**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**:- 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**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 l

📌 Ai-Powered Systems & Automation Specialist (Xico)
🏢 Trolley
📍 Xico