
Ask HN: Is a starting an enterprise software startup worth the hassle? - diminium
I was talking to a few people who worked for a big company.  The software they use are some of the worst software I've ever seen.  The workers there hate it and it makes them unproductive.  Sounds like a good place to make a start-up, right?<p>That is until I found out the people who use the software have virtually no input in purchasing it.  Not even the IT people who have to maintain it has any input in it.  All purchasing decisions are made three states away in a purchasing department that buys stuff by list of features - whether or not those features work efficiently or even correctly for that matter.<p>How is this maze navigated?  Is it worth the hassle if you don't have deep contacts and relationships inside every big company?
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calinet6
This is a very difficult market to break into, and lots of people are trying
right now.

My first piece of advice is to build up your size and trustworthiness as much
as possible. Large companies won't buy from you if you have no standing in the
market. That's what you need most, after you have quality software to sell of
course.

I'd recommend starting with smaller companies and building up from there—the
long tail contains a huge untapped market that you can take advantage of and
build up your size.

Next, know your domain exceedingly well. Don't show flashy software, _solve
problems._ Find out what the true problems are with their current software,
and solve those. Unfortunately, their problem is NOT that their users don't
like using it (well, it's a problem, but not the top problem). The top problem
is likely that it isn't fully capturing their process, or it misses certain
savings or benefits to the bottom line that it should make obvious. Business
problems are the real problems, never forget that.

Don't be afraid of investment. Use it to grow when you need to, because your
small size will be your biggest downside. Even through all that, never forget
that your software quality holds up the rest of your business in the end; you
must balance all these factors at once.

And lastly, buy a really sharp looking suit. Sorry.

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mrkurt
Now's actually a pretty good time to tackle these problems since "users" are
becoming accustomed to using tools they like. You just have to be clever about
how you tackle a particular problem, you're not going to take down PeopleSoft
by trying to sell companies a PeopleSoft replacement. Rather, you're going to
build something like Expensify that saves individual employees from some of
the more irritating things they may have to do with PeopleSoft.

A good general trick is to build something that solves some portion of an
enterprise's need, make it free to try out and cheap to use at work. There are
a huge number of people out there that can pay some nominal amount for a
service and expense it, it's just a matter of finding some need people with
that level of autonomy have and getting them to pay you to fix it. Easy,
right?

I wouldn't start by trying to navigate the maze, just avoid it altogether
until you have a compelling reason to take that burden on.

~~~
ericingram
> you're not going to take down PeopleSoft by trying to sell companies a
> PeopleSoft replacement. Rather, you're going to build something like
> Expensify that saves individual employees from some of the more irritating
> things they may have to do with PeopleSoft.

Brilliant way to put this. The way to compete with old enterprise software is
first by not doing it the way they're doing it. I would start with something
that appeals to individual employees, make their work easier, even joyful, and
eventually you'll work up to top level decision makers.

By then you'll have a fantastic user-centric product and a list of features an
exec team would drool over.

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kjhughes
Old school: Big sales forces addressing committees and execs, operating over
long sales cycles. Rewards: big contracts and institutional lock-in.

New school: Self-serve sales winning grass roots support from front line
workers. Rewards: high customer loyalty, quick sales cycles, quick feedback,
and lower sales costs:

[https://www.google.com/#q=consumerification+of+the+enterpris...](https://www.google.com/#q=consumerification+of+the+enterprise)

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diskdoctor
I'll start off by saying I'm a closeted entrepreneur in my heart, however by
day I've been selling Enterprise Software for 10yrs+. The latter is what's
kept me from doing my own startup for a decade, the income is addictive but
the business is not straightforward. To give some context, the average deal
size for me is around $250k, but I generally work on large enterprise deals
that run $2M+. Two years ago I sold over $70M in software to just two
companies, neither Fortune 500. Needless to say income is substantial in this
type of sales where base salaries are easily $100-$150k and you can find
yourself earning at least $250k in a slow year, and as good as maybe $1M in a
very good one. However, I'm different than most enterprise software sales
people. Before selling I spent years programming, architecting systems and
continue to work hard to keep my skills up b/c I love this stuff.

Marketing and selling software to enterprises is the most dysfunctional cycle
of decision making you will ever see in business. In almost all cases the
individuals in the business who actually derive value from the technology are
entirely disconnected from those who make the purchasing decisions. Many times
those purchasing decisions are made based on "perceived" synergies with other
software systems already owned from the same vendor, having never been vetted
by the actually consumer in the business. Enterprises represent a huge market
to be served by well designed/functional applications. Keep in mind that most
Enterprise SW contracts have customers paying yearly maintenance charges that
are 20% of the original license cost and sometimes more...

The thing to understand in selling into this market is you need to adapt your
"logical" marketing and sales strategy to the way enterprises buy. I say adapt
b/c you can't make or help a dysfunctional buyer behave differently. These
companies like centralizing technology decisions, large multi-year commitments
and have complex IT accounting considerations. You need to be aware of their
existing legacy infrastructures and have a story of how you "play nice". You
need to have partnerships with existing large Enterprise SW companies (IBM,
HP, Microsoft, Oracle,etc) and you need to have Rolex wearing sales guys who
have the connections and can get deals done -
<http://techcrunch.com/2010/11/13/new-enterprise-customer/>

If you do all that, just moderately well, a large SW company would swoop you
up really fast. They can't innovate new marketable products worth crap, all
they do is buy. And although we hear about some of those acquisitions there
are many, many more that don't get as much press...

However in contrast to the approach above I have been whiteness to a handfull
of startup business models that have done really well at infiltrating the
enterprise based on their distribution and user engagement model. Take Yammer
for example, their model allowed for people in large companies to start using
it (for free) without having to get any approval from their IT departments. I
had a CIO friend of mine who never heard of Yammer until I mentioned and
showed him where over 100 of his company employees were already active on it.
Large companies have to worry about compliance, document retention, etc. His
first reaction was to block it via the firewall, but then he was smart enough
to see it as an opportunity to invest in a technology that had actually been
proven to deliver value by people within his own company. Software or services
that can get into the enterprise like a cockroach, breed and spread under the
radar have a really good chance of getting a CIO's attention in a good way -
it's an opportunity for them to invest in a solution that works and guarantees
that their business will get value since its already been proven on an small
scale.

