
Ask HN: Describe your first enterprise sale - hackerews
What was it like to make the first enterprise sale at your startup?<p>How&#x27;d the enterprise hear about you? What was the first meeting like? What obstacles and challenges did you run into? Were there other companies in the mix? What did you do wrong? What did you do right?
======
mortona
About six years ago I set up a Dropbox-like service for real estate brokers to
handle the paperwork side of the sale and purchase of condominium blocks.

I built the product, which was basically a service for storing and
authenticating access to PDFs.

I'd previously built a news portal for the industry and had a mailing list of
around 8,000 professionals. I emailed them all and got nothing back. At the
same time I researched a few flagship developments and contacted the parties
involved. Eventually one agreed to use the service as a trial at zero cost. I
was excited - this was a big business. But they weren't interested in
continuing and I saw nothing back.

About a month later I received a phone call from the technology manager at a
top 5 national firm who'd seen our product being used by this company and
thought it was exactly what they needed. I flew for a meeting with them, I
copy and pasted my way through a template SaaS contract. They made me fill in
a disaster recovery questionnaire and quite a bit of other paperwork - no-one
ever checked anything. They wanted the source code for this website in Escrow
but in the end they never made any arrangements.

They signed the contract and six years on they still use the service, are the
only client, and absolutely love it.

My only helpful advice would be that enterprise sales are actually way more
personal than consumer stuff. Me and this technology manager get on well, and
have worked well together for years. As the client, they expect to be bought
lunch and dinners - that's just the way it is. After all, they sign the
checks. Over time my contact has gradually realized that this is a one-man
operation. At the same time he's risen high in this company because his
initiative has delivered a service that really works for them. Meanwhile all
their competitors spurned my 'simple' service to do it in-house, and most of
them still haven't built anything. My client merged with another company who
had sunk $220,000 into developing the same system and it didn't work. They
scrapped it and now just use mine.

I don't want to talk about the service (or grow it) - I keep it going because
the monthly check is good, and because they rely on the service.

~~~
mzarate06
> They made me fill in a disaster recovery questionnaire ... They wanted the
> source code for this website in Escrow ...

Can you elaborate on the details or circumstances these parts outlined?
Particularly in regard to provisions or protocols to be followed in the event
you become unable to render product service (due to disaster against the
product or its infrastructure, personal circumstances, or otherwise).

I'm in a similar position that you've described. I'm mostly a one-man shop
with a SAAS product that has a Fortune 100 customer. As it becomes
increasingly integrated within their company they've voiced concern over what
happens if I become unable to render service. We likely have contract
amendments coming for code escrow, but I've no experience in this particular
area, so thought I'd ask what you learned from these parts of your contract.

If it matters, the product is tightly customized to the customer's work flow,
and provides a solution they've been unable to readily find elsewhere. So in
the event that service can no longer be rendered, having them subscribe to
another product wouldn't be immediately viable.

~~~
FireBeyond
Where I've worked has been an <10 man shop with 2 critical personnel who wrote
software that was responsible for the healthcare of hundreds of thousands of
individuals, actually probably in the low millions.

We were required to have code escrow contingencies, and one company required
those two key personnel not to travel on the same flights.

~~~
usaphp
> not to travel on the same flight.

Did they also asked them not to travel in the same car? Chances of dying in a
car accident are considerably higher than a plane, unless I am missing the
reasoning behind it

~~~
haser_au
Part of this is about making sure people are available at last minute
notification. If you're in transit from Sydney, Australia to London, UK,
you're out of action for 30+ hours plus the time to get over jet lag.

~~~
usaphp
I am not buying that, People sleep and do morning routine for 10+ hours and on
top of that they have personal life and weekends, you won't ask them to stop
doing that so they will be available for you at last minute notification.

~~~
tamana
Whoever is oncall rotation for that week does.

------
enricotal
I created a order taking ios app for companies in Italy with Sales reps.

Here's all my first sale story.

-Inbound marketing

I setup a web site...and eventually got some leads (name email phone).

-Qualifying call

I call them up and asked them about the problem they were trying to solve.
Many of them were just Software tourists (people that sign up just for fun)
but some looked promising.

