EPISODE 581: Building Sales Training that Sticks for Women in Sales with Brooke Bachesta

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[EDITOR’S NOTE: This podcast featured an interview with Brooke Bachesta, Head of Commercial Learning Design at JLL Technologies. The interview was conducted by Gina Stracuzzi, Institute for Excellence in Sales Women in Sales Program Director. Both Brooke and Gina were named in Demandbase’s 100 Most Powerful Women in Sales.]

Find Brooke on LinkedIn.

BROOKE’S TIP: “Run towards the fire. There is always something going wrong. Whether it’s a process that’s busted, a team that’s not performing, a product that needs help. There’s always something wrong in a business and if you can just identify that and instead of avoiding it, say, “Hey, I think I can help out with this.” 


Gina Stracuzzi: I am talking to Brooke Bachesta from JLL Technologies. Welcome, Brooke.

Brooke Bachesta: Thanks so much for having me. It’s an honor to be here.

Gina Stracuzzi: I like to let our guests tell us a bit about themselves rather than me reading your bio. How did you get into sales and where you are today?

Brooke Bachesta: I got into sales I think like a lot of people, completely on accident. I graduated school with a degree in English and Sociology and I had no idea what I wanted to do with that. I was considering, do I go get an MBA? Do I put something else to study? Then applying to a bunch of roles, I was realizing that I was actually getting offers to interview for positions in sales. At that point, my perception of sales wasn’t great I will say.

I thought to myself, like hey, I’m not a Wolf of Wall Street girl, I’m not a smooth-talking person. I don’t think this is what I want to do. Little did I know that solution selling or B2B sales is so the opposite of that. When I had an opportunity to interview for a BDR role in the Bay Area, I was blown away. I was like, “Man, this is like consulting. I get to talk to people all day, I get to learn about people’s businesses.”

Well, you certainly have to be persistent. It’s not as pushy as I had made it out to be in my mind. Once I started doing it, I was hooked. I was an athlete in college and so I loved the competitive aspect of being able to be on a team while also owning your own number. It’s very clear input output. That really set me on this trajectory in software sales, specifically inside sales.

I was a BDR twice at two different companies. I was an account executive two times. I worked my way up to BDR management. Most recently, I was at a company called outreach.io, which helps salespeople to sell more. Got into an enablement position where I was tasked with enabling the global team of about 100 BDRs in the US and Europe, as well as their managers and a couple other roles in that department.

Now I’m leading instructional design development at a company called JLLT, where I get some exposure to the entire sales team. Not just the BDRs, but the BDRs, the account executives, the specialty sales folks, their managers, all that jazz, and it’s my job to help create trainings that stick and revamp the way that we think about training the sales floor in 2023.

Gina Stracuzzi: I love everything you said, and I am a big fan of Outreach. Just went to their Women in Sales revenue conference in California. I love everything you had to say there. That is awesome. Today we’re going to be talking about building sales trainings that far exceed expectations and as you say, stick. What can you tell us in your world that is different from other sales trainers? What do you do that’s different?

Brooke Bachesta: There’s a lot of appetite right now it seems to improve sales training and shift away from the model of like, hey, we’re going to bring everybody in and talk, ask them about a product, hope they retain it, and then send them back into the field. Quite frankly, I think a lot of that has been spurred by the pandemic, everybody was at home so we had to find ways to be a bit more dynamic in our training.

Now that we’re in this hybrid environment, people are semi-back on the road, they’re in the office, they’re working at home. It’s finding ways to meet your sales force where they’re at. Some things that I’m really excited about, that we’re building out at JLL is a recurring model of training. Making sure that people know what it is they’re getting into before they show up. It’s less of a like, “Oh, I just have this random training on my calendar, I suppose I’ll go.”

Setting the expectations and really working with stakeholders. That was something that my previous bosses, Whitney Sieck and Nikki Schanzer at Outreach really drilled into our team of like, training for training’s sake is a futile effort. If we’re just doing it to check the box, it’s never going to stick and you’ll be back in your same spot that you were three months from now doing the exact same thing. It’s really important to sell the dream with not just the frontline managers, but their executive team, because without any reinforcement, the training is kind of moot.

