The Most Surefire Way I’ve Found to Win Enterprise Deals

The Most Surefire Way I’ve Found to Win Enterprise Deals


At barely a year old, General Assembly (GA) had already come to a crossroads. The company had just pivoted from providing workspaces to companies to focusing solely on educational offerings for individuals. In that transition, its founders spotted a new and somewhat daunting opportunity: Could such a young company put together a week-long Digital Bootcamp for leaders for one of the world’s largest industrial conglomerates?

As often happens in the startup world, GA said “yes” first, planning to figure out the “how” later. Fast forward to today, and GA is working with thousands of employers, including 20% of the Fortune 500. Not only does GA offer courses directly to individuals around the world but companies come to GA to help train and uplevel their talent — in everything from data science to UX to digital marketing and more.

Luckily, they had a few secret weapons to help propel the business — including Anand Chopra-McGowan. Core to the establishment and growth of GA’s enterprise business, his and he have been responsible for millions in revenue from deals with some of the largest companies in the world like GE, Visa, Walmart, L’Oreal and more.

He’s the first to admit that success didn’t happen overnight — not by a long shot. It took many conversations, post-mortems and iteration cycles to get to a formula that worked in conference rooms packed with corporate stakeholders. Today, Chopra-McGowan leads GA’s European expansion — and his most impactful discovery over the last few years is this: The shorter the sales cycle, the likelier the win. As a result, most of the tweaks that were (and are still) made to GA’s sales strategy drove toward tighter timeframes. And they learned a lot along the way.

In this exclusive interview, he shares the exact tactics that helped GA achieve the shorter sales cycle that helped them nail deals with huge companies — and how other enterprise sales teams can do the same.


Lead with insight and direction.

Too many tech startups kick of conversations by talking about their novel products, services and underlying technology. Sounds good, but it obscures the benefits to the customer (i.e. why they should be listening to you) — and ends up extending the conversation. Instead, companies should lead with a clear vision of how the relationship between your companies will work and what they stand to gain by having it (tailored tightly to the customer).

Develop an objective, data-driven qualification model and apply it ruthlessly.

When you’re just starting out and have few customers, it’s hard to say no to any meeting. But it’s at precisely this stage of company growth when you need to be judicious about where to spend your time. This is why effective sales teams tend to have very clear qualification models that they apply throughout their sales cycle. This model should be refined over time, and use past experience to build an objective checklist at each step of the process so that sales execs know with confidence whether a sale is progressing.

Add boosters to each buyer interaction.

Most buyers at large companies have expectations around how long each phase of a sale process should take — and they tend to be longer than most young companies can tolerate. To survive, you must challenge these expectations wherever possible — how you prep for meetings, how you use time in meetings, in producing a proposal, in incorporating client feedback. A few cuts to each of these can substantially reduce your total cycle.


Okay, so those three themes might make sense, but how do you actually execute on them? Let’s take a closer look at each and unpack the actions you can take to put them into practice.

Bring insight and direction.

First sales meetings tend to be all blue sky. This isn’t great. People like structure, and they’ll have more confidence in your ability to deliver if you strongly frame your thoughts and your process. Ideally, the structure you give them focuses on what you plan to deliver, says Chopra-McGowan.

For example, General Assembly’s sales team says its core offering is helping companies and their people build new capabilities. “We keep it short: We’ll help you source, assess and train your talent,” he says. “Sure, we could go into all the hackathons, events, social impact initiatives and sponsored courses we offer too, but that would have dulled focus on what we can do for them. It’s all about the rule of three — a three-part framework is easy to wrap your mind around.”

The “source, assess and train” model gives the customer something concrete to envision. If your first conversation is too broad, you risk getting pulled far off topic, promising features you can’t deliver, and requiring another meeting just to cover the basics. Start with a clear, simple model for purchase, and trust you’ll have the chance to go into detail later.

As you get more experience, you can offer several different models for purchase and lead with the one most relevant to the client in question. This demonstrates insight into what they really need and establishes credibility.