-Skype meeting Setup.

Some of them asked me to visit them... I said yes, but I told them that I
would to set up a short Skype meeting first to understand their problem
better... In reality I just wanted to know I there where really App-Worthy
before doing the human brochure.

-Skype meeting.

At the beginning of the skype meeting I would try to know more about them,
their role in the company etc.. After a little warm up I would dive into the
problems list and asked them what my app should do for them rather then just
presenting my app.

I asked them if they already have a budget, and when they would like to solve
the problem

I show them part of my app (only the parts they asked for) and clearly asked
them from 1 to 10 if they think my app would solves their problem.

If I got a vote 8 or below I asked what it would take to reach a 10.

If I got a vote above 8 I asked what we should next..

Most of them usually reply "send me a proposal"

-End of story

After few days... I received my first signed proposal... without meetng them.

~~~
beachstartup
this all sounds about right. refinements i would add:

* don't ask the customer what the next step is, tell them, show them, push them in the right direction. they have a job to do, and don't want to think about yours.

* also setup a final proposal review meeting for last minute q&a. ask what any last hurdles might be. then push hard for the signature, buyers respect a seller who is confidently trying to drive the schedule forward. be polite but drive forward.

* include a deposit, if not the entire licensing fee as a requirement to start work/deployment. a customer that does not pay you is not a real customer, they are trying to manipulate you for some other purpose i.e. reducing their incumbent vendor's price.

* if you have a working product, do not, under any circumstances, offer any kind of "30 day out" clause, or refund, or whatever. this just means you are going to waste 30 days of your time and money. this is fine for SaaS with freemium, but not enterprisey sales/services driven deals.

in larger businesses you can be flexible on the last point (i.e. accepting a
purchase order instead of cash), but as a small shop you can't afford to waste
your time or be jerked around by assholes.

but honestly i wouldn't even worry about it, if you're a newbie at sales, it's
100% guaranteed you're going to learn that the hard way. c'est la vie.

~~~
mapster
the 'what happens next' question should be answered or asked depending on the
client's personality. sometimes the client wants to be a little important in
the negotiations or the company clearly has their own way of doing things, so
I ask them 'now what', but it is never asked so bluntly. More along the lines
of "To move forward, I typically would send you a proposal/invoice, but I
would defer to you on how you company handles this. What works for you?"

------
DizzyDoo
I don't have a story about enterprise sales, but if you'll allow me I will
just slip in the story of the first copy of software that I sold. I hope no
one minds.

I wrote a silly computer game about cats
([http://store.steampowered.com/app/386900](http://store.steampowered.com/app/386900)),
essentially making a puzzle game out of finite-state automata questions you
get during the computation course of a Computer Science degree. Of course, the
abstraction on the mechanics involve cats, because it's a good way to trick
people into doing computer science.

Now, three weeks before I released the product, I stuck up a webpage where
people could purchase the game for a higher price, but the twist was that they
could send me a picture of their cat, and I'd put the cat in the game, in a
level somewhere. I didn't really know if anyone would be interested, I didn't
do any marketing, but since it didn't take long to hook Stripe up and the idea
amused me, I went for it. The next day I received my first customer, someone
from Peru, who in broken English described their cat 'Missy', and attached a
dozen or so photos of her. So, I draw an in-game representation of the
Peruvian cat, place her in the game, and add a feature where when the user
mouses-over Missy, an overlay pops up with a photo inside. I still have no
idea how this customer found me, but I do know who their cat is, what food it
likes, what toys are its favourite. Over the course of the three weeks, a
little more than a dozen people preordered and sent me (usually loads) of
pictures of their cat(s), which was quite a personal subject for some. More
than one had recently lost their pet, and wished me to memorialise the cat
inside the game, either for them, or their wife/husband, as a gift or as a
surprise when they played it through. I did not expect to be in some way apart
of people's grieving. Some of them wrote me much later to express their
thanks. What stuck with me most though was the feeling of making a personal
connection with someone on the otherside of the globe, Peru, Singapore,
Algeria, etc, and effectively being introduced to a member of their family. It
was a surprisingly meaningful experience.

