Best Practices for Winning 3x More Deals in Enterprise Accounts

Yulia Mihlin

As competition and account complexity increase, sellers today face mounting pressure to win more enterprise deals in less time. Which strategies help most?

In a webinar with Salesforce, Databook, and Prolifiq, we aimed to uncover best practices used by high-performing sales teams to win 3x more deals on average in enterprise accounts. Together with Jack Gallo, VP of Sales at Prolifiq, I spoke with an executive panel featuring fellow Databooker Dave Graswick, RVP of Strategic Accounts and Channels, and Scott Barghaan, GM and VP of Sales at Salesforce.

Here are the top tactics we surfaced during our discussion.

Find Enterprise Accounts Most Likely to Close

All of our experts agreed: You’ll be most productive if you prioritize the accounts you can win. So how do you quickly uncover the best targets? Research, research, research.

  • You can’t win if you don’t understand your customer. Period. Your first step should always include a deep-dive into your customer’s business, financials, industry—and even your customer’s customers. If you’re targeting a public company, all of the data you need is readily available in things like quarterly business reports, analyst call transcripts, and so on.
  • Approach the research process efficiently. Use the natural breaks in your sales cycles (like early Q1, for example) for dedicated account planning and learning. And use technology to your advantage. Databook users, for example, can grab actionable insights from all of these documents with just a few clicks, cutting literal weeks off your prep time.
  • Assess how your solutions align with your customer’s needs. Look for details on how a company intends to spend its purchasing dollars. Is management talking a lot about certain projects or innovations? What does investor sentiment look like? Where can your offerings fill a critical gap to drive value that executives will notice?

“What separates average enterprise sellers from those that triple deals is the quality of their discovery conversations. The former run with questions like Ted Koppel for the sake of writing an article, which drives other executives and me crazy because they sound like an idiot. In contrast, the latter asks different questions that focus on solving their problems and show that you have the experience to address such problems because you have a perspective and context that’s valuable to them.”

Scott Barghaan, GM and VP of Sales, Salesforce

Coordinate and Conquer with Strategic Account Plans

The most successful account strategies are backed by teams that are heavily invested in the culture and process behind the planning. How can you keep everyone working together towards a common goal?

  • Make it a visible group effort. Many departments are involved in crafting a winning account plan, from marketing to value engineering and beyond. Show others that you recognize their contributions to the process. Be sure that real-time information is readily accessible by all the groups that need it.
  • Get everyone on the same page. Our executive experts repeatedly stated the importance of having a single source of truth for everyone involved in account planning. Align on the common objectives, and make sure everyone is referencing the same data as you work to execute your plan.
  • Keep it alive. An account plan is a living, breathing, dynamic thing—not some “set it and forget it” exercise. Have regular meetings to discuss what’s happening on the account. Remember that account planning only becomes ingrained in the company culture if people continue to work on it and see how progress is made toward the goal.
  • Don’t ignore the obstacles. When you meet for status updates on the account plan, don’t forget to discuss what is not working. What challenges have you or others faced thus far? Are there resources you need but aren’t getting? Is the customer pushing back on something? Determining the barriers to your success and how to overcome them is part of the planning process. Too many obstacles might signify an account that’s not worth your time.

“As a seller a few years back, I chose a customer account with high-level engagement that used our tool for account planning. I went ahead and started to identify the different business units within their account and got our foot in the door with one single business unit. This strategy alone, backed up by research, made me successful in the enterprise space versus hoping someone responds across various automation and engagement platforms.”

Jack Gallo, VP of Sales, Prolifiq

Accelerate Deals and Improve Pipeline Velocity

Winning more deals and keeping the pipeline moving means working faster and more productively. Which approaches give you the greatest acceleration power?

