Cloudflare TV

Yes We Can

Presented by Michelle Zatlyn, Brittany Hamilton
Originally aired on 

A recurring series presented by Cloudflare co-founder and COO Michelle Zatlyn, featuring interviews with women entrepreneurs and tech leaders who clearly debunk the myth that there are no women in tech.

This week's guest: Brittany Hamilton is the Senior Director of Operations at Bench, a company that is on a mission to bring financial mastery to one million entrepreneurs. After joining Bench seven years ago as an intern, Brittany has grown with the company and today leads a team of more than 200 people. During Brittany's time at Bench, the company has seen exponential growth fueled by multiple funding rounds totaling $53 million to date.

Women in Tech

Transcript (Beta)

All right. Good morning, everyone. Welcome to this week's episode of Yes We Can. I am so honored to have Brittany Hamilton here this morning.

Good morning, Brittany. Good morning.

Thanks so much for having me. Yeah, I'm so excited. It's always the highlight of my week.

And so Brittany's joining us from beautiful British Columbia, so it's great to have you on.

A couple things. If you have any questions, you can always email yeswecan at and we'll try and get to them.

Or if you have ideas for great guests you would like me to interview in the future, please also send it to yeswecan at

So let's dig in.

Brittany, it's such an honor. We got introduced through a mutual friend and it's been great getting to know you.

And so you've been working at a company called Bench, which I would say is more like a startup, about 500 people startup for the last seven years, which is a long time in any company, especially a tech startup.

Maybe you can start by telling the audience, what is Bench?

For sure. And I think when a lot of people hear Bench, they're like, oh, do you sell clothing?

We're not Bench the clothing company, we're Bench Accounting.

And in short, what we do is we use this combination of in -house built tech and a whole lot of human power, honestly, to give small businesses access to affordable, easy to use, and easy to understand financial services completed for them.

And so I think when people hear that, like financial services, what does that actually mean?

What are financial services?

In brief, what it looks like right now is bookkeeping. So we do monthly bookkeeping and tax filing for small businesses and super small businesses.

Like we're talking under 10 employees and a lot of our clients actually are solo entrepreneurs.

They're just getting started. They're on their own, often for the first time, stepping out of kind of a long-term career in a lot of cases.

And so that's what we're up to. And then we've got a couple of really cool products on the very near horizon that folks will be hearing about pretty soon that are further geared at making what we do, giving people access to really solid financial information, more and more accessible and affordable and more streamlined so that they can actually focus on doing what they love to do, not bookkeeping.

Oh, I love that. Okay, great. And you, I mean, Bench Accounting has many customers, like almost 10,000 small businesses and entrepreneurs that are using your service for your financial mastery wizardry, right?

Correct. Right. Almost 10,000.

Right. So that's a lot, 10 ,000. You're helping 10,000 small businesses with their bookkeeping and accounting.

And I was joking, I was thinking about this where I imagine you go to parties and you tell people, hey, I work in bookkeeping and they think their eyes kind of glaze over.

So why is accounting and bookkeeping and financial services for small businesses so important?

Why should people's eyes glaze over, Brittany? I mean, literally bookkeeping is the backbone of the business and it can be really simple stuff like, okay, last month, was my revenue, was the income that I had last month greater or less than the cost that I incurred?

Literally, did I make or lose money?

Bookkeeping answers really basic questions like that. And then it can also get a whole lot more complicated.

But there are things that are absolutely required to know in order to make great decisions about your business, decisions that will literally keep you in business or not.

Being able to look back and say, do I have a seasonal business?

Do I have more revenue in the summer or the winter, for example?

Do my costs go up or down accordingly? Are there new decisions that I could make?

Like, should I be spending less in the winter because my revenue goes down?

It's stuff that, without actually having some level of record-keeping, accurate record-keeping, you can't answer those questions.

And then there's places where things get really interesting.

With bookkeeping and accounting, it's the difference, especially for very small businesses, between life or death for the business.

I mean, if you're not able to say, okay, in two months, I've invoiced all these customers.

How much have I invoiced them for? Here are what my, I know my monthly expenses are.

Am I literally going to have enough money in two months to be able to cover my expenses?

