
Pilot.com raises $15M to bring bookkeeping into the modern era - aston
https://techcrunch.com/2018/03/14/pilot-raises-15m-to-bring-bookkeeping-into-the-modern-era/
======
curun1r
Having worked at Intuit, I'm always amazed at the number of people that look
at how crap Quickbooks is and think that beating them is a matter of just
making better software. There's some really important psychology that most
competitors completely miss.

First, Quickbooks is frequently not chosen directly. Many, many small
businesses choose their bookkeeper first and use whatever they use. One trick
Intuit uses both in Quickbooks (bookkeepers) and TurboTax (CPAs) is to put a
lot of effort/money into focusing on those relationships knowing that they
have a huge indirect impact on acquiring and keeping customers.

Second, the fact that Quickbooks is so awkward and inconsistent to use isn't a
UI problem, it's a feature. This is an important lesson in designing software
that people use for their jobs. When you make elegant, intuitive software that
almost anyone can use in short order, it stops being an impressive item to put
on a resume. And it stops being a barrier to entry for competing
professionals. Software like Quickbooks that's hard to use correctly becomes a
selling point for bookkeepers and almost accomplishes the same purpose (though
to a lesser degree) than professional licensing organizations...it limits the
competition and keeps the rates they can charge high.

So many Quickbooks competitors have failed to knock them off their perch by
not realizing that their customers aren't really their target audience and
what should be their target audience doesn't want easy.

~~~
Dwolb
I really hope you weren't a product manager at Intuit.

>Second, the fact that Quickbooks is so awkward and inconsistent to use isn't
a UI problem, it's a feature. This is an important lesson in designing
software that people use for their jobs. When you make elegant, intuitive
software that almost anyone can use in short order, it stops being an
impressive item to put on a resume. And it stops being a barrier to entry for
competing professionals.

A good professional product does not have "awkward or inconsistent" UI. It has
consistent, useful UI that can expand as user's sophistication grows. i.e. it
has a learning curve

The curve for learning an "awkard and inconsistent" UI you highlighted is
useless and a detriment to SMB's everywhere. A proper SMB accounting approach
would to have standard patterns for doing simple accounting with the ability
to grow and extend as sophistication of your org grows.

~~~
curun1r
I was a dev manager for a team that was working on a Quickbooks-adjacent
product. I had a lot of meetings with core Quickbooks teams and met many of
their PMs. They are, for the most part, really good at their jobs.

Your comment comes off as incredibly naive. It's the same naivete that I had
before seeing the internal perspective and it's what my comment was
addressing. There are psychological phenomena in play that make an existing,
market dominant piece of software more successful and harder to displace when
it's objectively harder to use when that software forms the basis for
someone's job.

And it's important to realize this because this is counterintuitive to what
those of us that create software for a living have been taught. We're taught
to think like you. We're taught to make software that delights our users and
is as easy as possible to use. But understanding a specific set of
circumstances when that approach is destined to fail can be important.

~~~
Dwolb
>There are psychological phenomena in play that make an existing, market
dominant piece of software more successful and harder to displace when it's
objectively harder to use when that software forms the basis for someone's
job.

For the record and from the GP's context, I'm going to assume by 'harder' you
mean 'difficult to use UI'.

I'd assert 'difficult to use UI' is the incorrect type of 'hardness' or
'difficulty' that should be present in an enterprise piece of software. Mainly
because fighting a UI is non-value add to the goal of the user. The user's
goal, in this case is to manage their books.

Because of this tension of QB _purposefully_ being at odds with the user goal,
I'd expect start-ups and new software products to gobble up QB market share
over time. If this is the case, all QB can do is make it more difficult for
current users to switch off them (.QBW file extension?) as their market share
slowly dwindles and their channel sellers slowly disappear.

Good 'difficulty' should come from the learning curve it takes to master (i.e.
accurately, quickly, and reliably) the task at hand.

FWIW I'd expect purposefully building difficult-to-use products has many
negative externalities for the company culture and this would be a big red
flag for any future Intuiters.

