Digital Compliance Attorney Samantha is a Software Expert—and FreshBooks is Her Accounting Software of Choice

FreshBooks helps digital nomad Samantha run her U.K.-based business from around the globe with ease.

Case study: Samantha Simms, The Information Collective | FreshBooks

case study highlights - The Information Collective x FreshBooksOnce exclusively the domain of software developers, data privacy and regulation has been making front-page headlines in the past few years.

“I went from nobody ever really understanding what I do to everyone now telling me what I do,” says Samantha Simms, CEO of The Information Collective, a U.K.-based digital compliance consultancy.

Samantha, an attorney by trade, has spent roughly two decades working on data privacy and compliance for large corporate legal departments. In 2017, she set out on her own.  “I’m a bit of a tech geek,” she says,  “I love tech and love to see new software developed and brought to the market.”

Today, she works with clients to help them develop new technology products and scale in an ethically compliant way while remaining commercially viable. Her focus is on helping businesses that have some social impact and on supporting underrepresented communities, including Black software developers.

We spoke with Samantha to learn what makes a great piece of software—and why she thinks FreshBooks fits the profile.

built to scale

Can you tell me a bit about why you started the Information Collective?

Samantha: The more expertise I gained in my area of law, the less I felt I knew about everything else. I felt there was much more than I could bring to the global table, and I wanted to explore more of myself as a leader. I was looking for a certain freedom, as well, to live my life on my own terms. I also wanted to have more impact—for myself and the wider world.

My clients are largely what I call Black tech and big tech. My focus is on giving underrepresented communities who are trying to enter the tech world the professional support that they may not have access to otherwise. I also work with big tech to ensure that there is fairness built into their tech products.

With so many data privacy legislation changes recently, I can imagine you’ve had a big couple of years!

Samantha: The Information Collective started in the boom time of digital privacy. GDPR was just about to be brought into force, harmonizing the European data privacy landscape. With the new legislation, people have recognized the need for digital privacy, so my services don’t require as much of a “sell” as pre-GDPR.

We’re now at the frontier of a newer digital era, where I help clients be prepared for a lot more than data privacy compliance requirements. Our team also assists clients with e-commerce regulations, advertising and marketing rules, and compliant e-communications. We make sure those are handled in a fair, transparent, and secure way.

What surprised you about starting your business?

Samantha: I remember somebody saying to me, “You will always work for someone.” At that time I didn’t understand it, because I was thinking, “Well, if I’m running my own company, I’m not working for anyone.” But I get it now. I am working for my clients. And that is not a problem. That is exactly what I love. But it does mean that I have to be fully present and available As the leader and the principal consultant of my business, everyone looks to me. There is a lot more required of me now than ever before. So now I have more work-life harmony, but I’m not as focused on achieving work-life balance.

Some of the other accounting software seems to have been designed with big business in mind. FreshBooks has been designed with a small business in mind from its DNA. That simplicity saves me a lot of time.

What was your accounting experience prior to starting your own business?

Samantha: I had absolutely no clue about accounting or cash flow or anything like that for a small business when I first started out. When I first started The Information Collective, I had been working in large corporate organizations for a very long time. I knew how large enterprises operated, but I had very little knowledge of the operations of small businesses.

How did you find out about FreshBooks?

Samantha: I literally did a Google search for “small business accounting software.” What came up was a range of options. I read through a lot of marketing materials and comparative studies. What jumped out at me was that people talked about FreshBooks being simpler to use. And it was more suited to my needs because I only work with a handful of clients at any one time. I didn’t typically need to invoice more than 4 clients in a given month.

It was also easier for my personal assistant, trainees, and the contractors I work with to come onto FreshBooks. They charge their time to me through FreshBooks, and that works really well for us.

Which FreshBooks features do you use the most?

Samantha: I love the Dashboard. When I go in, I’m immediately able to see exactly what’s going on and get a snapshot of the financial health of my business. I love the invoicing function as well. I was able to create a more-or-less bespoke invoice straight out the gate. As a fledgling small business working with enterprise clients, branding my own invoice was really important to me. FreshBooks was able to give me a more professional look and feel, even when I was just starting out.

I also use Expenses, Proposals, Time Tracking, and Projects. All those features have really helped me to quantify and qualify effectiveness in my business.

For instance, since the U.K. has allowed open banking, I’ve linked my bank account and my expenses are automatically imported and categorized in FreshBooks. So when it comes to doing the accounts, or looking at disbursements for my clients, I can easily link those back to the actual expense itself. It’s very seamless.

And then, as I continued to grow I started using the Retainers, which is linked to Time Tracking, and also Projects. Those have worked fantastically for me.

project management

Can you talk a bit about how you use Projects?

Samantha: After I, say, send a proposal, within a new project I’m able to see—because of the tight time-tracking system—how effective my team has been against the number of hours we set for the delivery of the project. Using the Project Profitability tools (Team Cost Rates, Project Estimates, Profitability Reports) I can see what it actually costs to deliver a project versus the profit made. And I can then use that information for other projects of a similar nature. So it’s helped me a great amount with my pricing as a result.

As a U.K.-based business operating globally, how have you found payments with FreshBooks?

Samantha: I run my business across the U.K., U.S., Canada, and the Caribbean, and get paid in U.S. dollars, Canadian dollars, and British pounds. Using the integration with Stripe for payment processing means that my clients who are not in the U.K. have a familiar way to make payments quite easily and simply. I know funds are coming in and we don’t have to go through convoluted banking systems. It’s really enabled me to expand the business beyond the U.K. market.

Since business accounting was new to you, I’m guessing you’ve had a question or two! How has your experience been with FreshBooks’ Support?

Samantha: That’s one thing I liked about FreshBooks from the very beginning. Early on I had a query. The FreshBooks staff member I spoke with was very friendly and helpful, and able to get things done to the extent that I actually assumed I was one of the only people using it. To be honest with you, I was like, “Oh bless, he’s probably the CEO.” And then not long after that, I realized, “Oh, FreshBooks has been around for a long time and they have quite a few customers, so that couldn’t possibly be true.”

A year-and-a-half into my time using the software, FreshBooks invited me to a dinner in London where I met other FreshBooks users and the executive team. I just thought that was such a nice touch—bringing us all together and showing interest in us as clients and customers.

I work with a lot of software companies. I’ve helped to develop a lot of software on the legal side of things. That customer care is not something that you often see in the software business.

more of the work you love less paperwork

Why would you recommend FreshBooks?

Samantha: I’m not an accountant; I’m a lawyer. I have to spend a lot of time either doing client delivery or learning or marketing. I have little interest in learning accounting, beyond what I need to do to keep my business operating. FreshBooks built something because they understood where their customers were coming from. Some of the other accounting software seemed to have been designed with big business in mind, whereas FreshBooks has been designed with a small business in mind from its DNA. And that simplicity, I think, saves me a lot of time.

I’ve been at the forefront of developing a large number of consumer-facing and business-facing software technologies as a specialist in digital compliance. I would say I’m a very good test use case for whether something works well or doesn’t work well. If it feels simple to use, it gets my tick in the box. And for me, that’s FreshBooks.

Jessica Wynne Lockhart
about the author

Jessica Wynne Lockhart is an award-winning journalist and fact-checker, who splits her time between Canada and Australia. She has bylines in the Toronto Star, Chatelaine, and The New Zealand Herald. She writes about e-commerce, personal finance, health, and travel. Learn more about her work at