When you’re working a high-quality B2B deal, the biggest enemy to success is time.

We interviewed Tim Sanders, CEO of Deeper Media and author of several sales and business books, including Dealstorming: The Secret Weapon That Will Solve Your Toughest Sales Challenges to ask him more about closing big, complex deals.

Time Is the Enemy of High-Quality, Complex Deals. Team Selling Is the Solution (Interview with Tim Sanders)

“Big sales are just problem-solving exercises,” Tim told us. “They’re not pitch exercises and you can’t rely solely on ‘Closing Academy’ tricks.”

Simple transactions may benefit from pitching close mechanics, and Tim’s not against studying them. But complex B2B deals require a lot more than closing techniques.

Time—more than anything else—is the enemy of complex deals. In a high-value deal with multiple stakeholders, the salesperson’s job is to solve problems—and fast.

“If you’re fast enough,” Tim said, “you get the problems solved before the people you’re working with leave the company, something changes in the market, or a new nimble competitor comes in and disrupts the deal.”

The key to going fast in a complex deal?

Team selling.

Note: At Troops, we’re building an Account Based Collaboration solution to help close big deals faster. Want to win more enterprise deals? Get early access here.

Team Selling: Tall Team vs. Wide Team

When you hear the term “team selling,” your first impulse might be to think about collaborative sales efforts within your sales team—a “tall” team as Tim described it.

That’s a mistake, Tim told us.

A “tall” team is usually a collection of account managers, product specialists, sales managers and other professionals within the sales group.

When everyone on the team has a full Salesforce license (or whatever CRM you use), you probably have a “tall” team, which is not ideal for high-quality complex deals.

“A tall team doesn’t have people who have a stake in the outcome and expertise that can solve their blind spots,” Tim said. “They usually end up doing what they’ve always done.”

“Wide” teams, however, include team members from across the organization and beyond.

If your team includes people who don’t work from Salesforce every day—or who might not even work at your organization—you probably have a “wide team.” And you’re much better positioned to keep a high-quality complex deal moving.

Why? Because you can call upon a diverse set of experts and stakeholders in order to address problems and build buyer confidence quickly.

“Team selling is most effective when the team goes wide early in the sales process, when all the little challenges signal to the salespeople that the normal sales process is not going to win,” Tim said.

How to Build a Wide Team for a Complex, High-Value Deal

Who should you invite to your team when you have a complex, high-value deal?

Here are six groups to consider:

1. Pricing & Finance: Turn the Police into the Pep Squad

Pricing and finance - "I don't recall having invited you in my party" GIF

When do we usually bring in pricing and finance?

At the end. Once we have an agreement on price from the customer.

We do this because we want leverage. We want pricing to have no choice but to approve the deal we worked so hard to negotiate. They’re holding up a $7 million dollar deal if they don’t.

When we do this, we’re making enemies out of our finance team—treating them like adversaries instead of team members.

“The next five deals you have that are at the margin, they’ll say no,” Tim said. “They may not be big deals, but all slights get settled.”

Instead, Tim told us, by involving finance and profitability early on, you turn the “police into the pep squad.”

“The earlier you bring in finance, the more likely they’ll be to get really creative about what they can do,” he said. “Bring them in so early it feels a little uncomfortable to you. They can help you solve your problems so you can win.”

2. Marketing: Dramatically Cut Close Times (And Lift Win Rates)

Team selling: "I'm not a creative, I'm a digital invention officer" GIF

Too often, we treat marketing as a lead generation machine or creators of sales collateral—not as strategic partners.

But marketing has much to contribute to team selling efforts, especially marketing teams executing an account-based marketing program (which was shown to double win rates in one recent study).

“We did research at Deeper Media and showed that close collaboration with marketing can dramatically reduce the sales cycle—sometimes cutting the time from a year down to a couple of months,” Tim said.

What can marketing do for you?

In addition to building a new pipeline, marketing can direct their efforts at educating and evangelizing the buying unit within an account during the sales process.

If—by the time your sales rep engages with new members of the buying unit—they’ve heard or read about you multiple times, they’re going to be more receptive in the initial conversations vs. completely cold contacts.

3. Customer Success: Early Collaboration Can Equal 50% Happier Clients After One Year

Team selling: "Ohh... you didn't tell them how long it would REALLY take, did you?" GIF

Customer success is another group that often gets left out of early sales conversations.

“We don’t want to invite customer success though because we’re afraid they’re going to say no,” Tim said. “But what actually happens is they respond to us bringing them in early by trying to find ways to say yes.”

Bringing in customer success early on in complex deals is especially important when the proposal is outside the normal template—as it often is for high-value deals.

To prove the effectiveness of this approach, Deeper Media researched the effect of bringing in customer success early across 200 clients.

“We found customer satisfaction was dramatically higher one year after the deal—sometimes up to 50% higher,” Tim said.

4. Lookalike Decision Makers from Your Existing Customer Base: Access to Unique Insights

Team selling: Lookalike decision makers help you to access unique insights.

Lookalike decision makers are people in your existing customer base that are in similar situations to a key decision maker in the account you’re hoping to sell.

If you’re selling to a CTO, for example, find a CTO you know and have a relationship with from your existing customers. This can even be someone within your organization.

