What is Agile Selling, and Why Does it Matter to Sales Organizations?

By: Teresa Weirich

November 29, 2017

“Agile” is a term we hear in almost every industry today. In the SaaS world, agile development is one of the most adopted forms of software programming, which follows a “set of values and principles under which requirements and solutions evolve through the collaborative effort of self-organizing cross-functional teams”. In the context of development, “agile” results in adaptive planning, evolutionary development, early delivery, and continuous improvement. One of the most important parts of agile development, however, is that it encourages a rapid and flexible response to change.

While agile development is a simple example to use because of its wide adoption in the technology world, we also hear about business agility, agile organizations, and even agile methodology (a project management process). All of these examples have one thing in common: they’re open to making adjustments and process changes—and in many cases, are actually on the lookout for ways to make continuous improvement in real-time.

In the traditional world of sales, selling methodologies often included a rigorous process of prospecting, discovery sessions, and a flurry of emails, phone calls and dinners that were chalked up as “relationship building” events. But in today’s modern sales age, traditional methods on their own can no longer cut it. According to CSO Insights only 57% of sales reps hit their quotas with the average company coming at 80% of the revenue plan.

What’s the reasoning behind this major shift from traditional selling? Companies are investing in software that helps their team to be more efficient, but not necessarily more effective. Fortunately, though, by adopting an agile selling methodology, sales organizations can be both efficient and effective.

What is Agile Selling?

While others may have their own take on what agile selling means and why it’s important, we’d like to share ours and the reasoning behind why we believe it’s a critical success factor for enterprise selling. In our definition, agile selling breaks complex deliverables into manageable pieces to deliver value faster. Obviously, VPs of Sales care immensely about improving sales velocity, which Salesforce defines as a function of the number of sales opportunities being worked, the average deal value, the win rate, and the length of the sales cycle.

In order to positively affect sales velocity, there are 3 core values of agile selling that must be addressed:

1. Align: Customers + Solution

The first core value of the agile sales process is aligning customers with the appropriate solution. Sales leaders know firsthand that developing a thorough sales methodology and discovery process is a key element to long-term success. Not only is it important to ensure customers are aligned to a particular solution, but sales professionals must also be up front as to whether their organization and/or solution actually aligns to the customer’s perceived needs.

For example, as a best practice at Costello, we open every sales call with an honest dialogue about why we may not be a good fit for that particular prospect, and we ask them to be candid with us if we don’t check all of their boxes after the first call. You can imagine that most prospects are caught off guard by this approach, but the response is almost always overwhelmingly positive. By taking this first agile selling core value to heart, we can be sure that our solution is aligned to the best interests of our prospects—and we don’t waste anyone’s time by dragging on a sales cycle that was dead on arrival.

2. Iterate: Frequently + Collaboratively

As we’ve discussed in previous posts, making changes within the sales organization is inevitable and necessary—especially in the complex enterprise world. That’s why frequent iteration and optimization of the sales process is not only recommended, but required.

Sales leadership should constantly be working several quarters in advance to spot trends, mitigate procedural issues, and work collaboratively with other teams to feed the top of the funnel with qualified leads and nurture existing opportunities through the sales cycle. Without marketing, customer success, procurement, IT, and even implementation teams working in sync, agile selling doesn’t work—it simply cannot be effective if operating within a silo. But by identifying patterns, targeting trouble spots, and working with other teams in an ongoing manner, sales organizations can make tremendous strides towards being agile.

3. Support: Process + Tools

Hubspot recently reported that companies in North America are already spending more than $15B on sales acceleration tools. Clearly, sales teams care about being efficient with their time, and for good reason since sales professionals are already pulled in many directions. According to Hubspot, only one-third of their day is actually spent selling, with most of their time being allocated to admin work or CRM data entry.

Many sales leaders believe that adding tools to help reps be more efficient will simultaneously solve the sales velocity challenge. But the problem is, they often neglect solutions that help sales professionals be more effective with the limited time that they have. Taking an inventory of current solutions and processes is a critical step within the final agile sales core value. Understanding the true state of the sales organization will help uncover what’s working, but more importantly, what gaps may have previously been overlooked.

What Prevents Sales From Operating In An Agile Way?

Patching together ad-hoc tools leads to ad-hoc execution and from there, a negative spiral of missing data, little visibility, and low confidence in the pipeline usually follows. The problem is, sales leaders live in CRM data, but we’ve all heard the expression, “the data is only as good as what’s entered” or the other classic, “junk in, junk out”. Despite the best intentions of sales professionals to capture every note and prospect interaction, CRMs simply aren’t meant to be used as a real-time deal platform.

Despite the 1:1 meetings, the pipeline reviews, and painful win/loss analysis, no amount of reactive sales coaching can improve the sales process if VPs of Sales aren’t given the appropriate level of visibility into specific deals. Similarly, if sales professionals don’t have a consistent sales methodology to follow, then every deal can veer off course in a matter of minutes. No amount of “good” CRM data or even the best of intentions from sales professionals to capture every prospect interaction is enough to turn the ship around.

Making The Transition to Agile Sales

Teams that move to an agile sales methodology see more sales professionals hit quota and along with that, enjoy a healthy 111% average company revenue attainment when 72% of professionals meet quota. Sounds too good to be true, right?

When companies make a full transition to agile, it benefits stakeholders from sales professionals to sales managers to VPs of Sales alike. With an agile sales platform, sales professionals have access to the most up-to-date sales methodology framework so they always ask the right questions and provide the right information to prospects, all while keeping deals on track. Within the same platform, managers can access key insights for each deal in real-time so they can iterate quickly and collaborate to get deals across the finish line. Finally, with a true agile sales platform, VPs of Sales can access visuals and stats to see what’s working, what’s not working, and what needs to be adjusted and iterated upon for future quarters.

The benefits of an agile sales process are endless, but organizations are often slow to adopt a new framework for selling, despite how critical it is for long-term success. We all know from experience how easy it is to get caught up in the quarterly whirlwind and only focus on the fire drill deals that require attention in the here and now. But well prepared sales leaders are adopting agile deal management platforms that will help them not only navigate complex deals today, but plan effectively for many quarters to come.


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    Teresa Weirich

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