If you can't answer that question, you're literally just going in the day-to-day, in the dark, unsure of what's going to happen.

So there's the piece that's about decision-making. Like, any large business that is running for a long term has an internal finance team that's thinking about this stuff.

Small businesses also need to think about this. They just don't have the internal finance team to do it.

And then there's the other part of accounting, which, you know, it admittedly isn't super fun, but it's like governments decide that, great, once a year, because you've decided to go do something cool like run a bakery, oh, by the way, you're also going to have to do this really complicated thing called filing taxes.

And if you get it wrong, you're going to be in a ton of trouble, and it's really hard to do.

Good luck. And so the other part of having your accounting taken care of for you is you don't have to worry about that.

Like, it's something that will be done for you. So there's the piece of it about decision -making, and there's the piece of that that's about, like, literally compliance with the law and making sure that you're in line.

I could go on forever, obviously. I talk about this stuff all the time. But ultimately, like, finance and great bookkeeping, great record keeping gives you power over your business.

It's amazing. I see if someone's eyes glazed over, they certainly just, like, pop wide open.

You ooze the passion, which is great.

And, you know, I think that you said the backbone of the business. I kept thinking as you were just talking an illustration of, like, the spinal cord where businesses either can stand up straighter and walk around.

Otherwise, they're kind of humped over, and you feel, like, paralyzed.

So that's a, I like that. 100%.

Yeah, and nobody questions, like, you know, why does a large business, why does a corporation need a finance team?

Why is there forecasting? Why is all that done?

But, you know, it's almost bizarre to talk about in terms of small businesses or a solo entrepreneur simply because that kind of information is complicated and often therefore expensive.

And so when you're just starting out, you're on your own figuring things out.

The idea of having somebody who can provide that for you is totally inaccessible.

I mean, even a lot of the services that exist, like, there's, like, CFO, on-call CFO kind of services are still really expensive.

And so what we're trying to do is say, okay, what does it look like for us to be able to provide more and more of that to somebody for, you know, $100 or less per month, where it starts to get really accessible, even for people who are just kicking off?

Yeah, that's amazing. Actually, that's been a theme that I've heard through a lot of conversations where it's, you know, again, I think you described bench accounting as both technology and people, where it's using the technology to help make it efficient and affordable and accessible, and then also keeping the human element, which is great.

It kind of makes it more accessible to all these small businesses entrepreneurs, which is, I think, feels good.

Yeah, 100%. Okay, so you've been at Bench for seven years, which, I mean, again, any company that's a long time.

In an early stage company, that's a really long time.

Like, that is kind of, like, unheard of. I mean, you joined that company when there were 15 people, and today you're at about 500.

Like, why did you get into this field?

And like, why did you get into this field? I'd love to hear a little bit about that story.

How did you find Bench? I feel like my, you know, my backstory is probably common with a lot of people who are listening in with who are millennials of my generation.

My journey into accounting and into tech is, was not like a perfectly linear one.

I initially had a background in classical archaeology and Latin.

So that was my, that was my initial background. Graduating into 2008 in a financial crisis made that quite an interesting decision to make, needless to say, for education.

And so, you know, given everything that was going on, I kind of had this running joke.

I'm going to go back to school and I'm going to pick a career that's recession proof.

You know, and let's be either a lawyer or an accountant.

And as it turns out, that broadly actually does, that does work out. So I decided to go back and study accounting.

And I kind of had this moment while I was studying where I thought, okay, I'm learning a lot here.

And it's like, it's quite complex stuff.

And this is really interesting. And it was like, it's like puzzles and everything.

I love accounting. I could also talk about that for a long time.

But I kind of had this moment where I thought, you know, okay, but what do I want to do for the world?

Like, what do I want to do? What is the impact I want to have?

And if you've been, if you're studying accounting or if you're in business school, you're doing a lot of networking, you're meeting people, you're feeling out different like firms and figuring out what you could do.

And none of it really felt quite right.

And so I had this moment of realization that actually took me longer than perhaps most people would have, but where I kind of realized, you know, I'm the child of two small business owners.

And I had heard stories for a long time from my mom in particular about the struggles that she had with the financial side.

I literally remember her like every night at this dining room table that we had with like her old laptop and a pile of documents around her spending hours and hours doing at the time for me as a teenager, who knows what?