Gina Stracuzzi: We do fall back on our old habits very easily. Something has to be moved forward with more intent than just sending someone to training, especially just plug and play trainings. Those really do very little to change the trajectory of the sales organization.

It sounds like you’ve also been around a lot of really awesome women in sales who take a different philosophy on training than just your standard models. You’re an executive sponsor for WINS, which is women in sales execution, which is not something that I have heard of before. Can you talk to us a little bit about that?

Brooke Bachesta: Actually, I was really proud, I started this program with a pal of mine named Mandy, she still is a recruiter there, and one of the other SDRs on the floor but that was about four years ago when Outreach had, I think it was only 30 SDRs on the team. We recognized that we really needed more women in sales, not only from like a diversity is good for business but like from an optics perspective. We had three women on and I think it was 30 people and we were like, this is not a good look.

That if we wanted to make a change, we really had to make some intentional shifts to the way that we ran our organization and our recruiting and not to say like, “Hey, women, come apply and like, test it out.” Step one was, we got together with the VP of the SDR team and the CRO at the time, Anna Baird and Steve Ross and we said, “Hey, let’s revamp our job descriptions to be more gender neutral.”

We took out a lot of the words like crushing quota and a lot of the requirements. We had this whole laundry list of things like you had to have, but in reality, it’s an entry level role that didn’t require any experience. We were just looking for soft skills. Like are you persistent? Do you like to help people? Are you comfortable having a deadline or a quota at the end of every month?

That was really helpful. Changing the language for one, and then going outbound and going out to universities or communities, programs in the Seattle area and saying, like, “Hey, we are hiring”, and we would specifically target women. That was step one.

Step two was we had to make them want to work here. We had to demonstrate like, this is a place where you will have a community. We started out just doing happy hours and realize that while happy hours are fun, there’s not necessarily a clear line that you can draw to professional development.

We started to add some professional programming to that in the form of panels with female executives who were in at the company. Maybe Anna Baird would come and do a Q&A and just an overview of her career. People will get to ask her questions in a really small environment. We would pull up people within our network, senior level sales reps, CROs, CFOs around the area just to come and do. Essentially what we were doing is we were trying to demystify networking because it can be such an intimidating term especially for folks who are new to sales or new to the industry.

If we just put on a “networking event” I was pretty sure we weren’t going to get a lot of people. But if we turned it into like a, this is a cozy event just for our internal folks, we’re going to have some kind of activity, we would normally do some kind of like paint and sip or like we did terrarium building, something to futz with your hands. You have an excuse to do something while putting them in the room with all these executive women. We saw huge success.

We ended up doing that every single quarter. When we started the program in 2018, 10% of our sales force was women. Fast forward to 2019 right before the pandemic, that’s when we were doing a lot of live events. We had grown the team to about 100 people and 46% of our entire sales for our BDR team was women. We were super pleased with the impact that we had there.

Pandemic slowed us down a little bit because we didn’t have that in person goodness that we were so used to. I wanted to shout out, there’s two girls actually, or three, Peony Situ, Carson Boyle and another woman named Grace Presnick. They really helped to revitalize the program. We renamed it from, it used to be called GALs and SALs. Sales Accepted Lead is what it stood since it was so BDR focused.

We widened the audience to just anybody in sales, and since Outreach sold sales execution software, which called it WINS, women in sales execution. It’s anybody on the revenue team. CSMs, account executives, BDRs, their managers and it’s still running to this day. We’ve got remote environments with speakers. When there is an in-person hub like we have an Atlanta office and there’s a Seattle office, we try and put things together just to foster that sense of community. That was a very long-winded answer, Gina.

Gina Stracuzzi: That’s okay. What’s interesting, too, is just shortly after the Outreach conference in California, I sat on a panel with Anna Baird at a conference in Texas for Girls Club and more women in sales activities and she’s fabulous. I loved her.

Brooke Bachesta: Sure, she is. I’m a huge fan.

Gina Stracuzzi: Yeah, me too. Let’s talk a little bit about, what are some of the easy ways, using your methodology, to engage with an audience?

