Candice Coots
Content Marketing at SetSail
Table of contents:

The win-loss analysis in sales is a fun endeavor. I don’t remember the exact moment this happened, but at some point, I stopped looking at wins. Because all the losses I would analyze listed a myriad of things that had gone wrong  - the product, the message, the market, the price. So much to learn and to fix! All the wins, however, had just one thing in common: the sales rep did a great job.

To be fair, in most cases, the reps were indeed great. It's just that it wasn't easy to know in what ways and how to replicate their success. Today, with every customer interaction with a sales rep imprinted onto our digital canvas - calls, emails, language, etc. it’s possible to track and understand what they did right.

What 500+ enterprise deals revealed about the small wins

Here at SetSail, we look at all the small wins of sales reps that lead to their big win. We collect and connect a treasure trove of deal progress data and use machine learning to unveil every deal milestone that matters. We call them signals. Our platform then turns those signals into little bits of easy guides to follow (or get rewarded for) every week to improve win rates.

Just this past week, we looked at a pool of 500+ wins to understand what leads to success in an enterprise deal. Here’s what we learned:

1. Consistently delivering on at least 5 signals improves win rates by 62%.

As one of our customers once wisely noted ‘There’s nothing revolutionary about what best reps do. They just do it consistently.' Our data confirmed it by showing that any combination of 5+ signals present in a deal improves win rates by 62.2%. But what are those signals you ask? They are machine learning-based templates of the best deal milestones unique to your business.

In the case of this enterprise customer, the key signals were things like the number of emails received (at least 10), or the number of active contacts (at least 6), and the sentiment and language of the conversation (positive and mentioning progress). So the magic number for an increase in win rate for the customer was a combination of 5 of those signals. For Sales Managers, that level of knowledge creates a repeatable, transparent, and consistent way to drive performance.

2. Multi-threading is more important than the frequency of interactions.

The data revealed that while more than 5 ‘meetings accepted’ improves win rate by 47% and more than 10 ‘emails received’ increases it by 28%, what really moves the needle is the number of ‘active contacts’: if you have more than 6 active contacts on an enterprise deal, your win rate goes up by a whopping 62%.

That was really eye-opening for the customer. They started to encourage less excitement about one great champion in a deal and more creativity in reaching out to involve more decision-makers. This finding is not surprising given today’s complex buying committees, but it’s much easier to act on when your reps are measured on it. The next step on this customer’s journey is to associate the multi-threading signal with more points and instant rewards so more sales reps get better at it.

3. What sales reps do isn’t important, the customer's response is.

This seems obvious, but the way we measure sales performance before a deal closes is ineffective. We have activity dashboards that focus on how many emails a rep sent, or how many calls she made. What matters is what the customer did and how they responded. 90% of the 400+ signals we track have to do with how the customer responds. Because that’s how you get your reps to become creative in engaging the customer. Imagine rewarding reps for that too. But that will be the subject of our next post in our Sales Science Thursday series.

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Every sales team wants to be more data-driven, but the truth is, more data creates more noise. We have more dashboards than ever, but when have dashboards ever closed a deal?

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