~~~
curun1r
You're still not getting it. A Bookkeeper's goal isn't to keep the books.
That's their product, but they have their own small business that has more
fundamental goals. Accounting software that's easy to use makes it easier to
keep the books, but it runs counter to that more fundamental goal of running a
successful small business. You're right that there are negative externalities.
Small business accounting costs more than it needs to and, by extension, small
businesses need to charge customers a bit more. But the people deciding which
accounting software to use are the ones benefiting from that negative
externality, not the ones paying for it. And as a software vendor, you always
target decision makers over users or you go out of business.

~~~
davemel37
I don't think anyone is misunderstanding your point, I just think its
ridiculously backwards. It's the equivalent of the government breaking roads
so they can create jobs fixing those roads. If software can simplify
bookkeeping and make the profession obsolete, and you deliberately make your
software in a way that keeps that inefficiency at play...you guys are gonna
wake up one day and realize you spent all your time serving the bloated
middleware instead of the true end user, and your market will evaporate before
you know what happened....

We get that from a short term perspective, it may make sense to keep it too
complicated for the end users, but efficient markets will prevail short of
forced intervention.

If that is how Intuit thinks, I cannot wait for the day when they get
displaced.

~~~
curun1r
Yes, it's ridiculously backwards. But it's reality. Intuit, at various times,
has tried to make the kinds of changes you guys are suggesting. And every time
they've run smack into reality and had to backpedal. Reality is like
that...you can try to deny, and fail, or accept it and adjust your thinking.
It isn't a how Intuit thinks issue, it's the way their customers think after
decades of getting comfortable using Intuit software.

Another example...Intuit has wanted to transition customers away from the
desktop version of Quickbooks for many years now. If you think Quickbooks
online has it's learning curve, just spend some time using the desktop
product. It's a maze that takes years to learn to navigate and many of the
"features" are horribly buggy from years of neglect. But pry it from their
cold, dead hands Intuit cannot, so you can still buy new versions of
Quickbooks Desktop.

That's why what you guys are saying is so ridiculous. You're denying a reality
in a field you're not familiar with. You're saying something should be
different because it's inefficient or other industries work differently. But
you haven't done the user research. You don't have decades of experience
dealing with the people who actually spend money on the software. You're in no
position to critique the way that Intuit thinks.

~~~
edraferi
I agree with you, and have seen other examples:

\- government managers are evaluated on budget and headcount because the core
services they provide are hard to measure. Thus they don’t want new software
to help them be more efficient, unless the alternative is catastrophic,
visible failure to provide their service.

\- Lawyers charge by the hour. They don’t want new software to dramatically
reduce the time spent in discovery. Then they would have to bill for outcomes
(cases won) and there are too many things out of their control.

Basically nobody wants to charge for value, because value is hard to quantify
accurately and quickly. You wind up showing costs to prove value, so nobody
wants to reduce costs.

~~~
dragonwriter
> government managers are evaluated on budget and headcount because the core
> services they provide are hard to measure.

That’s... untrue. Government managers are judged (in terms of evaluation of
job performance) largely on _minimizing_ both costs and negative public
attention.

OTOH, managers _generally_ (and not just in the public sector) like to have
big budget and headcount numbers _on their résumés_ as proof of scope of
responsibility.

------
adam_gyroscope
Pilot customer here; they are amazing. It's pretty different from a regular
bookkeeper largely in that Pilot is super accurate and timely. My time spent
doing bookkeeping for my small startup went from an hour or two a week to zero
hours a week - those are pretty important hours. Highly recommended.

~~~
andruby
Can you explain how it saves those hours? Do you no longer have to input
invoices and expenses? Is that all automated?

~~~
adam_gyroscope
Yep - all of that is automated. Importantly, all the the classification of the
transactions is automated as well, so I no longer have to look at a charge
like "GUS99PWR-T __BILL.COM __" on my credit card statement and figure out a)
where it is from and b) that it should be categorized as a
marketing/promotional expense.

~~~
MarkMc
How do they know that "GUS99PWR-T BILL.COM" is a marketing expense? Do they
use the fact that other users have previously classified "GUS99PWR-T BILL.COM"
as 'Marketing'?

