
My Losing Battle with Enterprise Sales - aberoham
https://lukekanies.com/my-losing-battle-with-enterprise-sales/
======
gumby
On thing he didn't mention (but surely must know -- this guy clearly has the
enterprise scars) is the importance of the "coach" at the customer.

He well describes the team of people that need to be involved in actually
sending you a PO and payment(s): someone from purchasing, someone in middle
management, possibly someone from legal, and the hapless folks who actually
have to use your product. You never get them all in one room, which is
probably a good thing.

The coach is the person who will get the deal done: they know the product is
needed, they know who needs to be convinced, they can make the case, and they
will sherpa you around to the appropriate stakeholders so you can make your
pitch. Typically they are middle management for the people who will use the
product, but they can also end up being someone who reports to the CTO or
whomever.

Another key thing is go in at the right level. You might get an intro to the
CEO, and she may end up convinced that your product is the greatest thing
since sliced bread. That's unlikely to help: she'll come back from the week
end and tell the GM of some division "hey, we should really be using that
Foobartronix cloud solution!" and the GM will say "Wow, thanks, that's gonna
make a huge difference to us" and then nothing will happen. You'll want to
pitch the highest person responsible and no higher.

I once pitched our product the CEO of the Sony Computer Entertainment
(Playstation). He was really interested and asked good questions and I assume
forgot about us almost completely as soon as we had left the room. The
importance of that meeting was that the other people who had decided to work
with us (which happened in the blink of an eye...like 9 months) wanted him to
know they'd found a good solution to a big problem. We were crucial, yet in an
odd way irrelevant to that meeting.

~~~
stupidcar
And then after 6 months of effort, the coach moves to a different role or
leaves, and suddenly the whole deal deflates like a balloon.

~~~
barrkel
Your champion may move to a different company doing a similar role and spread
the religion there. I think this can go both ways.

~~~
blinky1456
'Wololo'

------
lefstathiou
I enjoyed this piece though some of the anecdotes felt apocryphal. Some broad
thoughts on enterprise sales (been doing it for 5 years with tremendous
coaching from my brother who has done it for 18):

I love love love the enterprise sale. It's complicated, strategic,
psychological, time intensive, stressful and so many other things. Cunning,
patience and integrity are key attributes that lead to success here and when
you win, you win big. The key is to ensure this type of sale aligns with your
temperament.

Years ago, a mentor gave me some advice (which I believe to be true): the key
to selling to the enterprise is that you need to be known, liked and trusted.

To be known, you need to be getting in front of the key decision makers and
influencers and build a real relationship with the long term in mind. There
are no short cuts and salesman should not be writing an intro email or going
into meeting 1 or 2 thinking (and pitching) like they will get the commitment
on the spot. Skip steps and you lose the sale. It's a relationship that must
be cultivated even after initial rejections. I can't count how many customers
said "not at this time" that eventually came around to become large accounts.

To be liked, you need to be respectful, genuine and interested in them (not
yourself). Find out who they are as people, what they value, what their goals
are, their kids names. Ego is your enemy here. Read Dale Carnegie.

Trust is about integrity. You must believe in the product and the benefits you
market must be realizable (that's not to say the customer will necessary place
much value on those benefits). The moment trust is compromised, it's over (and
not just for you, the company). It takes a sentence (perhaps just a word) to
destroy a personal and company reputation.

Which goes back to the ultimate prerequisite (as mentioned in this article) of
all enterprise solutions IMO - solve a problem that people care about.

------
markbnj
Great piece, and a lot of it rings very true, especially the part about
managing warring subgroups within enterprise sales prospects. Back in the
early 2ks a startup I cofounded to sell to huge banks (enterprise sales on
steroids) did a deal with a marketing group at one of the largest US banks. IT
was opposed, wanted to build internally, and we had many meetings like those
described by the author. We did a 600k deal but behind the scenes the battle
continued, and a couple of months after signing the IT guys won, the marketing
guy who did the deal with us left the bank, our contract was bought out and we
were sent packing.

------
bigbadgoose
In saas enterprise sales there's much more focus on the post-sales lifecycle.

Because the model is recurring revenue, elastic with workforce, and up/cross-
sell, there's huge focus on account management, service levels, and delivering
actual value.

If those aren't getting to the customer, it's likely they didn't actually need
your product, or … their product didn't need _you_.

~~~
mathattack
The SaaS vendors I’ve dealt with are pushing 2-3 year contracts due to churn
fears.

~~~
jjeaff
Exactly. And that contract will include a minimum number of seats in exchange
for a "discount". So they don't have to worry about you hating it and
downsizing.

~~~
mathattack
Pay more if you go over. No discount for under.

------
matchagaucho
_" Our products were built to solve problems that big companies have."_

That's really the crux of the challenge. Vendors like Atlassian can win over
an enterprise one seat at a time, and co-exist with competing tools in other
departments.

