How Skybound Bookkeeping Unlocked A Market for Bookkeeping Data

Skybound Bookkeeping is a cloud-based bookkeeping firm situated in Ontario.

Founder and lead bookkeeper, Scott Easter, started his career in accounting and became an advocate for the continuing relevance of good bookkeeping.

Here’s Scott’s story of his mission to go paperless, the courage to make a strategic shift back to the cloud with ideal clients and his vision for growth.


Passion for bookkeeping is rare. Passion for technology is exciting.

So reads Skybound Bookkeeping homepage. Scott Easter founded Skybound in 2015. At the time, he was working for a traditional accounting firm that decided to sell.

“I started to get my designation in accounting and realised there was a lot of room for good bookkeepers. I felt like many businesses were missing out on accurate, timely data. If they could have useful data all year round rather than a once-a-year turnaround, those numbers could actually mean something. Rather than six to nine months later, once the business had succeeded or struggled, real-time data identifies areas to focus on. I believed there was a market for it. I took on a couple of clients and began Skybound as a cloud only business. Our goal is to create useful data used in a timely manner.”

“We were incorporated in early January. I brought a CPA onboard and we are now fine-tuning processes to create a higher level service, working on the intricacies needed to deliver the next level of bookkeeping services.”

“I actually dislike bookkeeping. I spend more time trying to figure out how not to do my job. I spent a lot of time in research, trying out different tools. Other products’ data extraction felt clunky compared to Receipt Bank.”

Yet, moving to the cloud was not a linear progression. “I broke off from the [cloud-based] business model for the sake of making money,” admits Scott.

“Then, I dropped the desktop-based clients who didn’t adopt the new system, or were not looking to update. We’ve been growing steadily ever since. The clients that updated love it.”

This shift resulted in a period of little to no growth, as Scott replaced clients with new clients that fit his vision of the ideal client. 


Before Receipt Bank, Scott had twelve clients and spent much of the week driving to and from clients, picking up and dropping off paperwork.

“Once a week, I would pick up my clients’ files. It would take half a day to get everything in. Then, I’d return to the office to have paperwork everywhere, key in all the data, then bring everything back to pick up the next round of paperwork. It involved lots of driving, manual data entry and fighting to file paperwork. I did this for about a year and a half.”

“My hours were spent simply on bookkeeping. I spent a lot of time playing catch-up if a client couldn’t provide paperwork on time. It was not how I wanted to run my business. This wasn’t my vision for Skybound. I wanted to go paperless, yet I had more paper than ever in my office. I realised I’d need to take a step back and restart the whole process.”

“There was a lightbulb moment when I spent six hours catching up on filing because of a family emergency the week before. That day, I decided to change things. My wife and I both work from home. She was just starting her own business, so we didn’t have the cash-flow to take a large risk. Yet, for my sake and sanity, I knew I needed to do this. We made it work, and we pulled through.”


“We now have 35 monthly recurring clients, with ten in the pipeline. Some clients are not looking for monthly correspondence. We build a billing structure that makes working with us month-to-month more affordable.”

“For the most part, our ideal client falls into three key categories. First, a freelancer, such as a freelance graphic designer or marketer. Second, a contractor, such as a construction company or plumber. And third, a healthcare practitioner, such as a massage therapist or radiologist.”

“We find that contractors file a lot more receipts from Home Depot or supplier stores. We encourage them to take photos of receipts as soon as they get them. Currently, I’m investigating the needs of healthcare practitioners to see how we can improve the process.”


For the very client Scott used to drive to, pick up paperwork from then return printed cheques, the process is now much simpler without having to drive to and from.

“I auto-forward around 50% of his paperwork to Receipt Bank, upload on Wednesday and spend just 45 minutes approving everything. Once a month, I upload any straggling cash receipts.”

“The feature, ‘Boost’, is pretty cool. On Wednesdays, I upload a batch of invoices, switch on boost and go make a coffee. By the time I’ve come back, it’s all set to review.”

“On average, I used to spend 2-3 hours per month per client. Now with Receipt Bank, that has been knocked down to just 30 minutes.”


“Right now, we’re focusing on selling. Our tech stack puts accuracy first, efficiency second, and key performance indicators (KPIs) third.”

“I want to get ready to scale, then spend more time working with Receipt Bank integrations. We are always trying to adapt and change what works. The industry is changing so quickly, you have to get someone’s full-time job to maximise technology.”

“That’s our foreseeable future: growth, training, more training and learning. It’s an exciting time to be in bookkeeping. It’s changing so quickly now.”

Related posts