~~~
wdaher
The first time we see something totally unknown to us, just like a normal
human bookkeeper, we'll have to ask you about it (assuming there isn't
metadata somewhere else that helps us categorize it).

But then once you've told us, _unlike_ a normal human bookkeeper, we won't
forget about it later — we'll actually encode a rule in our software that will
enforce this check going forward.

(And yes, you also do benefit from "If our system has seen this type of
transaction somewhere else, we can make a more intelligent guess")

~~~
enraged_camel
So let's say I have a $29.99 expense from AMAZON.COM and tag it as a marketing
expense. Then I buy something else from Amazon tomorrow for $44.99.

Are you telling me that it gets automatically tagged as marketing? Because
that seems... naive at best, and hugely problematic at worst (as it can result
in a huge amount of expenses getting incorrectly tagged).

~~~
ckeck
Exactly what I came to ask, because I have at least a handful of vendors
(perhaps more) that I have to key in across multiple categories.

Rules cannot be applied to these transactions. For the obvious ones, I already
have automatic rules build right into QuickBooks Online.

What is different here?

~~~
fma
My guess...they use quickbooks in the background, which allows you to upload
receipts. If the description of your amazon receipt looks like furniture, then
they'll mark it as such...if it looks like office supplies...office supplies.

I use Wave, which lets you upload receipts and it will perform OCR to extract
vendor info, date, total cost. It's not much of a leap to go 1 step further
and look at the line items and categorize...again just a guess.

------
lancewiggs
In NZ, UK and Australia we have been using Xero for years, and there is a
vibrant ecosystem around it. And yes - it’s turned bookkeepers and accountants
into advisors, completely changing their professions. Xero is listed, worth
$3-4 billion and growing quickly.

So how is this different, and how is it going to integrate with Xero, QBO and
other cloud accounting software? And why does the article not mention these
elephants in the room?

~~~
Lazare
That was my first thought too. Xero is quite good and very large, and it's
absolutely in the "modern era". And it's growing a very large ecosystem of
accountants and consultants that are building on the platform to offer the
_exact_ service that Pilot is (apparently) offering.

Launching a Xero killer is ambitious but doable. Launching some new
bookkeeping software (or...service? what even are they doing?) seemingly
without being aware of Xero seems...deeply myopic. Xero is big, their product
is solid, and they're able to move a lot quicker than the legacy vendors. And
this:

> When a company starts working with Pilot, the actual core experience on the
> customer side doesn’t really change all that much: they still work with a
> human on the other end. But the bookkeeper from Pilot is working with the
> internal tools they have built to bring in the data from the company,
> organize it and structure it, and produce a set of books that are more
> accurate than someone might have produced than just doing it by hand.

That's a bizarrely accurate description of _how stuff works today_. That's not
new, that's standard. I'm not sure if the article is terrible or the product
is terrible, but something is clearly not coming through.

Similarly, all the stuff about categorization of expenses? Again, that's just
a core feature in modern bookkeeping software; Xero allows you to configure
very detailed rules. And then since the rules can't be 100% accurate in all
cases, your actual bookkeeper (the one who _uses_ the software) is going to
ask you about the ambiguous ones.

I'm just mystified as to what the value prop is. "Bookkeeping firm raises $15m
to provide the same services everyone else does"? How is this tech news? Or
even news? (Caveat: My experience is outside the US, maybe this is less
common/standard in the US?)

~~~
wdaher
Pilot is not replacing Xero or QuickBooks (in fact, we do all our work in
QuickBooks -- and we're definitely aware of Xero.)

Pilot is _a better bookkeeper_ , and the reason we can be a better bookkeeper
is that, even with a tool like QBO or Xero, there's still a bunch of
incredibly manual work that happens ON TOP of those platforms, and a lot of
that work is very well-suited to being done in software.

Do Xero and QBO get better and smarter with time? Sure, yes, of course they
do. But the problem is: no one software company (i.e. a company with the
ability to develop software) owns the problem end-to-end, so it's never going
to be seamless.

(It's not obviously Xero's problem if the Xero/Gusto sync isn't very good, and
it's also not obviously Gusto's problem either. Net result: the bookkeeper
does a bunch of work by hand to fix it all up themselves--work that's super-
manual and tedious.)

That's where we come in; we're the bookkeeper, but we also have the ability to
write software when it's appropriate for solving the problem.

