Small Business Bookkeeper + Operations/Administrative Assistant

I am looking for an experienced, highly organized, proactive bookkeeper/virtual administrative assistant who can help me create systems around the financial and administrative side of my small businesses and, most importantly, reduce the amount of information and recurring responsibility that currently lives in my head. I am a small-business owner and therapist in a small mountain town in Colorado. My husband and I own and operate multiple businesses, and our lives have become increasingly complex as those businesses have grown. I am at the point where continuing to personally remember every bill, loan payment, payroll date, vendor issue, insurance renewal, employee document, bookkeeping question, grant deadline, receipt, follow-up, and administrative task is no longer sustainable. I don't necessarily need more advice about how to be organized. I need another capable person inside the system who can take ownership of recurring administrative and bookkeeping work, create reliable processes, notice when something needs attention, and bring me the things that genuinely require my decision. My goal is to move from reactive small-business management to predictable systems. THE BUSINESSES My primary areas of responsibility are: 1. 'Dera Deli 'Dera Deli is a small restaurant/deli in Silverton, Colorado. It is a highly seasonal business, with a busy summer tourism season and a much quieter winter season. The business has employees, payroll, vendors, food orders, equipment, licenses, insurance, recurring bills, loans, employee paperwork, bookkeeping, and all of the normal administrative demands of a restaurant. Because it is seasonal, cash-flow planning matters tremendously. A good summer does not necessarily mean we have unlimited cash available because the business needs to prepare for slower winter months. I am increasingly taking responsibility for the operational and financial direction of the deli and want to create systems that allow me to oversee the business without personally carrying every administrative detail. My goal is eventually to have the deli operate with a manager and well-documented systems rather than requiring an owner to physically manage every aspect of it every day. 2. My Therapy Practice I am also a therapist with a growing private/contract practice. The therapy practice is much simpler operationally than the restaurant, but I still need good organization around income, expenses, tax documentation, professional expenses, licensing-related items, insurance, and general bookkeeping. I am actively growing my clinical caseload, which means that my available administrative time is becoming increasingly valuable. An hour I spend chasing receipts or reconciling transactions is an hour I cannot spend seeing clients or with my family. 3. Other Family Businesses My husband operates other businesses, including a bike-related business and a transportation/shuttle business. Initially, I do NOT want this role to automatically absorb administration for every business we own. This is important. One of my goals is to create clearer ownership and responsibility boundaries between our businesses. The initial focus should be the businesses and responsibilities that are specifically assigned to me. If we later decide that bookkeeping or administrative support should expand to additional businesses, we can explicitly discuss the scope, hours, access, compensation, and expectations at that time. I do not want responsibilities to quietly migrate into this role simply because another business needs administrative help. WHY I AM HIRING The central problem I am trying to solve is cognitive load. Right now, too many things depend on me remembering that they exist. For example: A loan payment may be coming due. Payroll may be approaching. A vendor invoice may need to be paid. An insurance renewal may be coming. A grant may require documentation. An employee document may be missing. A bank account may need reconciliation. A piece of equipment may need repair and an invoice or warranty claim followed up on. A business license may need renewal. An accountant may be waiting for information. A credit card payment may need to be planned around cash flow. None of these tasks individually is especially complicated. The problem is that there are dozens of them happening simultaneously. I want to build a system where these things are tracked automatically and surfaced before they become urgent. I want someone who can eventually tell me: “Here are the five things that need your attention this week.” Rather than me waking up in the middle of the night remembering the fifth thing. WHAT SUCCESS LOOKS LIKE The ideal outcome is that I can open one simple dashboard, email, spreadsheet, or weekly report and understand: * Current operating cash * Upcoming payroll * Bills due this week * Bills due within the next 30 days * Loan