Operations Manager – Chief of Staff to the Founder, AI-First

About

Outsourced Staff is a company that specializes in providing high-caliber remote teams for various roles including software development, IT support, digital marketing, and customer service. With over 25 years of experience, they focus on matching businesses with exceptional talent to aid in their growth, ensuring candidates are thoroughly screened for skills and cultural fit.

The company offers a wide range of outsourced solutions, including virtual assistance, software development, and customer support, promoting efficiency and productivity for their clients.

Description

• Coordinate the content and client success teams under the Founder's direction, growing into full ownership and management of both as trust builds
• Set the operating rhythm. Chase deliverables, track client health, escalate issues, ensure SLAs are met
• Run the operational backbone so the Founder can focus on growth
• Track and flag operational issues before they reach the Founder's desk
• Drive the rollout of new tools, processes, and team initiatives
• Shadow and observe how the Founder and the teams spend their time, week by week
• Map every recurring task, decision point, and workflow across sales, recruiting, ops, content, client success, and finance admin
• Document each one as a clear, repeatable SOP, including triggers, steps, tools used, decision criteria, and handoff points
• Build a central SOP library that is searchable, maintained, and version-controlled
• Apply process-improvement principles (Six Sigma, Lean, or equivalent) to identify waste, reduce variation, cut cycle time, and improve quality
• Measure before and after. Show the numbers
• Identify which workflows can be delegated or automated with AI agents
• Turn the business from a set of habits living in the Founder's head into a documented, measurable system
• Manage the Founder's inbox across Outsourced Staff and Conversational AI. Triage, draft replies, send under direction, escalate what needs his eyes
• Run his calendar. Book meetings, defend his focus time, send reminders, prep him for what's next
• Attend meetings with the Founder. Take notes, capture decisions and actions, own the follow-through
• Daily and weekly check-ins covering priorities, deals in motion, follow-ups due, and blockers
• Post-meeting summaries drafted and sent within one to two hours of a call ending
• Sales proposals drafted and sent the same day if a request comes through before noon
• Follow up warm leads by phone when they go quiet. Typically five calls per week. ("Dom sent that proposal, where are you at?")
• Keep HubSpot hygienically moving. Update deal stages, log activity, flag stale deals, ensure leads are in follow-up sequences
• Pull together pre-call briefs so the Founder walks into every meeting prepared
• Default to Claude as your primary AI tool. Training will be provided on Claude, Claude Projects, prompt engineering, and the internal AI stack
• Use AI to draft, summarise, research, and prep faster on everything you touch
• Build and maintain light agents and automations under the Founder's direction
• Spot repetitive tasks and propose an AI-assisted way to handle them

Requirements

• 5+ years in operations, with real experience supporting a founder, CEO, or business owner directly
• Background in an outsourcing, BPO, or support services business. You understand ho