~~~
Lazare
> Pilot is a better bookkeeper, and the reason we can be a better bookkeeper
> is that, even with a tool like QBO or Xero, there's still a bunch of
> incredibly manual work that happens ON TOP of those platforms, and a lot of
> that work is very well-suited to being done in software.

Xero is a platform with an extensive API, partner program, app marketplace,
etc., and a large ecosystem of partners, including bookkeepers, that offer
what sounds to me like exact thing. If you want a better bookkeeper that uses
automation to provide a slick experience on top of a modern software
platform...I have no reason to think Pilot can't do a great job of that, but
that's _totally_ the value prop of the Xero partner program too...right?

If the sync isn't very good and your doing some manual work categorising
stuff, why not...write some tools to automate the categorising, and then feed
it back into their API?

I'm sure I'm just being obtuse, but every explanation of what Pilot is doing
just sounds very "standard". Are you trying to do this cheaper, or better,
or...?

> That's where we come in; we're the bookkeeper, but we also have the ability
> to write software when it's appropriate for solving the problem.

Okay, right, but...Xero has a pretty great API. I've written software that
solves problems by working with the Xero API; I didn't need to write my own
bookkeeping software to do it. Xero is outright targeting "bookkeepers that
can write software" for their partner programs and developer APIs, no?

(Sorry, if I seem like a Xero fanboy, but I do like them, and their offices
are right down the road, so I suppose I might feel some local pride.)

------
ivankirigin
If you're new to being a startup founder, you might be surprised by how much
time you must waste on this area. Getting it right isn't optional, but most
technical founders have a weak finance background. Spend money on tools like
this to get your time back.

~~~
fma
Agreed...started using Wave but I feel like I should have used quickbooks.

Though they have payroll, they do not pay your taxes for you (only in a few
select states). You need to do it manually...and at times I've forgotten and
had to pay penalty. Now I use square - and they do it all automatically. I
didn't know I had to 'turn off' payroll in wave and was charged the $15 a
month even though I didn't run payroll for any employees.

Payments...their recurring invoices are good, but you need to do some manual
work. They create the invoices and it adds to your sales. When they deposit
your money to your bank it adds to your sales as well. So you need to find the
one they deposit and manually delete. I asked if there's like a report they
generate that tells me everything they've deposited...it doesn't exist. So you
could mistakenly delete something, or forget to delete something...and it
throws everything out of whack. You could be underpaying or overpaying taxes.

Their 'ACH' requires people to log into their bank. I'm not going to try to
convince my customers to click on a link on my invoice and put in their bank
credentials.

I have other gripes...there's definitely room for improvement. I haven't seen
_that_ much changed in the last few years...not sure if they cut back on their
development team or what. I probably should have looked more heavily into
Quickbooks since that's the industry standard. I will look into pilot, though.