And I had this realization. I'm like, oh my gosh, she was dealing with the bookkeeping.

That's what she was spending hours doing. And so I literally, there was a moment where I called her up and I'm in school and I'm having like a slight existential crisis.

What am I going to do with my life? And I called her up and I asked her, you know, okay, it's been about 15 years that you've had this business.

Has anything gotten better for you around accounting? And she's like, no, it's still the same thing.

You go out, you buy software, you do it yourself. There was nothing really new that had changed.

And I'm like, oh my gosh, why? Okay. Maybe I could help people who are in a similar situation as what my mom is dealing with.

So through like a bit of a serendipitous Google search, I at the time had no idea about like tech.

It wasn't something I was thinking about. I wasn't thinking about startups at all.

Random Google search of a small business bookkeeping, Vancouver and Bench popped up.

So I applied, show up. It's literally a condo in like downtown Vancouver with 15 people.

There's like brick wall, you know, like that kind of brick walls, people have like wine, we're chatting and, you know, networking.

Dogs, Brittany, were there dogs?

There's dogs. There's like the whole, there's snacks, the whole deal.

I had no idea what hit me, needless to say. And ultimately while that was really cool, more than that, I just started talking with these people who were like big nerds like me, who just wanted to make things better for small business owners who are doing this like super creative stuff.

And it was like, I just felt like I had kind of been knocked out and like woke up in a dream.

And frankly, seven years later, the reason I'm still here is because I still feel that way.

You know, like we went from helping, I think when I started, we maybe had 50 clients, if that, to, you know, coming up to 10,000 and have these big dreams about a million.

And getting to be a part of that at different levels, like the experience of Bench today is miles apart from what it was at the beginning.

It's almost like every year you're working at a bit of a new company because you're at a new stage.

Getting to have such a big part of that, it's been really incredible.

So for me, ultimately, like my journey into tech wasn't entirely intentional.

Tech kind of found me and met me halfway in the mission that I was on.

And even into accounting. People always said, you know, say when you're growing up, you might not know what field you're going to end up in.

And I'm like, no, I'm going to be, I'm definitely going to be an archaeologist.

I'm not one. But ultimately, I end up finding something that, you know, I can take what I know and what I've learned.

And what I can see is this huge gap in the world for small business owners and work with an ever growing group of people to make it better for people.

And it's incredible, truly. Wow, that's great.

I love that story, Brittany. I feel like there were definitely moments where I could see Hollywood shooting this movie.

Everything you just described from your mom, like it's you could just admit, like I literally had flashes of me watching this on the big screen.

So you did a really good job describing that.

And I think what you what you described is really common, where people are just passionate about a problem, and they go find groups of people to go solve it.

And you describe yourselves as a bunch of nerds who are doing it.

And then you end up creating something really special to help a lot of people, which is pretty cool.

And I think like, I've heard that advice quite a bit, which is, you know, instead of choosing a person or even a company to follow and saying, Oh, I'm stuck with this, you say, like, what is the mission that you're on?

And then you pursue that person that relentlessly with whoever you you meet along the way, whichever company is the most up to it and really tie yourself to that mission.

Now, I recognize in saying that, that I have been incredibly lucky in a lot of ways to just happen to have found this group of people who were already there.

And, you know, it's not necessarily as easy as a Google search to come across an incredible group of people who are on that same mission.

But I think for me, what it has allowed me to do is through really challenging times, startups are not easy changes in in the business.

And, you know, as as a company grows from 50 people to 500 and more, there are shifts in even the feeling of the company in a great way, you know, and when you really are anchored to the mission that you're on and what you're doing for people, you start to kind of relate to, you know, your team or the company or even things like, you know, whatever processes or whatever's in place as tools in pursuit of the mission, as opposed to something that's important in and of itself.

And it's allowed me certainly to avoid what can often happen when you're really in the early stages of a startup, which is to get the rose colored glasses of like, remember back then when it was so much better.

For me, I think by being anchored to the mission, all that goes away.

And it's like, what is it going to take to this company to get this company to the next level where we can reach more people with this thing that I'm really passionate about?

Wow, that's great.

