4 Ways to Convert Enterprise Customers Using Project Management Principles

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Jack Matsen
Jack Matsen



Selling software B2B is more involved than ever before.

Enterprise sales team discusses project management tactics

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When a company brings on new technology, they need to consider the impact it will have on their existing systems. Will the new solution adequately replace what we already have in place? How will it connect and speak with our current systems? What is the integration process for coordinating these systems?

The questions a buyer needs to consider when purchasing enterprise software can go on and on. Because these questions are important to your prospective customer, you as a seller, should be ready to help answer them.

Answering these questions involves seamless coordination between both your own company and your prospect’s organization. It’s up to you as the seller to communicate across teams, anticipate potential challenges and blockers, secure your next steps, and keep the buying committee updated along the way.

While our opportunities are organized into a nice and easy set of stages, we all know deals are rarely that easy.

An enterprise deal typically starts with discovery, where you hop on a call with your prospect to understand their pain points, what goals they are looking to achieve, and what timeline they are working towards. From there, you’re mapping those goals and pain points to solutions within your platform through a demo.

After the demo, it takes a number of additional meetings to scope and confirm feasibility between technical teams. Then you have to get buy-in from their legal and information security teams, which bounce back and forth as they share assessments with one another. Lastly, you have to hunt down the signer and anxiously refresh your inbox until the signed documents arrive, signaling a successful deal.

Juggling all of these tasks — keeping your key stakeholders' attention and getting their buy-in, logging and organizing key information, and drafting deliverables — is complicated and can get more complex as your company grows. To keep up with the ever-growing complexity of today’s sales cycles, salespeople need to start thinking and operating like project managers.

What Do Project Managers Do?

Project managers oversee the success of projects or initiatives within their organizations. Their role starts by identifying an organizational pain point or an opportunity that aligns with specific goals or objectives. From there, they are tasked with bringing a solution to life through the creation and execution of project plans.

This typically involves working cross-functionally with a team with a diverse set of skill sets and backgrounds to successfully complete the project. To organize a team, a project manager needs to secure a budget for their initiative by convincing the budget holders that investing in the project will help the company reach an important goal.

Sound familiar?

While project managers don’t have a quota, they know what it takes to bring an idea to life. Their process includes very similar steps to what sales professionals go through — discovery, connecting a solution to company objectives, winning buy-in from stakeholders, working cross-functionally, launching the product, and continuing to improve it post launch.

As sales processes become more complex, sales professionals should look to borrow a few key practices project managers do when they’re bringing their projects from ideation to completion.

Key Practices Project Managers Have Mastered that Salespeople Should Borrow

1. Establish timelines and benchmarks to promote accountability.

Project managers and salespeople are both working against time. You’ve probably heard the saying, "time kills deals". Time also kills projects. Both project managers and salespeople are working on specific timelines and have the challenges of setbacks, personnel changes, objections, and resource constraints that can compromise schedules.

Effective project managers stay on track by setting benchmarks — or mini deadlines and regular check-ins within their project timeline to ensure all areas are on schedule. Benchmarks keep their team aligned on what’s expected of them and when specific deliverables are due.

Sales people deal with a similar set of steps. First, are sales timelines. Timelines should be driven by an external event important to a prospective customer. External events are normally aligned with the prospects goals, an upcoming project, or something going on within a prospect’s organization that is a motivating factor. These events will set the timeline and target close date of an opportunity.

For example, a client might share they have a goal need to raise revenue by 3% or cut costs by 10% by a specific date to fund a new product launch. Make sure to uncover these external events before committing to the sales cycle. If you’re not solving a critical problem for your prospect, why would they consider buying from you? Use their priorities as your north star to keep things moving towards close.

2. Have regular check-ins with key stakeholders.

Additionally, project teams typically have weekly stand-up meetings to discuss what they’re going to accomplish in the given week and any blockers that are in their way. It’s up to the project manager to oversee these conversations, providing space to mitigate any issues and keep the team on track.

Salespeople should consider adopting this practice with their enterprise prospects to speed up their sales cycle. Emails are easy to lose track of, but standing meetings can promote accountability and open communication. With permission from your prospect, set up a recurring calendar invite as soon as possible in your cycle. Use this time to build a stronger relationship with your prospect, mitigate challenges that could inhibit the sale, and gain insight into what’s happening in their business.

Stand ups should be clear in their agenda and always based on a set of key goals or next steps needed to push the deal forward.

3. Set clear expectations.

Project managers are held accountable for successful project implementation along with their teams. In many organizations, project managers report to leaders on the product or operations teams. These stakeholders control the budget and resources available to their team. If you’re a salesperson this sounds familiar, doesn’t it?

In sales, you are often at the mercy of the boss that your main point of contact needs approval from, the last person you meet before final sign offs, or the person who torpedos your deal right at the one yard line. We often know these people as decision makers.

To successfully launch a project, project managers need to keep key stakeholders involved, interested in, and supportive of their initiative. They also need to set expectations up front. Expectations can include the length of the project, how much the project is going to cost, the resources required to successfully tackle the project, and potential hurdles and challenges that may occur along the way.

From a sales perspective, giving insight into the specifics of onboarding is a great way to set expectations with your prospect. I personally like to send onboarding steps to a prospect as soon as we hit the legal phase of the deal cycle. Legal normally takes some time to iron out terms and during that time onboarding items will keep your champion engaged and will lead to an easy transition with your customer success counterparts.

4. Anticipate issues and requirements.

The role of a sales rep is often compared to the quarterback of a football team. As a rep, your job is to guide your prospect through the buying process, and in return your buyer should help you understand their challenges, goals, and organizational structure so you can guide them to success.

The best project managers do a great job of developing a blueprint of the steps needed to complete a project on time and within budget. To do this, PMs start developing these plans from day one of the project. They know where they are starting from and where they want to end. With this information they are able to compile requirements, assemble the correct personnel, and ultimately bring the project to life. Having a plan in place also allows project managers to parallel path certain tasks to make sure no time is wasted.

The same goes for deal cycles. It’s important to give insight to your prospect about the steps required to successfully bring the deal to close. This should come after the value is established with them but shouldn’t go unspoken. The more insight your prospect or champion has into your sales process the more likely they’ll be able to add value to you during the deal cycle. Yes, I know as salespeople we are the ones that are supposed to be adding value, but remember your prospect or champion knows more about the internal workings of their company than you do.

A perfect example of this is briefing your prospect on the teams who play a role in the purchasing decision. Let's say you’re working with mobile marketers but implementation requires involvement from the product and creative teams. Letting your prospect know this will heighten your chances of bringing these teams into the conversation earlier. This will allow you to build more champions, prevent from being single threaded, and avoid any last minute miscommunications.

Putting Project Management Principles Into Action

Project managers and salespeople follow a set of eerily similar steps. They’re tasked with identifying a challenge or opportunity, deeply understanding it, coming up with solutions, navigating stakeholders, and driving the project or sale to completion.

To continue your success in a complex sales cycle, I encourage you to establish how long a deal should take and identify the key benchmarks all while staying in touch with your prospect. In addition, make sure you’re keeping the entire buying committee informed on the value you’re bringing and the progress of the deal. Lastly, make sure you know what resources and personnel are needed to successfully close a deal and set up your customer up for success.

Ready to close more B2B sales? Check out this post for more insider tips.

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