Onboarding an Outsourced Accounting Team: The 90-Day Playbook

You've decided to move to outsourced accounting. You've selected a provider. Now comes the transition—the process of handing off your financial operations to someone new.

This is where many engagements stumble. The old bookkeeper is gone (or leaving), the new team doesn't know your business, and suddenly you're missing payment deadlines and scrambling to answer basic questions.

A structured transition prevents this. Plan for 90 days from kickoff to full operation. Rush it, and you'll pay with errors and stress later.

Before Day 1: Pre-Transition Preparation

Before the engagement officially starts, lay the groundwork.

Gather Historical Records

• Financial statements: Last 2-3 years of P&L, balance sheet, cash flow
• Tax returns: Last 2-3 years of business tax returns
• Chart of accounts: Export from your accounting system
• Bank statements: Last 12 months for all accounts
• Contracts: Key customer and vendor agreements
• Prior work papers: Any CPA work papers, reconciliations, schedules

Document Current Processes

Even if informal, document how things work today:

• How do invoices get entered? Who approves payments?
• What's the monthly close process? When does it typically happen?
• Who handles payroll? Benefits? 401(k)?
• What reports do you receive? When? From whom?
• What are the key vendor relationships (bank, CPA, benefits broker)?

Clean Up Known Issues

If there are known problems—unreconciled accounts, missing documentation, messy records—address what you can before transition. It's easier to hand off clean books than to have the new team clean up while also learning your business.

Weeks 1-2: Discovery and Access

The first two weeks are about understanding and access.

Discovery Meeting

A deep-dive meeting (2-3 hours) covering:

• Business overview: What do you do? How do you make money? Who are your customers?
• Revenue model: How do you bill? Subscription, project-based, product sales?
• Expense drivers: What are the major cost categories? Any unusual expenses?
• Banking structure: How many accounts? What do they do? Credit facilities?
• Pain points: What's not working? What keeps you up at night?
• Priorities: What do you need first? What can wait?

System Access Setup

Grant access to all necessary systems:

• Accounting system: QuickBooks, Xero, NetSuite—admin or accountant access
• Banking: Read-only access or view-only user for bank feeds
• Bill pay: Bill.com, Melio, etc.—appropriate user role
• Expense management: Ramp, Brex, Expensify—admin access
• Payroll: Gusto, Rippling, ADP—accountant access
• Document storage: Google Drive, SharePoint—shared folder access

Historical Review

The outsourced team reviews your books:

• Chart of accounts structure—does it make sense? Need reorganization?
• Open balances—AR, AP, bank reconciliations, accruals
• Historical trends—revenue patterns, expense ratios, seasonality
• Red flags—unusual items, unexplained variances, potential errors

Weeks 3-6: First Close and Parallel Operations

Now the real work begins. The outsourced team closes their first month.

The First Month-End Close

This close will take longer than normal. The team is learning your business while also doing the work. Expect:

• Lots of questions: "What is this vendor? Why this expense category?"
• Discovery of issues: "This account hasn't been reconciled in 6 months"
• Process gaps: "How do you currently handle X?"
• Extended timeline: First close may take 15-20 business days instead of 10

Parallel Operations (If Possible)

Ideally, run parallel operations for the first month:

• Both teams (old and new) close the same month
• Compare results—they should match within reasonable tolerance
• Investigate differences—often reveals misunderstandings or prior errors
• Document learnings for future reference

If your prior bookkeeper is already gone, parallel isn't possible. The new team will need more support from you to answer questions.

Establish Communication Cadence

Set up regular touchpoints:

• Daily (first two weeks): Quick check-in on open questions, blockers
• Weekly (ongoing): 15-30 minute status meeting—what's done, what's pending, any issues
• Ad hoc: Slack/Teams channel for quick questions between meetings

Define Deliverables

Agree on what you'll receive and when:

• Monthly financial package: P&L, balance sheet, cash flow—by day 10?
• AP aging and upcoming payments—weekly?
• AR aging and collection status—weekly?
• Any custom reports specific to your business

Weeks 7-12: Optimization and Steady State

By month two, the outsourced team knows your business. Now focus on improvement.

Process Refinement

• AP workflow: Finalize invoice routing, approval thresholds, payment schedule
• AR process: Invoice templates, collection cadence, customer communication
• Close process: Documented close calendar with deadlines and responsibilities
• Reporting: Refine reports based on what's actually useful vs. what was assumed

Address Historical Issues

The first close often surfaces prior issues:

• Accounts that were never reconciled—clean them up
• Miscategorized expenses—correct going forward, evaluate whether to fix history
• Missing documentation—gather what's findable, document what's missing
• Prior period errors—assess materiality, decide whether to adjust

Implement Improvements

This is where outsourcing pays dividends. Good providers bring best practices:

• Automation opportunities identified during transition
• Process improvements from experience with other clients
• Technology upgrades—better integrations, new tools
• Controls improvements—segregation of duties, approval workflows

Reduce Communication Frequency

As things stabilize, shift from daily touchpoints to weekly:

• Weekly check-in becomes the norm
• Monthly financial review (post-close discussion of results)
• Quarterly business review (engagement health, scope, improvements)

Measuring Transition Success

How do you know if the transition is successful? Track these metrics.

Close Timeline

• Month 1: Close within 20 business days (grace period for learning)
• Month 2: Close within 15 business days
• Month 3+: Close within 10 business days (steady state)

Accuracy

• No material adjustments discovered after close
• Bank reconciliations match to the penny
• Intercompany (if applicable) balances net to zero
• CPA tax prep finds no significant adjustments

Responsiveness

• Questions answered within 24 hours
• Ad hoc requests completed within agreed timeframes
• No missed deadlines (tax filings, payroll, vendor payments)

Business Value

• You trust the numbers you're seeing
• You have visibility you didn't have before
• You're spending less time on accounting issues
• Your CPA/auditor comments positively on book quality

Common Transition Pitfalls

Rushing the Timeline

Trying to complete transition in 30 days instead of 90 leads to missed items, stressed teams, and errors that persist for months. Take the time to do it right.

Insufficient Discovery

Skipping the deep-dive discovery meeting means the team doesn't understand your business. They'll make assumptions—often wrong ones—that create problems later.

Incomplete Access

If the team can't access systems, they can't do their job. Delays in getting access cascade through the entire timeline.

No Internal Owner

Someone internally needs to own the relationship—answer questions, approve decisions, review output. If this person isn't designated, things fall through cracks.

Expecting Perfection Immediately

Month one will have questions and issues. That's normal. The measure of success isn't "no problems"—it's "problems get identified and resolved quickly."