~~~
acct1771
Off-Topic, but anyone else here regret using Wave? Have started with them, but
it's not too late for me to move.

~~~
kitcar
I want Wave to succeed but can't recommend their accounting product to anyone.

Ran into major issues with their accounting product (especially around
reporting, and dealing with multiple currencies). Reached out to their team to
explain the problem, they agreed it was a significant problem, but didn't
really have a desire to fix it. Fast forward 12 months, core problem is still
there. My only thought is when your product is free its not always easy to
figure out how to prioritize what you work on.

I have found Xero to be the best intersection of function and price for SMB -
Quickbooks online also had some significant quirkyness (i.e. one thing Intuit
doesn't really highlight is Quickbooks online is not feature complete when
compared to Quickbooks desktop - hence there are many desktop features and
reports which just don't exist in the online product...)

------
amoorthy
I use two Intuit products at my startup: Online Payroll because my BofA
account easily integrates with it and Quickbooks to manage the books (because
my accountant suggested it). Both products are easy to use.

Online Payroll looks like a '90s UI but works. Some complications like if you
have some non-standard paperwork to file with a tax payment then you have to
do at irs.gov.

Quickbooks UI is actually pretty slick (perhaps recently updated?) The
automatic classification is ok, nothing special. One issue is duplicate
payroll transactions due to sync'ing with a bank account and Intuit Online
Payroll.

On the whole I spend about 5 min every pay cycle creating paychecks and
issuing tax payments. Once a quarter I classify expenses in Quickbooks - about
an hour. And once a year I spend a couple hours double checking things with my
accountant for the tax return.

These numbers may get more complicated when we're > 3 employees and have
revenues.

------
whitepoplar
As someone who's currently looking at Bench and Pilot, it seems that Bench is
a similar product, albeit much cheaper once one's revenues start to grow. How
does Pilot compare to Bench?

~~~
wdaher
Three key differences:

* Our books are stored in QuickBooks Online, and you have access, so you're never locked in. If you need to work with another provider or just don't like us anymore, you can hand your data to any bookkeeper in the world, because it's just QuickBooks (vs. being handed an Excel export from a custom accounting system)

* All we do is startup company bookkeeping, so we've developed super-deep expertise in it (vs. aiming to solve it for, e.g. the bakery or yoga studio)

* We do accrual-basis bookkeeping (vs. only supporting cash-based bookkeeping)—this is a pretty inside-baseball thing, but it matters as the startup gets larger

I don't know how much automation Bench has already built, or if it's all just
humans under the hood, but one structural advantage of #1 for us is that it
means our engineers can spend all their time focusing on automating error-
prone work (rather than needing to build out a QuickBooks clone).

~~~
whitepoplar
Thanks! This...makes a lot of sense.

Since you're focused exclusively on startups, is there any chance y'all can
write up a "tools" guide for people just starting out, not just for
bookkeeping? i.e. "Here's stack that new companies have a lot of luck with,
that minimizes headaches and saves time: Pilot, Expensify, Gusto, Stripe etc."
Speaking of which, any recommendations for things I can do now that will save
me headaches down the road?

~~~
wdaher
Yes! "Pilot recommended financial stack" is definitely at the top of the list
of blog posts we want to write because it's just super-nice to get set up on
the right stack from day one, rather than having to worry about it when things
are more complicated.

The short, spoiler version for now is: Gusto, Chase corp card, Stripe,
Expensify, bill.com if you do a lot of invoicing.

(And then the more 101 stuff, like, "Please don't mix business and personal
expenses")

------
Meekro
I run a SaaS company, and I'm curious why I would need a product like this.
Here's how I handle things now:

1\. Stripe charges my customers' credit cards every month, and deposits money
into my bank account once a week. If I want to check my revenues, I just go to
Stripe's website and download the CSVs.

2\. All expenses are run through a company credit card. If I want to check my
expenses, I just go to my bank's site and download transaction CSVs for the
card. If I want to graph them by month or whatever, I can just import that CSV
into Excel.

3\. For tax purposes, I need to break down #2 into categories of deductible
expenses. I just wrote a perl script parse the credit card CSVs and match
descriptions. So for example, it'd have a rule like "/digitalocean/ -> Cloud
Hosting" and so on.

