The Enterprise Sales Strategy General Assembly Used to Cut Their Sales Cycle, Accelerate Growth, and Get Acquired for $413 Million


Giants move slowly.

As someone focused on closing high-value, enterprise-level sales, this is a reality you know all too well.

Sure, the bigger the sales, the bigger the payoff – that’s why you’re in this business, after all – but that doesn’t make it any less stressful when the 6+ figure deals you’re trying to wrap up take weeks (or months) longer than you’d like.

Enterprises have notoriously long buying cycles. Between all that red tape, scheduling conflicts, and the need to please multiple stakeholders, it’s not unusual for a typical buying cycle to take six months – or longer. That’s at least half a year between the moment you make contact and the moment you sign a deal.

To say a lengthy sales cycle is frustrating? That would be an understatement. Fortunately, there are several practical steps you can take to actively shorten the cycle.

Even better, you can learn from the failures and successes of other sales team who’ve already figured out the secret sauce – without experiencing their mistakes firsthand.

Today, we’re going to look at a company that managed to reduce their sales cycle, win Fortune 500 clients, and recently sold for $413 million.

More specifically, we’re going to dig into how General Assembly managed to shorten their sales cycle, look at the lessons they learned along the way, and break down the enterprise sales strategy they developed to close high-value deals faster.

But first, let’s talk about why it matters.

Why should you care about shortening your sales cycle?

Is reducing your sales cycle really something you should prioritize?

Well, the longer your sales cycle, the more time and money your business ends up sinking into every single deal – so that’s a big fat YES.

Not only is a lengthy sales cycle frustrating to the seller, but it’s also expensive. The more time you spend stuck in stalled deals, the less time you have left to dedicate to closing more lucrative opportunities.

Still not convinced? Consider that anything you do to cut down your sales cycle length is guaranteed to boost your bottom line.

Why? Because shorter sales cycles equal higher close rates, more profit, and faster wins. This allows your sales reps to focus their energy on the next big win – which we both know you’ve already set your sights on.

Every moment cuts out of your sales cycle is extra time your reps can spend building relationships with prospects and closing more deals.

If you aren’t actively trying to shorten your sales cycle, you’re wasting valuable company resources.

The simple formula for calculating your average sales cycle

If you want to sell faster – or optimize your selling process in any way – then understanding the steps in your existing sales cycle is key.

You can’t improve what you don’t understand. So, before you can streamline your sales cycle, you need to have well-defined steps and an idea of how long it currently takes to close a typical deal. Plus, if you know your average sales cycle length, you’ll be able to forecast future deals more accurately and look for ways to increase your sales velocity.

The length of your sales cycle is affected by a range of factors, including your industry, deal size, customer profile, and the stages your sales reps typically follow.

To calculate your average sales cycle length, use the following formula:


Simply add up the number of days each deal took to close over the time frame you want to measure. Then, divide the total by the number of deals that took place during that period.

For example: Say in 2017, you closed 3 enterprise deals. One deal took 60 days, one deal took 100 days, and one deal took 200 days to close. Then your average sales cycle length is (60 + 100 + 200) / 3. That’s 120 days – or about 4 months – to close the average deal.

This calculation requires looking at the data from your past sales to see how many days each took to close. Whether you begin tracking from the moment a lead is contacted or from the moment you qualify them as an opportunity is up to you – just make sure the same starting point is used consistently by all of your sales reps.

Once you have the average length in days, you can use it to predict future close dates and as a benchmark to measure your progress against.

What factors lead to a lengthy sales cycle?

Now that you know how to measure your average sales cycle length, what can you do to pick up the pace? To figure this out, we need to look at why enterprise sales tend to take so long – and which factors you can manipulate to reduce your sales cycle.

Unfortunately, there’s more than one culprit.

The more stakeholders involved, the more obstacles there are standing between you and the sale. These include everything from coordinating meetings around everyone’s busy schedules and connecting with decision-makers to obtaining total buy-in from all parties and waiting on budget approvals.

But one of the biggest time-sucks is gathering intelligence on your prospect so you can go into every meeting fully prepared.

