Nobody starts a business because they want to run a business.
As a founder, I know this personally. You start a company to solve a problem you’re passionate about, to offer a service that helps your community, or to build a product you believe simply must exist. And then the reality sets in: running the business is often the single worst part.
Through my experience building and selling companies, I've become intimately familiar with the tedium and frustration that goes along with business finance, the arcane knowledge you feel embarrassed not to know, and the impatience you feel each month waiting for the books to close.
I felt there had to be a better way.
Today, there finally is! Alongside our incredible team, I’m excited to announce the launch of Digits AI, the world’s first private, accurate, and secure finance AI for small businesses. All you have to do is ask…
Finally: AI-Powered Business Finance
In today's fast-paced world, you need to make business decisions in real-time, in the moment. You can't afford to wait days or weeks for financial reports, and you have better things to do than open QuickBooks, export data, and fiddle around in Excel.
With Digits AI, your finances are never a puzzle.
Starting today, instant answers to critical questions are at your fingertips. Just ask:
“What is my burn rate?”
“Who are my top five customers this month?”
“How much did we spend on marketing so far this year?”
While Digits AI might not tell you who will win the 2026 FIFA World Cup, all your finance questions get answered in seconds, with clear explanations and intuitive charts that you can drop into a presentation or investor update.
Trained on over $300 Billion in small-business transaction volume, Digits AI represents a technological breakthrough in the application of state-of-the-art machine learning models to business finance.
You've seen all the hype around ChatGPT. Finally, you can experience the full power of large language models applied privately and securely to your business—saving you hours!
For too long, accountants and business operators have struggled with manual and repetitive financial tasks that waste valuable time. It’s finally time to replace tedium and confusion with fast and accurate automation—and regain hours of lost productivity.
Today, we're tackling one of the most frustrating and time-consuming parts of the accountant-client relationship: classifying and reconciling uncategorized transactions.
Every month, the process repeats itself:
"What is Figma?"
"Is this a business expense or personal?"
"What was this Home Depot purchase for?"
"What customer is this Stripe transaction for?"
Clients are too busy to answer. Accountants get blocked.
Enough is enough.
Turn Annoy into Joy
We’re excited to introduce Digits Transaction Review, our end-to-end solution for automatically identifying and booking uncategorized transactions and seamlessly collecting client input. Built on top of Digits underlying architecture, Transaction Review leverages the latest machine learning models to intelligently do the work for you, becoming smarter and more accurate with each use. Closing the books each month has never been faster or more delightful for your clients, turning them from annoyed to joyed.
Today’s finance tools fall far short of what accountants and finance teams deserve—immersive storytelling backed by intelligent analysis, powerful visuals, and instant answers.
It’s time to bid farewell to stale, black and white reports, tedious Excel models, and unsecured email attachments.
Let relics go the way of relics.
Financial reports are meant to tell a story. Today, that story is confusing—it’s told in a format that’s complicated, tough to understand, and hasn’t changed in decades. When business owners receive their monthly financials, they struggle to grasp the takeaway or what they should do about it. The burden falls upon them, their accountant, or their finance team to make sense of it all.
SoftBank Vision Fund 2 and Harry Stebbing’s 20VC Growth Back our Vision for the Future of Finance
Today, we’re excited to announce the next chapter: our $65 Million Series C, led by SoftBank Vision Fund 2 with participation from Harry Stebbings’ 20VC Growth, as well as Benchmark and GV.
SoftBank’s extensive experience in global fintech and their shared commitment to long-term, meaningful impact in the spaces they invest in is an ideal partnership as we shift to our next stage of growth.
Meet Digits Reports
Welcome to the future of financial reporting. Digits Reports is a modern and secure format for live, interactive, collaborative financial statements.
Go ahead, play with the numbers. Features like Hover to Discover allow you to quickly see trends, deltas, and actionable insights.
Deep-dive on demand. Live connections to your underlying accounting software enable infinite exploration, with endless visualizations.
Collaborate seamlessly. With one-click secure sharing, send and receive reports that invite exploration while keeping sensitive information safe.
The true power of Digits Reports lies in the editor.
Behind the scenes, Digits Reports Builder is the pro-tool we’re giving to accountants and finance professionals, letting you create highly-visual, interactive reports in a fraction of the time.
Go ahead, tell the story you’ve always wanted.
A picture’s worth a thousand words, and now you can paint a story your clients can comprehend, told the way you want it.
Drag and drop charts, insights, and top performer graphs directly into a report. See an intelligent insight you like? Click and instantly add it to the executive summary. Don’t worry, Digits has already calculated and verified the math for you.
For the first time, you can generate dynamic documents your clients can explore, visually and intuitively, from a high level down to individual transaction details—all in one place.
Digits Reports Builder works just as you’d expect, allowing you to create stunning reports from the moment you open it. Fine-tune your reports to match client goals and highlight insights that surface what they need to know. Adding charts and refining financials have never been this easy or beautiful. Just drag. Drop. Done.
Peek behind the curtain as we build the financial engine of tomorrow.
Our recent launch of Digits Search represented the culmination of over 30 human-years of software engineering work, from a team with hundreds of years of combined experience. All to make a financial search box… work.