So no, not at all about big enterprise sales, instead a $10 game involving
cats, but, there you go.

~~~
chris_st
That's a great story, and it looks like a good game.

Could you elaborate on Steam sales? Non-steam? Thanks!

~~~
DizzyDoo
I released on Steam, and Steam's been great. Since I just developed the game
by myself, I only needed to sell a couple thousand copies to break even, and
that happened fairly quickly. Releasing on my site
([http://cranktrain.com](http://cranktrain.com)) and on other stores like the
Humble Store, the Mac Store, that's all rather worthwhile too, it all adds up.
My site is a small Django site with Stripe, so that gives me the biggest
margins, though I then have to sort out things like European VAT payments,
which is a pain, but hopefully I'll grow that for my next game and it'll
become worthwhile.

The Cat Machine has done modestly well, but it's let me work on games full-
time. And it all started with that one cat-owner in Peru.

~~~
agopaul
Have a look at [https://quaderno.io/](https://quaderno.io/) for handling the
EU VAT stuff. I actually don't use it, but I remember that they provided a
checkout experience similar to Stripe.

------
syedkarim
We recently had our first huge sale to a single customer. It started out as an
inbound inquiry to the general email address. I wasn't involved at this time
(there are 6 of us, but only one other person handles anything sales/customer
related). I believe there were a total of 4 emails outlining the general
service, our products, current pricing, and what we could offer in the future.
I later learned it was a very junior member of their team who was collecting
this information.

The final email, which included a presentation, led to the scheduling of a
call with about six people from their side on the call (and two of us). This
call lasted about 90 minutes with me talking almost non-stop. After the call
they asked for an NDA so that we could share more details. It took about two
weeks to get the NDA in place.

The NDA was followed by a request for me to visit them in person for a couple
of days. We're based in Chicago and it was a three hour flight. The meeting
lasted about 10 hours, with about a half-dozen of their staffers involved,
including their consultants. Consultants were involved to offer advice on
build-versus-buy.

After I went home, I was asked if their management team could come to Chicago.
This ended up being an 8-hour meeting. At the close of that meeting, I had a
verbal approval. The paperwork took another week or so to get in order. The
initial funds were wired immediately after the contract was signed.

~~~
statictype
_The initial funds were wired immediately after the contract was signed._

For those who are new to enterprise sales and reading this - this is highly
unusual for enterprise sales.

Be prepared to waste many man-days chasing after payments to be payed and
expect months of delays in receiving them.

The larger the contract the more the delays.

That's the nature of the game

~~~
danieltillett
It is amazing what not giving the customer the product until they have paid
does for speeding up the payment process. I have yet to have a customer who
can't manage to get the bill paid when they really want the product.

~~~
statictype
In large enterprise sales, you would typically structure the payments into
various milestones.

You may be able to invoice the first one before you actually give them
anything but there is a vanishingly small chance of collecting the full
payment until well after the product is deployed, probably in-use and
occasionally after demands for features that were not agreed upon have been
delivered.

------
enterprisethrow
A Fortune 100 company reached out to one of our advisors looking for
technology that was right in our wheel house. We didn't yet have a product but
we had the technical underpinnings of a product. I think when they first
agreed to talk to us they thought it would just be a way to educate some of
their engineers on state of the art techniques in our field. Sort of
continuing education for their staff. But we threw together a demo in a week
and it impressed them enough that we kept talking and the tone shifted to the
potential for a commercial relationship. We put together a few more custom
demos and got them to the point where they believed we could deliver
technologically. From there we went to a 3-month trial where we gave them the
"real product" but only on about 1/10th of their full data. I think we charged
about $15k/month for that. The trial was a success and it came time to iron
out the full-blown contract. This was a huge ordeal. Because they had so much
leverage in the relationship, they threw every awful thing you can imagine in
the contract. The negotiation process was stressful and got pretty nasty at
points. We caved on many things but held firm on a couple and actually had to
walk at one point. They played dead for a couple weeks and then came back to
the table. It took about 4 or 5 _months_ to get it over the finish line and we
were able to get them to pay the trial fee for all of the months the contract
was in limbo (that felt like a big win). The contract was worth just north of
$1M and in retrospect I think we got a good deal. What did we do right? We
came in very high on price initially and that helped us settled on the higher
end. What did we do wrong? We probably fought more than we should have on some
of the terms since now we know they were mostly just CYA. It would have been
nice to have wrapped it up much more quickly.

