This article is based on a presentation from the Future of SaaS Festival 2022 when Amy was Senior Manager of Sales Enablement at Calendly. Catch the full unedited talk right here.

Many of you have probably heard of Calendly. We’re experiencing hyper-growth right now, but how have we built our enablement function to keep up with this growth, and what does it look like today? Stick around and I’ll tell you.

In this article, I’m going to walk you through…

Let’s get into it.

How we approach enablement

People in enablement tend to fall into one of two camps. Sometimes they’ve been salespeople who don’t want to carry a quota anymore. Sometimes they have an HR background and they know learning and development, so they decide to pivot into enablement.

This is because people tend to think of enablement as sales training. I'd like to challenge that way of thinking and highlight enablement teams’ strategic ability.

Seven factors impact sales and go-to-market performance, and enablement helps inform each of them. Let’s take a closer look at how we serve our teams across each factor.

Capacity: is everyone on the team able to do the job that they're in?

To support our teams’ capacities, we sit in on job interviews as needed. More than that, we help inform the competencies we need to identify during the interview process, and we look at what new starters should get out of onboarding. Ultimately, we help narrow that gap.

A lot of times, enablement teams will run an onboarding program, and then after a new recruit has gone through that program, the company will realize that person doesn't know basic selling.

Well, that should have been uncovered during the interview process. You can't solve that in a one-week, two-week, or even four-week enablement onboarding program. We've got to make sure that they can do the job first.

gears on a table

Conditions: do they have the tools, resources, and tech stack to do the job?

Then we look at the conditions our teams are working with. Have we set them up for success with our tech stack?

Have we made all of our tools and resources findable? Product marketing is churning out some really powerful content; we make sure that everybody on the teams we serve can find the information they need when they need it.

Standards: have we defined all of our processes so that even the newest team member understands what's expected of them?

When we look at our sales process, we want it to be crystal clear when AEs should convert. That helps sales leaders predict revenue, but only if the processes and reporting are clear and objective.

Knowledge and skill: are team members getting the training they need?

A lot of people think of our role in knowledge sharing as an enablement hour that appears on the calendar every week, but there's a lot more to it than that.

Sometimes live sessions are warranted; sometimes asynchronous learning sent out through an LMS is the best solution because it allows AEs to weave in training around their schedule. Sometimes it's as easy as providing a job aid.

In enablement, we need to be experts in how adults learn and get them the information they need when they need it.

Measurement: what does good look like and how do we prove it when we get there?

We need to know what winning looks like in the minds of the leaders we serve, then we look at how enablement can weigh in on that. We hone in on all the levers that impact sales velocity – number of opportunities, win rate, average contract value – and divide it by the days in a sales cycle.

We need to know the ACV so we can work to refine how our AEs run discovery. That way, we can increase it from the beginning of the sales cycle, and we can fine-tune the procurement and negotiation stages to help drive that ACV up.

Feedback: are they getting timely and consistent assessment and coaching?

Feedback is a big one because a lot of times you assume that, whether an AE is making quota or not, they know where they stand and how they're achieving, but that might not always be the case. We've got to equip sales leaders with regular feedback loops, and we need to be receiving regular feedback from the leaders that we serve.

A training session

Motivation and incentives: are they motivated to do the job at or above the level we define?

If you're serving a sales org, you want your AEs to be motivated to consume all the training. We've got to lean into that and when we're asked to deliver another sales training session, we have to understand if they’re looking for fresh intel or if people just weren’t motivated to listen the first time around.

Enablement maturity model

In everything enablement does, we need to assess our current state. When I came to Calendly to launch enablement, we built a maturity model to assess four aspects of the function: processes, tools, and tech; onboarding; sales and marketing content; and competencies.

Where we started

Let’s start with processes, tools, and tech. We had a great tech stack, but it wasn't optimized. AEs didn't necessarily know which tool to use at what stage. Plus, our sales processing and reporting standards weren't followed as consistently as they should be, so our forecast accuracy just wasn't there.

