How I joined Chairish as its second finance hire, mapped the full outsourced finance operation, determined what to insource, and built the internal infrastructure that saved $200K per year while improving speed and control.
Chairish was a rapidly growing Series A marketplace for vintage and high-end furniture. In the company's earliest stage, outsourcing accounting, payroll, tax, and other finance activities had been practical — external providers gave Chairish access to specialized support without requiring a full internal finance organization.
As transaction volume, headcount, and reporting requirements increased, however, the outsourced model became more expensive and less responsive to the company's needs. I joined as its second finance hire and helped determine which financial processes the company was ready to own internally.
Chairish's finance operations were distributed across several external service providers. The outsourced model had created challenges that became more visible as the company grew: financial information spread across multiple providers and systems, routine questions requiring back-and-forth with external teams, internal leaders lacking immediate access to the information they needed, and processes that had developed separately rather than as one connected operating system.
The company was paying for external support across accounting, payroll, tax, and finance operations — but much of the institutional knowledge remained outside the business.
The question was not simply whether employees could perform the same tasks for less money. It was whether Chairish had reached the point where internal ownership would produce better financial information, faster decision-making, and stronger operating controls.
Bringing finance operations in-house would affect nearly every employee and department. Accounting needed to remain accurate and timely. Employees still needed to be paid correctly. Tax filings could not be missed. A poorly managed transition could have resulted in missed payroll, delayed financial reporting, inaccurate account balances, or tax compliance issues.
At the same time, leaving the structure unchanged would preserve an expensive and increasingly fragmented model.
I first documented the work being performed across accounting, payroll, tax, and finance operations — which providers performed each activity, what the company paid for those services, how frequently the work occurred, which systems were involved, and where errors most frequently occurred.
This process revealed that the company was not only paying for technical work. It was also absorbing the cost of coordinating multiple providers, reconciling different sources of information, and responding to questions from people who lacked day-to-day context on the business.
I did not assume that every activity should be brought in-house. I evaluated each function based on cost, frequency, complexity, risk, required expertise, need for company-specific context, and responsiveness requirements. Some work — particularly specialized tax or legal matters — could still benefit from external expertise. Other recurring activities were closely tied to daily operations and could be performed more effectively internally.
I compared the ongoing cost of the outsourced model with the cost of an internal structure, including employees, systems, software, and continued specialist support.
The recommendation was based on both economics and operating effectiveness.
I developed a plan for how accounting, payroll, tax coordination, and finance operations would function after the transition. For each process, I defined the process owner, required inputs, key deadlines, review and approval responsibilities, systems of record, reconciliation procedures, escalation paths, and documentation requirements. The goal was not simply to transfer existing tasks — it was to redesign the processes so they worked as one connected finance operation.
I coordinated the transfer of accounting records, reconciliation schedules, payroll information, tax filings and supporting documentation, vendor records, process calendars, login and system access, and historical reports. I also reviewed the transferred information to identify gaps before external relationships were reduced or ended.
I documented recurring activities and established operating calendars for monthly, quarterly, and annual responsibilities — including month-end close, account reconciliations, payroll review, vendor payments, cash reporting, tax coordination, management reporting, and budget-versus-actual analysis. Standardizing the work reduced reliance on individual memory and made responsibilities easier to transfer as the finance team grew.
The work had to be phased carefully. We continued using external support where necessary while internal capabilities were established. Processes were moved only after the company had the access, documentation, systems, and internal ownership required to perform them reliably. This reduced the risk of operational gaps and allowed us to validate each new process before fully completing the transition.
Chairish successfully brought accounting, payroll, tax coordination, and core finance operations in-house. Additional outcomes included:
What began as a cost-reduction opportunity ultimately became an exercise in building the company's internal operating infrastructure.
A startup should not bring a function in-house simply because it believes employees can perform the work more cheaply. The better question is whether internal ownership will improve speed, context, control, and decision quality enough to justify the added responsibility.
I also learned that insourcing is not a vendor-termination project — it is a function-building project. The most important work was not ending the old structure. It was mapping the processes, transferring knowledge, establishing ownership, and building a new system that could operate reliably after the external support was reduced.
For an early-stage company, the right finance infrastructure should not add unnecessary bureaucracy. It should give leadership better information, reduce operational friction, and help the business make decisions with greater confidence.