payments approaching * Credit card payments approaching * Major expected income * Outstanding invoices * Bookkeeping questions requiring clarification * Administrative deadlines * Items waiting on someone else * Items requiring my approval or decision I do not want a complicated dashboard that takes an hour to understand. I want something simple enough that I can review it in approximately 10–15 minutes and know where things stand. BOOKKEEPING RESPONSIBILITIES Depending on experience and access, responsibilities may include: * Reconciling bank accounts * Reconciling credit card accounts * Categorizing transactions * Identifying uncategorized or questionable transactions * Maintaining clean books * Reviewing bookkeeping for obvious inconsistencies * Organizing receipts * Matching receipts with transactions when necessary * Organizing vendor invoices * Tracking accounts payable * Tracking recurring bills * Maintaining a payment calendar * Tracking loans and recurring loan payments * Helping prepare information for our accountant * Communicating with our accountant/bookkeeper when appropriate * Maintaining organized financial documentation * Helping identify expenses that appear duplicated or unusual * Monitoring subscriptions and recurring expenses * Helping us understand where administrative cleanup is needed I am not asking this person to provide tax, legal, investment, or financial-planning advice. Those decisions will continue to involve our CPA/accountant and other professionals. What I need is accurate information and organization so that I can make informed decisions with those professionals. CASH-FLOW ORGANIZATION This is particularly important to me. Because our restaurant is seasonal, simply knowing the current bank balance is not enough. I want help developing a rolling view of cash requirements. For example: If the bank account contains $20,000 but: * payroll will require $12,000, * a loan payment of $2,000 is due, * a credit card payment of $3,000 is approaching, * and $5,000 of vendor invoices are outstanding, I don't want to mentally experience that as “we have $20,000.” I want the system to tell me what is actually available after known obligations. I would like help developing a very simple rolling 30-, 60-, and eventually 90-day cash-flow picture. It does not need to be sophisticated financial modeling. It needs to be accurate enough to help us anticipate problems. ACCOUNTS PAYABLE / DEADLINE MANAGEMENT I would like one centralized system for recurring financial obligations. This might include: * Loan payments * Credit cards * Utilities * Insurance * Payroll * Payroll taxes * Vendor payments * Rent or mortgage-related obligations * Software subscriptions * Licenses * Professional fees * Equipment payments * Annual renewals * Other recurring expenses Each obligation should ideally include: * Amount, if fixed * Typical amount, if variable * Due date * Frequency * Payment method * Account it is paid from * Whether it is automatic * Any relevant login/document information * Person responsible * Notes I want to eliminate situations where a payment becomes urgent because someone remembered it three days before it was due. RESTAURANT ADMINISTRATION 'Dera Deli has a number of administrative responsibilities beyond traditional bookkeeping. Depending on the candidate's skills and available hours, I would eventually like help with: * Vendor documentation * Invoice organization * Employee files * Onboarding checklists * Payroll documentation * Workers' compensation paperwork organization * Insurance documents * License and permit tracking * Food-service-related renewals * Employee certification tracking * Grant documentation * Equipment records * Warranty information * Maintenance records * Recurring ordering information * Standard operating procedures * Staff contact information * Digital file organization I am NOT necessarily expecting one person to immediately take responsibility for all of these things. I am describing the larger environment so that candidates understand where this role could eventually grow. SYSTEM CREATION One of the most valuable things this person can do is help turn recurring tasks into documented processes. If something happens every week, month, quarter, or year, I would like it documented. For example: **Weekly:** * Reconcile certain transactions * Review cash * Review upcoming bills * Review payroll needs * Identify bookkeeping questions * Send owner summary **Monthly:** * Complete bank reconciliations * Complete credit card reconciliations * Review P&L * Review recurring subscriptions * Review outstanding payables * Prepare information for accountant if needed **Quarterly:** * Review licenses/renewals * Review insurance documentation * Review employee records * Review major upcoming seasonal expenses **Annually:** * Prepare bookkeeping for tax season * Organize contractor/employee documentation * Review business licenses * Archive previous