We didn’t have a formal onboarding process. There was a sales leader that was expected to bring in new hires and ramp them while also managing a team.

There was an informal buddy system, but there weren't any measures of success outside of whether they hit their ramp quota, so it was hard to know whether AEs were being effectively onboarded.

Next up, we have sales and marketing content. Before we ramped to the size that Calendly is today, we didn't have a product marketing team.

All the content that had been spun up was really feature-centric, so it wasn't driving the value proposition and the messaging that we wanted our customers to receive from us.

Finally, we looked at competencies and learning paths, and we saw that every time we led a training session, every salesperson sat through it whether they needed that information or not. We weren't protecting their selling time.

Where we want to be

That was our starting point, but where did we want to be? It's really important to identify not just our current state but our destination, which is a fully optimized function. So what would that look like?

For processes, tools, and tech, we needed to make sure that everything was automated and living within widgets in our Salesforce instance. We wanted to make sure that content and training were helping inform how sellers sell, and that comes through having a well-integrated tech stack.

We needed to customize onboarding by role. We don't need SDRs and enterprise AEs going through the exact onboarding program – it makes sense for a section of it, but then they need to follow a more specialized learning path.

To optimize our content, we decided to purchase Highspot as our enablement platform. We use this to deliver all of the information an AE needs at each sales stage.

Say you're going into the discovery stage, we want to make sure that the follow-up content, case studies, and relevant training all surface as soon as you need them.

When we come to competencies, the really important part is identifying the winning ones. Then, we can figure out where there are gaps in the rest of the team and level them up in those areas.

We use our top-performing AEs to help level up the rest. They serve as our subject matter experts as we're building training. They help speak to how customers use features when we're rolling out something new, so we can lean into the impact tool drives and the pain it solves, rather than just talking about the features.

Calendly’s enablement journey

So we knew where we were, and we knew where we wanted to be, but how would we get there? There are four crucial steps to follow if you want to build an enablement function that can keep up with hyper-growth.

A woman looking down from a hillside on a winding road

Step one: establish a sales onboarding program

The very first thing we had to tackle was onboarding. Between looking after new hires and managing existing teams, our sales managers had conflicting priorities, so we decided to add a headcount devoted to building a scalable onboarding program.

That way, whether we were hiring two people or 25, we’d have something that worked. Now, enablement serves our sales leaders by taking care of the first three weeks of all new sellers’ learning journey.

Week one

We focus on the basic product knowledge that everyone in SDR, sales, customer success, or marketing needs. We also look at ideal customer profiles, our use cases, and the problems that our customers are trying to solve.

Week two

We go into what customers want to see from us as we're running a demo. Whether we’re in pre-sale, customer onboarding, or a train-the-trainer session, there's a way that we position value when we talk about our product and our tool to customers; we cover that in the second week of onboarding.

We narrow the focus of the onboarding even more in week three. We work with new SDRs and salespeople on understanding customer pain points and decision processes. We want to identify the critical events that lead people to buy.

This is all cohort-based. All of our stakeholders are aligned along start dates because the best experience for the new hire is when they quickly find a community in an onboarding program.

Step two: implement a sales methodology

Once we got our onboarding program in place, we were able to start building the remaining three pillars. The second thing that we did was to bring in a sales methodology. This is how we adopt a common language across all customer-facing roles so that customers know what to expect when they interact with us.

Choosing a sales methodology is somewhat subjective – a lot of it looks the same – but diagnosing where you have friction in your sales cycle will help you select the methodology that’ll work best for your team.

If you've got a lot of friction at the top of your funnel, something like Force Management, MEDDIC, or MEDDPICC is probably a great choice for you.

If you're having a lot of friction in the later stages of your funnel, Challenger might work better. Challenger likes to talk about price, leaning in on value, and honing in on why customers need your product. It’s great for upskilling teams in late-stage conversions.

