6 Secrets to the Art of Team Selling

Sales has a reputation for being a very individual sport. All the best sales advice out there talks about personal motivation, individual incentives, and team-wide competition could lead you to believe that there’s no such thing as a team player when it comes to making a sale.

This isn’t the case within fields like SaaS. It’s tough to be completely independent when highly complex products and lengthy sales cycles are the norm. Team selling has become an integral part of the art of selling.

Sometimes, the team might simply involve another rep or tech support specialist weighing in to answer client questions. Or it might involve a complex, cross-functional unit aimed at winning the biggest and most challenging of deals. We thrive off of and encourage teams to work together for best results.

Either way, SaaS and B2B companies are rapidly coming around to the wisdom of the team-selling approach. Read on to find out how the art of team selling can benefit your company and the secrets to success.

Read on to discover:

What Is Team Selling

Team selling is the process where a sales department deploys more than one rep to win an account. While the exact makeup of this kind of team will vary, the process involves multiple members working together and pooling resources and expertise to give themselves a better shot at closing.

For example: Let’s say a company providing time-keeping software pitched its product to a multinational construction company. The sheer size of the deal, the number of decision-makers involved, and the variety of use cases the prospect might have would make this much harder for a single rep to handle.

The seller might try to increase their credibility by having more than one person participate in calls and answer questions. Including a supervisor can reassure the buyer’s management about issues around the process, a DevOps pro can clear up any questions about UX or scaling, and so on.

The team may work together throughout each phase of the sales cycle, like so:

  • A primary sales rep to handle all major calls and act as a go-between
  • An engineer to build a bespoke demo
  • A manager to act as discovery-call scripter or to head up late-stage discussions with senior decision-makers at the prospect company

In team selling, you might need separate individuals to help with particular stages in the call cycle, like so:

  • A primary sales rep to qualify interest on an initial call
  • The rep, a manager, and a DevOps on the subsequent discovery call
  • The rep and a manager or executive on the deal-closing call
  • A sales rep and a technical support specialist on the first post-deal call

It all breaks down to the idea that, in a world where businesses grow ever more complex, two (or more) heads are often better than one.

Why Team Selling

The art of selling SaaS, and B2B sales in general, is all about simplifying the buying process for your prospects. Whenever a sales cycle looks complex, team selling is a great way to make things easier.

Of course, in some ways, team selling flouts traditional wisdom about how sales should work — if selling is not a competitive practice between reps, how will your sales team collectively generate the motivation they need to succeed?

Team selling reflects the broader change in sales culture in recent years — in the same way that reps are encouraged to think of prospects as friends in need as opposed to opponents to be defeated, team culture is to be embraced. Team play can be turned into an excellent motivator by a skilled sales leader.

The reason, simply put, that you should embrace team selling is because it works.

Team selling has been shown to increase the likelihood of closing a deal by 258% and is particularly effective for enterprise-level sales.

SaaS products are often complex, and the prospects who are most buy-ready are also the most informed about the product. Therefore, you can sell your own product more effectively by engaging expertise across a team.

Team selling also allows a prospect to connect with nodes of your company beyond a sales team. It allows your prospect to make themselves familiar not only with account managers but also with but tech support, DevOps, and/or management. Particularly if the deal is a big one, this can be reassuring for decision-makers on the buyer’s side — your company is painted as a picture of internal harmony and efficiency, with plenty of knowledge sharing happening.

You can also better tailor your approach with team selling, and, if you’re flexible, the product offering, too. If you have a tech lead on a call with your sales rep and the client asks about a particular bespoke feature, the rep doesn’t have to hesitate or reply with a tentative “no." Instead, the tech lead can gauge the feasibility of adding the new feature or discuss workarounds. Such small details can be decisive factors in huge deals being won or lost and are more accessible with team selling.

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When Should I Use Team Selling

The basic principle of team selling is this: If the account is too large or complex for a rep to manage it solo, then other team members (technical specialists, support, etc.) should get involved in the sale.

For complex, account-based sales, mobilizing the breadth of your company’s expertise and building direct links between departments at your business and corresponding contacts at your prospect’s, team selling makes sense. Not only does it increase the likelihood of a win for the reasons detailed above, but it will also make the ongoing customer relationship more straightforward to manage.

As we’ve mentioned, enterprise-level selling is also a prime opportunity to make use of the team-sell. The sales cycle for enterprise deals is the longest of all SaaS deal types, often requiring up to six months to move from prospecting to closing — there are more decision-makers to engage and more variables to consider. You can dramatically increase the likelihood of success by sharing that burden with other team members.

