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HOUSEKEEPING 📨

Howdy! Coming to you today from the final week or so of my 8-week ‘off-season’ from writing in the newsletter. If you didn’t notice, the months of July and August were guest posts and interviews only. This was something I had been wanting to do for a while to freshen up my mind.

I don’t think I am the only person who feels that way. Lenny barely writes these days. Packy moved from a weekly piece to a ‘when I feel like shipping’ cadence. My other creator mates feel the same. I feel super blessed to be able to write this newsletter, though, and plan to keep doing it for the long run. So this little break from putting pen to paper has been great. While we are talking about it, though, I’d like to ask your opinion on something.

I’m planning on ramping back top two (or maybe even three) pieces per week from September onwards so this will help shape the future of the content. Anyway, enjoy today’s interview.

INTERVIEW 🎙️

Jeff Seibert, Co-Founder & CEO at Digits

Jeff Seibert is the CEO and Co-Founder of Digits, an AI-native accounting platform transforming how startups manage their finances. A Stanford computer science graduate, he previously co-founded Increo (acquired by Box) and Crashlytics (acquired by Twitter), later helping lead Twitter’s developer platform and consumer products. He also played a key role in Fabric, which Google acquired.

Digits has raised over $100 million from top investors like Benchmark and GV, with a valuation exceeding $500 million. Seibert is a prolific angel investor with over 100 startup investments, including Opendoor, Gusto, and Planet Labs. He has spoken at Stanford, Harvard, and MIT, and appeared in Netflix’s The Social Dilemma, highlighting his impact on both technology and startup ecosystems.

Tell us about the problem you're trying to solve? And why this?

Digits is the world’s first AI-native accounting platform, and it automates basically all of the tedium that goes into doing your bookkeeping, your accounting, and the month-end close. This came from my journey as a serial startup founder. This is my third company, and in my prior two startups, I was just so frustrated by the lack of data.

You’d sit there waiting two to three weeks after the end of each month for your accountant to get you your black-and-white profit and loss statement, balance sheet, etc. By comparison, on the product and engineering side, you had real-time dashboards, Google Analytics, A/B testing tools, all this stuff that's live and insightful. And I was just like, ‘Why doesn’t that exist in the finance world?’

That’s why we started the company. That’s what we built. Digits brings together all of your banks, cards, payroll, and payment processing data in real time. Our AI bookkeeping models—which we’ve spent five years training—automatically book about 95% of it. The rest gets surfaced in an inbox, so it’s super easy and quick to clean up. You go in, handle the remaining bits, and the models learn instantly. You get live, real-time finance dashboards so you can actually understand your business.

What was the most difficult when going from zero to one?

By far, the hardest part was building out the complete feature set and getting the data clean enough to train models on. As you can imagine, Australia actually has it a little easier, but in the U.S., pulling data from your banks, credit cards, and all the different systems is really complicated because there are no open banking laws.

Cleaning that data and making sense of it so we could do the accounting accurately has been the hardest challenge. We’ve spent years building the product—this isn’t something you can stand up overnight. We’ve been really disciplined. We raised $100 million to go on this journey and spent basically five years in stealth mode building before we launched earlier this year.

Did you have some error rate initially?

Yes! And it’s improved dramatically over time. A few years ago, Digits was only about 50% accurate. Half the time, it would book a transaction incorrectly. Obviously, we didn’t release the product then, we just kept working on it. The big realization was that accounting is not generative. You don’t want an LLM hallucinating your books or making up categories in your chart of accounts. So instead, we use our own custom-trained predictive models—classification models that can’t hallucinate. That’s where we’ve focused all our engineering effort. Now, those models are extremely accurate. Across our entire dataset, we auto-book 98% of transactions correctly, which is incredible.

In some companies, it even gets to 100%. The system learns each business, so as you go through your inbox and clean up the remaining transactions, it learns immediately. The next month, it’s even better.

Tell me about your day-to-day job as CEO?