But a solution close the hardware, like Puppet, is a company-wide cultural
decision. There's a propensity for the enterprise to choose one winner.

~~~
detaro
Depends on the enterprise I'd guess? Yes if you have strict, centralized IT
rules, not if your department has flexibility in running the stuff under its
control.

------
yesimahuman
I didn’t quite follow the story arc at the end. Somehow Puppet is back to
enterprise sales (i.e. it’s inevitable for a product like this), or are you
rejecting it? Very timely for me so I’m trying to understand the point...

~~~
hurflmurfl
I'm with you on this one. A very nice read on an interesting topic, but there
seems to be no point to it?

Maybe it was meant as a sort of excursion into enterprise sales for people who
have no idea on how those work and align with customer sales?

------
RyanShook
I understand enterprise sales to be a necessary evil but man it is annoying
when I want to try a service or software but have to talk to a sales rep
before being able to test out the product.

~~~
confiscate
ya but that sounds like you are not the target audience.

Most of the time in enterprise sales, the potential customer is too busy to
try software himself. Learning a new piece of software takes a lot of time and
effort.

Unless you are a techie, it's easier to just have salespeople do the work of
walking you through quick demos. Or have someone junior at your own company,
take care of the "dirty work" of figuring out new software and tell you the
results. It sounds like you are that junior person at your company :)

~~~
thirdsun
> Most of the time in enterprise sales, the potential customer is too busy to
> try software himself. Learning a new piece of software takes a lot of time
> and effort.

That's exactly why I want to deep dive into specifics and see the product in
action and detail on my own, without a sales person behind my back.

I understand that there are customers that need the guidance, but please make
it optional. For me it's just an additional barrier that will most likely
result in me not considering the product at all.

------
LaserToy
I also lost couple battles with enterprise sales. Somebody makes a decision
and engineering has to deal with it.

------
parasubvert
I used to hate enterprise sales, until I learned the most successful sales
motions and sales teams are all about successful outcomes. If the product
mostly does something value-able, and customer is taken care of, the money
will come.

There are some sales processes/books that get into this (Insight Selling,
Let's Get Real, Ninety-Five-Five etc.) and really can open your eyes as an
engineer that there is an ethical, effective way to manage enterprise sales to
solve user problems.

Luke mentions Bladelogic. I worked for BMC for a while, and it rings true to
me that there was a night-and-day cultural split between sales and R&D. Sales
at Bladelogic under John McMahon were maniacally customer focused, similar to
Mark Cranney's approach at Opsware (he's now at Andreesen Horowitz). BMC was
run by Bob Beauchamp for many years, the ultimate salesman, and for all the
flaws of that company, for many, they really cared about customer success,
which explained how they could maintain $2B in revenue with aging, middling
products. They just never seemed to be able to reconcile the cultural divide
between R&D (which did whatever it wanted), consulting (which also did what
ever it wanted), and sales.

The difference between a consultant and sales is that the consultant gets paid
by the hour, the sales person gets paid by the success of the customer,
assuming the incentives are properly structured. These incentives are, for
example: subscription software commission, with an emphasis on renewals (i.e.
lower pay on 1 year bullshit deals), maintaining customer satisfaction, and
consumption, i.e. customer actually using the software, not it sitting on the
shelf, is a good proxy for "they're getting value out of it".

I also find that enterprise sales generally requires a fairly intensive free
consulting engagement called a "proof of concept" (POC) usually 1-3 weeks of
intense work and commitment of time from both the company and customer to
enumerate all the technical risks/benefits of the software, and to run through
every single one of them until the customer (a) feels the product does what it
says on the tin (b) can work in their political and technical legacy
environment.

Getting to a POC as the last step before negotiation & deal close is a major
theme in large enterprise sales motions, as it forces a crucible: users (not
just buyers) have to learn the software, and their concerns are directly
aired.

Sometimes POCs are poorly scoped and drag on forever, or worse, are
inconclusive leaving the deal in limbo for months or years. This is where the
better enterprise sales teams shine, as they focus on what will make the
customer successful and address the concerns from the administration team and
users.

I wouldn't underestimate the cost/benefit of sales. Sales execs make $250k+
OTE and the best ones top $500k to $1M or more with accelerators, because they
have to coordinate across customer teams AND internal teams (support,
consulting, R&D, sales engineering, sales desk, legal, procurement, etc.). AND
they have to be personable and social. It's a tough gig. Sales engineers OTOH
have to be a bit of a sales person in soft skills but also know 20+ years of
legacy technology and IT culture along with the deep technical innards of a
product to properly sell, demo, and POC it. On top of that, a POC takes
several of them them out of other customers for 1-3 weeks, which is like $50k
or more of investment alone. And after the first deal, they're often
continuing to demo, teach, make friends, provide white glove support, etc., to
make sure the customer stays happy with the solution.