I admit I'm super-ignorant in this area, but the above solution seems to work
without requiring any ongoing effort on my part. How would something like
Pilot improve things for me?

~~~
awad
Being completely ignorant of your business and noting that all businesses are
different, here are some generic considerations around each of the points you
raise.

1) Do customers prepay for a month or pay after services have been rendered?
Cancellation terms and prorating? There are accounting nuances to each which
of course can matter greatly or not very much depending on the particulars of
your set up.

2) Running expenses through a company credit card certainly makes things
easier but the same considerations as above can also apply...do you prepay for
any services? Have long term service contracts even if you pay monthly?

3) Speaking of taxes, do you have a payroll? That's a whole rabbit hole onto
itself.

As with most things, context is everything here. Having a proper set of
financials that adhere to generally accepted accounting principles (GAAP) are
absolutely needed for any fundraising or M&A activities you might do. At
minimum, a more precise set of financials can help with understanding the
nitty gritty of the business when it comes to forecasting and at-glance health
of the business.

------
aresant
A startup I would love to see is one that could provide detailed personal
bookkeeping.

Mint.com invented this at some level, but there's still an awful lot of manual
classification to drive accuracy in my experience.

In my own household Amazon Prime, for instance, is a major line item expense.

But I'm unaware of a solution that can sort through and properly classify each
purchase within Amazon.

~~~
dalore
I find the same thing with classifying purchases. Most shops can be classified
by the shop itself. But with Amazon purchases it can be anything. I have half
a mind to write a script that looks up the purchase and finds the category on
the Amazon shop page and updates the qif file.

------
diffeomorphism
Any relation to pilot.co , Pilot Corporation
([https://www.bloomberg.com/research/stocks/private/snapshot.a...](https://www.bloomberg.com/research/stocks/private/snapshot.asp?privcapid=4182636)),
Pilot ([https://www.pilotfiber.com/](https://www.pilotfiber.com/)) or Pilot
([https://pilotpen.us/](https://pilotpen.us/)) ?

~~~
wccrawford
I think this is a perfectly valid question, especially considering that Pilot
once sued Palm for naming their device Pilot.

~~~
Infernal
Which Pilot sued Palm?

~~~
wccrawford
[https://en.wikipedia.org/wiki/Pilot_1000](https://en.wikipedia.org/wiki/Pilot_1000)

------
rglover
I'm a Pilot customer. Loving the service and communication with the folks
there. Highly recommended if you're looking to get your books straight.

------
jimnotgym
This seems to me like an attempt to get into the small end of SME space and
also those simpler cases where there is

a) No stock involved

b) A small number of expenses (like items on a credit card)

I guess a saas startup or a freelancer tend to be relatively naive to finance
so generally hire an accountant. This is not just to do their books of course,
in the UK they are looking for someone to advise on structure, and this often
means forming a corporation, which they will do for you. Then there is the
issue of VAT (sales tax) which people don't find easy and are scared of. The
accountant will do all of this for you for a fee. To save you money they might
suggest that you post your expenses to some kind of portal based on xero or
quickbooks. Typing in the few expenses of these kind of businesses is
absolutely the most trivial of thing to any bookkeeper. They might also use
this system to raise invoices from if they are a free lancer.

In a small Saas business the sales are most likely automated, the Stripe
charges are a one liner, and the expenses are often all on a credit card
(hosting etc). Payroll is a doddle if you are on fixed salaries and a complete
PITA if variable hours no matter what the accounting system. If I was to do
the monthly bookkeeping for one of these businesses I would spend more time
opening the files and administering my billing to them than I would doing the
books. My point here is you either a) know what you are doing and could use a
spreadsheet or intuit or xero or Sage or b) need an accountant for advice
beyond 'what code do I post hosting costs to'. Maybe this fills a particular
niche in the US, but I don't see it troubling the accounts world in general.

I work in a different space. We have stock, and an ERP keeping count of sales,
cos etc. This is the space your Oracle, Sage, SAP are operating in with big
money implementations, and i don't see anything to trouble that here.

------
plinkplonk
Due Disclosure: Worked at Intuit, once upon a time

QuickBooks has network effects (most accountants use it and are familiar with
it) and lockin effects (once you have many years of your data in it, there is
no way to get it out and into another software. at least that is the way it
was when I worked there).

Other products with these characteristics have been disrupted and so can QB.
But it will take a lot of work, or a powerful change in perspective. That
said, from the article on TC, I don't think Pilot is actually competing with
QB.Seems to be more like a layer on top.

I also agree with most of what curun1r says. Intuit is a weird company in many
ways, but they do know what they are doing businesswise.

------
samcampbell
As a former Big 4 accountant in SF, I see Pilot addressing a huge need for
startups with a fresh technology layer. I'm sure customers will be happy to
get back to building their companies!

------
happertiger
Good. We need a substantive competitor for Quickbooks and some real innovation
in the space.

You can’t underestimate the complexity and specific requirements of accounting
software. Startups in the space begin their journey in a nuclear minefield of
customer requirements, and have to navigate not only the professions inane
nuances, but also continually evolving bureaucracies and the accounting and
tax realities they create. Not. Easy. Stuff.

I wish them luck. Seriously. It’s nice to see entrepreneurs attacking the
boring companies. :)

------
chrischen
Their pricing seems to be on par with hiring a regular bookkeeper.