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6 Secrets to the Art of Team Selling

Now, the moment you’ve all been waiting for: We reveal some of the secrets to getting the best out of your team-selling approach. As with so much of sales, the art of team selling lives or dies by the care and diligence you put into your preparation beforehand. In other words, how you assess the use of team selling, how you build your units, and how you engage each professional at each stage of the sales cycle will make all the difference.

1. Qualify First

As excited as you might be about team selling, it’s important to qualify your leads and determine where a team-based approach is most likely to be effective.

Team selling is most effective for deals between 5x and 10x your average deal size. For most companies, this will come under mid-market (deals worth between $51k-$100k) and enterprise ($100k+) selling. Here, the benefits of burden-sharing and the introduction of different perspectives to the sales cycle make team selling a great option.

For SMB-level sales (deals between $5k-$20k), you may not need a team sell at all, as single sales reps can ably handle the ins and outs of the process while possessing all the expertise required to make the sale. SMB+ level deals (up to $50k) may only need partial input from other members, a DevOps dropping in on a call here or a friendly word from one of your executives there. By going with the team approach on these leads, you might tie more resources up in smaller deals than needed.

2. Build to Last

Team selling is about leveraging the personal connections between your own team and the decision-makers at your target company. You bring a tech lead on a call with your client’s tech lead because they can relate to one another, share information more easily, and build a solid connection between your company and theirs.

You should apply the same logic to building the team itself. In team sales, the pressure of selling falls not just on the lead rep but also on all members of the team. So, build teams with well-suited individuals who will be able to share in that responsibility happily, which is as much a question of making sure your team personalities match as it is of what skill profiles you have on the team proper.

Once you’ve matched skills and personalities between your team members, have them work together frequently on team sales to build familiarity and experience and promote bonding. Team sales is still sales: it’s a race to the finish line and a high-pressure, competitive environment. A team that can rely on one another is built to last.

3. Clearly Defined Roles

While team sales is meant to make complicated deals simpler, team selling can, in fact, be more complex and unwieldy if participants don’t know how to make an impact.

On calls, make sure your script is rehearsed. Select a leader, preferably your main sales rep, and have them cue other participants from your side to give their input when it’s effective. Ensure everyone has familiarity with any demo technology you’ll use. If a team member is making their debut late in the cycle, see to it that they are thoroughly briefed on the details of the deal to this point. Knowledge sharing between members of a team sale is paramount.

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4. Strategically Deploy Your Team

Sales reps, DevOps, managers, and executives can all take center stage at different points in the sales cycle. Knowing when to roll them out is key.

When strategizing, consider where each team member is likely to make the biggest impact. Your main sales rep should establish which decision-maker from the prospect company will be on the subsequent call — whether that’s senior management or a senior technician. Then, plan accordingly, bringing the corresponding specialist from your side to each call.

5. Know Your Target

Speaking of the various decision-makers: If marketing is involved in the team, have them prioritize identifying decision-makers at your target company. Team sales gives you opportunities to engage tech personnel as well as managers/executives. This is especially true with mid-market or enterprise-sized deals. The more people you can convince of the worth of your product, the better chance you’ll have to close the deal.

6. Leverage Your Tech Stack

Team selling, effective as it is, is complex enough. There will be multiple moving parts and a lot of contexts that each of your team members will need to keep track of. As a result of your engaging multiple decision-makers, you may find that progress is slightly harder to gauge on team sells than on smaller deals.

Organization, as a result, is of vital importance. To stay on top of all the details, make use of your tech stack. Your main sales rep should, once again, act as the fulcrum, managing the use of your CRM throughout the cycle.

Simplify otherwise unwieldy extra tasks with a few well-chosen additions to your stack, for example:

  • A conversational intelligence platform will keep a record of your calls and improve your team’s sales performance.
  • Who you entrust team sales to makes a big difference, and there are tools out there offering routing logic solutions for selecting the best rep (or team) for each prospect.
  • If you do decide to upgrade your CRM in advance of adopting team selling and chasing the really big deals, make sure it’s a platform that’s customizable with easy integrations.

However well-put-together your team is, however well-run your sales process, there’s only so much you can simplify in an enterprise-level sales cycle. The right tech can make enterprise-level sales easier on the whole team.

The Team That Sells Together...

Team selling is still a relatively young discipline and is still evolving. But, as business structures and products become more complex, it’s more difficult for a single sales rep to have all the knowledge needed to make the necessary impact.

Incorporating team-selling approaches is a fundamental way your company can respond to the challenges of larger, less responsive, or less accessible prospects. Not only will you find that your win rate increases, but you’ll also see your sales team become less siloed.

Working together, we all can win!

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