This is why enterprise software gets expensive, into the millions, all of this
high-touch time adds up.

Enterprise sales isn't something to avoid, it's still the nature of engaging
with a large complicated company, or the government, where most of the users
or technical folks aren't necessarily focused on the market, or upleveling
their skills, they're focused on their internal problems. They need someone
from the outside to expose them to the new ideas.

We keep thinking some next generation of knowledge workers will fix this, that
everyone will be self-starting, self-educating, and will buy things
transactionally with low-medium touch... we thought it might be the case with
Open Source, and it hasn't (the biggest OSS companies have large enterprise
sales teams). we also thought it might be the case with SaaS companies (but
they too have large teams).

~~~
drieddust
I used to hate enterprise sales, until I learned the most successful sales
motions and sales teams are all about successful outcomes. If the product
mostly does something value-able, and customer is taken care of, the money
will come.

> This is not true always. Enterprise sales is also made by massaging the ego,
> or creating false sense of urgency (a 60% discount offer with an expiry
> deadline of 15 days ) of those who hold the purse and does not have common
> sense. I have seen millions spend this way.

There are some sales processes/books that get into this (Insight Selling,
Let's Get Real, Ninety-Five-Five etc.) and really can open your eyes as an
engineer that there is an ethical, effective way to manage enterprise sales to
solve user problems.

> These books probably portray humans as logical rational machines who will
> decided based on some rules. Emotions, alliances, and personal gains are
> more important to decision makers.

Luke mentions Bladelogic. I worked for BMC for a while, and it rings ……

> This paragraph negates itself. If R&D and consulting did not listen to
> sales. How they were able to keep the customers happy. As a customer if I
> cannot get what I need in the product, sales will have to lie to me to make
> a sale.

The difference between a consultant and sales is that the consultant gets paid
by the hour, the sales person gets paid by the success of the customer…...

> This is becoming true with subscription models but there also sales pushes
> for muti-year deals with minimum spend. In my view, once the contract is
> signed sales just runs away leaving delivery guys to deal with the customer
> who expects what product can’t deliver. Any post-sales issue simply becomes
> delivery team’s problem, customer education etc.

I also find that enterprise sales generally requires a fairly intensive free
consulting engagement called a "proof of concept" (POC) …………

> This exercise provides a certain level of risk mitigation. However,
> requirements get modified to clear the POC because customer gets invited to
> dinner parties, conferences in vegas etc.

We keep thinking some next generation of knowledge workers will fix this, that
everyone will be self-starting, self-educating, and will buy things
transactionally with low-medium touch... we thought it might be the case with
Open Source, and it hasn't (the biggest OSS companies have large enterprise
sales teams). we also thought it might be the case with SaaS companies (but
they too have large teams).

> You are right this system exists for a reason and it can’t be fixed.
> However, its not all rosy and ethical. In most cases their is so much at
> stake that unethical behavior creeps in. It is just human behavior and
> that's the way it is going to remain.

~~~
ptx
You got your response passages and quoted passages reversed.

[https://en.wikipedia.org/wiki/Posting_style#Interleaved_styl...](https://en.wikipedia.org/wiki/Posting_style#Interleaved_style)

------
ewams
All the comments and the story seem to be coming from people that have been
around sales or briefly touched it but never been full in a sales position.
It's definitely true that "enterprise" sales has a different sales cycle than
commercial or smb. I've had seven and eight figure deals close faster than a
small 6 figure deal. I also have found smaller organizations need much more
care and feeding after the sale than larger companies. But of course this is
not true for every organization or sale.

I empathize with his part on gear that sat there for years after the sale.
Welcome to business, it happens everywhere. I've been on both the purchasing
side and the selling side of it. Things just happen, just like we all mean to
change the world or pick up a hobby but something else shiny gets in the way.
But it's not a reason to give up on sales.

Politics are a part of everything. Engineers (or anyone) that refuse to accept
this are just cutting their eyes out to spite their brain. If, on the sales
side, you ignore the politics of the organization it is no wonder you
struggle. The same is true for people in their own organization that can't get
anything done, don't get promoted, or can't make friends.

Sales sucks. When you spend days, weeks, months, even years on a deal and you
don't win you get nothing. Sometimes you even lose your job. Sales is
expensive in more ways than just money or time and it is not for everyone.

I enjoyed reading your piece but the negativity in it is from frustration at
lack of understanding. Just because you are not good at something does not
mean it is bad or evil. I love basketball, but I am horrible at it, so I know
realistically I will never be in the NBA. But because I do know what goes in
to it I can truly respect those people that do. You can learn from others for
things you are not good it, but why kid yourself? Focus what you are good at
and become even better.