In short: takes forever, prepare for pain due to power inequality, and aim
high on price.

~~~
hackerews
If you don't mind me asking, how much higher was your initial price?

~~~
enterprisethrow
About 3x that.

------
zupa-hu
We ran a web scraper startup selling leads to London property agencies.

I built the product in 3 months in Hungary after which my partner was about to
sell it but couldn't due to a vis major.

I extracted the addresses of all London agencies (~2000) from a website
collecting them. Then I built a simple CRM system in about a week that was
essentially a Google Maps frontend with all of them on it + ability to add
notes & color mark them according to their status (if I have visited,
interest, etc.).

Than I flew to London, printed some brochures and walked in ~500 of them in a
week. (London is/was packed with them, there were sometimes 3 in a row.) I ran
around with a brand new iPad 2 which brought me lots of interest - in the
iPad..

We got 1 big sale, where I bumped into the CEO of a small chain. He was very
entrepreneurial and simply wanted to give it a try. It took a couple of days
of negotiation over the phone to iron out the terms. There was no second in-
person meeting.

FYI, we got some 10 smaller sales but the marked proved way smaller than
anticipated so we shut down.

~~~
dasboth
Nice story! With the large volume of Hungarians moving to London, was there
not a way you could use your data to help them find a place to live? Having a
web scraper that finds appropriate listings before you could physically comb
through the websites sounds like it would gain some traction.

------
nxzero
Simple, contacted VPs of sales for of a large consultancies and offered to
give them a percentage of any sale I got from leads they provided. Found one,
and required their CEO sign-off on it. After that, all the leads I got were
hot and for me, larger than I would have gotten on my own; for the company
feeding me the leads, the project sizes were too small.

~~~
mmansoor78
Did that really worked ?

~~~
nxzero
Yes, got enough clients to grow on just cashflow; one leads turned client I
got from it was a very well known globally recognized brand, publicly traded
and a market-cap of half-billion+.

------
matt4077
I was 17, skipped the last days of school and sold a forum-/chat-/etc.
software to the largest german TV channel. The software didn't actually exist
at that time, I had to make do with a prototype built in powerpoint.

We got about 20k€ iirc, and later learnt that we should have probably added a
zero to that. Took us quite a while to build it and became a bit much for me
to manage that project, but we got it done mostly intact.

The whole thing was quite a mess of php spaghetti-code, though. Still had a
lot to learn.

------
abraae
We had a good idea where we wanted to be - HR software. We built our
enterprise product by looking online at what others were doing in the space,
then building something that had a single key screen in it that was better
than anything else we could find. It seems one good page is often all you need
to entice prospects (we certainly didn't have a fully formed product).

Then we got lucky, which is something you probably need at some stage. We came
across (chance networking) a giant Telco who needed our product. They'd just 6
months earlier been through a typically elaborate and baroque RFP process to
pick their incumbent, a big US player with an exceptionally ugly legacy
product. Despite doing their due diligence up the wazoo, they got shafted when
the vendor decided to stop selling that product and asked them to pony up
again for a multi-100K re-implementation fee onto their new platform.

Telco was enormously pissed off, and we lucked across them just at that
moment. They were open to procuring their replacement product in a more
lightweight way, so we side-stepped the RFP process and snuck in (also found
out afterwards we were about an order of magnitude cheaper - though cost is
often not that big a factor in enterprise sales).

From there on we were on a roll, because Telco was so ginourmous, we got
plenty of other people signing up just off the back of the halo effect of that
one deal.

Then we did all the hard yards - converting those steadily growing revenues
into product improvements, and all the stuff that's less luck and more
execution. We did awesome, great work, but its questionable whether we'd have
got the chance to even run onto the field if not for an initial lucky break.

Things you need for enterprise sales:

\- luck

\- a likeable, trustworthy front person with a cultural affinity with target
customers

\- the illusion of a solid, well managed company, i.e. not a one man band

\- the patience to do a swag of accompany paperwork - RFPs, disaster recovery
plans, external audits, etc. All a PITA, but worth gold

\- the balls to ask for large amounts of money for your product, because its
worth it, and you're worth it

\- perseverance

~~~
ak39
Great story!