For example, one of GA’s first corporate customers wanted it to customize a portion of the curriculum for a leadership offsite. GA was able to develop an offering to fit the need. And once they had it, they could go into other conversations immediately offering this type of programming for retreats and offsites. “That one suggestion crystallized a whole new way we could initiate relationships and cut down on time we would have been going through the whole menu of options,” says Chopra-McGowan.

The other strategy for setting strong direction: Prescribe a timeline.

If you’re at a startup, most people will not have bought what you’re selling before. They won’t know how you plan to go from pitch to launch, unintentionally giving them permission to delay and dawdle.

Chopra-McGowan lays out a detailed timeline outlining each step with customers — typically on a single slide with color-coded line items showing who is responsible for what. His team tries to get clients to explicitly confirm their acceptance of that plan. Even if they don’t end up sticking to it exactly, it still establishes a shared understanding of what’s about to happen, and the clearer it is the faster things go.

Qualify ruthlessly.

To make sure GA is investing its time wisely with the right customers, Chopra-McGowan and his team apply the relatively common BANT system, which stands for Budget, Authority, Needs and Timing. New founders may not be familiar. If you’ve been selling at IBM for 30 years, it’s old news.

“Like many frameworks, it has its supporters and its detractors, but honestly if all four of those factors are a fit, the deal probably has a great chance,” he says. “What’s new is that we’ve focused less on the framework itself and more on developing an objective way to determine if a new opportunity actually meets what the framework is trying to prove.” The following is an insights-driven way to frame qualification questions that the GA team routinely uses in sales meetings:

The questions on the right tend to yield answers that are more objectively reliable qualifiers for a new opportunity. “You want to present proper context and then ask the question,” says Chopra-McGowan. “When you ask people a completely open-ended question like, ‘How much money do you have?’ it’s tough for them to answer, and you come off as unprofessional. Instead say, ‘An engagement with us costs this much — is that in line with your expectations?’ If they seem surprised by how direct you’re being, it’s powerful to acknowledge that you’re busy, you know they’re busy and you just don’t want to beat around the bush. Generally, there’s appreciation for that.”

A lot of startups end up skipping over basic qualifiers. They’d prefer to spend time on a sales call listing all the various things they can do, as opposed to addressing the potentially awkward and difficult questions. “My colleague Nate Castro, who spent years as one of Apple’s most successful sales leaders says all the time – ‘we’ll succeed in this role based on where we spend our time, and where we don’t’. In other words, it’s as important for us to qualify out of a sales conversation as it is to qualify into one,” says Chopra-McGowan.

The more conversations you have, the more qualifiers will emerge specific to your product or service. You’ll hear new objections and questions you should absolutely bake into a matrix like the one above. In prepping for this article, Chopra-McGowan spoke to Paul Hlatky, who runs west coast sales for email sales startup Yesware.

“Based on prior experience, Yesware’s sales team has created this rigorous internal qualification framework that has helped them dramatically improve the productivity of their sales team,” he says. “If a prospect says they don’t have an inside sales team or dedicated resources for lead generation, they’re less likely to buy Yesware. Sales reps also ask what other sales tools they use to see if they’ve made any similar investments.” It pays off to add 2-3 qualifiers like this to your own BANT system to make sure you won’t hit surprise roadblocks later.

Regardless of the qualifying questions you choose, be prepared for buyers at these companies to hedge and dodge. Very rarely will they give you an iron clad answer. That doesn’t mean they aren’t giving you valuable information though. Listen and put in context. “For instance, if they say they’re ‘just shopping around’ or can’t provide even a ballpark answer to ‘do you have a learning and development budget?’ we know we should move on and we’ve only wasted half an hour — not two weeks — of both parties’ time.

Talking about money can be very hard for salespeople and buyers alike. It feels awkward to ask questions about it if they’re nervous to offend. If you’re on the sales side, you have to get over it. “Think about it as having confidence in your product,” says Chopra-McGowan. “The more directly and clearly you’re able to talk about money, the more confident you appear in your product.”

Behave like you’re not selling, but simply facilitating the buying process. Have trust in the level of value you’re offering.

Turbo-boost your process.

If you take a hard look at your current sales cycle and list all the way you could save time, you’re sure to spot opportunities. But there’s a difference between shortcuts and boosters. If you cut steps for the sake of cutting, you could end up pushing your customer too much, failing to share crucial information, or missing out on even greater possibilities. Below are the five booster techniques that tend to pay off the most.