I love that the tools in pursuit of the mission, I think that you're right, it does change when you're growing, growing and changes, you do reinvent yourself.

So I think that that's, that's a great insight.

You know, can you, obviously, you're so passionate about what you do, and, and, and the pursuit of this mission of helping small businesses realize their dreams, which is awesome.

What are maybe what are two projects that you're really proud of, and that you can share with the audience, just maybe can set content to contextualize a little bit better, like, okay, I love Brittany's passion, but like, what are some things that you actually do?

So, you know, one of the times where this has become really real for us as a company, and I'm going to, you know, use an example that is obviously something that is on a lot of people's mind, which is what's going on with COVID and businesses in general, but in particular, how that's impacted small businesses and the project around that.

So back at about mid to late March, our entire company went remote, which is, I think, a pretty common theme for a lot of office spaces.

And at the same time, as we were adapting to that, inevitably, as we had economic slowdown across Canada and the States, people either had to stop going and shopping at local businesses, or were deciding to kind of like, tighten the belt up and not have the spending that they had previously.

We started to hear, unsurprisingly, from a lot of small business owners, that they were going to be in financial trouble, if not immediately, then quite quickly from our clients.

In April, early April, we started to see a really sharp increase in client cancellation of our service.

Suddenly, bookkeeping at the time was like, well, you know, my business might not even be around, so I'm going to cut business, I'm going to cut bookkeeping, I'm going to cut a bunch of costs.

And we also saw an increase in folks going out of business right out the gate.

So as all that was happening, we got kind of really early wind of a government program that was coming down from the US government called the Payroll Protection Program.

And then there was also the EIDL, which are different grants and loans that were aimed at keeping small businesses, keeping businesses in general, but really for us small businesses, open and running and able to pay their employees.

As it turned out, we were incredibly poised to take advantage of the incredibly complex programs, combined with the fact that we've got people in house who have become incredibly adept at reading and understanding a lot of the legal jargon.

I mean, we spend probably more time than most businesses would on the IRS website trying to read what's going on.

And we're incredibly well poised to say, great, we've got these people in house who can understand these bills.

Let's jump on this, let's understand these, let's interpret these for the average person so they understand what it means to actually take advantage of these programs.

And then let's go the step further and say, for literally any of our clients, we will do absolutely everything we can possibly do to make sure that you get access to these loans if you are eligible for them, period, full stop.

So the project, and I can't take, I can take a very sliver of credit because this is literally an example of like a business mobilizing all 500 people to turn on a dime on this.

This started with a really simple message, a Slack message from our CEO, Ian Crosby, saying, so like, what if we helped people with the Triple P program?

And it turned into like, everybody just said, okay, let's do this.

We created an in-house team that was focused on research, we started writing blog articles, we had this incredible person, employee who was at bench for a co-op, a student co-op program who wrote this blog article that exploded explaining the Triple P program, which 10x'd our blog traffic.

We ended up ultimately supporting our clients in securing over $375 million in financial relief through grants and loans.

And now we're looking ahead and saying, okay, great, what's next?

It looks like the Senate is actually planning on voting on another bill next week, potentially for an extension of this payroll protection program, we got to figure out how to help people get forgiveness.

And ultimately, it was like, okay, this is not to say that bookkeeping is on hold.

As it turns out, people needed their bookkeeping done in order to be eligible for these loans.

But what it did do is it kind of galvanized us to say, like, more than ever, we're really fighting for our clients' businesses alongside them.

And here are these tools that we have that we're capable of, we can deliver advice at scale, we can deliver these bookkeeping, you know, the pieces of bookkeeping or their tax forms that they need to apply to these programs at scale, we can interpret complicated bills and legal jargon, we can help people understand if they're eligible, we can leverage the partnerships that we've got with lenders already to streamline the process for application.

And then we, you know, we had groups of people working over the weekend, literally on the phone with clients just trying to, like, get a hold of people that we hadn't heard from, saying, like, the deadline to apply is in, like, on Monday, we need, like, it looks like you need this.

Is this something you want to apply for? Here's the documents we need, like, turning around years of bookkeeping in hours.

And so for me, it was, like, unbelievable pride in the team, of course, to see people going and really fighting for their clients like this.

And it was really incredible to see, kind of, take this superpower and come together and say, okay, here's something unexpected.

