Bench in 2019: A Look Forward


Ian Crosby


Reviewed by


January 8, 2019

This article is Tax Professional approved


Below is a message that Bench CEO Ian Crosby shared with the Bench team at the beginning of 2019—a look at where we’re going and why we’re committed to helping a million entrepreneurs master their finances.

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Happy new year everyone! Bench has an exciting 2019 ahead. I’d like to spend a moment to step back and discuss the big picture of where we’re going as a team.

But let me preface this with an admission, which is: my wife and I really don’t have mastery of our family’s finances. Money comes in, money goes out, and I feel like we’re always scratching our heads about how our bank balance ends up being so much lower than expected at the end of each month. Then at the end of the year, I struggle to piece together what the process will be for filing taxes for myself, my wife, and our holding company.

I have no idea what services we need a tax accountant for, and I’m always left wondering if we’re paying them way too much or if they’re even necessary. At the end of all this, my wife and I are so stressed out that we end up having an argument about how we spend our money!

All this to say, while our Bench books are pristine, we still don’t have mastery of our finances.

Financial mastery for a million entrepreneurs

The issue with finances is if you don’t like that area of your life, you can’t just opt out. If you don’t like meat, no problem. Be vegetarian. Don’t like finances? Too bad. You’re a grown up. This is your life now. Avoiding it doesn’t make it go away.

I imagine most of you are in the same boat, because most human beings are. And unfortunately, making more money doesn’t cure it. Because without mastery, inevitably your expenses will just increase to match or exceed your income. But getting financial mastery, that makes a huge difference. Being on top of whatever one’s finances happen to be makes a real improvement in the quality of life of human beings.

This is what Bench is about. It’s a company about people and the quality of their lives. This is why we want to bring financial mastery to a million people.

And we’re starting with entrepreneurs. There are more people in the world than just entrepreneurs. And there’s way more than a million people. But we’re sticking a stake in the ground-we’re going to win this first game. And when this game is won, we’re going to have an incredible foundation for an even bigger game.

Growing beyond bookkeeping

Some people, when I tell them this have said, “but that can’t be what Bench is really about, because if you were about helping a million people master their finances, wouldn’t you be doing (X)?” The answer is, you are completely right, and that’s why Bench is going to have to start doing a lot more for people.

If we think about financial mastery, we pretty quickly realize that business bookkeeping isn’t really sufficient. There are all kinds of issues that people struggle with in their finances. Understanding what happened in their business is an important first step. But there are a lot of steps after that.

And to an entrepreneur, there isn’t much of a difference between business and personal. All of their personal income comes from their business! So if we want to help them, we can’t focus on one and not the other.

So we’ll need to think much bigger about the role we play in people’s lives. And we’ll need to think about what pieces of mastery we provide, and what pieces we simply diagnose and plug in world-class partners (e.g. Gusto). And before we’ve built all that, we won’t simply throw up our hands and say, “I guess some day once we’ve figured it out, we’ll begin bringing financial mastery to people.” For anything we can’t directly help people with yet, we’ll educate them on these topics so they at least have the possibility of mastery by applying some of their own effort.

Measuring financial mastery

As I mentioned at the recent all-hands, one of the most important things we’re going to build in the new year is a test that tells us whether an individual has financial mastery or not. So our daily measurement of success will not be “we’re closer to a million people paying us money” but instead “we’re closer to a million people having financial mastery, as determined by our test.”

We’re going to spend some time and resources to define financial mastery. What are the components? What does it look like? We’ll come up with a questionnaire, then we’ll use it on our customers and ourselves to assess where we fail to bring people financial mastery. We can even open up this questionnaire on our website so any entrepreneur can evaluate where they fall short of financial mastery.

Then we’ll track it like we track our other business metrics. How many people have we actually brought financial mastery to? How many this week? This month? Then we can make company decisions in a way that gets us to a million people passing the test the fastest.

What are we working on this quarter?

2019 is going to be an exciting year of figuring out how to bring financial mastery to people. This quarter, we’re going to make some giant leaps that get us closer:


Our sign-up flow, app and sales processes were built to survive our flawed Yodlee bank connect experience when it comes time to connect accounts. But Plaid is here now, it’s pretty amazing, and that flawed Yodlee bank connect experience is going to disappear. This is going to allow us to rethink how we do sign-up and sales and many parts of the app. We already have the Plaid connection working, and over the next few months we will be about ironing out the last bugs and rolling it out.

Real-time financials

For years we’ve heard our clients tell us they need to see the real-time status of their finances. Our new feature addresses this, giving clients access to their real-time balances and transactions. We plan to roll it out to all customers within the next few months. And the quality of this experience is going to be amplified by Plaid.

Bench for Accountants

Bench for Accountants started as a way to get clients from tax accountants. What we’re realizing is just as important will be getting clients to tax accountants (for those that need them). Coupled with our financial mastery test, we aim to make sure every client has the tax and advisory services they need, even if we don’t make money on it. This will take longer than a quarter to achieve, but we’re setting off on this trajectory now.


In order to start simple and small and get things right at the start, Bench started as a cash-based bookkeeping service. We turned away many potential clients that needed accruals. Over the past year, Bench Pro has continued to chip away at accruals, adding more and more types of accruals to the list of things we can serve. This coming quarter we plan to move closer by adding some challenging items to our arsenal of accruals: accounts receivable and inventory tracking. By the end of the year, there should be very few accrual clients we can’t handle bookkeeping for!

Hyperlocal marketing

For small businesses that aren’t aware of online bookkeeping, they go straight to looking for a local bookkeeper without realizing there’s another option out there. This year we plan to make sure that they come across Bench during their local search, by being in the places they expect a bookkeeper to be—Craigslist, Yelp listings, and even at co-working spaces through our partnerships with WeWork and Industrious.


In order to go big on our vision this year and invest in building the new products and services we’re going to need to bring people financial mastery, we’re going to raise a Series C equity financing.

That’s it for today. I’m looking forward to working with each of you this year to make a difference in a lot of people’s lives.


This post is to be used for informational purposes only and does not constitute legal, business, or tax advice. Each person should consult his or her own attorney, business advisor, or tax advisor with respect to matters referenced in this post. Bench assumes no liability for actions taken in reliance upon the information contained herein.
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