~~~
skrish
Fantastic answer.

It is not impossible but just takes its own cycle and hard as @diskdoctor has
mentioned above.

To add to this there are a bunch of questions that you should answer well
before Indirect Purchasing department (yes, the department that makes the
purchasing decisions on all items that are to be used internally).

1\. What is your business continuity plan?

2\. Annual revenue. Would you remain in business long enough?

3\. Technology stack - what does it take to maintain it?

4\. Does it align with their tech stack recommended by architectural team?
(not necessary if there is a good justification).

5\. Partnerships / integrations.

6\. Customer references of similar scale.

...

The best way for a startup could be the Yammer way - make it very attractive
for users within the organization to drive it bottom up or have some real
strong partnerships to drive it through.

~~~
diskdoctor
thanks, I am glad to could contribute something here... I have often enjoyed
the thoughtful dialog this community provides...

skrish, I agree, especially for a community such as Hacker News the Yammer way
is the best way. If I were to start a company right now I would look to build
something that an individual within an enterprise could acquire and get value
from w/o involving their IT departments. As a bonus I would try to engineer
some type of social, sharing or collaboration element where that individual
would get exponentially more value if their coworkers also used the
technology. I would closely study the technologies enterprises use at their
core and figure out a way to expand, enhance or even exploit. As an example
companies like Geckoboard or Leftronic could find opportunities in the
enterprise by providing tight integrations into Salesforce.com, workflow/rules
(Pega) data warehouses (DB2, TeraData, etc) and analytics (Cognos) - that is
how large companies like IBM, PG, and GE run and manage large parts of their
organization. And they could charge 10x for those features and companies would
pay. CIOs like to buy software that will logically fit within their enterprise
architecture. Sure, systems like DB2, SAP, Websphere, Cognos, OmegaMon,
Dynatrace and Linux on z/OS (Mainframe) don't sound as sexy as working with
MongoDB, Redis and Node.js but in my experience that's where the real money
is. Some would argue that the future isn't DB2 or Linux running on a
mainframe, but take a look at DB2 it supports in memory key/value stores.
Linux on Mainframe is probably the most stable, cost effective way to run
Linux on a large scale, especially if you must have a mainframe for legacy
CICS apps anyway. No CIO of a large company is going to stake their career on
something mission critical that relies on Cassandra or MongoDB, they go with
something that works with DB2 b/c its their corporate standard and you simply
don't get fired for "Buying IBM". They may experiment with new technologies on
noncritical tactical projects, but face it that's not where the real money is.
Companies like iRise, Roambi, Apptio, ITKO (acquired already), Splunk, Jive
and Okta have the enterprise "hook" figured out in my opinion... Sure, some
are "mature" now but they all started as startups...

rdl, on hiring sales people... We are a unique bread as we are hungry and
heavily coin operated. The key to hiring sales people is finding those that
have a track record of success. Track records not only demonstrate their
ability to do the job, but they have existing networks, know how to build
partnerships and most importantly know when and where not to waste their time
and your time. So where do you find us/these people? Search Linkedin profiles,
poach within other enterprise software companies and your network of other
founders/mentors/executives who have been sold to by or employed good sales
people. I was a sales manager for Rational Software for several years, the
latter is how I filled almost every opening. Interviewing sales people can be
tricky, they are trained to "sell" and "close". I usually look at a couple
things... 1) Do they job hop? a new job for a sales person every 2-4 years is
ok, but any shorter may indicate they can not sell and just keep getting
pushed out. 2) Demand to see their W2 to validate past earnings. This may
sound overboard but every software company I've interviewed with recently asks