Of course, there’s a lot going on under the covers.
From stateless request authentication to streaming data processing pipelines to search index generation and efficient view serving, the Digits engineering team continues to push the bounds on how modern, secure, highly-scalable, and highly-available SaaS products are built, tested, and (continuously) deployed.
Today, we’re excited to launch Building Digits, an engineering blog dedicated to sharing the details behind what we’ve built, how it works, and the tips and techniques we’ve learned along the way.
Deep Learning, live, in production
And to kick things off, what better topic than machine learning? While seemingly every startup pitch now mentions AI and ML, the harsh truth today remains that very few companies run deep-learning models live, in production, and that efficiently training, deploying, and tuning these models is still quite challenging.
At Digits, we’re firm believers in the benefits of continuous deployment across our entire stack, and we’ve invested heavily in ML infrastructure to address those challenges and support these workflows.
Digits stands at the unique intersection of big data, continuous development, and consumer-grade design—focused by our team’s shared obsession to modernize business finance.
From designing Ferraris, to building the origins of Twitter Mobile, to authoring Building Machine Learning Pipelines, our team brings a diverse array of backgrounds and unique skillsets to tackle the most impactful problems in this space.
If you have a passion for hard problems, deep technology, and human-centered design, we would love your help shaping the future of business finance.
Today’s finance software falls far short of what business leaders need—intelligent, powerful analysis and instant answers.
We’re excited to introduce Digits Search, a brand new way to know and understand your business.
Digits Search was born from the frustrations we experienced building and growing our first companies. But the discomfort went beyond just frustration—to pain and constant uncertainty. After speaking with hundreds of business owners, we realized we weren’t alone.
For a growing business, nothing is more important than knowing the numbers.
Before now, even with the best software and teams of accountants and analysts, entrepreneurs couldn’t get the answers they were looking for without sending out requests and twiddling their thumbs. They might be waiting hours or days until their books were updated, those reports were run, the figures exported, and finally shared. Just imagine if something came up over the weekend.
Finance, meet search.
For 99% of businesses out there, the flow of financial information is slow and fragmented. Needed receipts are strewn about like Legos on the living room floor—mountains of financial figures buried under emails, Slack threads, and random account statements.
It’s time someone applied some order to the madness. We realized that the unassuming, familiar search bar could be the gateway to financial super-intelligence.
Digits Search changes the game.
Imagine trying to find something on the Internet without a search bar… what a nightmare. Now, imagine getting instant intel on all of your company’s finances with just a few keystrokes, immediately saving you both time and money.
Digits Search unlocks answers to all of your questions in one powerful, yet easy-to-use tool. And the best part is, you don’t have to ask anyone for help! Your finances are now right at your fingertips, instantly.
The future of finance is instant and informed.
Put Digits Search under your company’s hood in just a few clicks, and you’re in the driver’s seat. One-click suggestions draw your attention to what matters most, and anything you’re curious about is just a few keystrokes away.
Digits sits on top of your existing accounting software and your existing accountant’s work. You change nothing.
Digits gives you a living, learning, hyper-aware model of your business, and it never stops working. Digits gets smarter and more accurate with every new transaction or account change and automatically learns what drives your business forward.
Oceans of financial data? No problem.
Once activated, Digits starts running machine-learning algorithms that absorb your transactions and perform millions of calculations to form a living model of your finances, working for you 24/7.
Digits seamlessly blends historical data from QuickBooks with live, real-time transaction streams from your banks, corporate cards, and more, giving you a complete picture of your business.
Financial clarity is a beautiful thing.
Gone are the days of dense spreadsheets and black & white reports. We’ve designed Digits Search from the ground up to make your company’s finances visually immersive, easy to understand, intuitive, even dare we say… beautiful?
With just a click, instant search results give way to deep-dive insights and analysis, all performed automatically on your behalf. Vendors, customers, budget categories, and more dance at your fingertips, with plenty of helpful graphs and nary a pivot table in sight.
Get Digits Search today, for free.
The power to know how your company’s money flows, gets invested, and is spent is priceless… but today it’s free.
We want every small-business owner and startup founder to experience the power of Digits Search, and you can get started today, for free, in just a few clicks. Digits Search integrates seamlessly with your existing accounting software and your existing finance workflows, with no configuration or manual data wrangling required.
Advanced features and upgraded pricing plans are coming soon, but the core features of Digits Search will always be free.
It’s simple. We wanted better financial tools to run our own company, but we wanted to build them for everyone.
Our goal with Digits is to usher in a paradigm-shift in business finance, and we couldn’t be more honored to work with the incredible band of engineers, data scientists, product designers, and so many other talented folks that form the Digits team.
They have poured their hearts and souls into this launch, and we have quite a bit more we’re cooking up behind the scenes. Search is where we start. Just wait ’til you see what’s next.
The past year has been quite a journey for us all. Thinking back to just over a year ago, when we announced our Series A, feels like a distant memory of an antique land… We sincerely hope that you’ve stayed safe and healthy during this time.
Through the travails, uncertainty, and drama of 2020, we have done our best to stay heads-down building, fully-remotely, and in focused pursuit of our mission to bring business finance into the modern, real-time era.
