Amy McClain gave this presentation at the Sales Enablement Festival in October 2021

My name’s Amy McClain, I’m the Senior Manager of Sales Enablement at Calendly.

I've been at Calendly over a year and a half, in which we've established the enablement function, scaling up from a team of one (me) to a team of six.

We've implemented several different initiatives that made a big impact on the business.

Reporting on what we're doing, has allowed us to continue to get funding. In this article, I’ll get into how this has worked for us and how it might work for you as well as why it’s important to measure your outcomes and report out to the business.

Here’s a breakdown of our main talking points:

  • Why is it important to measure enablement outcomes?
  • How to get from current state to future state with enablement
  • Diagnose the right problem, deliver the right solution
  • What are the metrics you deliver back to your business?

Let’s go ahead and dive in 👇

Why is it important to measure enablement outcomes?

We're all here to serve one purpose: help our sales teams sell more.

The more we can lean in on the ROI of what we're doing to empower and enable our teams to sell better, we’ll gain alignment and buy-in around our initiatives.

Sales leaders will get on board seeing how you are contributing to moving the needle for them and more of what you do will start to come to life.

As you're looking at new tools or new headcount, proving the value of what you're doing will also aid in securing future investments.

How to get from current state to future state with enablement

Image: Establishing enablement benchmarks. Where are we now? Where do we want to be? Enablement is the "how do we get there?" in between.

First of all, you want to establish enablement benchmarks. In order to do this, you first need to identify where you're starting and then where you want to be.

Enablement is what connects the dots in between. Here are three examples of how enablement efforts can help getting you where you want to be:

  1. Sales velocity

If your current velocity is from lead coming into your funnel to converting to close/won takes about 100 days, it would be remarkable if you were able to find ways to shorten the sales cycle by 10 days - in turn getting more deals through the funnel faster and realizing revenue.

  1. Ramp time

We want to shorten the time to the first deal sold as new hires average 60 days to their first deal. Then, we also look at how long it takes reps to consistently hit quota. For us at Calendly, consistently means three consecutive months.

I want to be able to tie efforts around onboarding and ramping AEs back to getting them to close their first deal faster and getting them to consecutively achieve quota.

  1. Win/loss rate

An important outcome for any enablement team would be: once deals are in funnel, 40% of them end up in a close win - to be able to move the needle to 60% is big.

Achieving this will mean great wins and lots of investment and excitement around all of the initiatives you bring to the table.

Identify specific performance gaps and solve the right problem: sales velocity. Average sales cycle is 100 days, including: prospecting, qualification, needs analysis, proposal, negotiation, closed/won. Where is the drag in the sales cycle? How can we shorten the time to convert between sales stages?

Above is a standard sales cycle. We’re looking to shorten our 100 days by 10 days, bringing it down to 90.

Where is there drag in the sales funnel, and how can we shorten time to convert between stages?

Our approach will vary depending on where in the sales cycle we're feeling a drag. If it’s around prospecting, you need to understand and dig a little deeper.

If it's converting between stages like qualification to needs analysis, your solution will look very different than if you've got a stall in your negotiation to close/won.

Diagnose the right problem, deliver the right solution

Process, Training, Tools: These are factors we asses when diagnosing performance gaps. When enablement solves for gaps in these areas, there's a measurable impact on business outcomes.

There are three pillars that show how to diagnose the right problems and deliver the right solutions around performance gaps.

Oftentimes, when sales leaders are seeing a need for something more or when something's not working quite right, they'll call on enablement and ask for training.

We don't want to be order takers here, we want to be performance consultants and help diagnose the right problem and look across: process, training and tools.

Once we lean into the right performance gap and solve it in the right way, we'll be able to show our measurable impacts on business outcomes.