Executive Assistant / Operations Coordinator

We're a fast-growing home maintenance startup on a mission to take the stress, guesswork, and dropped balls out of home ownership — so our clients can actually enjoy their homes instead of worrying about them. We partner with homeowners to keep their properties safe, healthy, and running the way they should. We're growing fast. Things move quickly, priorities shift, and no two days look the same. We need someone who doesn't just keep up with that pace — they thrive on it. If you are looking for a predictable, process-heavy role inside a large organization, this is probably not the right fit. But if you want to be right next to the founder, own things from day one, and help build something that actually matters to people's lives and health — keep reading. The Basics Title: Executive Assistant / Operations Coordinator Location: High preference for candidates in Mamaroneck, New Rochelle, Larchmont area of Westchester County, NY Work Style: Primarily hybrid/remote to start — but we love having you close, and are securing office/garage space this summer for some office days Schedule: Full-time, Monday–Friday, 40 hours/week Salary: $75,000–$90,000 depending on experience Benefits: No health insurance currently (we're working towards that asap!) Health stipend open to discussion. Reports To: Founder, directly Key Tools: Jobber, HubSpot, CompanyCam, Google Workspace (Gmail, Calendar, Sheets) The Market Opportunity Home maintenance in the United States is a $600 billion market — and it is almost entirely broken. Most homeowners manage a patchwork of unreliable vendors with no coordination, no follow-through, and no single point of trust. Things fall through the cracks. Homes deteriorate. Families live with nagging problems because finding the right help is too hard. Every home has a maintenance schedule that should be followed—just like cars need regular oil changes and people need regular dental visits, our homes are no different. Most homeowners don't know this. We're on a mission to change that: helping homeowners live healthier and bringing awareness to a subject that's long been overlooked. The Growth Story In just over a year, we have grown from 75 recurring client households to over 160 — and we are still climbing. Almost entirely on referrals. Clients do not just use us, they tell their neighbors. That kind of organic, word-of-mouth growth in a market this large is not an accident — it is proof of something real. We have found product-market fit. Now we need to build the operational foundation to scale it. That is where you come in. The person who steps into this role is not filling a seat. They are helping to build the infrastructure of a company with the potential to become the defining brand in residential home maintenance. The ceiling here is genuinely high — and we are just getting started. The Opportunity You will be one of the first full-time hires at Home Upkeepers. That means you will have a front-row seat to how a company gets built — and a real hand in building it. You will work directly alongside the founder, which means you will see and touch every part of the business. You will know what's on his plate before he does. You will be the person who makes sure the important things don't fall through the cracks — with the crews, with clients, with operations, with everything in between. This is not a role where you wait to be told what to do. The best version of this person spots a problem before it becomes a fire, builds a solution before anyone asks for one, and takes genuine pride in running things well. We are not a perfect company. We are figuring things out as we grow. What we are is honest, ambitious, scrappy, and deeply committed to the people we serve. The opportunity for growth is limitless, and if that excites you, you will fit right in. Why This Matters Our clients are real people — busy families, working professionals, older homeowners — who depend on us to keep their homes safe and healthy. A dryer that doesn't dry, a disgusting dishwasher, dirty HVAC filters — these aren't inconveniences, they're health and energy problems. The work we do has a direct impact on how people live. The person in this role is a big part of making that work happen. What You'll Do The honest answer is: a lot. And that list will evolve as we grow. Here is what the core of the role looks like right now: Own the founder's calendar, inbox, and communications — proactively, not reactively Serve as the trusted first point of contact for incoming calls, emails, and texts on the founder's behalf — know when to handle independently and when to loop him in Draft, send, and monitor business correspondence: lead follow-ups, client confirmations, vendor outreach, and ad hoc communications Triage the daily priority list with the founder each morning; anticipate needs and surface action items before they become bottlenecks Draft communications, proposals, and updates on the founder's behalf Operations Coordination Own the full pre-visit workflow: scheduling, renewal tracking, reminder emails, materials orders, and client prep communications Manage day-of-visit operations: monitor crew progress, update Jobber and CompanyCam in real time, send client updates, and handle any job-day communications Handle post-visit tasks: receipts, visit checklists, new-client sneak-peek previews, and polished summary emails Coordinate crews, clients, and gear to deliver the best possible experience for our clients Maintain the lead-to-client funnel: enter new leads into Jobber and HubSpot, prepare new customer sheets, upload property photos, and trigger CompanyCam setup Track inventory across company supplies and client-managed materials; coordinate restocking with the operations team Build and manage operational processes that don't exist yet — and make them stick Maintain accurate, up-to-date client records across all platforms (Jobber, HubSpot, Google Sheets) Process and organize invoices; manage pre-visit administrative preparation for upcoming jobs Support weekly payroll processing and financial record-keeping Maintain and expand the company's email template library; audit Google Calendar invites for accuracy and proper scheduling cadence Maintain procedural documentation and flag opportunities to streamline existing workflows Client & Crew Relations Send timely, warm client communications: ahead-of-visit emails, arrival-window reminders, and renewal notices Manage the client referral gift program: track referrals, write thank-you notes, and coordinate gift sends Administer the tip thank-you card program: log tips, coordinate with crew leads, and ensure cards are written and mailed regularly Serve as the communication bridge between the office and crew leads for operational needs, troubleshooting, and real-time updates Spot problems before they become crises and solve them without being asked Over time, you will grow into whatever you are capable of. If you want more responsibility, you will have it. If you want to build a team under you, that opportunity will come. We promote from within and we invest in the people who invest in us. Who You Are We care more about how you think and operate than where you went to school or what your last title was. Here is what matters to us: Detail-obsessed — you notice the wrong name in a template before it goes out, and you care that it matters Flexible by nature — you can hold a structured daily cadence and drop it mid-sentence to handle something urgent without losing your place A clear, professional communicator — in writing especially; you represent a brand clients trust with their homes Self-directed — you manage your own time, flag issues proactively, and don't need to be reminded twice Comfortable managing up — you can be direct with a busy founder, keep conversations on track, and advocate for your own time and priorities Tech-comfortable — you pick up new tools quickly; CRM or scheduling platform experience is a strong plus Service-minded — you understand that in a home services business, the client experience starts with the first email and every communication in between Genuinely adaptable — you are okay with a job description that grows, because in a business growing this fast, it will You thrive in ambiguity and get energized, not anxious, when there is no playbook You are locally rooted in or near Westchester County and available in person when it counts Especially Exciting You've worked at a startup or small company before. You know what it feels like to figure things out as you go, to wear three hats at once, and to take real pride in a company's success because you helped build it. Nice to Have Prior experience in home services, field services, or a similarly logistics-heavy industry Familiarity with Jobber, HubSpot, or CompanyCam Background in office administration, executive assistance, or operations coordination at a small business Experience supporting a small business owner in a high-trust, high-autonomy environment Comfort working independently with minimal oversight while remaining communicative and accountable How to Apply Please submit your application using this link: We read every response carefully — your answers matter more than your resume, which is optional to include. No cover letter required. We will be responding to every application, targeting initial conversations with top candidates, starting the week of June 15th. #J-18808-Ljbffr Home Upkeepers