Embroker went even further, naming Digits the #1 fintech startup (and #6 overall) on their Top 200 list of the world’s “fastest growing companies that… will fundamentally transform our society.” We’re honored to be included!
What Digits is doing for businesses is truly phenomenal. Being able to analyze and visualize financials in real-time is especially huge for startups and other high-growth companies where KPIs are always moving quickly and changing rapidly.
-Yotam Shacham, Co-Founder,
The Digits Real-time Engine
Every financial transaction impacts your business’ bottom line. But today, businesses are forced to rely on a web of antiquated, manual, and time-consuming processes to record and model their financial activity to understand these impacts.
While unwieldy, historical data is straightforward—it’s studiously recorded in the general ledgers of businesses worldwide, but it’s static and outdated. Real-time transaction streams are increasingly available from financial institutions, but they are raw and unreconciled. Forward projections are still powered by spreadsheets and approximations, each one manually maintained—delaying leadership teams from making crucial decisions.
As serial-entrepreneurs, with 6 companies between us over the past 20 years, we realized that the holy grail of business was having a real-time, living model that empowers decision-making in the moment.
Two years ago, we embarked on our journey to solve this problem, and we believe we’ve now achieved this with the Digits Real-time Engine, which seamlessly (and accurately!) combines full-historical data, current real-time activity, and forward looking projections into a single, immersive, and intuitive financial dashboard for business owners, finance leads, and their department heads.
The Digits Real-time Engine has been the missing link in business finance. It’s the infrastructure that converts your data into a living model of your business, enabling an entirely new class of business software. With each change in your business, our Real-time Engine re-analyzes everything to give you the latest, most accurate view of your world… With Every. Single. Transaction.
It’s the 21st century. Business happens in real-time. What is your finance stack waiting for?
We’re truly honored by the recognition we’ve received so far as well as the feedback and feature requests from our Early Access community.
Over the past few months, we’ve been working hard on a number of exciting new tools, supercharged by our Real-time Engine. We can’t wait to show you what’s behind the curtain—stay tuned for our next major announcement!
Back in early March, before the full extent of this pandemic set in, I kicked off our introduction to remote work at Digits as follows:
To be sure, working remotely is not for every business, and not for every individual.
Little did I know how soon so many businesses and individuals would be forced to make do, and how quickly fully-remote work would become mainstream.
It’s been an abrupt transition… and for many, it hasn’t been easy.
Over the course of the year, I’ve heard from countless startup founders, small business owners, and team leads looking for more advice on how to build effective, collaborative, productive, and happy fully-distributed teams. The last, of course, being the most challenging.
For those of you that have held-off implementing major process and collaboration changes to optimize for remote work, the time to reconsider is now.
While there may soon be light at the end of this tunnel — thanks to the incredible vaccine development efforts by scientists and researchers worldwide — I foresee no quick reversion to “normal”. Remote work is here to stay, and every industry that can do so will embrace it.
Success in 2021 and beyond will be defined by those who adapt to remote work most effectively.
Digits went fully-remote the day we started the company in 2018, with my co-founder Wayne in Los Angeles and I in San Francisco. We knew it would be a fools-errand to try to build the company we envisioned in just one city (there’s simply too much great talent everywhere) and we both shared distinct, negative prior experiences managing multiple remote offices: the “second-class citizen” effect felt by those not frequently present at HQ is hard to overcome.
So (and despite distinct skepticism from a few of our investors — don’t worry, we appreciated the push-back!), Wayne and I made the decision to embrace remote work wholesale: Digits would never own a physical, shared office, and we would design our approaches and processes from the ground-up to champion distributed work.
After seeing so many different attempts at remote work by so many companies over the course of this year, and after reflecting on the most effective aspects of our own culture at Digits, it’s become more clear to us than ever what’s really important.
There are now thousands of online articles pitching countless techniques for improving the remote work lifestyle — it’s overwhelming.
As founders, here are the practices we believe have had the most positive impact at Digits, and the ones that we would recommend you try out with your teams today, even if you’ve previously preferred an in-person work experience.
For many, remote work is black and white: you’re either in the office together, or you aren’t. But degrees matter. Time zones matter.
In our experience, productivity and happiness go hand-in-hand with collaborating live, so we’ve made a conscious decision at Digits to agree to all work roughly the same hours: in our case, US Central Time. Folks out West tend to fire up their computers a bit earlier than they otherwise would, and those back East tend to stay on a bit later, or check back in after dinner, or once their kids are asleep. There is still a bit of skew on each side, but to have our entire team online together, every day, simultaneously, for the core hours of US Central Time is magical.
Sure, there are downsides. There are incredible folks (and former colleagues from prior companies!) in EMEA and APAC that we would adore the opportunity to work with, but we have assembled an incredible team that can collaborate live across North, Central, and South America synchronously. The pros outweigh the cons dramatically, and we communicate this upfront in our recruiting materials: when you join Digits, you’re free to move wherever you want within continental American timezones.
For those of you who already have colleagues spread around the globe, our advice would be to strive for team synchronicity. Here’s how.