But ultimately, we're here to fight for small businesses.

And here's the fight. The fight is help them stay in business by getting them access to these programs.

So that, to me, puts so into, like, such sharp relief, really an example of Bench being on the mission that we're on for people.

And it was pretty incredible to continue to be a part of because it's certainly not over.

Wow, I have, like, chills hearing this story.

And, you know, I love, again, this is back to tech plus people.

It's like, you use technology to make it accessible to many and the people to have the human touch, which is really powerful.

And this, you know, it is, you're, like, democratizing access to pretty sophisticated, complex things and making it available to many, many more.

And in your case, almost 10,000 small businesses.

That leverage you get, that impact you get is like, I, I'm constantly in awe when as I work in technology of those moments where that happens, because that's prior to working technology, I found it hard to find those moments.

Well, and like you said, with democratization of financial services is really exactly what it is.

We're taking things that otherwise were inaccessible, impossible to afford, or even just literally to get your foot in the door to get access to and saying, well, let's make this something that even somebody who's just getting started, solo entrepreneur can afford and have access to.

And we actually saw that show up in the payroll protection program, the triple P program, where literally the moment that the small business administration opened the door to applications in the first wave of applications, a significant portion, almost all of the funding was consumed immediately by very large businesses who have very sophisticated systems to make sure, they've got a whole finance team who's literally there ready to snap their fingers and apply.

Small business owners were kind of left in the lurch initially. And so we had a moment where we're like, okay, there's another round coming in.

Our clients are going to be the first ones in the door.

And you can see how without tech available to do that, you get people who are left behind.

Yeah. Amazing. Great. You mentioned COVID and small businesses and you gave a great example about how you're helping access.

I mean, $375 million in loans is like no small number. So huge congratulations.

And thank you for you and your team's work. Do you see any other trends with small businesses during this pandemic that the audience might want to hear about?

Yeah, I think, so there's a couple. The obvious ones that we're seeing is a greater hunger for information that I think typically people would just have kind of running in the background.

What's going on? We have clients who are reaching out now, literally checking in on like what's going on with progress in the Senate, like what's going on with the bills, like what's going on here.

So things that otherwise would be in the background, I think people are tuning in or trying to tune in more and more to understand how political processes are going to impact their business.

That's one that's been really interesting. The other one, this, of course, I put this as number two as being the most impactful, is that businesses with great record-keeping have been able to withstand in a lot of cases, a lot of the swings that come with COVID in a way that folks who are kind of scrambling just to get caught up and then have access to what's going on have struggled with.

So like great record -keeping has been very powerful, both for access to these programs and also for people just to understand what is the impact of COVID on their business, number one, has there been one, and to what extent.

The other one is that we have seen this really incredible transformation in small businesses to adapt to the needs of their communities in COVID.

So there was one that was really inspiring, a business that was manufacturing cases for musical instruments, literally turned on a dime and is suddenly creating face shields, building face shields for like thousands of face shields and delivering them within a few weeks.

So we've also seen small businesses pivot in a way that completely blows my mind how quickly they've managed to make this happen to adapt their business to what's needed in the community, which is absolutely incredible.

On kind of the more unfortunate side of sort of trends and themes we're seeing, small businesses are definitely closing at a higher rate.

We've seen about double the rate of small business closures amongst our customers that we had seen prior to, and then one that I mentioned before is businesses are looking to cut costs in lean times.

That has included a lot of conversations we've had with our clients around things like that we talked about a subscription relief.

So for Bench, it's like, okay, great, what can we do for you for three months, six months, so that you don't lose access to this record keeping.

Our mission is to help you stay in business.

You're going to need this. And then let's help you get back on your feet and then talk about like, what does payment look like later?

And so I would say if you're working with small businesses, if you're a company that serves small businesses, I imagine people have seen this, but it is something to keep an eye out for.

And we found that folks are incredibly receptive and certainly grateful for different versions of like a subscription relief program that can help them continue to use services that will keep them in business long term.

It's really an investment in them being a client and staying in business long term by making some of those short term changes.

Yeah, and then, you know, ultimately, three months of a subscription versus two years of somebody staying in business or longer, completely worth the conversation.