And after you’ve prepared to meet one prospect, you’ll likely be introduced to additional stakeholders at various points of the sales process – each with their own set of interests and intentions.

Imagine that you go into an initial discussion cold.

You have to start from square one, so that first meeting is just focused on understanding their company and their needs. This means that you need at least two meetings (discovery and pitch) to explain the benefits of your product in a relevant context.

Then, every time they introduce another stakeholder or add a new element to the discussion, you have to repeat this process – two separate meetings for each new step.

So, instead of looking like this:

Ideal Enterprise Sales Process…your extended sales cycle might look something like this:

Actual Sales Cycle

If this looks familiar, you’re not alone.

Complicated sales cycles that don’t unfold linearly are all too common when pitching enterprise clients. The addition of new stakeholders can set you back a full two steps in the sales cycle, adding extra time to an already lengthy process.

Here’s why this is particularly problematic: top salespeople are good at selling. They’re able to connect, build relationships, and establish rapport. Their talents are not put to best use by spending time researching – especially if they have to stop and dig up intel at multiple steps of the sales cycle.

If they have access to the information they need in advance, they can cut out an entire step (the discovery meeting) and use their time most effectively.

The enterprise sales strategy General Assembly used to shorten their sales cycle

To help you optimize your own sale cycle, we wanted to share a real-world success story that could inspire other sales team and provide practical, tactical advice anyone can apply.

So, let’s take a look at how General Assembly (GA) managed to significantly cut down their sales cycle – and find out why they’re the perfect model for enterprise sales teams to learn from.

GA offers courses that teach critical skills for the digital age to individual students and employers (including 20% of Fortune 500 companies). Since launching in 2011, they’ve scaled up to 20 campuses in 25 cities around the world, with over 50,000 alumni. Recently, GA was acquired by the Adecco Group for a cool $413 million.

One of the keys to their success? Honing their enterprise sales strategy to close major clients more quickly.

According to GA’s own Anand Chopra-McGowan, the road to success is paved with mistakes. Chopra-McGowan is a long-term team member who played an integral role in expanding GA’s enterprise business and is now Head of EMEA and Global Head of Consumer Practice.

His sales team helped develop the enterprise sales strategy that GA uses to win over conference rooms full of stakeholders. Since a shorter sales cycle boosts the chances of a closed-won outcome, GA focused heavily on tightening up their sales process.

Let’s take a look at the specific tactics and strategies they use to accelerate sales and win deals with major enterprise clients.

1. Qualify ruthlessly

GA discovered that a better, faster qualification process is driven by hard data.

They recommend building a qualification checklist and questions to refer to at each step of the sales process.

They use a modified version of the BANT system (based on whether the client’s budget, authority, need, and timing align with the offering), adding a few qualifiers of their own based on personal experience with past clients. You’ll be able to refine your qualification process over time as learn more about what your customers want.

Remember the importance of not only to qualifying ideal customers but also of qualifying out of certain conversations – not everyone is the perfect fit for your solution. This allows your reps to focus on clients who are most likely to close.

2. Communicate a clear timeline to all parties

General Assembly finds it most effective to send each prospect a detailed, color-coded timeline to make sure it’s clear who is responsible for each step (whether it’s GA or the client). They submit a visual representation of the plan broken down into specific stages, including pre-contract and post-contract requirements.

The goal here is to get clients to sign off on the plan early in the process so that everyone is on the same page in terms of expectations. This sounds simple, but it can really speed things up, even if the deal doesn’t play out 100% according to the original plan.

pre contract enterprise sales process

(Source: First Round)

3. Double down on face-to-face meetings

General Assembly’s enterprise sales team realized the value of in-person meetings early on. Not only does it show you’re serious about working with the prospect, it also allows reps to develop a more authentic personal connection.

They now encourage their sales reps to meet face-to-face with clients whenever possible – and use it as an opportunity to lock in a second meeting within 24 hours of the initial discussion. Chopra-McGowan claims this double meeting strategy can cut a solid two weeks off your sales cycle – just like that!

Most clients are happy to accommodate you for both meetings, especially if you explain that it makes the best use of your time. This creates a greater sense of urgency and allows for faster progress by taking you from discovery to proposal in less than a day.

