How to shorten your sales cycle

By Leigh Famigliette | February 27, 2023

When it comes to increasing revenue, most B2B teams focus on three core areas:

  1. Increasing win rates
  2. Growing your annual contract value (ACV)
  3. Winning deals faster

While the 3rd of these options is usually considered the easiest and quickest to achieve, it’s also often the most misunderstood. Here, we’re breaking down how to shorten your sales cycle and start bringing in more revenue in just three phases.

Phase 1: Understand your actual sales cycle

Shortening your sales cycle starts with truly understanding it. Here are some tips to uncover key information about your sales cycle.

Identify the dimensions of your sales cycle

The length of your sales cycle is not based on a single number. Everything from industry type, product, deal size, team, region, lead source, buyer roles, etc. all play an important role in establishing the time it takes for a deal to close. While some elements should be given more weight, it is crucial to consider all of these data points, across all of your deals, when assessing sales cycle length.

That may seem like a daunting task. But, if you start by inspecting your wins and looking at commonalities across both your shorter and longer deals, you will start to understand your sales cycle and how to shorten it.

Find the bottlenecks

Another key aspect of understanding your sales cycle is identifying what affects your sales cycle the most. Sales leaders should focus on the areas that have the largest impact and what contributes to the shortest and longest sales cycles. 

For example, if you can see that deal age is a key contributor to your sales cycle, start by only viewing deals by how long they’ve been in your funnel. If you can see that deals in your funnel for 30-50 days are your sweet spot, look at deals that have been in your funnel for 51+ days, assessing by industry, region, lead source, etc. to uncover why these deals are taking longer than the norm. Likewise, look at deals approaching 30 days with a new lens to determine the likelihood of closing with the new information you uncovered.

Highlight the information that matters

Once you know which areas are soaking up the bulk of your sales team’s time, you can start identifying ways to reduce it. A conversation intelligence tool makes it easy to inspect actual calls and highlight the information that matters. Do sales cycles lengthen when a competitor is mentioned? Do they accelerate if there’s a specific role involved or a key use case? Once you identify these aspects, you can take corrective action– which we’ll discuss later on.

Phase 2: Avoid wasting time on deals you won’t win

A sales rep’s most precious resource is their time. Sinking sales capacity into deals that the team is simply not set up to win wastes time. It also inflates the pipeline and makes it impossible to understand the true health of the sales funnel and create an accurate and predictable forecast. Here are some tips to avoid wasting time on deals you won’t win.

Analyze your pipeline by activity

As a sales leader, the biggest challenge in analyzing a sales funnel has always been: “Do I trust what my reps put in the CRM? Do we have enough activity? Are we engaged with the right contacts?” These should all be captured automatically to get a real-time, authentic pulse on your pipeline. This level of visibility helps sales leaders understand deal health by easily seeing activity like the next meeting date, gaps between emails, and overall engagement. It also leads to improved decision-making and predictability.

Leverage machine learning to predict outcomes

As mentioned, with the advancements in digital selling, there are far too many factors for even the best Operations team to analyze using spreadsheets or other ad-hoc methods. The good news is advanced technology has vastly reduced this burden. Today, Revenue Intelligence platforms can automatically capture, analyze, and predict outcomes, providing sales leaders with opportunity scores and other alerts. From there, reps, managers, and CROs are all aligned, with clear views of where teams should be spending their time.

Use automation to encourage rep behavior

Simply collecting the data is great, but what’s more important is what you do with it. The key to shortening the sales cycle is taking more effective actions. And that starts with coaching and enabling reps. Consider a deal that has sat in a stage for too long– or even more alarming, a committed deal that hasn’t had email activity in more than a week. Automated prompts (often called guided selling) can drive a rep to take action, shaving days or perhaps weeks off your sales cycle.

Phase 3: Compare your won and lost deals

Activating automation and machine learning are important elements when it comes to shortening the sales cycle, but you shouldn’t stop there. To run an efficient sales process, it’s not enough to understand why you win, you must also understand why you lose.

Coach with conversation intelligence

Analyzing wins and losses can be challenging, especially when you rely heavily on CRM data, which is often outdated and includes human bias. For example, after an opportunity has closed, are you confident the rep selected the true loss reason?

That’s where conversation intelligence comes in. Analyzing call recordings and transcripts gives you a rich, authentic analysis of conversation themes and topics, talk time, competitive questions and positioning, pricing discussions, next steps, and more. Managers should then use this data in open opportunities to pinpoint risk and coach as well as post-deal to ensure the same messaging challenges don’t wreak havoc on future deals.

Conversation intelligence alongside other activity and engagement metrics can help your entire team improve talk tracks and narratives for future calls and as a result, shorten the sales cycle.

Keep the funnel clean

As you might imagine, non-buyers tend to spend longer in your funnel than buyers, especially toward the top of the funnel where they often drag their heels and string along overly-optimistic sales reps. In fact, our analysis of more than 100 sales teams showed that the average sales team’s loss cycle is 2.7x as long as its win cycle.

If your sales team has a similar trend, you can use your loss cycle to help weed out dead deals.

Key takeaway: analyze from every angle

In order to shorten your sales cycle, you must truly understand it– and this means going beyond measuring it based on a single factor. Slice your sales cycle up based on a variety of factors and use every data point available, bringing in machine learning to inspect for risk, alert for stalled deals, and evaluate deal health. Activity data, whether from emails, meetings, attachments, contacts, or even conversations, is your key to ensuring reps are always focused on the right areas, and put deals on the fast path to close. 

Are you looking to shorten your sales cycle with machine learning and automated activity capture? Get a personalized demo of Intelligence360 and see what’s possible.

Leigh joined the content strategy and growth marketing team at Mediafly in January 2022 where she helps with all content marketing initiatives to drive traffic, demand, and growth. She attended the University of Massachusetts Amherst Isenberg School of Management and graduated with a Bachelor’s of Business Administration degree in Marketing.

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