The Buddy System: Scaling Synchronicity by Shrinking Teams
The traditional “two-pizza” team of 8–10 folks gathered around a conference table may work well in person, but we’ve come to realize it’s unwieldy on Zoom.
Even on fast Internet connections, latency often makes it awkward to get a word in edgewise in group settings, and inevitable background noise from pets, children, construction, or everyday city life motivates a default-to-mute culture, which adds another layer of friction to highly-participatory group dialogue.
That’s ok — we’ve never found large group meetings to be productive to begin with 😉
At Digits, we consciously break teams down into their smallest possible units: every project is tackled by tiny teams of 2–4 people, and in practice we found that 4-person teams often self-divide pairwise to get work done more effectively. We call this the Buddy System.
Working on something by yourself is lonely.
Working on it by yourself, in your home, with nobody else around, is just sad.
Working on it with a buddy is awesome.
In practice, substantially everything we do at Digits is tackled collaboratively by 2–3 people. They work together, synchronously, throughout the day, and decide when they want to pair on Zoom, Tuple, or Slack Audio, and when they want to go heads-down and sync back up in an hour or two. But they always know who they can count on to brainstorm with, or get feedback from, or have review their work, and they know they won’t have to wait around for it because that person isn’t elsewhere working on something else.
Yes, this means we take on fewer projects simultaneously than we otherwise might, but in exchange, each work-stream gets completed far faster, at a far higher quality level, and the work day is far more enjoyable.
We default to coordinating work between teams asynchronously: via shared Google Docs and Trello, in order to minimize meetings and maximize flow. Input is welcomed, and actively sought from broad groups across the company, but that doesn’t take a meeting to accomplish. Let people chime in on a doc when they have time, and then grab time with them and their buddy directly if it deserves a live conversation. After all, they’re unlikely to be in another meeting…
The Maker Schedule, Writ Large
One of the most challenging aspects of almost any large organization is the meetings. An endless parade of prescheduled time-blocks, which require abrupt context switching and leave little time for thought, creativity, or even a snack. How easy it is to end the day exhausted, yet with the gnawing feeling that you didn’t actually accomplish anything of note?
For those with the maker mindset — with roles that require creativity and execution — this sparks terror. There is no better way to ruin the productivity of your design and engineering teams than a few poorly placed meetings. Losing half a day or more due to a couple preset commitments is not an exaggeration. At large companies, it’s a way of life.
At Digits, we discovered something we hadn’t realized: scarce resources are largely to blame.
Conference rooms are evil.
At a traditional company (all of Silicon Valley included), I need a place to hold a meeting. It would be rude to stand around and make noise somewhere public, where others are trying to work, so I book a conference room. Genius.
Except, conference rooms are in high demand, so I must reserve one in advance, and my meeting must conform to the room’s list of available slots. Without thinking about it, my meeting must now be 30 minutes or an hour long, and the time it will happen is now fixed on the calendar and broadcast in advance.
This is a nightmare.
It turns out that the maker schedule is not all that disrupted by the meeting itself… but rather by the presage of said meeting.
There is nothing more distracting than seeing a hard-stop on your calendar in 90 minutes. Do I have enough time to build out this feature before then? Can I really sink my teeth into this design problem in less than two hours? Should I just spend this time replying to email, or triaging bug reports, or grabbing coffee?
Don’t worry, I’ll dive into my real work after that meeting. (I tell myself)
Oh no. I also have a 2pm!?
At Digits, we have full-company, all-hands meetings 3 times a week, spaced every 48 hours:
Monday morning Kick-off (30 mins)
Wednesday morning Check-ins (30 minutes)
Friday afternoon Show & Tell (75 minutes)
They are scheduled to fall at the beginning or end of the day, to minimize disruption.
More importantly, we aim to schedule no other internal meetings.
Sure, interviews need to be booked, and customer and partnership calls need to happen, but it’s easy to distribute interviews across the team (and monitor how frequently any given engineer is pulled into an interview) and external-facing roles tend to be less maker-schedule driven.
This does not mean people don’t talk! Instead, we highly prioritize an ad hoc, interrupt-driven culture. Remember, the meeting itself is far less painful than the upcoming hard-stop on the calendar. And with no conference rooms to book, there’s no need to schedule anything in advance, so we don’t bother.
Much to our initial surprise, this has lead to a bit of a utopia: our typical “meeting” is 5–7 minutes long, includes less than 6 people, and happens with just a couple minutes of notice. Everyone is typically available because they’re all working US Central Time, and they aren’t tied up with any other pre-scheduled commitments, so why not join? And in just 7 minutes, they’re right back to being productive, because the meeting wasn’t long enough to “page out” or forget what they were doing and shift them out of flow.
This sounds too good to be true. It isn’t. It’s reality.
Remote Work At Digits
Taken together, our days and weeks at Digits look like the following:
High-bandwidth all-hands, every other day, so we all know what everyone else is working on and how it’s all progressing. The complete, cross-functional visibility these provide builds confidence that the whole company is rowing in the same direction, and immediately surfaces any duplicate or conflicting efforts.