~~~
rabidonrails
I'm no Intuit fan but this seems to be more expensive that Quickbooks with all
of the add-on features.

That said, bookkepping is a major pain and stellar support is definitely worth
something.

~~~
chrischen
It says they use Quickbooks Online. They are replacing the regular human
accountant.

------
orthecreedence
Somewhat off-topic, but are there products that do this for home accounting?
Like it hooks into my bank account(s), grabs all the transactions, categorizes
them, and lets me run reports on them? I have a hodge-podge setup going right
now with ledger/plaid.com/custom web UI, but missing things like notifications
and budgeting.

I've looked around a bit but not found anything that lets me just set it up
once and leave it (and learns from categorization data).

------
vinhboy
I've been working, unsuccessfully, on accounting software for small businesses
for like 8+ years now. I am surprised they got so much funding to come into
the space. Good luck to them. It's a great space to build software for because
people rely on it and they are willing to pay for it. I wish I had that kind
of funding to continue doing it.

~~~
tc7
Did you release a product that didn't get customers, or how were you
unsuccessful?

~~~
vinhboy
Had some customers. But never got that hockey-stick growth all VCs want. And
you're always competing with the big boys, Quickbooks, Netsuite, etc... It's a
constant arms race to add more features, more integrations, etc... A lot of
customer support because your customers rely on you to run their business.

I enjoyed it, but it's a tough nut to crack.

------
pgt
What's the secret sauce? I tried signing up but it demands a consultation
time. Just show me the product, please

~~~
wdaher
(Pilot CEO here).

Here's the thing that's a bit different about Pilot: it's not a software
product — it's "You have a bookkeeper who does your books (in QuickBooks
Online), that you can call and email when you have questions, and that sends
you a report every month."

Under the hood, we're building the Iron Man suit for the bookkeepers—letting
our team do all the heavy lifting to make sure the work is super-accurate in a
way that your typical bookkeeper definitely can't.

Basically, the last thing I wanted as a startup founder was "Yet another
software product"—I wanted someone to just take care of the problem for me
—which is why we built it this way.

I also find it annoying when people gate software behind sales forms — "Just
let me try it!" — but in this case, there really is nothing for you to try, by
design. _We_ do all the work for you.

(The next steps today are: we quickly chat with you to better understand your
business, and if it's a fit, we pair you with an account manager here, and
then send you through a web flow to get read-only access to all the systems we
need — your bank, payroll processor, etc.)

~~~
a_d
Brilliant model. PayPal's fraud detection is usually the most cited human
intervention model for building "smart systems", but the idea goes back
further: Amazon's backend in the 90s, CD baby's recommendation engine [1] and
one can probably find examples that are decades old. I have built large
operations teams around this central idea. Happy to chat if you want to
compare notes and experience doing this.

[1] [https://sivers.org/hi](https://sivers.org/hi)

------
awad
I think there are some employees active on this thread...how do you position
against, say, Indinero?

~~~
wdaher
Biggest differences vs. inDinero are:

1\. Our books are stored in QuickBooks Online, and you have access, so you're
never locked in. (The "Leave inDinero" migration is a pretty rough one.)

(Strategically this is also important for us because it lets our engineering
team focus on building software to assist with the most thorny/painful parts
of the process, as opposed to making a QuickBooks clone.)