Double Meetings. “When traveling to meet a client, we’ve found it works great to request a follow-up meeting within 24 hours of the first one (schedule both at the same time upfront) — sometimes even the same day,” says Chopra-McGowan. This allows you to take some time and digest what you learned at the first meeting and come right back with rough draft proposal to get quick feedback.

Ideally, you set things up to meet with the larger group of stakeholders first, and then only with your primary client the second time. That makes it easier to schedule, and protects against a scenario where a large group meeting ends without clear next steps — a common pitfall. This departs from the normal cadence of having a meeting, sending a proposal within a few days, and scheduling follow up the next week.

Double meetings can shave as much as two weeks off your sales cycle.

“We met with a big bank recently in Stockholm, and we decided to ask for two meetings — when you’ve traveled to see them that adds pressure for them to say yes to that second meeting,” says Chopra-McGowan, whose team is based in London. “Say you will only be there for a day and want to make the best use of everyone’s time. We were able to leave the meeting with the bank with a word doc full of notes about what was most relevant to them. We were able to polish that up into a rough proposal we sent and got feedback on in the follow-up meeting that same afternoon.”

The Agile Proposal. The idea here is to create very rough versions of your proposals in deals very quickly, and the goal is to get great feedback before moving forward with full fleshed out proposals. The first version could be as rough as a simple word document, the second could be one or two Keynote slides, and the final would be detailed and on-brand — and would be much more likely to be a slam dunk for the client.

In addition to speeding up feedback loops, this has the extra benefit of building a client’s investment in the ultimate final proposal, keeping both parties tightly aligned throughout the cycle.

“It’s critical that the first version get put together within 24 hours of your first meeting, and that you’ve been clear with the client upfront that you’re going to send them something very rough with the express purpose of getting feedback,” Chopra-McGowan says. “We tell them at GA we like to practice what we preach re: rapid prototyping, that we’ll be sending a document with initial thoughts later today, and we’d like to get 20 minutes on everyone’s calendar to continue to get feedback tomorrow.”

He has a team member, Alexandre Terrien, who takes it a step further: He prepares the rough proposal before even going to his first meeting with a client. “He makes his best educated guess about what the company will need and goes in with these thoughts to get even more immediate feedback,” he says. “That shaves an entire step off his sales cycle and works incredibly well.”

Another strategy he’s seen is drafting a first proposal in a shared Google Doc, allowing customers to make comments or edits directly in between meetings. That way there’s even more feedback to go on before an official follow-up.

You want to make reviewing an early proposal as low lift as possible for your customer. Tell them simply to glance over it, maybe jot down some thoughts, and tell you if you’re on the right track.

Pre-Intros. When you’re meeting with larger groups of people at your customer, it’s extremely helpful to set up very short 1-on-1 calls with anyone who’s going to be new to the conversation. This ensures that when you’re meeting with the whole group less time is wasted on introductions and getting everyone up to speed. It also gives you a bit of a heads up on the issues or questions you should be prepared to address in the group setting.

“I’ve been in meetings where 8 people are on a deal on the customer side — we did pre-calls with each of them and it saved us so much time when we were all in the room together,” says Chopra-McGowan. “You don’t have to rehash everything, and you get valuable intel to make any group interaction smoother.”

Often with a group meeting, it gets put on everyone’s calendar and they show up with no idea about who you are or why they’re there. “We’ve even had people ask if we work for their own company,” he says. “With that starting point, the chance they can go from not knowing us to a productive conversation is virtually nil.”

But if you managed to get them on the phone for just 10 minutes in the couple days leading up the meeting, they’ll be much more oriented and ready to talk about something substantial. All the call has to be is a 3 minute summary of what your company does; a 3 minute proposal for how you think you might work together; 2 minutes you to ask about their role; and 2 minutes for them to ask any questions.

“It can be that short and sweet if you want it to be, but we’re surprised by how often people want to stay on the phone,” says Chopra-McGowan. “Sometimes these conversations go on for a while and we learn all kinds of things that will be helpful. For example, one person told us their company had a training program the previous year that didn’t work out. We got to ask a bunch of questions to learn why and what we could do differently. We were able to bring these insights to the group meeting a couple of days later.”