Michael Jordan was an amazing athlete, totally dominating basketball. He tried
his hand at baseball and did decently but realized being just "decent" at it
was all he would probably be and went back to what he excelled in, basketball.

I need to finish my book on sales and consulting geared towards engineers.

~~~
EGreg
Any chapters done yet, that we could read?

~~~
ewams
Just in a poorly formatted word doc currently. I'd be happy to contact you
when its closer. Thanks for asking!

~~~
confiscate
ewams, I would like to see this word doc too. Would like to learn since it
sounds helpful. Would be happy to contribute as well.

I checked your website but it looks like it's down due to PHP errors. How can
I contact you? My email is in my HN profile. confiscate [at] gmail

------
briancl
Enterprise software sales has changed dramatically in the last 10 years,
largely due to the shift to SaaS and the shifting strategy from land big to
land fast.

If you look around the younger generation succeeding in enterprise sales,
you'll find that many come from a far more technical background. Maybe they
transitioned via sales engineering roles first, but the next generation of
field sales reps often have real world experience to apply in a consultative
sales process.

The days of closing deals over steak dinners or on the golf course are over.
Providing real business value in the short term during a quick POC is a must-
have. Delivering on real business objectives over the first 6-12 months to
ensure the expansion is too.

Some of the old guard, at least the ones that are any good, have adapted. A
lot of the old skills are still useful for building relationships and trust.
Being able to manage complex organizational challenges that getting more and
more complex is an asset as well.

------
voiper1
>Always listen to what customers tell you, but never do what they say.

Great line.

------
avinium
Great article and spot on for anyone who's ever dipped their toe into the
waters of selling to enterprises.

It's a draining and frustrating experience.

The problem - as the author mentions - is that it can be so incredibly
lucrative.

------
mlthoughts2018
““What does it matter what the customer thinks? They already bought the
product.” Astoundingly, the CTO did not fire him on the spot, and instead just
moved on, ignoring the comment entirely.”

The author lost a lot of credibility to me when I read that part, because it’s
often critical for the life and success of a product to be skeptical of
customer requests or feedback, especially bespoke custom work requests that
come up all the time in enterprise sales. Your company wants to grow and needs
the revenue, but accepting custom requests takes you off-strategy and often
wastes resources on things that won’t generate value beyond one isolated sale
/ renewal.

The Recurly founder had a great quote about this, related to why Dropbox
succeeded (by ignoring feature requests from customers and imposing their own
vision if a simple interface, and only adding features later). It’s discussed
here: < [https://zurb.com/blog/don-t-add-features-to-make-
customers-h...](https://zurb.com/blog/don-t-add-features-to-make-customers-
happ) >.

Anyway, this author’s rants actually strike me like someone who doesn’t have a
good sense about product design or product management.

------
bernardlunn
Speaking as somebody who used to lead enterprise sales teams, my take is a)
the company did not know how to do enterprise sales properly b) they raised
far too much capital. If you bootstrap (most great enterprise software
companies were bootstrapped) you cannot afford to deviate too far from
customer needs.

------
lucio
beautiful.

------
ziont
modern day enterprise sales is essentially providing free consulting work.

------
anoncoward111
Sales sucks. I have always preferred selling to consumers and handling support
in a humane and friendly way.

I simply don't have the moral fibre in me to fuck someone out of their money
like a "b2b" guy does, or car salesman does.

~~~
stupidcar
Sales does suck, but as the article says, enterprise sales aren't the way they
are because the salespeople are necessarily immoral or trying to fuck anyone
out of their money, they're the way they are because big companies need to be
sold to in a particular way. When the buyer is not the user, and there are
multiple departments and decision makers involved, you can't just rely on the
quality of your product to win out. You can have a fantastic product that you
know will help the customer immensely, and you _still_ have to follow the
enterprise sales process if you want to sell it.

~~~
anoncoward111
Agreed. The beautiful thing is that the power of creating anything is
increasingly being put back into the hands of the consumer. We are rapidly
approaching the point where anything you could ever want is buyable with the
click of the button on Amazon or etc.

I am really glad the days are over where we used to have go negotiate with
some sales guy to buy paper for the office :)

------
jbmsf
Rings true to me.

------
blihp
The author sounds like they were confused as to who the customer is for
Enterprise Sales. It's always the person / team who is paying for, not the
person / team who is using your product or service. The companies that do well
selling into political environments, which most large companies are, get an
Executive on board who can navigate the environment / clear a path. So that
Executive and whoever they tell you matters, who will probably never use your
product, is the customer and who you work to keep happy. Sure, it helps if the
product works and is good but sadly this isn't always a requirement. It's a
very different and dysfunctional world compared to selling to small / mid-size
companies where the customer often is the user where things are a bit more
sane.

~~~
gk1
As I say: Make the _user_ want your product, make the _buyer_ want to pay for
it.