year's documents * Establish new annual administrative calendar I want the system documented so that the business does not become dependent on one person's memory—including the VA/bookkeeper's memory. DIGITAL ORGANIZATION Our digital files also need structure. I would like help developing a straightforward folder system for documents such as: * Banking * Taxes * Payroll * Employees * Insurance * Loans * Vendors * Grants * Licenses * Equipment * Legal documents * Accountant correspondence * Monthly financial reports * Receipts * Contracts The goal is that if I need an insurance policy, loan document, employee form, or vendor invoice six months from now, I know where it is. COMMUNICATION STYLE I am busy and do not want dozens of messages throughout the day unless something is genuinely urgent (email is a nightmare for me to manage). I would prefer a communication system where routine questions are grouped together. For example: **Needs decision:** 1. Vendor invoice needs approval. 2. Transaction needs categorization. 3. Insurance renewal has two options. **FYI:** 1. Bank account reconciled. 2. Payroll documentation filed. 3. Vendor statement received. **Upcoming:** 1. Loan payment due Friday. 2. Payroll next Tuesday. 3. Insurance renewal due next month. That style of communication would be extremely helpful. I want someone who knows the difference between: “This can wait until our weekly check-in.” and “Megan needs to know about this today.” PROACTIVITY This is probably the single most important personality characteristic for this role. I do not want someone who sees a potential problem and assumes I already know about it. If you notice that a $2,000 loan payment is due in five days and the account contains $1,200, I want you to tell me. Ideally, I want something like: “The $2,000 payment is scheduled for Friday. The account currently has $1,200. I see $600 of expected deposits, which would still leave us approximately $200 short. How would you like to handle this?” That is incredibly useful. A message on Friday saying: “The payment bounced.” is not useful. I am hiring someone specifically to help us move from reactive management to proactive management. INDEPENDENCE WITHOUT OVERSTEPPING I want someone comfortable taking ownership of processes while understanding where owner approval is necessary. For example: I would be comfortable with someone independently: * Organizing documents * Reconciling transactions * Updating spreadsheets * Maintaining calendars * Following up for routine documentation * Flagging missing receipts * Preparing reports * Identifying deadlines I would expect approval before: * Moving significant amounts of money * Paying unusual/non-recurring expenses * Opening or closing financial accounts * Changing payroll * Entering contracts * Making legal decisions * Making tax decisions * Making significant operational commitments Good judgment around this distinction is important. CONFIDENTIALITY This role will involve access to sensitive business and financial information. Discretion is essential. The candidate must be comfortable following secure practices for: * Passwords * Banking information * Employee information * Financial documents * Tax records * Business records Because I am also a therapist, it is especially important that the person understands that my clinical work involves confidential information. This role should NOT require access to psychotherapy notes or unnecessary protected client information. The bookkeeping/administrative system for my therapy business should be designed to minimize access to confidential clinical information. IDEAL EXPERIENCE Strong candidates may have experience with: * Small-business bookkeeping * QuickBooks * Square * Restaurant bookkeeping * Hospitality businesses * Seasonal businesses * Owner-operated businesses * Multiple business entities * Payroll * Accounts payable * Cash-flow tracking * Google Workspace * Excel or Google Sheets * Digital document organization * Administrative operations * Professional practices * Working directly with entrepreneurs or family-owned businesses Restaurant experience would be especially useful because restaurant finances and operations can be messy and fast-moving. Experience with seasonal businesses would also be valuable because our cash flow changes dramatically throughout the year. PERSONALITY FIT I would probably work best with someone who is: * Calm * Extremely organized * Direct but kind * Comfortable with imperfect systems * Curious * Resourceful * Nonjudgmental * Reliable * Proactive * Good at follow-through * Able to prioritize * Comfortable saying, “I noticed something we should look at.” * Comfortable asking for clarification * Not easily overwhelmed by a backlog I do not need someone to be impressed by how busy we are. I need someone who looks at the situation and thinks: “Okay. Let's build a system.” WHAT I DON'T WANT I do not want: * Someone I have to