How did you manage this: >>\- the illusion of a solid, well managed company,
i.e. not a one man band<<?

~~~
abraae
Really a matter of faking it until you've made it..

\- have a physical address

\- have photos of your employees (even if some were drafted in from the office
next door)

\- be highly responsive to strange (to you) requests for documentation etc.
from their IT, procurement, exec and management teams

\- this is hard but don't over stress when they are late paying you. It takes
a hideously long time for corporates to actually cut you a check. They always
pay - eventually. But its not impossible to wait for 9 months longer than you
thought to get paid, just because of their process. You have to somehow
survive this

\- have a lawyer

We bootstrapped off of consulting revenue to cover the costs in the start

------
robterrell
Our first customer was a lead from one of my co-founders. He'd been in another
company a few years prior in the same space, and that company went bust, and
the customer needed a new solution. An easy first sale. Later sales proved to
be extremely difficult.

IIRC our original price list ranged form $15k to $100k. The typical sale
included hardware, a 1U rank-mount server that we pre-instated our software
on.

Why were sales so difficult?

\- Enterprise sales can take a long time to close. I think our average close
time was a year. That's not surprising when you think about the process most
companies have to go through -- getting buy-in across divisions, waiting for
an annual budget period to arrive, etc. Educational institutions took the
longest -- over a year. You need a lot of runway.

\- Enterprise sales are very high-touch. Lots of phone calls, lots of demos,
lots of on-site visits. Prepare to buy lots of meals for decision-makers! It's
reasonable for a large company to want to spend time to get comfortable with a
start-up... you're competing with HP, Microsoft, EMC, etc. for these
customers, and none of them are going away anytime soon, but your startup
needs to prove it's real and has staying power.

\- During one of your first get-to-know-you calls, I highly recommend learning
about the internal process of the company. What's the signature authority of
your contact? Who has to sign off to approve a payment of the size you're
thinking of? It's not uncommon to believe you have all the approvals you need,
and actually be wrong. We had situations where we installed gear on-site and
later learned that a VP needed to sign a check of that size. Don't be rude,
but make sure you ask the right questions. You may need to get the name of
someone in Payables to get the real deal.

\- To avoid the lengthy approvals process... a trick I liked was to make a
custom product just below the expense limit cutoff. For one company I talked
to, they could authorize and expense anything under $1k, so we made a product
that was $1k/month that they could pay with a credit card and expense.

\- Contracts are part of the long lead time. Expect lots of modifications. If
you don't have an attorney handy, this can be a real expense.

\- Source code escrow came up a lot. You may want to investigate options ahead
of time and bake the cost into your pricing structure.

By the end of my time there, I was convinced that enterprise sales weren't
worth the trouble.

------
throwaway_62304
I won't give too many details as negotiations have only just closed, but we
are product development engineers building a physical hardware/software system
and selling to operators to whom product development is a completely foreign
concept.

We knew who our target customers were, and made contact with one who came to
us at a trade-show. This went through a few rounds of talks, but although the
initial contact and his manager were dead keen, the decision maker stalled and
we gave up.

Simultaneously, we found a contact in our network who got us to near the top
of the hierarchy of a second much bigger customer. They sent a single manager
to have a demo, and we must have blown him away because they brought the CEO,
CFO, some VPs and even a board member around for the same demo a few days
later. They proposed a partnership that day and left us to iron out the
details. Direct access to the decision makers was a HUGE part of making this
happen.

It took about four weeks of meetings and emails to get alignment, but we're
now preparing for a paid trial with an MOU for a much longer partnership
assuming all goes well. The biggest challenge was withholding their desired
exclusivity in different ways until we reached alignment on the upside to us,
at which point we gave them the lockouts and distribution rights they wanted.

Fortunately this deal went well for us, but had it not we'd be talking about
how much time we wasted preparing models and spreadsheets and refining terms
of agreement. We had other paths we could have gone down, and the interest
from this customer was validation that the product was valuable so we weren't
short of options. I think that gave us good negotiating leverage, and we were
ready to walk away at one point. The biggest irritation was probably the
translation from verbal discussions to written form, as it seemed like terms
we'd talked through and removed were being re-added in different flavours each
round. Careless (or perhaps deliberate...) wording could have cost us half our
upside, but we spotted that and resolved it.

I don't believe any other companies were in the mix. I suspect they saw that
our product was a distinct improvement over their existing capability on so
many counts that they just jumped at the prospect of getting it exclusively
before their competitors did.

------