The methodologies that we’ve used separately and at different times are Winning by Design and Sandler. Both these methodologies encompass the entire funnel.

Step three: revise the sales process

Once you've got your methodology in place, it's time to take a hard look at your sales process. It needs to be objective and repeatable so you can drive a predictable pipeline. If there’s any subjectivity, then your stakeholders' reporting is not going to be consistent, and your forecast is not going to be reliable.

We have six sales stages: qualify, discovery, validation, proposal, trade, and close. In each of these stages, there are three things that it’s vital to document:

  1. Stage goal – What is the customer doing? Are they just exploring options? Are they trying to understand how different tools can fit their needs? We need to align on their motivations at each stage.
  2. Exit criteria – What MUST occur in each stage before converting to the next? You cannot convert until you hit that criteria. This is the most critical piece because every AE needs to know what they're trying to achieve in each stage. This creates meaningfully weighted stages that give you predictability and add value to your forecast.
  3. Meetings – What conversations should reps have with the customer during each stage? Listing out the types of calls helps to provide more context and cues for your salespeople.

Step four: build a sales playbook

The last of the foundational pillars of enablement is your playbook. Of course, you want to have a playbook from the time people go through onboarding, but it should be informed by your methodology and your process.

Everything in the playbook should revolve around selling value to your ideal customer profile. Whatever your go-to-market strategy, whether you’re aiming for expansion or net new customers, you want to make sure that all your plays are outlined.

The playbook will become a critical part of your onboarding program, and as you're reviewing your programs, you can go back through and check that your methodology is working. Are people using your sales process? Is there a drag someplace that you can solve?

A notebook

Our enablement org structure

By building these four pillars for your enablement function, you can unlock maximum sales productivity and create value as an enablement team. But building those pillars is not a one-person job – it takes a village, or in this case, an org. So what does Calendly’s enablement org look like?

Year one

When I was brought in to lead the team, I was an individual contributor. In the interview process, I helped define growth projections for the future of the enablement team.

As I said, this is not a one-person role, so I asked for direct reports. Our function provided so much value that in year one, I was able to get five enablement managers.

We started with the onboarding manager, then we worked to align managers to teams. Each manager works with department leaders to make sure that we’re delivering everything they need for their teams to sell efficiently and effectively.

We have somebody aligned with SMB and mid-market. The enterprise sales team and the SDR org both report to our head of enterprise sales, so we have one enablement manager aligned with that team. We have another enablement manager aligned with customer success.

And then, to make everything we're doing predictable, scalable, and repeatable, we needed an instructional designer who knows adult learning principles and can make sure that everybody’s getting the information they need when they need it.

Like me, other sales leaders like to weave, “Hey, this is a good time to remind them about this,” into every meeting and training session. Sticking to need-to-know information is a specific skill that instructional designers bring.

Year two and beyond

Now we’re in year two, and our org has grown and evolved. We've added a second enablement manager to help create learning paths so each function has a tailored onboarding experience.

We’re also adding a team leader so that all of these strategy-driving enablement managers that are aligned to teams can report up to one person.

We were building so much asynchronous training that we needed to split it across two roles. One is focused on product and tech, and the second one is working on making sure our methodology sticks and our sales process is seamless; they’re also leaning on metrics to uncover future training topics.

Lastly, we added an enablement program manager who’s in charge of all sales communications, including our weekly newsletter and the manager guides that provide talking points for weekly team meetings.

The enablement program manager is also responsible for reporting the impact of all of the programs we're leading – we want to make sure that the business always knows what we have going on and how we're moving things forward.

I got these four additional managers because we were able to communicate our vision for the org.

In 2023, I hope that we will break enterprise AEs away from SDRs and serve each of those roles separately in the way that they need. I’d also like for us to have a manager looking after the instructional designers and onboarding.

This is the team that I think we need to exist all through the future growth of Calendly.