4. Scoop up any openings in VIP prospects’ schedules

Your prospects are busy people. If you’re selling to C-level execs and other bigwigs, you know how quickly their calendars fill up. It can take ages to get a meeting, and you’ll often find yourself scheduling an initial discussion weeks or months in advance.

But cancellations or schedule changes can give you an opportunity to meet with them sooner. You just have to be diligent about calling to ask if any time slots have opened up.

This is the strategy that GA uses for bumping up important meeting with executives. Once they set a meeting with a high-level executive, GA’s sales team checks in with their assistant every few days to find out whether any upcoming times slots have opened up in their calendar. It sounds simple, but it works!

5. Submit a proposal ASAP

After your initial meeting, send over a draft of the proposal as quickly as possible to keep the momentum going. Chopra-McGowan says it is vital to get that first version of the proposal written up and sent to the client within 24 hours of the first meeting.

To prevent the client from procrastinating on reviewing the proposal, explain during the meeting (and in your follow-up message) that you’re sending over a very rough proposal specifically to get their feedback.

This serves the double purpose of getting them to look at the draft and gives you an early opportunity to incorporate their feedback in the next version – which should make everyone happy and keep the process moving along.

Even better, you could draw up a rough proposal based on your understanding of the company and any intelligence you have before your first meeting. This makes it possible to get immediate feedback during that very first discussion and has potential to cut out an entire step of your sales cycle.

6. Get to know your prospects ahead of time

Pitching to a group of stakeholders for the first time isn’t easy. Especially if there are 6 or 7 people in the room who you’ve never met before.

How can you establish a connection with each person as an individual? How can you learn about each of them and find out what they want and expect from your company?

There are two possible solutions here. The first is what General Assembly calls pre-intros. Essentially, you would try to get each stakeholder on the phone for a quick ten-minute call. This gives you a chance to introduce yourself, get to know them, learn about their goals, needs, and concerns so you know what to address in your pitch.

However, since it’s not always easy to get every stakeholder on the phone in advance of a meeting, you can seek out that information elsewhere. For instance, human-powered sales intelligence from Prepperz arms you with the same level of personalized, high-quality, relevant data before you’ve even met the prospect.

Key Takeaways from General Assembly’s success

  • The fewer meetings, the better. Not only does this reduce friction and cut back on the number of steps involved, but it can also speed up your sales cycle substantially.
  • The more you know about your customer and their specific needs, the more power you have to accelerate the discussions.
  • If you enter each sales meeting with a pitch tailored to the prospect, you can make a deeper connection, draw up a proposal draft immediately after, and cut down on the number of meetings needed.
  • Don’t overlook the value of personal relationships, face-to-face meetings, and emotional drivers.
  • Go beyond collecting data on your prospects; aim to truly understand your clients, what it is they’re after, and what they value.

Sell smarter, not harder: Using sales intelligence to pick up the pace

Let’s go back to our example from earlier. You’re meeting with a new enterprise client for the first time. If you go into that initial meeting completely cold, your entire first discussion will focus on discovery.

At your second meeting, you can use what you’ve learned about the company and their needs to deliver a tailored sales pitch.
Whenever another stakeholder is introduced, you need to rinse and repeat: complete the same discovery and pitch steps for each new person.

However, you can cut those two steps down to one by arriving at that first meeting fully prepared and knowledgeable about the prospect you’re meeting with, their needs, and their company.

Take a look:

sales cycle with prepperz

Shortening your sales cycle isn’t just about booking more meetings in a shorter time frame, it’s also about reducing the number of total meetings required.

Having actionable intelligence will put some of the steps in your cycle parallel rather than making them sequential.

That is, you’ll get more done in less time, and close your next enterprise sale faster.

Shorten your sales cycle with powerful sales intelligence

When you’re going after enterprise sales, you need to go in armed with accurate intelligence and relevant insights about the company and the individual prospect.

That’s where Prepperz comes in. We can help you cut down your sales cycle by providing actionable intelligence ahead of each meeting.

Want to shorten your sales cycle and close high-value deals faster? Get in touch today to find out how sales intelligence from Prepperz can supercharge your selling process and accelerate your sales cycle.

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