every sales candidate for that. The W2 doesn't lie, you want to hire the
person that consistently makes $300k+ a year. They know how to do the job and
they also know where not to waste their time trying to sell something they
don't understand well enough.

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abiekatz
I find this post on the topic to be interesting:
[http://www.julesmaltz.com/post/3376586698/if-you-like-
saas-t...](http://www.julesmaltz.com/post/3376586698/if-you-like-saas-try-
freemium)

I think if you don't have the sales rolodex to sell traditional enterprise
software going freemium or low cost SaaS is the way to go. Or to team up with
some one who can sell into enterprises. You may be able to learn the ropes as
you go but that is unlikely. If you look at the background of a lot of the top
enterprise software entrepreneurs, you will see that they have worked at other
enterprise software companies previously.

Like anything, it is difficult to give a sweeping answer. There are a lot of
great opportunities in enterprise software that are worth pursuing. The
"hassle" of selling can be reduced by have more consumerized enterprise
software but selling will be a big issue. Plus it'll be more tricky as you
attempt to sell to larger organizations.

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fertel
A few points from my experience building a startup for the enterprise (these
examples are based entirely on my experience in the financial services
industry, although from what I understand they should be easy to extrapolate
across other fields):

The sales cycle can be/is excruciatingly long. Certain companies that signed
on took 1-2 years to get on board after initial engagement.

You need to partner up/find someone who has the deep contacts/relationships in
the big cos that would be your clients.

You need to prove to them that it will be cheaper (including the cost of
switching, training, etc...), Reduce Risk, and allow them to "reallocate
resources."

Inertia is very strong at large organizations. Building a product that
directly competes with an entrenched competitor sounds like a very risky
endeavor.

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serverascode
I am starting an "enterprise" software company. I agree that often enterprise
software is complete garbage, and the reasons organizations purchase said
software is not because it is actually good, or even does what its supposed
to.

But I don't think that should be a deterrent to building an enterprise
software startup--there's room for disruption, and room for good software,
good people, and good decisions. There are good organizations out there to
work with.

Smart startups can beat the big entrenched code.

That said my co-founder is a great salesman (I'm the techinical co-founder),
and having a sales team is high on my priority list.

~~~
ericingram
I'm also building software for the enterprise and as the technical founder, I
get excited about building a sales organization.

~~~
mindcrime
I'm also the founder of an enterprise focused startup[1]. We should start a
club or something, looks like there are a few of us here. :-)

[1]: Fogbeam Labs, the up-and-coming Open Source collaboration / knowledge-
management company that's bringing the Semantic Web + Social Web to the
Enterprise. <http://www.fogbeam.com> Go there now and sign up for our
newsletter.

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choffstein
Well, a new accelerator Acceleprise (acceleprise.vc) just started up to tackle
the space. At the very least, it might be worthing reaching out and talking to
some of their mentors.

Note: I have no affiliation with Acceleprise

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astrofinch
My question is what industries these dysfunctional enterprise companies who
buy terrible software are in and whether those industries could be disrupted.

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wheaties
Anything is worth the hassle if the rewards make up for it. If you don't
believe me think about cameras and photo fanatics. You just have to beat
someone at something to give yourself an edge. Then work that edge.

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pbreit
Don't attempt top-down enterprise sales unless you are ready for long,
expensive cycles.

Instead, look at what Yammer has done with a bottoms-up, freemium customer
acquisition approach.

