Chief Operations Specialist

About the RoleThis is not a typical executive assistant position.We're looking for a forward-thinking chief operations specialist with potential to lead future growth initiatives who builds efficient systems, owns outcomes, and drives productivity.You'll work directly with a strategic leader managing multiple high-growth ventures across commercial construction, lead generation, nonprofit leadership, property management, and family.The leader needs someone who can anticipate needs, convert ambiguity into actionable plans, and relentlessly close loops.The GoalExpand capacity and increase velocity of execution through process improvements, AI automation, and proactive operational support.About the VenturesAll ventures are in growth mode, and most do not have formal processes yet.You'll solve for and document processes to allow rapid onboarding of future hires with repeatable results.Strategic Markets Leader for Healthcare and Public Projects at this Commercial General ContractorIndustry networking agency launching a new high-ticket service offeringBoard Member for a nonprofit focused on workforce development in construction tradesRental Property – Management of two rental unitsWho We're Looking ForWe need a systems-thinker with high agency who is AI-native, proactive, and relentlessly follows through.You should be comfortable with ambiguity, able to convert loose ideas into structured action plans, and driven to improve workflows weekly.Critical mindset: We're looking for critical thinking over task-execution.You should anticipate needs, propose solutions, and own outcomes—not just execute orders.Personality Traits of Successful Candidates:Proactive and calm under pressureHighly organized and goal-orientedSystems-first thinker with high agencyPushes for clarity and closes loops consistentlyLow-ego, coachable, rigorous about details and dataComfortable saying 'no/next' to protect prioritiesOperational Cadence & ResponsibilitiesWeekly Rhythm:Owning and managing family/school/kids' activities, professional meetings, travel, and reservationsSending a Friday Weekly Brief: next week at a glance, risks flagged, top 3 priorities identifiedInbox & Communications:Triage emails and meeting invites dailyFiling receipts and managing reimbursementsMaintaining stakeholder communication loopsTask System:Maintaining a running capture board across all venturesConverting texts/voice notes ? tasks with deadlinesConfirming task owner and status; nudging until doneResearch & Automation:Conducting project research and generating executive summariesWeb scraping and competitive trackingAutomating report generation and research tasksContact enrichment and CRM loggingPublic records, permits, budgets researchSOP Engine:Recording Looms of recurring tasksShipping 1+ SOP per week to the vaultDocumenting processes to enable future team scalingIterating and refining edge casesFamily/Personal Operations:Managing school communications and kids' calendarsCoordinating family travel and summer camp planningHandling household-related administrative tasksAi & Systems Improvement:Proposing workflow automation improvements weeklyImplementing AI tools to increase efficiencyBuilding and optimizing capture ? triage ? plan ? execute systemsRaising quality bars continuouslyRequired Skills & ExperienceMust-Have:1–2 years minimum executive assistant or operations experienceAdvanced AI literacy: Fluent with ChatGPT, Copilot, and Perplexity; strong prompt crafting abilitiesCalendar triage & stakeholder management: Expert-level scheduling and communication coordinationResearch skills: Public records, permits, budgets, market intelligenceSOP creation: Ability to document processes via Loom-to-SOP workflowExcel/Power BI basics: Structured data work and simple reportingClear written English: Concise, action-oriented communication styleSecurity hygiene: Understanding of role-based access and data protectionDocumentation discipline: Rigorous attention to detailStrong interest in AI use cases and implementationNice-to-Have:Basic Python or no-code automation experience (Zapier, Make, n8n)AEC familiarity: Procore, RFQ/RFP exposureWeb scraping capabilitiesHubSpot or CRM management experienceContact enrichment skills (LinkedIn, research tools)Power BI visualization and dashboard creationGolf handicap lookup experience (when relevant for relationship building)Tools & Platforms You'll UseEmail/SMS (Google & Microsoft suites)Ninety.io (project/goal management)ChatGPT, Copilot, Perplexity (AI tools – critical)Slack, Discord, Telegram (team communication)SharePoint, Google Workspace, MS Teams (document management)Excel (data organization)Additional tools to be collaboratively identifiedWhat We OfferFull-time position: 40 hours per weekConsistent schedule: 8:00 AM – 5:00 PM EST, Monday–FridayFully remote: Work from anywhereDirect collaboration with an entrepreneurial leaderExposure to multiple industries: Construction, lead generation, nonprofit, real estateGround-floor opportunity: Help build foundational systems for scaling venturesLearning environment: Strong focus on AI implementation and automationCompany Culture & ValuesCulture in one line: We are problem solvers—systems over heroics—and the whole is greater than the sum of its parts.Core Values:IntegrityGrowth MindedIn Service to OthersProvide SolutionsOnboarding & SupportThere is currently no formal onboarding program—this will be part of the early partnership.You'll collaboratively identify the tools and support structures needed to achieve great outcomes.This is an opportunity to help shape the operational foundation from the ground up.Application ProcessPlease send the following to Resume: As a PDF titled (Lastname.Firstname.ExecutiveAssistant.pdf)Cover Letter addressing:How you meet the required skills and experienceSpecific examples of systems or SOPs you've builtYour experience with AI tools (ChatGPT, Copilot, Perplexity, automation tools)A time you anticipated a leader's needs and proactively solved a problemHow you've closed loops and driven projects to completionWhy you're interested in supporting multiple ventures simultaneouslyAi Competency Example: Share a specific example of how you've used AI tools to automate a workflow, solve a problem, or improve efficiencyEmail Subject: Systems Over HeroicsTimeline: We aim to fill this position within 2–3 weeks.Well-structured and thoughtful applications demonstrating critical thinking and systems-first approach will stand out.If you have questions about the role, feel free to include them in your message.