Empty calendars, devoid of pre-scheduled internal meetings, so everyone can stay in flow and focus on getting work done.
Tight-knit, synchronous collaboration with a buddy, day-in and day-out, so you’re never alone during the day, and you always have someone you count on to brainstorm with and get feedback from.
Asynchronous, cross-team collaboration via shared Google Docs and Trello cards. Input and feedback is actively sought, but never blocked on, and each team is empowered to deliver their work end-to-end.
Ad hoc check-ins throughout the day, as needed. With no notice or preparation that takes you out of flow, it’s trivial to pause for 5 minutes and share an update, or get input from another team and then go right back to being productive with your buddy.
With 2020 coming to a close, Stanford eCorner just recently published a recap of their key entrepreneurial takeaways from this year, and I was floored to be featured again. Thank you Tina 🙂
Enjoy our new mini-series w/ short podcasts highlighting insights from our summer ETL series. The first one showcases @jeffseibert of Digits on how to make remote work work - 2020 Insight: Innovating at a Distance https://t.co/LyTPUnTk8d@ECorner
At Digits, we have been strong and ongoing proponents of modern, secure connections between financial institutions. As part of our mission to give businesses real-time visibility into their finances, we believe in the need for common, open, interoperable standards for businesses to seamlessly transmit financial data.
For many years, the lack of a secure communication standard between financial institutions has led to one-off data sharing arrangements, proprietary, incompatible APIs, and a veritable cottage-industry of “screen scraping” approaches — which have significant downsides in implementation cost, reliability, and of course data security. This has led to the formation of FDX, the leading nonprofit consortium that’s unifying the North American financial sector around a single, secure communication standard.
Drawing from our own rigorous security practices, we are excited to collaborate with other FDX members and share our techniques and learnings to drive further innovation in the industry.
A More Reliable Experience for Digits Customers
By contributing to and supporting secure communication standards, we also help guarantee the security and performance of our data integrations on behalf of our customers, including:
More to Come
We’re looking forward to helping shape the next generation of transaction and authorization APIs that financial institutions use to securely interoperate. In parallel, we’re heads down gearing up for our next major launch this Fall. We can’t wait to share what’s behind the curtain when it’s time — stay tuned!
We are obsessed with the vision that business finance should be immediately accessible and intuitive. It should learn, in real-time, as the business evolves, and it should empower business owners and operators everywhere, without requiring any prior financial training.
Why? Because today’s business climate requires you to take action in the moment and react rapidly to changing market conditions. That means not waiting weeks to receive a standard packet of black & white financials—which honestly can be quite difficult to interpret—and instead demanding the visibility and insight you need to make decisions, right now.
The Power of Digits
The world’s largest companies have sophisticated finance teams and internal forecasting models that give them these capabilities. What about everyone else? What if synthesized, actionable financial insights were available to every business on earth? What if they were always in real-time, and always up-to-date?
For two years, we’ve been building the technical infrastructure to make this a reality: N-dimensional transaction attribution. Auto-reconciliation. Predictive classification. Vendor identification and profile synthesis. Sub-second, full-ledger search. Statistical analysis and anomaly detection. Per-secret envelope encryption. The list goes on.
Introducing Digits, for Expenses
We’ve been humbled by the glowing feedback from our early customers and we’ve been inundated with requests for access. And, in these unprecedented times, we feel the obligation to help as many business owners as we can, as quickly as possible.
So today, we’re launching a broad early-access program for Digits for Expenses. We’ve taken all of the power of our platform and focused it specifically on helping business owners navigate today’s challenging market dynamics, so they can see and manage how their company is spending money:
*Digits is a phenomenal and truly game-changing product. To be able to ask such a wide spectrum of financial questions and get to those answers immediately has been so empowering, and the team’s passion for the space is clear in all the small details.*
Thinking back to a finance world before Digits…feels like remembering Netflix as a DVD-by-mail service.
– Kenny Mendes, **Head of Finance, People, and Operations**
Digits for Expenses is the first real-time, intuitively visual, machine-learned expense monitoring dashboard for small businesses, and in light of current conditions, we are making it Free.
(Seriously. We have other paid products on our roadmap, but Digits for Expenses is and will continue to be free for all small businesses. In this quarantine, it’s the least we can do.)
GV leads $22M Series B
As we’ve built Digits, we’ve been overwhelmed by the energy and excitement for our mission from founders, accountants, and investors alike, and we’ve been honored to have the financial backing of Benchmark and over 70 passionate angel investors.
We see this as a long-term, sustained effort, and Digits for Expenses is just the first chapter: we believe that innovations in technology, algorithms, and design have unlocked a new realm of possibility for financial software, and we are committed to making this vision a reality for businesses around the world.
In support of this, we’re excited to share that we have closed $22M in Series B funding, led by Jessica Verrilli at GV, and we’re thrilled to welcome her to our Board. Jessica’s deep experience in corporate development at Twitter and in early-stage investing through GV and #Angels have given her unique insight into the challenges small businesses face during their most-defining moments, and we’re looking forward to imbuing the product with her knowledge.