crdb
We were building a price comparison company. I was trying to figure out ways
to make money after we were turned down by YC and unsatisfied with 4 months of
fundraising. Thought we'd try and sell our price lists to businesses who
wanted to be competitive.

I tracked down the biggest in the region, found someone there who had upvoted
a couple answers of mine on Quora, pinged him there, and he replied. Said it
was interesting, but he had no idea what price comparison was, so forwarded me
on to the COO.

I met the COO at Starbucks, we talked for a couple hours. Initially, he said
it was a very interesting concept, but he didn't understand how to integrate
our information into his product. I said it would be easy to integrate it in
his data warehouse. He asked me what that was. I explained, he asked me how
much we'd want to build it for them part time. The contract was signed the
next day after a 30 second meeting with the CEO, and so we were in the data
business.

I didn't get on well with the CEO, in great part because I was still
inexperienced at the political side of sales and would say what I thought in
emails, particularly about their existing BI efforts. So we parted ways after
6 months, but they had a data warehouse and automated reports by that point,
which afaik are still running there under a new team.

To this day it is my only cold pitch conversion. Every other client I ever had
came through connections (making me wonder the value of spending time on
pitching). Sometimes as random as - I met a guy in a conference I talked at,
he invites me to his next government event, he introduces me to his friend who
left the civil service for a VC, the VC likes what I'm saying and introduces
me to her portfolio companies, one of them signs.

------
cglee
I used to run a company called Active Interview. I say "used to" because the
product is on auto-pilot now, and just cruising along without any support with
MRR of around $1200.

The very first sale was done before our recurring pricing was even built. We
had a contact who sold video interviewing to One Laptop Per Child _without a
product_. He was a sales guy trying to build a product, but was having trouble
executing on the implementation (as programmers, this is probably an old
story). He saw our product and said it was exactly what he was trying to
build. He agree to split the revenue with us 50/50, if we allowed him to use
our product for his clients. That was our first and last enterprise check, and
this was before our product was even fully finished. The One Laptop Per Child
interviewing went very well, and we were able to get some minor publicity out
of it. At that point, we thought we had something big, and wanted to pursue
our vision of a SaaS product, instead of doing pure enterprise with the sales
person who found us. We were one of the first video interviewing products,
along with Hirevue, and was sure there was a market out there. At first, this
was true.

Our first enterprise sale on our own was Airbnb, and was relatively easy. A
lead from one of their departments sent in an email, and after a demo, they
signed up for our $500/month plan. We created that plan only to provide a
contrast to our $99/mo plan, which we thought would be the primary seller.
Turns out $500/mo is nothing for enterprises, and soon that's the only plan
anyone ever cared about. The Silicon Valley startups in general were much
easier to sell to. Wildfire Interactive (later bought by Google) was also an
early customer, as was odesk, and a couple of other startup companies. They
were all very easy to deal with. They were abnormal though, as we found out
later.

The real enterprise sales experience came from more traditional industries.
For our product, that meant mostly recruiting firms. No one used the free
trial, and everyone wanted a demo. They wanted to speak to someone over the
phone, and do several rounds of demos. The first was usually with a smaller
manager or analyst in HR. Then subsequent demos would be head of recruiting or
HR, or other senior executives. Almost every demo ended with the clients being
impressed by the product, but no commitment. We did demos with some of the
largest recruiting companies in the US, and with some of the largest retail
firms in the US (head of Marshalls/TJMaxx, for example). In the end they went
with a bigger company because they couldn't trust a couple of scrappy guys
with their business, even though the product was good. Our pricing was also
off-putting, because it was way too low. Low prices send a signal of poor
support and poor quality to senior executives. $500/mo is a rounding error to
them, and we probably would've made a better impression by asking for $10k
upfront and $2k/mo and assigned an account manager to each client so they have
a point of contact.

That taught us a lesson - if you want to go after enterprise, it's not really
about the product. It's all about sales and hiring account managers and
showing that you too are a big company. In that sort of field, you almost have
to take VC funding to "act big".

The alternative is to do what Basecamp did which is become thought leaders in
your field, but we really didn't love the recruiting industry enough to even
attempt to do that.

I'm not sure if this is the type of answer you're looking for, as this is more
of a failed enterprise company. I've talked to a lot of small companies who do
enterprise sales, and the success stories I've heard always revolve around
building an in-house sales team and ensuring a successful on-boarding
experience for customers by way of account managers.

That costs a lot. For bootstrapped companies, that's just not possible.

