharmacy ordering, and wellness, and in 2027 we are standing up a formal incubator with two more launching next year. Every one of them runs on AI agents from day one.

ClearDesk already runs on them too. Grok Bot screens our candidates, works our inboxes, manages calendars, updates HubSpot, and keeps Slack moving. We are hiring the person who owns that system and makes it bigger.

The role

You will own Grok Bot at ClearDesk end to end: the agents we have, the ones we need, and the integrations that connect them to the tools the team lives in. You work directly with the CEO and Chief of Staff, who bring the problems and the priorities. You bring working bots.

The job is half builder, half internal consultant. Some weeks you are writing and tuning the candidate-screening bot for our recruiting team. Other weeks you are sitting with a finance manager, mapping the twenty steps she repeats every Friday, and handing her an automation by Monday. As the incubated companies grow, you will stand up their first bots too.

This is a hands-on role with unusual scope. Your work touches every department at ClearDesk and every company we launch, and you have a direct line to the people who decide what gets built next.

What you'll do

• Build, tune, and maintain Grok Bot agents, routines, and skills across hiring, sales, operations, finance, and marketing.
• Connect and manage integrations with Gmail, Google Calendar, Slack, HubSpot, Google Drive, Asana, and whatever the team adopts next, through native connectors, APIs, and webhooks.
• Sit with team members, find their repetitive work, and automate it start to finish. You own the result, not just the setup.
• Write clear prompts and instructions, test the edge cases, and make sure every agent acts safely. Bots draft first and send only with approval; nothing touches a client, candidate, or bank account without a human in the loop.
• Track how each bot performs, fix what breaks before anyone notices, and keep a plain-English doc of how every agent works and who owns it.
• Train the team to work alongside their bots, and keep raising the bar on what they expect from them.
• Stand up the first agents for each new company we launch from the incubator.

What success looks like

First 30 days.

You have audited every bot we run, documented what each one does, and fixed the two or three that break most often. You have shipped at least one new automation that a team member uses daily.

By 60 days.

Every department has a prioritized automation backlog you built by sitting with the team. Recruiting, sales, and executive support each have at least one new agent in production with approval gates where they matter.

By 90 days.

You own the Grok Bot roadmap. The team brings you requests instead of workarounds, and you can show hours saved per week by department.

Ongoing.

Hours of manual work removed each month, bot uptime and error rates, adoption across teams, and how fast a new company gets its first working agents.

What we’re looking for

• Hands-on experience building with AI agents or LLM tools: Grok Bot, ChatGPT and GPT builders, Claude, Zapier or Make with AI, n8n, or similar. We will ask to see what you built.
• A systems thinker who loves automating workflows and can point to real business results from it, not demos.
• Strong written communication. Prompts are product, and so is the documentation the team reads.
• High ownership and quick follow-through. You ship a working v1 in days and iterate with whoever uses it.
• At home in a fast-moving startup where you get a problem, not a spec.
• You have automated recruiting, sales operations, or executive support before.
• You have worked in or with staffing, home care, real estate, or small-business services.
• You have run bots in HubSpot or Slack at scale.

Why ClearDesk

You will work directly with the CEO, see your work land across a 500-person operation within days, and help shape how an AI-first company runs. You also get a front-row seat as new companies get launched, and a real path to a senior role in one of them.

Compensation, location, and how to apply

• Compensation: DOE
• Type: [Full-time / Contract]