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The Fundamentals of Enterprise Sales

These days, people are starting to understand and even embrace remote work, but back in the early 2000s, it was a source of consternation for many a customer.

It’s fun to get mobbed after a talk—usually it means you picked the right topic for the audience and struck a chord. That’s what happened after I gave a talk at WordCamp Europe about the difference between selling $50K and $1M projects. While many people cringe at the words “sales” or “marketing,” I think they are a fundamental part of human culture. Both speaking and sales are the art of connecting people with what they truly want, adding value to their lives. They are both immensely rewarding. 

The people who attended my talk at WordCamp seem to agree—it turned out to be a very popular topic. Dozens of emails later, I decided to post my slides and a short writeup.

The majority of the opportunities I get pulled in to consult on fall into the category of enterprise sales. By enterprise I mean mid-six- and seven-figure projects of significant complexity, for global brands you know, often for multi-year contracts. We’ve done hundreds of projects since my start in 2000, and I’ve personally closed well over $20M in new work for Modern Tribe. While we also work with a wide range of startups, not-for-profits and regional businesses, this talk was focused on the big deals.

The Four Pillars of Enterprise Sales

As you develop your skills and grow your reach, focus your efforts on four key pillars:

Cultivate your credibility and tell the right stories.

First connect personally. Until they know you care, not much else matters. You don’t win deals from the void. Establish relatability, then layer on credibility. The best way to demonstrate that you understand their challenges and have the right experience is through relevant stories. And for that, the magic number is three stories (insert Holy Hand Grenade joke here). Guide them through brands and problems with which they identify. You’ll want to cultivate these stories actively as a team, as they’re powerful assets in your tool chest. And if you don’t have the right stories yet, partner with someone who does and lean on their credibility.

Great sales is actually consulting. You can’t sell what you don’t profoundly understand.

Very few people want another piece of software. They want an outcome: more customers,  increased efficiency, happier staff. If you sell custom purpose-built solutions, your job is to listen for the win and guide them to it—even if your company isn’t the answer. Few things build more trust than a well-shaped no: “What you’re asking for won’t actually solve the problem you are facing. Let me refer you to someone who specializes in that problem.” One of our first huge enterprise accounts with SAP actually came from us referring them to another path.

Be a master qualifier.

Sales isn’t about convincing someone they need what you have. It’s about uncovering the best fit. Spending a ton of time on the wrong fit is at best a waste of time, and at worst a loss of money. The faster you can identify scope, timeline, budget, and customer capabilities, the better.

Learn how to gracefully navigate corporate bureaucracy.

Nothing hurts more than working hard only to see delays in kickoffs or payment, or a contract that works against your best interest. Understanding the terminology, as well as how to craft and shape an MSA, get a PO and invoice properly might sound boring, but it is vital to the health of your company and the key pillar of a successful sale.

Why Big Companies Pay You Money

Time: They are slammed but can’t push deadlines. 

When Eventbrite acquired Ticketfly, their board gave them a drop-dead date to migrate hundreds of WordPress sites to a new platform on WordPress VIP. To pull it off, they needed to triple their capacity, and hiring and onboarding would be too slow.

Skills: The in-house staff lacks a specific specialty. 

Another enterprise client needed a partner that understood how to scale a WordPress Multisite network to manage 10,000 independent sites. Scaling wide happens to be one of our core specialties, as we have built massive site networks for radio stations, schools, restaurants, sports teams, events and more.

Partnership: You come bundled as part of a bigger offering.

MTV bought into a vision to create a movie news vertical targeting young teens. To do that, they partnered with a well-respected content and media company. We were the media company’s design and UX partner and were included in the offering of an end-to-end solution for MTV. 

Perspective: Your experience enables you to see solutions no one else has.

BigCommerce wanted to create a solution for the WordPress community and needed a partner who had the experience and know-how to build a headless ecommerce integration, as well as an understanding of the journey to launch, support and build a successful open-source freemium offering. We’ve built and managed the core plugins for Salesforce, Pardot and Eventbrite and have over 1 million users of our own WordPress plugins, so they knew we were up to the job.  

Bureaucracy: You can mobilize quickly, and they can’t. 

Sometimes, working at a major company means hearing, “Fill out Form 37A and we’ll get you an in-house designer 3 months from next Wednesday.” And often, three months from Wednesday isn’t fast enough. For years, we were the SAP Innovation team’s go-to partner for prototyping and UX overflow. Requisitioning resources was too slow when a VP or C-suite executive wanted an idea quickly run up the flagpole. The procurement team had a $25K minimum before open bids were required, so we got a steady stream of small, focused independent prototypes to dream up and build, bypassing all their bureaucracy.

Accountability: They just need someone they can count on to deliver.

This doesn’t happen out of the blue. This is the result of delivering consistently, time and time again. Bon Appetite is a subsidiary of Compass Foods, the largest food management company in the world, and we’ve worked with them on and off for nearly a decade. They recently came back to us and asked us to do a round of vision and production work for a group of 1,200 restaurants. Why? While we may be more expensive than their off-shore team, in their words we “solve real problems and get it done.” 

