AI-Powered Systems & Automation Specialist - REMOTE
Job Description :
- Location : Remote
- Hours : 40hrs / week
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 workflowsEnsure our tech stack (ClickUp, Zapier, Front, Slack, HubSpot, Google Suite) runs as an integrated systemDesign, document, and scale SOPs so that every process is standardized and easily repeatableStreamline onboarding, offboarding, and internal training for a self-sufficient teamAutomate financial operations, including QuickBooks, invoice tracking, and financial workflowsLock down company IP and ensure airtight permissions and access controlLead project management and communications, ensuring operational alignment across teamsOwn the onboarding of new hires into our systems, ensuring they ramp up quickly and efficientlyResponsibilities
AI-Powered Operations & System Optimization
Design a fully integrated, AI-powered workflow using ClickUp, Slack, Zapier, Front, and HubSpotImplement AI agents (ChatGPT, Claude AI, Loom AI) for internal operations, email automation, and reportingSet up automation layers to connect CRM, project management, and communications seamlesslyBuild a scalable AI-enhanced knowledge base so the team always has access to essential informationAutomate & Streamline Onboarding, Offboarding, and Training
Create AI-powered training modules with Loom AI and ChatGPTAutomate employee onboarding and access provisioning across 1Password, Google Suite, and SlackStreamline offboarding workflows to ensure security and complianceDevelop SOPs for every internal function to minimize HR dependencyEnsure every new hire is efficiently onboarded into systems, workflows, and automation toolsProject Management & Team Communication
Own project management in ClickUp, ensuring teams have clear workflows, tasks, and prioritiesLead cross-functional alignment to ensure operations support finance, sales, and growthStandardize communication workflows in Slack and Front to keep operations transparentEnsure team members understand and fully adopt AI-powered workflowsClickUp & Slack Workflow Engineering
Architect and automate ClickUp dashboards, task dependencies, and reportingSet up automated Slack workflows, including status updates, approvals, and team-wide alertsUse Zapier and Make (Integromat) to connect all operational toolsAutomate project and deal flow tracking for the VC fundAI-Driven Financial Operations & Compliance
Automate QuickBooks invoicing, reconciliations, and expense trackingSet up AI-generated financial reports and forecasting modelsImplement automated audit trails and document security controlsProtect Business IP & Ensure Security Compliance
Structure permissioning and access control for all tools, including 1Password, Google Suite, and DocSendImplement automated alerts for unauthorized access or security risksEnsure AI-driven documentation workflows meet compliance and data security standardsQualifications
Must-Have Skills
Expertise in ClickUp, including workflow automation, reporting, and dashboard creationProficiency in Zapier and Make (Integromat) for seamless tool integration and workflow automationExperience with Slack AI and automation, including bot setup and workflow optimizationStrong knowledge of HubSpot CRM and AI-driven lead tracking and deal flow automationExperience automating inbox management in FrontFamiliarity with Loom AI and ChatGPT for AI-powered documentation and trainingFinancial workflow automation experience, including QuickBooks, Xero, and AI reportingExperience in security and access management, including 1Password, Google Suite, and DocSendStrong project management and communication skillsProven experience onboarding teams to new systems and ensuring adoptionBonus Skills
Experience with API and Webhooks for deeper integrationsFamiliarity with Retool or Airtable for internal AI-powered dashboardsNote : 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 a fast-growing creative operations company delivering high-impact digital and marketing solutions. We collaborate with high-profile clients to strategize, produce, and optimize compelling content that drives engagement, brand visibility, and business growth. Our creative team functions as a fully integrated power-house, combining strategy, design, production, and performance analysis to deliver world-class results.
We Operate Under Founder Mode
Trolley is built on a Founder Mode mindset -an operating system rooted in ownership, strategic thinking, and execution at speed. Here, we look for people who take initiative, think like entrepreneurs, and use tools like AI to optimize how work gets done. But Founder Mode isn't about going it alone, it's about working within high-trust, collaborative teams where contribution matters more than control. We value creativity, resourcefulness, and clear communication. If you're driven by impact, thrive in dynamic environments, and believe in scaling through systems, not stress -this is the place for you.
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.
Required Skills : #J-18808-Ljbffr