How to Land Your First Enterprise Accounts
The GTM Newsletter
What does every normal person do after ten hours of Zoom meetings on a Friday evening?!
Well naturally, you sit down and write about how start-up founders and tech operators can break into large, enterprise logos and increase their ACV.
Man, I gotta get a life.
Luckily I’m fortunate to stand on the shoulders of GTM giants and in this issue you’ll hear directly from leaders that have sold multiple billions of services/software into slow-moving, overly bureaucratic, massively political, enterprise organizations.
That’s billions with a capital B baby.
One deal has the capacity to completely change the trajectory of your career or SaaS business…
caveat: there’s way too much to cover so we’ll likely revisit this topic multiple times in the future.
Anyway, let’s get into it.
How to Land Your First Enterprise Accounts
First, let’s start with a story.
…because who really wants to read an overly jargony, buzz-word filled business newsletters on a Friday night?
This story comes from Chris Donato, a dear friend of mine, and the CEO/Founder of Esellas who has previously held sales leadership roles at HPE, Axiom and Accenture:
“I’ve been selling things since the third grade. As a middle-class, little league playing, Catholic-school kid in suburban Philadelphia, it wasn’t hard to find a reason to raise money.
So my brothers and I went door to door selling candy, raffle tickets and magazine subscriptions in our neighborhood to moms in flowered, smeared aprons.
Years later the deals became bigger and had much longer sales cycles. I eventually sold billion dollar outsourcing contracts to men and women in expensive suits all over the world.
Throughout my career, I was always curious about what set the best apart from the rest. Was there something specific that they were doing that no one else did?
After years of studying salespeople, I learned that most effective sales people did three things more consistently than others. I also learned that the same things that worked in the neighborhood, also applied to the enterprise.
They originated business. The great ones don’t sit back and wait for the phone to ring. They are proactive at generating business. They had the courage to go out into the world and create demand. They do this consistently even when they’re pipeline is full of opportunities. The best are always prospecting.
They picked their spots. They knew which doors to knock on. Equally important, which ones not to waste time on. They have a nose for sniffing out the the people and businesses who are most likely to buy what they offer. In the neighborhood for example, it wasn’t necessarily the most expensive house or even someone they knew who bought something. Rather they figured out that people who recently moved into the neighborhood were good prospects. They realized that a new mom often wanted to make a good 1st impression on the rest of the neighborhood. New families almost always purchased something.
They asked for the business. More than anything else, the best sellers had the confidence to simply ask some version of the question “do you want to buy?”. As easy and straightforward as that sounds, it actually is one of the more rare skills. The most effective sales people know that if you don’t ask, you don’t receive it. They ask early by stating their clear intentions up front. They’re not shy about the fact that they sell something. They also close throughout the process by constantly asking for confirmation of the small decisions the buyer is making along the way.
There are course other skills that matter. Being prepared, listening more than you talk, asking great questions, and having discipline to play the long game set the really good ones apart. All of these things contribute to creating a positive buying experience for the customer. The best know that a great experience contributes more to customer loyalty than price, product and brand combined.
That’s said, a new style of buying has emerged in business. A buyer requires less interaction with a seller to make a purchase decision. Much of what a buyer needs is easily accessible; pricing information, product demonstrations, competitive comparisons and independent reviews are abundant. Meanwhile, More buyers are showing a preference for self service experiences over sales-assisted ones. And some of the over zealous antics from sales and marketing organizations are pushing buyers away at a faster rate.
This new buying paradigm has put pressure on every sales organization. It has also created a call to action for salespeople to improve their game and rethink their role.
Selling is not about driving volumes of activity that create frothy funnels. It’s all about building more predictable pipelines by demonstrating to a prospect that you can add value along their purchase journey.
What hasn’t and will never change is that people need solutions to their problems. And businesses make new problems everyday. Meanwhile, as more and more options come on the market, it’s harder than ever to distinguishing between two solutions. Buying on behalf of your colleagues has become more complicated and a scary thing to do. People enjoy having someone they trust to guide them along the way.
This is where a sales professional finds purpose - in a buyer’s moments of need. A good seller is the curious (not invasive), collaborative (not manipulative) and inspiring (not pushy) curator of the buying experience.
While things seems a little unclear today, I’m sure that sellers in the future will be trusted advisors with the ability to connect things, in order to solve problems for clients, that would otherwise be disconnected without their personal involvement.
Businesses need more competent, character-rich women and men in sales just as little-league teams and elementary schools need scrappy 10-year-old kids standing at our doorsteps because growth doesn't happen in business until a sale is made.
Someone has to knock...and that person is in sales because we are more afraid of letting down our customers, colleagues or company than we are of a virtual door getting closed on us.
Besides, There’s always one more door around the corner.”
I don’t know about you but that fired me up 🔥
📈 How to take action:
Never be ‘too senior’ to do your own prospecting.
Be ruthless with where you spend your time.
Have the courage to make the big asks, again and again.
In deals that can take multiple months or years: you need to draw your strength from purpose. Your buyer has a moment of need, you may be the only person in the world that can solve that problem for them - that’s your purpose.
Alright, story time has now concluded.
Now, if you’re not ready to dive right into this topic head first then maybe bookmark this for Monday morning.
For the rest of you, I want to introduce Jamal Reimer, former top 1% Strategic Account Manager at Oracle turned VP of Sales turned Founder, Author, Advisor.