How $1M gigs are different than $50K ones

Hurry Up and Wait

It’s not unusual for a deal cycle to take six to 24 months. With Unit Trust Corporation, a financial solutions provider in Trinidad and Tobago, we went back and forth on proposals, scope and procurement for nearly two years. This isn’t atypical with government projects. Be prepared to be quite patient, and when they are finally ready, act quickly.

Mo’ Money, Mo’ People

The bigger the project, the bigger the team. It’s important to learn the organizational landscape to identify the true decision-makers and enroll your advocates. Authority isn’t always based on role. We once worked on a rebrand directly with the CEO of a large company, only to learn that his company’s board vetoed him frequently, and that he had no brand design authority.

Keep in mind that project teams, project owners and project stakeholders/execs have different expectations from partners. Learn who you’re speaking to and hit the right altitude. As budgets get bigger, titles get grander, and someone’s job could be on the line. That means politics get real, and you need to help your internal champion navigate them to success.

I’ve found that the altitude of stakeholder involvement is often an interesting barometer of economic recessions. As the economy tightens, companies get more cautious. Decisions that were once made at the project level start to bump to the exec level. For something that would once have been approved by a director, we find ourselves talking to VPs. That pattern definitely kicked in during late 2018 and continues to play out.

With smaller projects, we are typically the only team solutioning. As the budgets get into the mid-six figures and above, you almost always find yourself collaborating with the customer and/or third party teams who are responsible for delivering other parts of the project.

Advice is Part of the Deal

It’s easy to think that with a website budget that’s ten times bigger, you simply have ten times more to build. That isn’t really the case. At larger budgets, the expectations are different. Nothing is order taking. Clients expect you to solve business problems and provide meaningful strategy, whether that’s explicitly sold in the statement of work or not. 

“I’ll Pay You Tuesday”

The nuance of fiscal policy makes or breaks projects. Your first sales call should always surface their fiscal budget cycle and how it plays a role in the opportunity in question. For a number of years, I would close nearly 60% of our annual volume in a two-week period. The first week of December, I started calling every budget holder in a large corporation and asked, “Do you have any budget you lose if you don’t use it by year-end? Let’s find a good project and put that to use.” Corporate finance reform in 2008 ruined that strategy for me, but it’s critical to understand when budgets renew.

Consider the impact of payment terms on fiscal health. For example, “MegaCorp’s” net 90 payment terms meant from the day we did work, payment would take over four months to show up—best case. You would think with that kind of turnaround time, they would honor their own schedule. But even those invoices are sometimes paid late. If you ever get into a pickle with a customer with long payment terms, the amount of exposure can be enormous. As a result, we require all customers to keep a security deposit for one month’s burn in escrow, simply to give us a hedge.

Everyone has a budget. With smaller projects, scope often shapes the budget. But as scope gets huge, budget tends to shape the scope, and aligning them is the real challenge. 

Billing Models

Hourly, fixed, retainer or value-based billing? That is the question, and the answer depends on who you ask. The right model is a tool to balance risk. The more you can define the scope, the better off you are with fixed billing with higher margins. With less clarity on scope, you’d be well advised to hedge your bets with hourly billing. Personally, I would never do fixed-bid R&D. Even with hourly billing, though, your customer has a budget; going over it consistently will damage your relationship.

The truth is, we are always experimenting. I’ve never believed in one model to rule them all. Right now, our team is working to determine whether offering a fixed discovery package would create better results. We are also experimenting with retainers, and we’re looking into trying paid hourly discovery followed by a fixed price buildout. In the last 12 months, our agency billed 75% T&M, 10% retainer and 15% fixed.

Procure This

At larger budgets, there is a third team besides project and exec. The procurement team(s) are in charge of managing the RFP and bid process, and if you make it past them, then you get to work with legal, too! While many of our smaller customers sign our Master Service Agreement (MSA), large projects either have their legal team mark up our MSA, or we have to dissect theirs. Don’t be afraid to push back on terms within an MSA. It’s natural to feel so relieved that you were selected as a finalist that you don’t want to mess anything up—but they EXPECT you to make edits. In most cases, the document is either horribly unfavorable to you or has inaccuracies. We almost always have to make edits to intellectual property and ownership clauses to account for GPL licensing and the realities of open source. Large companies will also commonly have large insurance asks. We carry a fair amount of coverage (general, E&O, workers comp, disability, etc.), and we usually have to tell clients that $2M of coverage is plenty. $5M is overkill. 

Caveat Venditor

As budgets get bigger, their impact can be outsized, both good and bad. Your largest account should NEVER make up more than 25% of your revenue. If you can, keep it under 10%. I just watched a friend lose their primary account (70% of their pipeline) as a result of a new CEO coming into a Fortune 100 company. Let’s just say, it’s been a heart-wrenching five months for them. In 2019, our largest account represents 8.7% of annualized revenue. While that’s still revenue we rely on, the balance gives us much more stability to weather any major changes.

I hope these tips are helpful for you as you continue to grow your business and land that next big client. Whether you’re chasing mammoth contracts or not-so-mammoth ones, I encourage you to go forth and pitch with confidence—even if you think the client might be a little out of your league. Enterprise clients typically require more energy and patience throughout the sales process, but it also helps you build trust and credibility as you negotiate and consult with your potential client. Once that budget and contract are nailed down, you’ll have a client that’s as eager to get started as you are.