chase * Someone who requires detailed instructions for every recurring task * Someone who creates overly complicated spreadsheets no one uses * Someone who waits until something becomes urgent to mention it * Someone who silently guesses how transactions should be categorized * Someone who makes financial decisions without authorization * Someone who tries to become our financial adviser without the appropriate credentials * Someone who casually expands their scope into other family businesses without discussion * Someone who makes me feel like I hired another person I have to manage FIRST 30 DAYS I envision the first month as an onboarding and cleanup period. **Week 1: Understand** Learn: * Business structure * Accounts * Existing bookkeeping systems * Major recurring expenses * Payroll schedule * Vendors * Loans * Credit cards * Current administrative systems * Who our professional advisers are * What information is currently missing Create a list of questions rather than trying to fix everything immediately. **Week 2: Organize** Begin: * Account reconciliation * Transaction cleanup * Document organization * Accounts-payable calendar * Recurring payment list * Administrative deadline list * Digital filing structure Identify obvious gaps. **Week 3: Systemize** Develop: * Weekly financial summary * Cash-flow snapshot * Owner decision list * Recurring task checklist * Bookkeeping workflow * Administrative calendar Begin documenting processes. **Week 4: Stabilize** Review: * What has been accomplished * What remains messy * What tasks should become recurring * What tasks should remain with the owner * What tasks should go to the accountant * What tasks may eventually be delegated elsewhere Then recommend an appropriate ongoing weekly workload. ONGOING HOURS I am thinking approximately five hours per week initially. I am open to adjusting that once we understand the actual workload. There may be weeks when fewer hours are needed and periods—tax preparation, seasonal transitions, employee onboarding, grant deadlines, etc.—when additional hours make sense. I am interested in building a long-term relationship with the right person rather than constantly hiring different freelancers for individual administrative tasks. LONGER-TERM VISION Over the next year, I want to significantly simplify how our businesses operate. For the restaurant specifically, my goal is to move toward: * Reduced owner dependence * Clear financial reporting * Predictable staffing systems * Documented procedures * Better seasonal planning * Better cash-flow forecasting * Cleaner bookkeeping * Organized employee administration * A management structure that eventually allows a manager to run day-to-day operations I want to remain involved in strategy, finances, hospitality, community relationships, and major decisions without being required to personally remember and execute every administrative detail. The right person could play an important role in helping us reach that point. THE CORE PROBLEM I NEED YOU TO SOLVE If I could summarize the entire job in one sentence, it would be: Help me build reliable systems so that running my businesses no longer depends on me remembering everything. I am capable of making decisions. I am capable of solving problems. I am capable of understanding the finances. What I don't have is unlimited bandwidth. I need the information organized, recurring tasks handled, deadlines anticipated, and problems surfaced early enough that I can make thoughtful decisions rather than constantly responding to emergencies. I want to spend more of my time on the things only I can do: * Seeing therapy clients * Leading the direction of the deli * Making strategic financial decisions * Supporting employees * Developing the business * Pursuing grants and opportunities * Spending time with my children and family * Having an actual life outside of administration And I want to spend considerably less time: * Searching for documents * Remembering due dates * Tracking down receipts * Wondering whether something was paid * Discovering upcoming payments at the last minute * Cleaning up bookkeeping * Maintaining mental lists * Repeatedly solving the same administrative problem HOW I WILL KNOW THIS IS WORKING Three months from now, I would like to feel that I can answer the following questions quickly: What cash do we actually have available? What is due this week? What is due this month? When is payroll? What major expenses are coming? Are the books current? What does the deli's financial performance look like? What administrative deadlines are approaching? What decisions do I personally need to make? What is waiting on someone else? And most importantly: What do I NOT need to think about because someone capable is already handling it? That last question is the reason I am hiring. I am looking for someone who can become a trusted administrative and bookkeeping partner—not another item on my to-do list.