Resources for Bookkeepers
The Back Office was created for bookkeepers who care deeply about clean systems, sustainable workflows, and doing this work well. This space is for professionals who want to build businesses that feel organized, efficient, and aligned with real life.
Inside, you will find process driven insights, systems thinking, and behind the scenes guidance from my own bookkeeping practice.
These posts lay the foundation for how I think about bookkeeping as a business, not just a service.
Latest Articles
more coming soon!
Systems Before Scale
The Back Office goes beyond debits and credits. It focuses on how to run a bookkeeping business that is efficient, sustainable, and built for the long term.
Topics include:
Workflow design and documentation
Client onboarding and boundaries
Software decisions and integrations
Balancing growth with real life capacity
Hi I’m Jessie,
I’m the founder of Oak and Ledger and the voice behind The Back Office.
Before starting my own bookkeeping practice, I spent nearly a decade doing the books for my family’s company after leaving public accounting to build a life that worked better for me. Because I worked from home for so long, I had very little local network when I decided to start my firm, and no clear roadmap for how to grow it.
I’m also a mom of two, and both of my kids were under the age of three when I felt the pull to build something of my own. My time was limited, my capacity was real, and my original goal for 2025 was simply to have five clients by the end of the year. I ended up with nine, without spending a single dollar on advertising or paid marketing.
What surprised me most was how much I genuinely loved the process. The systems. The learning curve. The small wins. Even the challenges. And through that experience, I realized I wanted a place to document what this journey actually looks like, not the polished version, but the real one.
I also wanted to step back from constant short form content and create something more intentional. A space to write, reflect, and share what I have learned without the pressure of algorithms or trends.
That is why I created The Back Office.
This blog is where I share the behind the scenes of building a bookkeeping business. What worked, what did not, the systems I rely on, and the parts of this work that often go unspoken. My background spans from micro businesses to mid sized companies, and that experience shapes how I approach both bookkeeping and business ownership.
If you are a bookkeeper who cares about structure, sustainability, and building something that fits your real life, you are in the right place.
If you want to start at the beginning, the first post shares the story behind this space and how it all started.
The tools that support our workflows
These are the systems I use inside Oak and Ledger to stay organized, protect client data, and create repeatable processes.
-
Method CRM
Method CRM is a flexible system that helps businesses manage leads and long sales cycles without losing track of past conversations. When inquiries come in before someone is ready to move forward, Method CRM makes it easy to log details, set follow ups, and reconnect at key moments like tax season or important deadlines. It also works seamlessly with Google Workspace, keeping emails, contacts, and communication organized in one connected workflow.
-
Squarespace
Squarespace is a clean, reliable website platform and a great resource for small business owners who want a professional online presence without managing complex tech. Oak and Ledger is a Squarespace Circle Silver Partner, which allows us to offer clients free access to Squarespace Circle benefits, including 10 percent off new annual subscriptions and extended three month free website trials, making it easier to build and maintain a polished website that supports your business as it grows.
-
1Password
1Password is a secure password management tool that helps protect sensitive information, streamline logins, and safely share access with team members or professionals. It is especially valuable when managing multiple logins across different client bank accounts and business systems, keeping credentials organized and secure without relying on spreadsheets or email. As a trusted system we recommend at Oak and Ledger, 1Password offers a 14 day free trial, making it easy to improve security and organization without added complexity.
-
Google Workspace
Google Workspace is a professional email and productivity platform that helps small business owners stay organized, collaborate easily, and present a polished brand through custom domain email. Through Oak and Ledger, clients can receive 10 percent off Google Workspace for the first 12 months, making it easier to implement a secure, reliable system for email, file storage, and day to day operations.
-
SaasAnt for QuickBooks Online
Saasant is an essential tool from a bookkeeper’s perspective, especially for large clean up projects and high volume files. It allows for accurate bulk importing of transactions, including POS data and repetitive entries, which significantly reduces manual work and helps restore structure and consistency in QuickBooks Online when cleaning up months or years of activity.
Learn alongside me
If you enjoy systems, structure, and thoughtful conversations about bookkeeping as a profession, you are in the right place.