I’m going to do my best to distill some of Jamal’s thoughts/ideas/strategies on this topic but for the full dose, I would recommend you check out his website: Mega Deal Secrets (I think you can even get a free copy of his book).
Below is one of his graphics depicting the typical SaaS company’s sales motion maturity model:
From my experience, most SaaS companies are lucky if they make it past the Transactional stage ever and only a very select few make the jump successfully to true Enterprise selling.
Of course, there is a case to be made that not every tech company should go after the enterprise but that’s not what we’re talking about.
So if you’re looking to mature, how do you make the jump?
First you have to know the differences between the two.
The buyer and seller journey is going to look vastly different and therefore requires a completely different approach as outlined by Jamal in Fig.1 and Fig.2 below.
Fig.1
Fig. 2
Old habits die hard and I’ve seen lots of teams try to squeeze an enterprise buyer through a run-rate sales process.
It makes sense. When you’ve seen a certain level of repeatable success with one model, it’s going to be hard to abandon it and adopt an entirely new way of thinking.
But that is the kiss of death 💋☠️
Here is how Jamal sums up the shift in thinking that has to happen:
“Moving into enterprise selling will require enabling a shift from "Batman and Robin" selling (seller + solutions engineer) to "Field Marshall of a Roman legion" selling, where the seller is a quarterback of an extended deal team which includes sales, presales, value engineering, an exec or two, product strategy and maybe engineering.”
Ok, now that you’re the “field Marshall of a Roman Legion”, you need to use that new found strength to feel comfortable getting to power early in a sales cycle.
SUPER IMPORTANT IN ENTERPRISE DEALS.
One more illustration to hammer this sentiment home:
📈 How to take action:
Diagnose where you currently are in your sales motion maturity model.
Map out your different buyer/seller journeys for the four models: founder-led, transactional, run-rate and enterprise (understand the differences in complexity, time and # of stakeholders)
For Ent. selling, you need to switch your mindset from sole contributor to the quarterback of a team.
Bring power in early (your executives) and get to power (their executives) as quick as you can.
Getting a quick NO is not a bad thing when selling to the Enterprise - it will save you a ton of time/resources.
Now with every topic we cover, we try to bring other perspectives to the table.
And just because you may have the ability to sell to the enterprise - should you?
Farlan Dowell, former VP of Sales at RainforestQA, Cleanshelf and active GTM Advisor at Iconic Air (one of the best in the biz from 0-10m ARR) has some candid thoughts:
“I generally hate dealing with Enterprise, Fortune 500 companies, until I’ve got a couple million in ARR and I’m not putting all my eggs in one basket.
I’ve seen many a startup go out of business chasing shiny exciting logos.
My advice: scrutinize the sh*t out of them and make sure it’s a real deal.
Do they actually need your product? Or are they doing ‘market research’; you’d be surprised how many ‘so-called-sunshine-pumping-deals’ fit into the latter.
Be optimistically cautious and overly paranoid.”
Ben Dietz, President and General Manager at Mintel Americas, also jumped in with some parting thoughts:
“No matter what price you think you should charge, add at least another zero. You are not taken as a serious player if the price seems like a bargain.”
📈 How to take action:
At the early-stage, make sure you don’t overly index time/resources to one deal.
Do ridiculously deep discovery, turn over every rock possible and make sure this opportunity is not a mirage.
Remain optimistically cautious and overly paranoid.
You won’t get a seat at the big boy table if you underprice your software/services.
👀 More for your eyeballs:
“Traditional AI (artificial intelligence) allows machines / computers to analyze reams of data finding patterns for many use cases (ranging from fraud detection to what you see when scrolling through social media). Until recently, the creativity possessed by humans was something that machines could not compete with – but that’s no longer the case..
This new development is called “Generative AI”
If you tend to go down rabbit holes like I do, then you can go deeper on this topic in an article that Sequoia published title “Generative AI: A Creative New World”
*more on how this technology will influence the future of GTM in an upcoming issue.
👂More for your eardrums:
Remember Chris Donato from the story above? We recorded an episode of the GTM pod together where he discussed his learnings from selling over $4bn in software/services throughout his career and how some back of the napkin scribbles turned into a deal worth $300m.
🚀 Start-ups to watch:
“While complex in execution, our goal at Channel99 is straightforward: make it easy for finance and marketing teams to use a common language to eliminate dollar inefficiencies and more predictably exceed sales pipeline goals.”
Channel99 just announced a a $5m raise led by Jackson square Ventures - and including Norwest Venture Partners, GTMfund and Bloomberg Data.
🔥Hottest GTM job of the week:
SDR (Brand Partnership Associate) at Statusphere, more details here.
See more top GTM jobs here.
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Ok, time to stop writing.
I’m going to go enjoy my Friday night and I hope you do the same.
We’ve seen a big bump in subscribers to the newsletter and listeners to the pod over the last two weeks so thank you to everyone who has shared this with a friend/colleague or two.
We write these in hopes of sparking some inspiration, helping to validate ideas you may already be having or giving you the push you need to run some new GTM tests/experiments.
It’s strange times out there - but we’re all in this together - so we might as well share whatever knowledge we have with each other.
See you next week.
Barker.
✌️
Fig 2 😂🤦
Thanks for writing these, keep it up!!
Thanks for the Friday night read, Scott