Finance & HR

Get a Rippling specialist working in your account

You already know what needs to happen inside Rippling. The problem is finding the time and the right person to do it correctly. Trusty Oak's fractional specialists work directly inside your Rippling account, handling the configuration, maintenance, and cross-functional workflows you've been putting off. This is not advisory support. This is someone who logs in, does the work, and documents what they built.

What our team does with Rippling

Concrete work our fractional specialists take on inside your Rippling account. No vague promises.

Build and configure employee onboarding workflows

We set up onboarding flows inside Rippling Workflow Automator, including task assignments, document requests, and app provisioning triggers tied to start date and department. Each workflow is configured to match your actual org structure, not a generic template. You get a documented flow you can hand to any new HR team member.

Administer payroll runs and resolve discrepancies

We manage scheduled payroll runs, verify hours and deductions before submission, and investigate any flagged discrepancies in pay stubs or tax withholdings. This includes reconciling PTO balances, commission inputs, and contractor payments within the same pay cycle. We flag anything that needs your sign-off before processing.

Manage benefits enrollment and carrier connections

We configure open enrollment windows, update plan options, and ensure carrier connections are syncing correctly through Rippling's benefits administration module. When employees have enrollment questions that require account-level answers, we pull the data and route it appropriately. We also audit dependent and beneficiary records for accuracy.

Audit and clean up your Rippling account structure

Over time, Rippling accounts accumulate orphaned roles, misconfigured permission groups, and outdated app assignments. We conduct a full audit of your company's org chart, custom fields, and security groups, then correct what's broken and document what changed. This is especially valuable before a compliance review or after a period of rapid hiring.

Set up custom reports and workforce analytics

We build custom reports inside Rippling using your actual workforce data, covering headcount by department, turnover trends, compensation bands, and time-off usage. Reports are scheduled to deliver to the right stakeholders on the cadence you define. Where Rippling's native reporting has gaps, we export and format data for use in connected tools like Google Sheets or Excel.

Integrate Rippling with your existing HR and finance stack

We configure and maintain Rippling's native integrations with tools like QuickBooks, Xero, Greenhouse, Slack, and Google Workspace, including field mapping, sync schedules, and error handling. For integrations not available natively, we build connections through Zapier or Make using Rippling's API endpoints. Every integration is documented with a data flow map so your team knows exactly what moves where.

How Trusty Oak supports Rippling workflows

How the Rippling handoff works

At the start of an engagement, your Client Success Manager reviews your existing Rippling setup with the assigned specialist, identifying what is configured correctly, what is broken or incomplete, and what is missing entirely. From that audit, we build a prioritized task list that maps to your immediate pain points first. Your specialist works inside your Rippling account using access you control, and every workflow, report, or configuration change is documented so you always know what was done and why. You approve anything that affects payroll, benefits elections, or employee records before it goes live. This is ongoing operational support, not a one-time project, and the scope adjusts as your needs change month to month.

Common Rippling workflows we build

A few of the most common workflows our team has deployed with Rippling.

New hire offer accepted → Rippling onboarding flow → app access provisioned on day one

When a new hire's status is updated in your ATS (such as Greenhouse or Lever), we trigger a Rippling onboarding workflow that assigns I-9 and direct deposit tasks, provisions role-appropriate apps, and notifies the manager. The employee arrives on day one with accounts ready, not waiting.

Payroll close → QuickBooks journal entry → finance team notified

After each payroll run is approved in Rippling, we verify the QuickBooks sync has posted correctly to the right expense accounts and cost centers. If the sync fails or maps incorrectly, we catch it before your books are closed and correct the entry manually.

Employee termination → app deprovisioning → final pay calculation reviewed

When a termination is initiated in Rippling, we execute the offboarding checklist: revoking app access in the correct sequence, verifying accrued PTO payout calculations, and confirming the final paycheck reflects any outstanding reimbursements or deductions.

Open enrollment window opens → employee completion tracked → stragglers flagged

We configure the enrollment window in Rippling, monitor completion rates by department throughout the period, and send targeted reminders to employees who have not yet made their elections. Before the window closes, we do a final audit to confirm all elections are saved and carrier connections have no sync errors.

Headcount report requested → Rippling data pulled → formatted dashboard delivered

We build a recurring headcount report inside Rippling that segments employees by department, location, employment type, and tenure, then exports to a formatted Google Sheet or Excel file on a weekly or monthly schedule. Stakeholders receive a clean, consistent view without having to log into Rippling themselves.

What Rippling support costs

Drag the sliders to build a monthly plan that fits your workload.

Executive Assistants

~$35/hour

10 hours $350

Specialists

~$50/hour

20 hours $1,000

Fractional Executives

~$95/hour

0 hours $0

Your monthly budget

$1,350

Starting at $1,000/month. One-time $300 onboarding fee includes your Strategic Delegation Plan.

Book a Discovery Call

Frequently asked questions

Do I have to give Trusty Oak admin access to my Rippling account?

You control the access level. Most clients create a dedicated user account for their specialist with the permissions needed for the specific tasks in scope, such as payroll admin, HR admin, or IT admin, without granting full super-admin access. We work within whatever permission structure you set up, and we recommend documenting the access level as part of your onboarding plan.

Is this a one-time setup project or ongoing support?

Engagements start with a 3-month commitment, which gives enough time to complete an audit, build out workflows, and establish a maintenance cadence. After that, it moves month-to-month. Most Rippling clients keep a specialist on retainer for recurring work like payroll runs, benefits administration, and report delivery rather than treating it as a one-time project.

What if I only need a few hours a month inside Rippling?

Trusty Oak's monthly talent budgets start at $1,000 per month, and Rippling specialists bill at $50 per hour, which works out to roughly 20 hours of capacity. Unused hours roll over, so lighter months do not go to waste. If your Rippling workload is genuinely minimal, your Client Success Manager can help you assess whether a blended engagement with an Executive Assistant at $35 per hour makes more sense for the mix of tasks you have.

We're considering switching from a competitor like Gusto or Deel to Rippling. Can you help with that migration?

Yes. We have handled migrations into Rippling from other payroll and HR platforms, including data mapping, historical record imports, and reconfiguring benefit carrier connections in the new environment. Migration work is scoped during onboarding so you know what to expect in terms of hours and sequencing before we start.

Rippling is expensive. What if we decide it's not the right platform after all?

That is a fair concern, and we will not push you to stay on a platform that is not working for your business. If during the audit we find that Rippling is underutilized or misconfigured in ways that make it feel more painful than it should be, we will tell you directly. In some cases the right fix is better configuration, not a platform switch. If a switch makes more sense, we can help you evaluate alternatives and manage the transition.

Get a Rippling audit this week

Book a discovery call and we will review your current Rippling setup, identify what is broken or missing, and hand you a prioritized action plan before your first billing cycle starts.