~~~
skewart
Thanks for sharing your story. It's super interesting.

I've seen the long, drawn out and high touch enterprise sales process shock a
lot of product and engineering driven startups.

It's too bad. I think this heavy sales process that enterprises usually demand
slows down the pace of innovation. I mean, I get why they want account
executives, and even why they feel more comfortable dealing with a seemingly
"bigger" company. But there are a lot of people with game-changing ideas who
can't get them off the ground because they can't build an effective sales org
on a shoestring.

I wonder if there's a way around this situation. I mean, maybe some kind of
AEs-as-a-service thing could be helpful (if that doesn't already exist).

~~~
cglee
There are sales-as-a-service type of companies out there, but most I've seen
are a bit sleezy. Premium ones, I imagine, would cost similarly to a good
salesperson.

The most successful model I've seen is hiring recent college grads who are
sharp and willing to learn. They are cheap and will dive into the industry
they're selling. A lot of funded startups operate this way, usually led by an
experienced salesperson.

------
throwthis
These are great. Could the OP please include a request for people to
optionally include their technology stack?

Thanks either way!

~~~
ctack
A wonderful thread indeed!

------
krambs
Selling software to law firms. Father of a friend's wife had heard I was
building the particular type of software his firm needed for a case. They
purchased the software almost sight unseen. Sometimes you need a little luck
with those first sales!

------
lefstathiou
Started a company that sells SAAS to US investment banks. I was a former
banker and spent a lot of time priming my colleagues for the service prior to
starting it assuming they would be willing customers when it was ready (we
addressed a niche that was quite a problem for the banks). I thought that if
we built a better mouse trap that significantly improved the user experience
(for investors, the under writers and the issuers - the companies that
actually raise the money) and saved everyone thousands of dollars it would be
a no brainier for the banks to use us. Didn't happen. When the time came,
bankers who, contrary to public perception are highly risk averse and focus on
risk mitigation, didn't want to migrate to something untested despite our
domain knowledge and demonstrable improvements. They didn't say this of course
- it was always another reason such as "it's not my choice" or whatever.

The way we established a foot hold was to go straight to the issuers. What
made our service unique is that while a bank was our user the service was
often chosen on behalf of someone else (their client, the issuer). 99% of the
time the issuer is silent on which service the banks use, after all they pay
the banks to advise them. So we instead sold the service to them (well in the
beginning let them use it for free). They in turn told the banks that they
needed to use our service and the banks, who ultimately serve the issuers,
simply complied. Once we had 2-3 of the banks onboard, network effects kicked
in. With each sale we would go to another bank and say "let me show you what
we did for XYZ"