  • Transparency and truth prevail. Always be upfront about your strategy and the methods you plan to use to execute that strategy. Additionally, be clear on the legitimacy of your opportunities and where you stand. Honesty is a time-tested accelerator.
  • Get to the champion. Don’t waste meetings on people who lack decision-making power or who don’t have a vested interest in fighting for your solution’s value. Keep asking for referrals. Who needs to be involved on the customer side? Push for them to attend meetings, too, to further cement the validity of the deal. If your customer won’t engage those people for you, your time might be better spent elsewhere.
  • Ramp up faster. Getting sellers educated and on board quickly is paramount to your ability to accelerate deal cycles. You have to become an expert not only on your own solutions, but on your customer’s entire business and industry. This is where having the right technology in play can make or break your success. Solutions that help you scrape data and parse insights in mere minutes are game changers—not just because they do the heavy lifting for you, but because they make the onboarding process scalable and repeatable across the entire go-to-market team.

“This is really where Databook and our account planning process came together. We were asking teams to get comfortable with an industry, and a level of context, in weeks—when that normally takes months and years. By plugging Databook into our account planning process, we were able to get roughly 40 new sellers caught up on our industry in less than 60 days.”

Scott Barghaan, GM and VP of Sales, Salesforce

“What separates average enterprise sellers from those that win 3x deals is getting real smart, real fast, from the industry perspective. You turn the calendar one day, you’re in a new territory the next day, and suddenly, you’re a logistics expert. You've got to find ways to gather that intelligence, and you have to do it fast.”

Dave Graswick, RVP of Strategic Accounts and Channels, Databook

Create Hyper-Accurate Forecasts for Pipeline Production

If you’re looking to exponentially increase your wins, you have to have pipeline ready. That makes accurate forecasting—and the research behind your forecasts—even more essential to your success. Is there a trick to setting ultra-realistic expectations?

  • Create an audit checklist. You need some kind of framework for how you’ll review your deals and strategies on a regular basis. Who isn’t aligned and needs to be? Where are you short team members or resources? You have to look at the potential obstacles to a deal and talk about plans to clear them. The accuracy of your forecast depends on the validity of your opportunities, so check them and recheck them.
  • Align your expectations to your customer’s expectations. Get to know the specific priorities of your accounts so you can map your offerings to their needs, and then you’ll gain a better understanding of how well you can meet expectations in the coming months. Do your solutions drive value-based outcomes for your accounts? The more value you bring to the table, the better your chances to close—and the more accurate your forecasting will be.
  • Be ready for more buyers. Enterprise deals are known for their complexity, and that means most involve an ever-increasing number of buyers in the process. In other words, you don’t just have to get one person to say yes—sometimes you’re after the approval of five or even eight people. Be sure you’re equipped to understand all the people in play. You need to know their unique points of view and be able to speak their language, down to the specific ROI points they’re looking for. Again, this is all part of your research and planning. And no forecast is accurate if you’re not prepared to win this kind of deal.

“We talk about the importance of understanding strategic priorities, but it's also important to speak the language of your customer. Forget the buzzwords you use internally. Listen to what people say in demonstrations. Listen to what your customers say. What are the acronyms that they use? What are the ways in which they're talking about the value of your product? Make sure you're aware of those, because those small things show that you care. They show that you're listening to how they operate their business and best serve their customers. And the more you can start to make yourself an expert not just in your product and what it does, but in what their business does and how they speak about their business, the easier you'll be able to connect the dots.”

Jack Gallo, VP of Sales, Prolifiq

We talked at greater length about these best practices and more in our webinar. If you’d like to watch the entire discussion, just click below.

About the Author
  • Yulia Mihlin

    Yulia is a self-driven marketing leader with 17 years of experience in building revenue-generating marketing programs from the ground up in Fortune 500 companies and startups. Her areas of expertise include account-based marketing, demand generation, product marketing, digital marketing, and sales enablement. She is experienced in partnering closely with sales, executives, and marketing peers to develop and execute integrated account-based marketing motions that accelerate business growth.

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