*Jeff and Wayne are masterful at creating intuitive, high-utility products from complicated data. I saw this up close with Crashlytics and Twitter, and I’m thrilled to partner with them on Digits as they reimagine financial software for startups.*
– Jessica Verrilli, **General Partner**
This round gives us the stability we need to become the partner that businesses can trust: at current burn, Digits’ runway now extends over 10 years.
$8+ Billion and counting…
When we announced our Series A in November, Digits’ production systems saw over $1.5 Billion in transaction value across our early customer base. Today, that number is already over $8 Billion, and growing daily.
Digits for Expenses is available today, for free, for US-based startups and small businesses. We plan to add support for international markets later this year.
Digits takes just a few clicks to set up, and sits on top of your existing ledger and your existing accountant’s work—you change nothing. Sign up here to get started.
(If you’re an investor, startup incubator, or accounting firm and want priority access for your portfolio companies, contact us at email@example.com.)
As founders, we would like to thank the entire Digits team for their tireless work over the past two years to bring us to this point. We still see this as just the beginning of our Digits journey, and we look forward to building powerful tools to help businesses of every shape and size chart their course.
We can’t wait for you to experience Digits, and we can’t wait to hear what you think.
To be sure, working remotely is not for every business, and not for every individual.
If your team needs to huddle together to prototype a physical product, that will be tricky. Or if you work for a biotech startup with special lab equipment, it’s likely infeasible to provision it for every home-office. Or if you’re a big-time extrovert who lives for lunchroom gossip and 5pm team socials, this work-style may not be your cup of tea.
But remarkably, we’re now at the point where most software/digital/service-based businesses, and most knowledge-based employees, are well-suited to going fully-remote, and many will be better off if they do! In fact, remote work has already jumped 159% in the past 12 years, but that’s just the tip of the iceberg.
Wayne and I founded Digits 2 years ago to create the next generation of delightful, powerful business finance software, and we had a choice: how should we structure the business? When we landed on building a fully-remote startup, even some of our closest supporters were skeptical.
Can a fully-distributed team be productive?
Won’t everyone just slack off all day?
How do you brainstorm and make product decisions?
But, but… whiteboarding??
We immediately faced these and countless other questions, but we were convinced that we could not build the scale of business we envisioned in San Francisco, and we had a strong distaste for the known challenges of distributed offices.
With the full benefit of hindsight, we could not be happier with our decision. Working as a fully-remote team has been a joy, and we have relentlessly iterated on the tools and techniques we’ve used to make it so.
Here’s just a few of the lessons we’ve learned over the past 2 years building a fully-remote company:
The Key Difference: No HQ
“Remote” isn’t new, and isn’t great. “Fully-remote” is a totally different concept.
Most peoples’ understanding of remote work has been a scattering of remote employees and a big HQ somewhere. As a result, the remote teams miss out on a lot of the ad hoc conversation/culture that develops in the colocated offices, are frequently left out of some meetings (sorry, who forgot to dial-in?), and inevitably begin to feel like 2nd-class citizens.
Trust me, I’ve been there.
A fully-remote team, by contrast, means no conversations are happening in an office somewhere to miss out on. At Digits, the pulse and culture of the company is pushed online for everyone to partake in: what would normally be hallway conversations now happen in some digital form. Chats are quickly upgraded to voice/video calls when written communication is not enough—and there is no stigma towards, or friction preventing, those who were passively following along in the chat room now asking to join live. Everyone is on the same level playing field.
This makes our fully-remote team feel like we aren’t remote at all. We’re all working right next to each other, at adjacent desks, despite being thousands of miles apart. Our remote interactions are a real and meaningful replacement for stopping by a coworker’s desk to chat something out or chasing them down in the hallway.
The moment any part of your team is physically together in an office, all of these critical distinctions begin to break down.
The Buddy System
We aim to run all projects at Digits in micro-teams of 2-3 people. Sometimes 4, but in practice we’ve found they tend to immediately split themselves into pairwise sub-teams.
The major benefit is you always have a buddy. From the moment we kick off the week, you know what your goals are and who you’ll be working with to achieve them, so you can dive right in together.
On the engineering side, this means you always have a designated code-review partner to keep things moving. It varies, but over the last 2 years many of our teams organically started to pair-program (yes, fully remotely) to further align and accelerate their work.
On the business and product sides, it’s the same story. We pair on strategy docs, product wireframes, marketing copy, blog post drafts—you get the idea. And pairing makes the work way more fun! You’re not sitting in your house toiling alone; you’re talking with at least one other colleague constantly, and you’re both working together to achieve a common goal.
It’s easy to think we’re wasting time having at least 2 people tackle every task, but the opposite is true: quality is much higher, each project moves at a faster pace, and in a distributed world, redundancy is critical to increasing the odds that someone knowledgeable about a thing is online and available.
The benefits have been dramatic: nobody is lost in their own world either slacking off or making unilateral (mediocre) decisions. Ideas are iterated and improved rapidly as they are discussed in small groups and then raised for broader awareness. And there is no unwanted overhead or design-by-committee: each micro-team is empowered with their own goals for the week, so they know the direction to head in and are trusted to seek input when and where they need it. If they haven’t, it will become very obvious at our next group check-in 🙂
The Death of 30-Minute Time Slots
To stay in sync and highly aligned as a remote team, we do (short) all-hands meetings every 48 hours. Apart from that, we aim to have no other scheduled meetings.