Moral of the story (for us at least): 1) someone may indicate they are a
champion but when the time comes, most are unlikely to be there. For every
team of 40-50 you can at best expect 1-2 people willing to be champions 2) if
possible (and I can appreciate that not all services can do this) sell to the
person that ultimately benefits from this. In our case, banks use our software
in relation to capital markets deals for other companies like John Deere so go
to John Deere directly. 3) random point not mentioned above but worth
highlighting ... I find that enterprise customers care more about making a
dollar than saving a dollar. Our sales improved dramatically by tweaking the
message to focus on this. If possible, focus on how you help these
organizations grow P&L 4) I am a HUGE believer in Trojan Horses (and I don't
mean hacking software). If possible, figure out a way to get your prospects
using or benefiting from your software immediately by giving some service away
(maybe not even your core service) weekly or if possible daily. The more they
interact with you, the easier it is to bridge the divide and get through the
process. 5) last point, don't get hung up on engagement letters. I know the
lawyers will advise against this but a lot of deals die in the engagement
letter phase. I appreciate not every business can do this but I made it
crystal clear to my accounts that if they don't like my service they don't
need to pay for it - that gave gem the comfort to use it regularly and at the
end, they all paid for every use.

I can go on further on some of the tactical nuances of the above and other
strategies. Feel free to ping me.

~~~
saeranv
Yeah I'd like to hear more. What are the specific ways you tweaked your
message to focus on making a dollar?

~~~
lefstathiou
In a typical enterprise sale, the people making the decision (to buy your
solution) are usually too senior to be the ones actually using it. There is a
subtle corollary to this that I did not appreciate at first... often, these
people are responsible for the profit of their group but less responsible for
the costs associated with the technology. Thus, teams are less sensitive to
cost than they are top-line revenue. There is a lot of theory about how silly
focusing on top line is instead of profit but we all know the difference
between theory and practice.

So how did I change my pitch: I ripped out all the slides that walked through
my site and all the neat ways we saved time, automated workflows, etc. I
focused on the data we generated (in one page) and threw in two case studies
that highlighted how decisions made with our data generated more revenue.

It is important to highlight that the pitch-deck is not what is selling your
solution, you are. The key is to tell a story worth listening to and I use my
pitch decks to guide that story. My pitch today has X pages:

\- Cover Page \- Page with client logos (demonstrating social acceptance) \-
Page with big picture showing our platform works on all browser enabled
devices (a major innovation on wall street) \- Page demonstrating the insights
our data creates \- 2x case studies

Hard to put an exact number on how well this new method of focusing on the
outcome rather than the solution has helped but I do not believe I am
exaggerating by saying it improved close rate by 1-2 order of magnitudes.

If you want to read some great books that I believe will dramatically improve
your close rate, I recommend the following in order:

1) Dale Carnegie's How to Win Friends and Influence People - if put in
practice, this will pay a life-time of dividends. I wish this was taught in
schools.

2) Getting to Yes (on negotiation theory) - a powerful negotiation framework
allows you to create and preserve value in very measurable ways.

3) the Psychology of Influence - great case studies on how people make
decisions, often in ways that are irrational. I incorporated a lot of the
learning points into my pitch and in our slides and absolutely saw a shift.

I love thinking through this stuff so to the extent you want to chat more,
happy to hop on a call or grab a coffee if you're in NYC. Shoot me an email
(in my profile).

~~~
saeranv
Thanks, it's so useful to get this kind of detailed advice from someone who
has worked through these challenges. I may take you up on that offer!

------
vpj
How we got our first enterprise customer (a company in Sri Lanka)

[http://vpj.github.io/b2b_customer.html](http://vpj.github.io/b2b_customer.html)

tl;dr; We got the contact from one of our investors. First meeting was a
product demo and a short presentation. There were long time gaps between
meetings (it took several months to get to the trial). We didn't have a
simpler way of doing the trial.

------
salilpa
went to a marketing tech conference and pitched our idea about AdWords
Automation : AdNabu to a bunch of people. Exchanged cards with a few of them.
We couldn't get meetings with any of them.

We got a call from from an enterprise with whom we couldn't interact
personally. Met them in their office twice, started a free trial, showed
positive results and they became a paying customer in a month

We had to sign a lot of documents but the contract is longer and more
profitable to us :)

------
murukesh_s
JGEWQ

