Our goal for the Sales Enablement Summit, and all our other events, is to provide a platform for sales enablement professionals to share experiences and advice with the wider community.

This panel session, from our San Francisco Summit in 2019, included fantastic insights shared by the following enablement experts:

  • Stacey Wells Justice, Workfront
  • Kyle Doerflein, LogicMonitor
  • Danny De Los Santos, Cloudera
  • Julie Newhouse, Lyft (Leading the panel and asking the questions)

We picked out a sample of the best questions below, but for OnDemand access to every single session from every single SEC event, become an SEC member today.

How do you build for a long term plan while managing that push and pull of the short term?

Stacey: Just start. Nothing's perfect.

When we launched, the first thing I did was create a sales process. But the second thing I did was start onboarding because you have new hires that are coming in at all times.

If you don't just start, you won't get anywhere.

I think that's the most critical thing, making sure that you've got people who can get to productivity.

So the model that we've at we've embraced since that time is continuous improvement. I'd like to say that every that we're very standardized, but we improve every month.

We take the feedback that we get; both immediate feedback, and we do a 90 day survey. We take all of that in, and we improve the next month.

So over the course of the last four years, that's where we've been able to expand into cohort onboarding, expand into focused solution advisor programs and also just to consistently improve on exactly what they need.

Danny: What's been really helpful is being able to be agile when it comes to the frequency of our boot camps.

Typically, we would run them once a quarter. Then once hiring really took off, and we started expanding, I relied on looking at workday to see which new hires were coming in and the forecasts, so it was a close partnership with HR to get those numbers on that data.

Based on that amount of frequency, that's how many boot camps we'll have.

So for example, since April, we've had one every month.

Another factor that has been mentioned that really stuck with me was just get started.

For us, boot camp is very iterative.

We also look at the feedback a lot and we make sure that we make improvements on every single cohort that progresses.

Also make sure that when it comes to onboarding, you really are taking in feedback and working with sales leadership, and trying to really understand what it is that they're expecting from their new hires, making sure that your course-correcting as needed.

Kyle: The first thing I do when I come into a new company and I need to build out a boot camp is to interview the leadership.

Figure out what is expected from a rep. What is that goal that we're trying to hit for a perfect rep coming out of boot camp? What is that expectation? What do they need to be able to do?

We'll try and chop that up to figure out okay, by the next cohort we have coming in what's possible for us to build out.

So when you're building from scratch, yes it’s great to get your end goal identified of what you want to get to, but then you're going to have to say if we know we have a cohort coming on this day, what's feasible that we can get there because it's an iterative process.

Every boot camp I've ever delivered has been different than the one before it in some way, shape or form.

We have to rely on other cross-functional stakeholders and partners to be able to build out our program. Who do we rely on to really get things done?

Kyle: My biggest partners are going to be the sales leadership. They're going to be the ones that I'm having post mortems with after every boot camp to understand; did we hit the mark? Where are we strong? Where are we weak? What should we iterate on for the next time through?

They're my eyes on the ground.

The other key component is going to be working really closely with recruiting.

Different companies have different strategies. My previous company liked to hire very seasoned reps, they were trying to build on the enterprise side. So I was getting candidates that had strengths that I didn't have to worry about training them on.

At my current company, working closely with recruiting, I was able to see that our strategy here is different. We're hiring junior-level people, and we're growing them into the role.

So we had to be a lot more prescriptive about things.

Understanding the candidate profile that's coming in, lets me identify the delta between what we're starting with and where we need to get them to.

That's going to dictate the curriculum of what we need to cover in onboarding.

Stacey: I think subject matter experts are really key.

Whether that's your high-level subject matter expert in product marketing, or if it's a demand gen expert or product expert, they're very key.

A huge lesson learned, as we were scaling, we had two people and then three people. So we were really tight. You have to manage that quality.

Because onboarding a lot of times for those subject matter experts, while you want it to be the most important thing they're doing in their day, it's not.

One of the things that we found, when we were bringing people in is they weren't updating their decks, they weren't updating their content. So six months later, they're using the same content.

