About Us

We are a fast-moving startup and boutique venture capital firm that thrives on efficiency, automation, and seamless operations. We need a systems-first, AI-driven operator who can architect workflows, automate processes, and scale our internal infrastructure to minimize manual effort while protecting our intellectual property.This is a high-leverage position that will:

• Eliminate inefficiencies and repetitive tasks by implementing AI and automation-first workflows
• Ensure our tech stack (ClickUp, Zapier, Front, Slack, HubSpot, Google Suite) runs as an integrated system
• Design, document, and scale SOPs so that every process is standardized and easily repeatable
• Streamline onboarding, offboarding, and internal training for a self-sufficient team
• Automate financial operations, including QuickBooks, invoice tracking, and financial workflows
• Lock down company IP and ensure airtight permissions and access control
• Lead project management and communications, ensuring operational alignment across teams
• Own the onboarding of new hires into our systems, ensuring they ramp up quickly and efficiently

AI-Powered Operations & System Optimization

• Design a fully integrated, AI-powered workflow using ClickUp, Slack, Zapier, Front, and HubSpot

Responsibilities

• Implement AI agents (ChatGPT, Claude AI, Loom AI) for internal operations, email automation, and reporting
• Set up automation layers to connect CRM, project management, and communications seamlessly
• Build a scalable AI-enhanced knowledge base so the team always has access to essential information

Automate & Streamline Onboarding, Offboarding, and Training

• Create AI-powered training modules with Loom AI and ChatGPT
• Automate employee onboarding and access provisioning across 1Password, Google Suite, and Slack
• Streamline offboarding workflows to ensure security and compliance
• Develop SOPs for every internal function to minimize HR dependency
• Ensure every new hire is efficiently onboarded into systems, workflows, and automation tools

Project Management & Team Communication

• Own project management in ClickUp, ensuring teams have clear workflows, tasks, and priorities
• Lead cross-functional alignment to ensure operations support finance, sales, and growth
• Standardize communication workflows in Slack and Front to keep operations transparent
• Ensure team members understand and fully adopt AI-powered workflows

ClickUp & Slack Workflow Engineering

• Architect and automate ClickUp dashboards, task dependencies, and reporting
• Set up automated Slack workflows, including status updates, approvals, and team-wide alerts
• Use Zapier and Make (Integromat) to connect all operational tools
• Automate project and deal flow tracking for the VC fund

AI-Driven Financial Operations & Compliance

• Automate QuickBooks invoicing, reconciliations, and expense tracking
• Set up AI-generated financial reports and forecasting models
• Implement automated audit trails and document security controls

Protect Business IP & Ensure Security Compliance

• Structure permissioning and access control for all tools, including 1Password, Google Suite, and DocSend
• Implement automated alerts for unauthorized access or security risks
• Ensure AI-driven documentation workflows meet compliance and data security standards

Qualifications

Must-Have Skills

• Expertise in ClickUp, including workflow automation, reporting, and dashboard creation
• Proficiency in Zapier and Make (Integromat) for seamless tool integration and workflow automation
• Experience with Slack AI and automation, including bot setup and workflow optimization
• Strong knowledge of HubSpot CRM and AI-driven lead tracking and deal flow automation
• Experience automating inbox management in Front
• Familiarity with Loom AI and ChatGPT for AI-powered documentation and training
• Financial workflow automation experience, including QuickBooks, Xero, and AI reporting
• Experience in security and access management, including 1Password, Google Suite, and DocSend
• Strong project management and communication skills
• Proven experience onboarding teams to new systems and ensuring adoption

Bonus Skills

• Experience with API and Webhooks for deeper integrations
• Python or JavaScript for AI-driven custom automation
• Familiarity with Retool or Airtable for internal AI-powered dashboards

Job Details

• Location: Remote
• Hours: 40hrs/week

Submit your application here

Note: We are not considering applications from agencies or recruiters at this time. Only individual candidates will be reviewed.

About Us

Who We Are: Trolley is an online marketplace and platform that pairs best-in-class people with best-in-class companies.   We are the future of work, create, and play, powered by our proprietary LiveWorkOS.

What We Do:  Trolley builds world-class teams using best-in-class SaaS tools, AI, and project management systems. Our mission is to empower professionals with world-class training and the latest tools to work smarter, faster, and more efficiently.

Why Join Us?

• Work with the Best: We recruit globally to connect top talent with forward-thinking companies.
• Tech-Driven Efficiency: Leverage the latest AI and tools to amplify your impact.
• Human-Centric Approach: Our systems are designed to support and elevate people, not replace them.
• Training for Success: We provide world-class training to ensure you excel in every aspect of your role.

Be Part of the Future of Work. Trolley is now accepting applications from ambitious professionals who want to work at the intersection of technology and creativity. Join us in shaping the next era of work.