It’s bouncing between too many things—way too many things. The way I view my role, and this is my third startup, so it’s something I’ve evolved over 17 years of doing startups, is that my goal is to keep everyone unblocked and help anyone in the company who needs support. So I bounce between writing marketing copy, reviewing designs in Figma, and talking through technical architecture with our engineers. I still code a little. I spend a small part of my time fixing bugs in the code.

I try to be involved in everything across the company at what I call the 10% phase and the 90% phase. I want to be part of things early on—helping with the strategy, roadmap, and rough design—and then again at the end, polishing things before we ship. That could be the pixels, the copy, or whatever we’re putting out into the world. So my day is really just bouncing around the company, talking with people, and making sure things move forward.

Who are your direct reports? And how do you manage them?

We have a head of engineering, a head of product strategy, and a head of go-to-market—those three run the rest of the company. I also have a chief of staff who handles recruiting, finance, operations, basically all the G&A stuff that doesn’t fall into one of those buckets. So overall, I have four direct reports.

We’ve done some things that are probably non-standard. We started the company seven years ago, and we’ve run the entire company on a weekly sprint cadence ever since. I lead an all-hands meeting every 48 hours—and I’ve done that for seven years. Here’s what it looks like: Monday is the kickoff. Every team—organized into workstreams—presents three to five key goals for the week. Right now, we have 12 workstreams and about 70 people total. Then on Wednesday, we do check-ins. Each workstream gives a quick update on how their goals are going—what's on track, who needs help, what’s falling behind, what might need to be re-scoped. We usually add a quick 10-minute internal presentation to share something interesting.

The cadence resets again on Monday, and this rhythm helps us move fast while keeping everyone aligned and in the loop.

What's your North Star? And who is your ICP?

At this stage of the business, it’s now ARR; annual recurring revenue. We’re focused on ramping revenue. Earlier on, we paid more attention to signups and, instead of DAU—since it's an accounting product—weekly active users and engagement with the platform. But now that we’re in full go-to-market mode and signing big deals with accounting firms, our real North Star is growing top-line revenue.

Our ICP is basically the QuickBooks and Xero market, which you're familiar with. Small businesses, startups, and the accounting firms that serve them. With accounting software, you have to work for both the business owner and the accountant, since they collaborate to get the bookkeeping done.

So that’s our core focus: SMBs, typically with $0 to $5 million in revenue and 0 to 50 employees. That’s our sweet spot. We also work with enterprise, which for us would be a large accounting firm with tons of clients.

Finding our ICP it came down to: do you sell primarily to the business owner, or do you sell primarily to the accounting firm? We spent years exploring both angles. And the real answer in our market is—you have to sell to both.

The business owner gets excited about a better accounting package, and the accounting firm gets excited about the AI and automation because it saves them a ton of time. So we’ve now designed what we call the ‘operator-accountant loop,’ where they each invite the other into the product. The accountant brings in more clients, and the business owner invites their accountant or friends who run businesses. We try to drive that whole loop.

What GTM channels do you have working today?

This spring, we’ve seen a lot of interest from accounting firms. The accounting channel in the U.S. is very tight-knit—there’s a lot of word of mouth and a lot of activity centered around a few major conferences each year. I just gave the keynote at Scaling New Heights in Orlando, Florida. It was 2,000 accountants in a massive ballroom, and we introduced Digits there. Our booth was flooded the entire conference—it was incredibly effective.

So that’s our strategy this year: reaching out to accounting firms and showing up at the events they attend. We still do the usual online advertising and marketing, but for this space, meeting people face-to-face works really well.

How do you set goals?

This will be another non-standard answer. Our weekly sprints roll up into what we call ‘horizons.’ We plan in terms of horizons because it represents, literally, as far as we can see. Right now, that’s about five weeks. So we plan in four- to five-week increments—here’s what we want to ship, here’s where we want to be, and here are the top metrics that matter. All of our weekly work builds up to that horizon goal.