You have to own that, even if you're bringing people in.

Danny: Another key group to partner with for me is EAs.

Boot camp is also a very big cultural experience. Everyone wants to fly in from all over the world to HQ and see what our headquarters look like. They're hoping for that chance to see our CEO in the hallway.

I really rely heavily on partnering with the EAs to know who's available. Sometimes it'll be a week where everyone's at HQ.

Sometimes I'm really digging for a Senior Director of someone to come in and talk. But it's really important and it goes miles.

One additional aspect to our boot camp is networking and happy hours. We want that to be a big takeaway as you are onboarding at Cloudera making the connections that you need to be successful.

We'll host on-site a barbecue and a mixer. We call it ‘meet the pros’, and I really rely heavily on our sales leadership and executives to show up and make the class feel welcome.

Are any of you doing anything with mentorship programs, buddy systems or other forms of peer to peer learning?

Kyle: We do have official mentorship where there's someone that they're going to shadow that's going to teach them and give that extra element of learning to the application of how to do it in the day-to-day.

We also teach a course in our boot camp on creating your own mentors, and encouraging people to go out meet different roles, different people, try and figure out what's the next step they want to do?

Then also work out who are my resources that I can reach out to if I need anything.

So there's an official mentorship program, then there's also the unofficial, that's highly encouraged.

Stacey: We have a mentorship program that we call the ambassador program.

Every new hire gets an ambassador that's a relative peer within the organization, which seems to work really well.

We've actually tried other programs where we have had the most recent new hire be the person's buddy. We found that to be really helpful, because while you'd think that that recent new hire doesn't have as much information as they should to be able to help them, they actually have more than you know, and it helps them to go figure it out too.

We also have an informal program.

We're really big right now on women in sales. So we have a mentorship program for women in sales.

When we have new women hires come into the sales team, we buddy them up as well.

If you have to pick one tool or system that you couldn't use can't live without for sales, onboarding, what would it be?

Kyle: I'll go first and my cop-out answer is a BI tool.

Stacey: I would say ours is our LMS just because we're moving a little bit more to that as we scale.

Danny: I’d say our LMS as well.

So much of the pre-work is a lot of video-based training.

So we can't really measure are they doing the work if we don't have that in an LMS.

I'm curious to know how big your onboarding classes are and how often you're onboarding?

Kyle: It depends on each cohort for me.

The first one we did in November was 36 people. In March we did 25. And then July, we did another 24.

We have one that's starting on Monday. That's going to be two overlapping boot camps, but it's gonna be a total of about 40 people.

Stacey: It also depends on cohort for us.

For our inside sales team, it averages between 3 to 5 a month, that can be up and down.

I will also say it's seasonal, especially on our AE side because you get into the end of the year and January hits and our numbers skyrocket in terms of new hires. That's just something we always have to plan on.

We have an onboarding going on right now, we have 5 people.

So it varies, it can go from 40, which is huge for us, to 3 or 4.

Danny: We cap it at 30. It's usually based on the number of new hires coming in.

I've run larger boot camps and I've run smaller boot camps, 30 seems to be the sweet spot to try to get as many in as you can, without it being overkill.

Think about a classroom setting, the teacher to student ratio, you would need more people in the room to help facilitate if it's bigger than that. So for us, 30 is manageable.

Do any of your companies offer any kind of compensation or reward incentive for your sales reps to be mentors?

Kyle: Right now, it's just me buying them alcohol to bribe them.

Stacey: We don't even go that far.

We find there are people who really like to be mentors.

But when you do look at new hires, and they're the next new hire, they feel like it's kind of a privilege. So we just go with that.

Danny: A lot of the guys that want to mentor our new hires also have an interest to go into management. So it's great exposure.

While we may maybe don't bribe them or give them gifts, we make sure that they're recognized, especially when it comes to leadership taking note.

Julie: I wish we had more of a program but our company award cash points for gift cards, so we use that or we just get something like an Amazon gift card.