Of course, interviews do need to be booked, and external customer/partner meetings get scheduled, but the principle holds: work within one’s micro-team is fluid and synchronous—you’re constantly on and off ad hoc video calls or pairing sessions with your buddy, but work between teams is async: via Google docs to review, large PRs that need broader buy-in, blog drafts that need editing, etc.
Digits is fully remote, has no office, and owns no conference rooms. This fact is critical.
Without conference rooms, there are no scarce resources to book, which means meetings don’t need to be planned in advance, which means they don’t need to be 30 minutes or an hour long. Chats can happen when the necessary people are available (which in practice is typically within minutes, because teams are small and independent, and no one else is over-scheduled either). You can add people to meetings when they are needed, and they drop off if the topic moves on. There is none of the awkwardness, friction, or wasted time of traveling between, waiting outside of, entering, or leaving, physical conference rooms. It’s truly remarkable.
This has made our typical internal “meeting” last on the order of 5-7 minutes: you hop on, get your questions answered or share your perspective, and return to execution. With the elimination of Parkinson’s Law, the Maker’s Schedule is complete: meetings usually aren’t long enough to knock you out of flow.
This flips the typical work day on its head: rather than running between recurring meetings and trying to “get stuff done” in between, we’re all free to focus on executing until pinged by someone who needs input. And since those interrupts are typically quite short, they aren’t disruptive—you’re right back at it without forgetting where you left off.
All of this creates an interesting reality: we’ve felt that we’ve reliably had more face-to-face interactions with colleagues than we ever did in physical settings. Everyone is more available. There is less friction to chatting—you don’t need to walk across the building to catch someone at their desk. And because the interactions are shorter, they tend to be much more frequent: I’d much rather chat with my teammates for a few minutes every day than a half hour once a week in a standing meeting!
The Remote Work Toolkit
Productivity tools often border on religious choices for many people and organizations, so I hesitate to make specific recommendations.
Instead, it’s more important to focus on the “jobs to be done”—what use case is each tool meant to solve—and then standardize on an answer for each, so everyone on the team knows where to go.
Over the past 2 years, we’ve converged on the following core roles for our tools:
Asynchronous & semi-synchronous lightweight chat (no important decisions, no expectation of reading scrollback)
Synchronous 1-1 (or small group) video/audio chats
We have preferred to find specific tools that really excel at each of these distinct use-cases (even if we only use a tiny fraction of the tool’s functionality), rather than consolidating on fewer tools that might be less ideal. In practice, we’ve not had much issue forgetting where something is because the use cases are sufficiently distinct and obvious.
We also constantly evaluate and explore new tools, as the pace of innovation in remote collaboration is currently exploding.
For those who insist on asking, our current toolchain at Digits is:
…but it can and will change as new options come on the scene 🙂
We do not use email for anything other than customer support, and I can hand-count the total number of internal emails we’ve sent since starting the company.
A New Set of Employee Benefits
As founders, Wayne and I care deeply about showing company personality through employee benefits. Above and beyond health insurance and 401ks, we try to embrace the remote-work lifestyle to ensure every team member’s day-to-day is as delightful as possible.
Wherever You Work Best
Not everyone “works remotely” the same way. Some people have a home office they have used for years, but that’s really not typical. Usually it’s a difficult choice—do I take over a spare bedroom or underutilized corner of my house or apartment, or do I find a co-working space nearby? Countless factors go into this decision and it would be unfair for us to motivate one over the other.
So we happily support both!
Every new Digits employee gets the choice: if you’d rather work from home, we give you a $2,000 budget to outfit your home office. A great chair. A new desk. Houseplants! A side-table with a coffee bar. Really anything you feel would make your day-to-day more enjoyable. Conversely, if you’d rather go the co-working route, awesome. Pick your favorite spot and we’ll cover your monthly membership fee for a desk.
The Need for Speed
Regardless of which direction you go, we have another perk up our sleeves. We’ve found that everyone works from home sometimes, for many reasons, even if they prefer a coworking environment. And ISP quality varies widely across the country.
Starting last year, we rolled out a new benefit: Digits pays for every employee’s home Internet service, and we immediately upgrade it to Gigabit (or the equivalent fastest available plan)!
Never have you seen a more butter-smooth video-chat experience from so many different homes across the country…
The New Power of Team Travel
Gone are the days of traveling between distributed offices for alignment sessions or making the monthly trek to HQ.
There’s no office at all, so there is nowhere you have to go just to make an appearance or get face-time! Instead, all internal business travel can be deeply intentional, and optimized for creating amazing shared experiences.
At our current stage, we’ve found the ideal cadence is quarterly. 3 times per year, we host our Digits Onsites: we rent a series of AirBnbs (or hotels, as we’ve scaled) and we bring the entire team together somewhere in the country for a jam-packed week of strategic planning, knowledge sharing, in-person work and collaboration, and fun team-building activities and celebratory dinners. During the 4th quarter, we throw our annual holiday party.