Now that we’re scaling, we’ve started discussing adding a higher-level layer we’re calling a ‘waypoint’—something like a quarterly target or a six-month vision. But all of our detailed planning happens at the horizon level. One of the advantages of how we structure our workstreams is that we can stop and start different workstreams each horizon. We spend the last week of every horizon planning for the next one.

During that final week, the leadership team and product managers focus heavily on planning. It works well because by the end of a Horizon, most of the engineering work is in the polishing phase—putting final touches on what’s about to ship. So while engineering wraps up, the PMs and leadership are setting goals and direction for the next Horizon.

What’s your recruitment process like?

Hiring is always the toughest part—the team is the single most important thing. So we’re very deliberate and thoughtful in how we hire. When I left Box to start Crashlytics back in 2011, Aaron Levie gave me a great piece of advice: “You should hire a full-time recruiter as your first employee.” I didn’t do it as employee #1, but I did around #7. And we did the same thing early at Digits; we brought on a full-time recruiter very early, and it completely changed the company.

We don’t post job openings. We do all of our own sourcing and outbound outreach to find talent. Every role has a take-home work sample—customized to that position—so we can see how candidates think and execute.

Then, when we bring them in for an ‘on-site’ (on Zoom), it’s an extension of that work sample. We get to talk through how they approached it, see how they work, and understand how they collaborate in real time. We also put a lot of effort into top grading—really understanding a candidate’s career path, who they’ve worked with, and what those people would say about them. It helps us get a well-rounded view of every candidate.

Oh and one question I love asking is, “As you look back on your career so far, what are you most proud of?” It’s a really revealing question. It shows what people value, what they believe they contributed, and how they think about their work. There’s no right or wrong answer—I’m not focused on the specific project. I care more about how they talk about it, because that reveals what matters to them.

How big are your take-home projects, and how collaborative are they?

Great question. We aim for the take-home projects to be about four hours of work. We want to be respectful of candidates’ time; everyone’s busy. I’ve found that if the project is too long or too demanding, you lose the top talent because they’re simply not willing to do it.

We think four hours is the right balance. It’s enough to show meaningful work but manageable for someone to complete over the course of a week if they’re serious about the opportunity.

What did you learn from the Box and Twitter acquisitions?

Every acquisition is different. When you start a company, people often ask, ‘Are you building this to sell or to IPO?’ And to me, that’s the worst possible question. The answer should always be: you’re building a great business. If an opportunity to be acquired comes along and it makes strategic sense, great. If you’re in a position to IPO, also great. But what matters most is: are you delivering real value to customers, and are they paying you for that value?

In any deal, the key is understanding the acquiring company’s motivation. There are basically three types of acquisitions. The smallest are usually acqui-hires; they just want the team. Then there are IP or product acquisitions. Maybe they want your tech stack, a feature set, or your customer base. And then there are strategic acquisitions, where your company actually changes something fundamental about the acquirer. Those are the most valuable and highest-dollar deals.

So my biggest advice to founders is: be blunt in those conversations. Ask directly, '‘What’s your goal with this acquisition?’ Because that answer will determine the value of the deal and how successful it ends up being.

How do you get the best out of yourself personally and professionally?

For me, every company I’ve started has come from a problem I personally experienced. Digits came out of the frustration I felt at Crashlytics, just not having any visibility into the finances. That’s a real motivator. I know exactly what I want, I know the problem I’m trying to solve, and I know we haven’t fully solved it yet—not until it’s 100% automated. So I keep pushing because I believe it’s possible. That drive keeps me going.

I wish I had a better answer for you. Honestly, my life is tech. When I’m not working on Digits, I’m coding something else or angel investing in startups. I’ve made over 100 direct angel investments. I live in San Francisco, right in the heart of Silicon Valley, so for me, life and tech are basically the same thing.

And that’s it! You can follow and connect with Jeff over on LinkedIn and Twitter, and don’t forget to check out Digits' website.

BRAIN FOOD 🧠 

HIRING ZONE 👀 

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TWEETS OF THE WEEK 🐣 

TOOLS WE USE 🛠️

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