Senior Associate, Accounting & Operations

Boring Stuff; United States; Remote; USD 85,000 - 125,000; Full time

Benefits offered by this job

Full health insurance

401k

Unlimited PTO

Remote-friendly

Job summary

Boring Stuff is seeking a Senior Associate, Accounting & Operations to handle core accounting and operations across client entities. You will own the close, AP/AR, payroll coordination, and HR/compliance tasks in a fast-growing, creator-focused firm.

You'll work across QuickBooks Online, Gusto, and multiple clients, requiring sharp technical skills, calmness under pressure, and strong communication with non-finance stakeholders.

Qualifications

• You know QuickBooks Online inside & out: reconciliations, chart of accounts, multi-entity management, close process.
• You’ve done real bookkeeping across multiple clients/entities.
• Understand basic entity structures: S-corps, LLCs, C-corps and related questions.
• Strong Excel/Google Sheets skills: SUMIFS, data cleanup, basic financial modeling.
• Experience with 1099s, payroll software, and tax prep coordination.
• Clear communication with non-finance people.
• Relentless follow-through; pursue missing docs and sign-offs.
• Discretion with sensitive financial information.
• Open to remote work with a preference for Greater LA and travel to LA.

Responsibilities

• Own month-end close and reconciliations across multiple client entities in QuickBooks Online.
• Produce monthly P&Ls, balance sheets, and cash flow statements on time.
• Support quarterly estimated tax calculations and client communications.
• Coordinate with CPAs and EAs for year-end returns and documentation.
• Prepare and file 1099s across client entities at year end.
• Run AP/AR and payroll coordination using Gusto and brand systems.
• Assist onboarding of new clients and assess their books for cleanup.
• Maintain internal tracking in Airtable and Google Drive.
• Draft and manage contractor agreements, onboarding documents, and HR compliance.

Skills

QuickBooks Online

Excel & Sheets

Multi-entity bookkeeping

Reconciliations

Communication

Attention to detail

1099s & payroll

Discretion

Tools

Gusto

Ramp

Bill.com

Lumanu

Airtable

Google Drive

Job description

About Boring Stuff

We’re a back-office partner for creators and creator-led companies — from solopreneurs to multi-entity production companies. We handle finance, accounting, operations, and HR so our clients can focus on building. We’re a small, serious team that gets results without a lot of noise. We’ve grown exponentially over the last year-and-a-half and are looking to add to our team.

The Role

We’re hiring a Senior Associate, Accounting & Operations to work across all aspects of our business. The accounting side is the foundation: you need to be able to open a client’s QuickBooks, understand what you’re looking at, and own the close. But this role is much bigger than bookkeeping. You’ll be in the middle of everything: AP/AR, payroll, tax prep coordination, HR compliance, client onboarding, vendor negotiations, and whatever else walks through the door on any given day.

Our clients are creator businesses. Some are solo operators making mid-six figures. Some are multi-entity production companies with W-2 staff, brand deals, and equity structures. No two are alike and no two days are alike. You’ll need to be technically sharp, calm under pressure, and able to shift gears constantly.

This is an early role at a growing company. The scope expands fast for the right person.

What You’ll Do

Accounting & Finance

• Own month-end close and reconciliations across multiple client entities in QuickBooks Online.
• Produce monthly P&Ls, balance sheets, and cash flow statements for clients on time, every month.
• Support quarterly estimated tax calculations and communicate proactively with clients about their liability.
• Liaise with our CPAs and enrolled agents to prep for year-end returns by organizing records, flagging issues and drafting client communications.
• Prepare and file 1099s across client entities at year end.
• Identify and flag entity structure issues: misclassified contractors, S-corp election problems, missing documentation.

Operations & AP/AR

• Run AP/AR for clients by coordinating with vendors, chasing invoices, navigating brand payment systems, ERPs, and whatever proprietary system a Fortune 500 brand insists you use.
• Coordinate payroll processing in Gusto and flag discrepancies before they become problems.
• Chase down missing documents, signatures, statements, and information persistently and professionally.
• Help onboard new clients, assess the state of their books, identify cleanup needed, and get them onto our systems.
• Maintain and improve internal tracking systems in Airtable and Google Drive.

HR & Compliance

• Draft and manage contractor agreements, offer letters, and onboarding documents.
• Run I-9 verifications and support HR compliance for clients adding W-2 staff.
• Coordinate benefits enrollment and flag compliance deadlines across clients.
• Liaise with attorneys and licensed professionals when matters exceed our scope.

What We’re Looking For

• You know QuickBooks Online inside & out. Reconciliations, chart of accounts, multi-entity management, the close process. This is non-negotiable.
• You’ve done real bookkeeping across multiple clients or entities simultaneously, not just one company’s books.
• You understand basic entity structures, S-corps, LLCs, C-corps, and know what questions to ask when something doesn’t look right.
• You’re strong in Excel and Google Sheets: SUMIFS, data cleanup, financial modeling at a basic level.
• You’ve worked with 1099s, payroll software, and tax prep coordination in a professional setting.
• You communicate clearly with non-finance people. Our clients are creators, not CFOs.
• You are relentless about follow-through. You chase missing statements, you follow up twice, you don’t let things stall.
• You handle sensitive financial information for prominent clients with complete discretion.
• You’re open to remote work, with a preference for candidates in the Greater LA area and willingness to travel to LA periodically.

Bonus

• Experience filing or preparing individual or business tax returns (PTIN a plus), or actively working toward an EA or CPA.
• Familiarity with Gusto, Ramp, Bill.com, or Lumanu.
• Experience working with entertainment, media, or creator-adjacent businesses.

How We Work

Execution over optics. No unnecessary meetings, no decks. Work is done when the job is done.

April 1–15 is all hands on deck — our tax season crunch, working directly alongside our CPAs and EAs on live client returns.

If you’re on an EA or CPA track, this is real, hands-on tax season experience most staff-level roles won’t give you this early. Outside of that window, your time is your own as long as the work is getting done.

What You Get

• Direct exposure to how creator businesses actually operate at the financial and operational level.
• A path to grow into senior responsibilities fast. We’re scaling and the scope expands with performance.
• High ownership, low politics, no busywork.
• Flexible and remote-friendly outside of tax season.
• Real tax season experience alongside our CPAs and EAs (valuable if you’re building toward an EA/CPA credential).
• Behind-the-scenes access to some of the most interesting businesses in the creator economy.
• Full health, 401k.
• Unlimited PTO (apart from April 1–April 15).