These are people who can provide deep insight into what matters to the prospect you’re working with. This is especially important when deals are being blocked.

“I’ve really seen that work well,” Tim told us. “It has a huge impact on the way you sell and how you tailor your message. When I worked at Oracle Cloud, we did this and were able to overcome objections that looked pretty formidable—like security.”

5. ‘Competi-mates’: Turn Competitors Into Teammates

Team selling: "Competi-mates" is key to being successful.

“Competi-mates” are companies that are in the same industry as you but who play nice with you.

It may be a someone you met at a conference, for example, and developed a relationship with.

Competi-mates can give you valuable insights into their experience selling in that industry or within a given target account such as how to navigate the buying process. And in return, you can help them achieve similar business goals by lending expertise from your company when needed.

If you work at a small company, developing a network of competi-mates can be a huge asset for you.

“For a smaller organization, you don’t have a lot of departments in your company to collaborate with,” Tim said.

Competi-mates can give you access to the experience and expertise you need to keep your deal moving forward.

6. Reps Who’ve Closed a Similar Deal: Learn from Those Who’ve Been There Before

Team Selling: "Perhaps I could be of assistance." GIFFinally, here’s one from our experience here on the Troops sales team.

If you have a big deal and another sales rep has closed a deal that looks like it—bring that second sales rep into the team as a resource.

Like many of the items on this list, this gives the team additional insight and experience they may not have from their own sales history.

How Big Should the Team Be?

There are different levels of team selling that can be applied to different types of sales opportunities.

Have a huge opportunity that could open new markets and opportunities for your company? Pull together everyone you know who can help you.

But there’s a political cost to doing that, Tim told us, which is why Deeper Media uses a qualification process to determine what kind of team they build for a particular sales opportunity.

“We quantify the political cost by qualifying based on opportunity and complexity,” Tim said.

A sample of the qualification process to determine the total team size.

Specifically, Deeper Media scores each opportunity on a 10 point scale across two factors:

  • Value
  • Difficulty

By multiplying the scores together, Tim and his team determine a resource score for every opportunity, then build their sales team accordingly.

“For a 72, we use the grid and we say, you need to have at least three unique perspectives on the team, which means you’re going to have to go outside the core sales group for two core team members,” Tim told us.

“We call that ‘The Beatles,’” Tim added, referring to deals that need around three unique perspectives. “For the deals that are a 10 on both complexity and revenue, call in your favors and build the Justice League.”

Team selling: Build the perfect Justice League within your own company.

How to Get People to Say ‘Yes’ When You Invite Them to the Team

Team selling means you’re going to be asking for help from people with no direct commission at stake in the deal.

Why would someone without a commission interest help you?

Because they have some other kind of stake in the deal. Or because you make it worth their while.

Whatever the motivation, you have to sell them on why they should help you.

Tim had two specific recommendations when asking someone to join your team:

1. Tell Them Why You’re Inviting Them to the Team

When you reach out to someone, be direct about what you’re asking for. Tell them about the opportunity and why they are exactly the right person to help.

“You have to let them know ‘why you?’” Tim said. “Say ‘I’m reaching out to you because your 10 years of experience as a CIO gives you a unique point of view that I can’t get anywhere else, and I trust your opinion.”

You’ll be surprised how many people will say yes. It’s flattering to be asked for your perspective, and people love to be thought of as an expert.

If you’re asking an outside expert to join the team and you have something to offer in return, make that clear as well.

2. Share the Numbers if You Can

Especially for internal employees, be open about the size of the deal if you can. If it’s a $7 million opportunity, tell them.

Sharing the numbers helps non-sales stakeholders understand the importance of the ask. They don’t want to have their time wasted. But if you explain why this deal is important and the opportunity it represents, most will be glad to help.

One Other Benefit: No More Lone Wolves

Team selling is the way to keep your biggest, most important deals moving.

But there’s one other benefit of team selling Tim mentioned toward the end of our conversation: a solution to the lone-wolf problem.

“For at least 15 years, quality sales leaders have worried about the impact of a lone wolf in their organizations,” Tim said.

Team Selling Time Sanders: Avoid lone wolves

Lone wolves are people who do everything on their own and typically strongarm other people into being compliant with them.

They often have outsize sales numbers, but they create a lot of dissatisfaction within the organization.

In Tim’s opinion, the lone-wolf problem is more than just identifying people with lone wolf tendencies.

It’s also about fixing the go-it-alone culture that’s so common in sales organizations.

“You can’t solve the lone-wolf issue if collaboration continues to be a last resort,” Tim said. “You’re literally institutionalizing lone-wolf behavior by working within your silo.”

Team selling fixes the lone-wolf problem from the inside out—replacing it with a collaborative culture of teamwork.

Why Team Selling Works

Have you had a deal die because your primary contact left the company?

Have you witnessed the trail of unhappiness that follows behind the lone-wolf salesperson?

Team selling is the solution to both of those problems.

It gives you the absolute best chance of closing those big deals that open new markets and new opportunities for your entire company. And it creates a culture of teamwork and collaboration, rather than one of competition and bitterness.

Isn’t it time to pull together your own Justice League?

Note: At Troops, we’re building an Account Based Collaboration solution to help close big deals faster. Want to win more enterprise deals? Get early access here.

Tommy Klouwers

Written by Tommy Klouwers

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