2\. We do accrual by default (inDinero will do it but only at the most premium
tiers)

3\. Most importantly: our customer service is way better—if you're seriously
considering inDinero, I'd encourage you to talk to a few current users and see
how they feel about it. (Not fearmongering, but the stuff we've heard has not
been great.)

~~~
awad
Fair enough. I actually used to use them and the above resonate with me. From
my perspective, your solution looks like something that would be worth looking
into if I were starting fresh, given that we're a SaaS startup with the added
nuances that entails.

------
SandersAK
I'm having a hard time understanding how this is worth it compared to Xero and
their rule-based functions. It's really easy for Xero to learn just the same
as a person (if not better).

Am I missing something?

~~~
wdaher
Pilot isn't "more bookkeeping software", it's "hire this company so that you
don't need to worry about getting into the weeds in QuickBooks Online every
month, because you have a person who will do all your work in QuickBooks
Online for you (assisted by our software)".

It's not that bookkeeping is rocket science or totally unlearnable (you can
definitely learn it), the question is really whether it's actually the best
use of your time to master it (when you could instead be focusing on running
your business).

~~~
ebcase
Thanks for all your replies in this thread, @wdaher!

Can you share how you are approaching growing / scaling the human side of your
bookkeeping army? E.g. the dedicated account managers — when I shared your
site with a CPA friend, he asked if you have outsourced teams in India doing
the categorizing.

~~~
wdaher
Great question, and definitely one of the operational complexities of the
business.

Our thesis is: by relying heavily on software from day one, we can actually do
it with a small, super-highly-skilled team (rather than a giant army of
folks.)

If the task can really be done by an arbitrary person somewhere without
context on the business itself, I suspect we can execute that same task
ourselves in software (only with much higher consistency and much lower cost).
Transaction categorization is a great example of this, actually.

I think the alternative—scaling by just hiring a ton of people—is compelling
because it's short-term easy but long-term hard. By analogy to a software
system: if you scale with an army of people, you're building a giant
distributed system of super-unreliable hardware (the error rate of people is
pretty high!), and you can't reprogram it by running "git push".

I'll venture to make a stronger statement: if you care at all about
consistency of quality, I think you _have_ to do this mostly in software --
because otherwise the quality of your service is going to be entirely the
quality of the individual bookkeeper you use, which is fundamentally going to
be pretty variable.

------
beaconstudios
on a somewhat tangential note, how on earth did they secure that domain?
Surely buying it would cost a fairly large fraction of that $15M investment if
they were to have done it at market rates.

~~~
wdaher
Pilot CEO here. Short answer is "A domain broker, some good timing, and a fair
bit of money".

Definitely not "a large fraction," but an amount that made us think hard about
it first.

~~~
niblettc
Do you guys also do payroll bookkeeping and processing? What about customers
who want project/job cost accounting for payroll and other expenses?

~~~
fma
A question I'll tack on...for payroll do you guys automatically pay and file
taxes for unemployment, medicare etc?

~~~
niblettc
These are good points. I've worked in this space and it's a huge time sink.
And you can't afford to get it wrong because you're dealing with people's
livelihood.

I'm currently working on a time attendance solution with an emphasis on
usability for non technical users. You'd be amazed at how much paper /
friction still exists in this domain.

~~~
fma
Funny I was working on the same thing (time/attendance solution). Square has
timekeeping using mobile app...punch in your ID, clock in. It had more
features than I needed...I also have volunteers so they don't get paid but
need to keep track of their time. I don't think it was the best solution for
me.

I ended up just having a sign in sheet....It works.

------
Kiro
Is this for US only?

~~~
wdaher
Yes.

~~~
cmer
Why wouldn't this work for Canada? Could it?

------
PerfectElement
Is there something like this for Canadian businesses?

~~~
sirkworraps
[http://origami.ca](http://origami.ca)

We're a small business all-in-one, flat fee, bookkeeping/accounting service
operating in the Canadian space.

We solve a similar problem space for Canadian business.