And what we’ve learned is that working remotely makes these in-person moments together even more memorable. Time is punctuated by Onsites. Product milestones are marked by the strategy we discussed at each one. Team members’ start dates are recalled by which Onsite they first joined.
There’s always the next one on the calendar to look forward to, and we go to great lengths to make each one special, in some way or another. With no corporate budget dedicated to facilities or inter-office travel (indeed, one month last year our cash burn was 91% payroll-related!), we instead shift those resources to Onsite logistics, with great effect.
The resulting work-life balance has been magical: we are home with our families, with no commute to speak of, day-in and day-out, with flexible schedules and an unlimited vacation policy, and then we’re all together each quarter, exploring someplace new and aligning on our next chapter.
The Future of Work
Without question, we will be forever adapting and refining our approaches to remote work with each new level of scale and degree of business complexity, but we foresee no structural reasons that would cause us to change this basic approach. Indeed, great companies such as GitLab, Invision, Buffer, and many others have pioneered this path with well-recognized success.
At Digits, we’re extremely energized by the growing interest in remote work and the explosion of new tools that are being built to facilitate it, and we’re excited to join the community in sharing and iterating best practices.
These past 2 years have honestly surpassed our wildest expectations: one of our teammates recently expressed that they don’t see themselves returning to an office environment for the rest of their career.
Everyone else nodded in agreement.
If you’re excited to join a passionate, fun-loving, fully-remote team that’s obsessed with building delightful business finance software, we’d love to meet you! See our open positions here.
Six months ago we shared a preview of our next adventure, and of our obsession with building modern, intuitive, intelligent, delightful financial software. And the response has left us overjoyed and even more focused.
We’ve heard from countless business owners, CFOs, and accountants who’ve all lost patience with the status quo and who share our hunger—and our vision—for a better solution. We’ve also been humbled by so many offers of support.
We’re also excited to share that Peter Fenton has brought his wealth of board experience from AirTable, Twitter, NewRelic, Yelp, and many others to Digits.
$1.5B+ And Counting
We’d like to thank our early customers and partners that have all generously shared their time, knowledge, ideas, and feedback with us over the past year as we’ve built out our core platform technologies. Digits’ production systems now see over $1.5 Billion in transactions across our customer base, and that figure grows daily.
As builders, there is nothing more gratifying than crafting a product that is used by millions. That saves them countless hours of effort. That turns something complex and frustrating into something accessible, intuitive, even delightful.
As founders, there is nothing more fulfilling than assembling a team of brilliant, passionate, customer-obsessed, kind people who you love working with every day. Who you trust deeply. Who you care for as friends and family.
When we set off to create Crashlytics in 2011, we were struck both by the potential of the nascent mobile ecosystem and by the frustration of actually building for it. How could it be so hard to make an app that didn’t crash? How could the bugs be so tricky to track down and fix, once the app did? We felt there was an opportunity to apply consumer-grade design and engineering to an obscure developer issue; an opportunity to bring enterprise-grade tooling to everyone on earth who aspired to write an app.
We got lucky.
We found a dream-team of like-minded builders who we owe everything to.
And we discovered that we had struck a chord with mobile developers around the world, from established tech companies in Silicon Valley to passionate indie devs in homes, in coffee houses, and in garages in almost every country on Earth.
And the scale left us humbled—today, Crashlytics processes trillions of events, from billions of mobile devices, across millions of apps. Every single month. Today, Crashlytics runs on substantially every active smartphone on Earth.
But that journey wasn’t all smooth.
Building a business is an endless rollercoaster of emotions, of challenges, of long explorations, of setbacks, of celebrations. And we unwittingly found our next project along the way.
The Next Puzzle
As builders, there is nothing more exciting than cracking the next engineering puzzle; than perfecting the next design; than delivering the next capability to customers.
And there is nothing more mind-numbing than the paperwork, and spreadsheets, and financial reports, and inscrutable transaction records that are all required to actually operate the business.
Globally, most entrepreneurs today have no formal training in business finance. We certainly didn’t. Today, you start a company to solve a real problem for real people, or to offer a service you’re skilled at, or to provide a living for you and your family. You don’t start a company because you want to operate a business—but you have to anyway.
Software has unlocked vast capabilities in some areas—you no longer must be a dedicated filmmaker to create a movie, or a professional travel agent to book a plane ticket—but it has stumbled in others. You still must be a trained accountant to understand your company’s financials, and even then they require tedious, manual work to keep updated.
We’ve become obsessed with solving this, but in the right way. Not with bots that replace human accountants, but with software experiences that pair design and machine learning to democratize financial savvy. That empower people of all backgrounds and skillsets to visualize, understand, and manage their businesses, and elevate their interactions with their accountants, investors, and advisors.
We feel there is an opportunity to apply consumer-grade design and engineering to the arcane world of business accounting; an opportunity to bring enterprise-grade tooling to everyone on Earth who aspires to own or operate a business.
From Digits, With Love
We’ve been lucky to reassemble a bit of the core team we loved so much to go build this together, along with some incredible new additions.
From the team that brought you Crashlytics, we hope you’ll wish us luck on this Digits adventure.