And then I think worth noting that all of these have varied significantly by state and industry.

Oh, I was going to say, have you seen an industry trend? Because I'm curious, the ones that are going out of business, do you see a certain industry?

I'd love to hear a little bit.

Yeah, businesses that aren't, especially they don't have an online platform.

I mean, e -commerce has like, there was a scary dip and then a rebound.

So anyone who's selling product online has broadly been in a pretty good state, if not higher.

On the other hand, anyone who was really focused on in-person services or who were selling kind of in like a brick and mortar situation and didn't have the online kind of aspect have struggled far more.

And also, it's very depending on the state.

State by state, there's been differences, obviously, in the level of kind of closures or restrictions.

So depending on what state businesses are in, that, again, could vary pretty widely.

Actually, now that you, as you were speaking, we've seen something similar where we had clients where they're also very in-person services, both big and small.

I mean, some big companies like movie theaters, depending on coming in.

And when COVID hit and that was hard, all of a sudden, these online-first strategies kind of took from a back burner to a front burner.

And the companies that could pivot and adjust, I love the story of this yoga teacher who was like, oh my God, no one come into my studio and created like an online and she's thriving and doing great to big companies saying, creating like a direct -to-consumer food company.

But it's, it is, or line, it's the agility.

It's like you want to, you want to, you have to be able to adjust.

Exactly. And it's like, if you either don't have the culture to adjust, or if you were already kind of running a thin, a thin line or a thin margin, and suddenly the idea of investing in something that might also be further risky or a new strategy, it, you know, it isn't possible.

That can be really tough. But exactly like you've said, we've seen really, really interesting adaptations, either to how do I literally manufacture a completely different thing that suddenly is in demand because we're set up to do that.

Like I can create face shields now for people or, you know, how can I deliver my service in an online way as opposed to previously in person?

So where possible, we, we've seen some really inspiring adaptations that truly, it blows my mind that a small business that already has limited resources can make a pivot like that as quickly as so many of them have.

It is, it kind of makes you think, but what have I done today?

Have I done enough?

I can do more, push us all to do more. I love that being inspired by the small business entrepreneurs.

It's great. Okay. So we're, we're, we're down to the last two minutes and I do want to just, you, you hire a lot of people.

I mean, you have a team of, you know, several hundred people of accountants and bookkeepers who are helping all these small businesses where it's technology plus people.

How do you hire, where do your people come from?

I think that this is really interesting. I just want to end here.

Yeah. I think, you know, there's generally the assumption that we hire a lot of former accountants, which isn't quite the case.

About 30% of the people that we hire do have a background in bookkeeping.

The other 70% are folks often with a customer service background or potentially right from university or college, I guess to use a more, the American term for it.

And you know, for us, the three things that we look for more than anything are people who are teachable, who are gritty and who are resilient.

And like, you want to talk about people who have that it's people who have been a waitress, who have dealt with the near unreasonable customer experiences, you know, things like that.

People who have this grit, who have really made it through something in their life and who can bring that to their role at a startup, because really that's what you need.

You need to be able to learn, you know, you need to be gritty and you need to be resilient to a lot of the changes.

So we teach people what they need to know in bookkeeping.

The technical tends to come significantly easier than what is difficult, which is finding people who have that kind of mindset and that background that's going to really work and mesh well in a startup.

Wow. So I, so just, so I, so this is not hypothetical.

It sounds like it's real. Like you literally hire people with customer service backgrounds.

So maybe like waitresses into pinch to, and then you train them to become bookkeepers to then go help these secure $375 million in loans for these 10,000 small businesses around the world and help build that skillset and learn more about technology.

That is a real story.

That's truly what is happening. 100%. It's, it's often the first step that people have into professional services or tech.

It was for me.

And it's been that for now at this point, hundreds and hundreds of the folks that we've brought on board and trained up to be bookkeepers.

Wow. Well, I love that. I love that you're providing an OMRA for folks in other backgrounds to come and learn more about technology and help.

We're, we're hiring hundreds of people right now.

So if you're looking to get into tech and don't have that tech background come and check us out.

Awesome. Thank you so much, Brittany. This was amazing.

Thanks everyone. See you next week on Yes, We Can.

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Yes We Can
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