Cancellation Pouncing. Especially if you’re trying to wrangle c-level executives, meetings might be scheduled weeks or even months in the future. Instead of just accepting this, General Assembly’s sales team checks with their assistants every few days leading up to a meeting to see if there have been any cancellations or any other surprise openings.

“We just met with a large Danish company — with the COO and CIO. We would have had to wait two months, and you better believe we took that slot, but Svetlana Knyazeva, who covers the region for our team, was in touch with their assistants three days after scheduling to see if anything opened up. We literally moved up the date by a month.”

“Startups have to think month-to-month. Big companies think in 3- to 5-year plans. Don’t let the length of one of their sales cycles dictate the length of your company’s whole life.”

Train the Softer Touches. “No one talks about it, but the energy a salesperson brings into the room for these types of conversations is critical to the sale,” says Chopra-McGowan. “The way customers make these decisions is often pretty nebulous. Especially if you’re a younger startup with limited data. A lot depends on human factors.”

A lot of startups also find themselves at a disadvantage because the age gap between the person selling and the person buying can be quite stark. “This means you really need to send someone in there who can own the room, who can overcompensate for any skepticism that will automatically exist. This is almost entirely about your professional posture, hand gestures and eye contact. They’ll render a judgment that fast and you want all signals to be on point.” There are a few rules here that should always be top of mind:

  • Always be on time, with no exceptions.

  • Have your materials prepared, customized to the client, with no dependence on their tech working to present.

  • Take notes. Even if the client isn’t saying anything new to you, write things down — it demonstrates engagement with what they’re saying.

“We used to fly much looser and never showed up with a presentation — thinking enterprises would appreciate the startup MO. We then realized it was much more impactful to show that work was invested upfront,” Chopra-McGowan says. “It’s fine to be agile, but you want to demonstrate you’re very serious about the opportunity too. People will discount you fast otherwise.”

The GA team also made the mistake of undervaluing face-to-face meetings early on, and now trains new salespeople to take every opportunity to get in the same room with clients.

“We assume digital is fast and better, but we miss so much of human communication when we can’t see each other — the body language, the attention being given,” he says. “On top of that, traveling to be there in person is a massive demonstration to the client of how important they are.”

Even though travel takes time, being in person can drastically reduce the number of meetings needed, because you get to place of mutual understanding and trust faster.

“Now after we reach some level of qualification and know there’s some potential there, we’ll immediately propose an in-person meeting. Even when clients push back and say they can do it over the phone, we insist again: ‘If it’s all the same to you and you’ll be in the office anyway, we’d like to talk face-to-face.’”


Getting your sales team to change their behavior and methods can be daunting. So here are the three simplest, most actionable things you can do in the next week to start seeing the impact of some of these approaches to sales:

Quick follow-up. The next time you schedule a meeting, also set up a follow-up meeting — and set it for much sooner than you normally would. For example, if you have a meeting with a customer in the morning, ask for another 30 minutes later that day, expressly noting that the follow-up meeting will be a chance for you to present some initial ideas, ask clarifying questions, and maybe draft a proposal.

“At worst, this will better validate your approach to solving the customer’s problem,” says Chopra-McGowan. “At best, it will shave meaningful time off your sales cycle.”

Start cancellation pouncing. Have your sales team make a list of every customer meeting that’s on the calendar for more than a month in the future. Then ask them to contact those customers and specifically ask if anything has been cancelled that might allow for the previously scheduled meeting to be brought forward.

Pattern match. Look at your 20 most successful customer relationships and see what objective patterns you can discern along a few factors: industry sector, company size, role of the key decision makers, average response time to emails, etc. The resulting list of common factors should be the starting point for your customized qualification framework. Make sure all the critical elements needed for a deal to be successful are included.

“Look at your current pipeline and see how each deal matches up to your new framework. Wherever there’s a gap, focus on either how to fill it or moving on.”

Photographs courtesy of General Assembly.

[First Round Capital]

September 13, 2016 / by / in , , ,

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