Brooke Bachesta: The first thing is whenever you put a training together knowing, what am I trying to get out of this? Outside of “I want people to know about a new product or sales process”, how am I going to know that it worked? Starting with the end in mind. If I’m doing a training on updating your pipeline, theoretically, we should be able to run a report in Salesforce and say, “Hey, are people’s notes up to date in Salesforce more so now after the training than before?” I think that’s step number one. Then when it comes to engaging with the audience, I had a teammate, her name is Malia Giselle. She taught me about this thing called the attention hammock. I think it comes from a organization called the Corporate Visions. Have you heard of it?

Gina Stracuzzi: Attention hammock?

Brooke Bachesta: Yeah. It’s this idea that when you’re presenting to folks, no matter how long your presentation is, at the beginning of your presentation, your audience will typically listen and retain about 70% of the stuff that you’re telling them because they’re like jazzed, the thing is starting, they’re paying attention. But the minute you get into content, that number dips down to about 20% because they might get distracted, they get lost in a train of thought.

Then when you reach the end and you start to use terminology like hey, we’re opening it up for questions, we’re about to end, we’ve got five minutes left on the clock, people’s attention suddenly ratchets up to 100%. The goal is you have to create these spikes in the middle of your presentation, like in 20% void. Attention span is difficult in general, not to mention when everyone’s at home, and they’ve got Slack and their email pinging them all the time.

Creating those opportunities, whether it is putting plants in the audience, like somebody who already knows the answer that I can call on and we have like a choreographed thing that we do. Breakout rooms are awesome. Using technology like Slido or Mentimeter to get people to engage, scan QR codes and ask questions that way. I think you really just have to be intentional. At the very least, it’s like beginning, middle and end you got to do something that engages the audience.

Gina Stracuzzi: Right. That is fabulous. With your training too, before you launch a new sales training in an organization, how do you gain buy-in? So perhaps you can figure out a way not to drop down to 20% in the middle of it.

Brooke Bachesta: There’s a couple of things there. One is, it’s important to know like what level of training is this going to be? A methodology that I’m really familiar with is this thing called awareness competency mastery model. Every training cannot be an 11 on a scale of 1 to 10 as far as important. Sometimes you just need to give people information so they know where to find it later. That would be awareness. Like bootcamp and onboarding, here’s where you sign up for your 401k. Here’s where you check where you’re tracking for your quota. You don’t need to memorize it as you need to be able to find it.

Competency is the next level up and that’s around, like, I need to make sure that you understand the concept and I can test you on it in a safe mock environment. If I’m teaching BDRs or cold call scripts, we do role plays, and if they can pass their roleplay on a basic rubric of like, was their tone good? Did they have the right intro? Did they say the right terms? Like, you’re a-okay.

Mastery is, are you able to execute these tasks in the field when there’s a lot of variables. Think of like a Solutions Consultant or Sales Architect, has to be able to run through a demo, fielding all these random questions from the buyer while also staying on track. That would be a mastery level of training. They all take different design to put together and to roll out into the field. That’s step number one is aligning with the frontline managers and the executives with the Department of, what priority level is this thing that you’re requesting?

Once you’ve got that, we’re a big fan of doing, we call them manager previews. Anytime that you’re ready to launch a training into the field, before the rep see it, usually a week beforehand. Like say, today’s Thursday, if next Tuesday I had a training with the field on something perhaps this week Wednesday, like yesterday or today, I’d run it by the frontline managers and I would run them through a full-on dry run and say, “Hey, does this content make sense to you and to your expectations?”

Part two of that is there’s always got to be some kind of reinforcement bit of like we’ve trained the reps on this, managers, you’re going to be asked to run this report, hold people accountable, maybe do a roleplay. Whatever the item is, just asking them point blank, is this something that you can commit to with your bandwidth and doing this month?

Like if you’re the manager, say like Gina, do you have time to check your reps, you got 10 of them, to make sure that they did this thing. Whether or not your stakeholders agree to that can be really telling of like, okay, maybe we’ve put too much on their plate and we’re going to shift this down to say an awareness level training because we just don’t have the bandwidth to test for it. Maybe next quarter, we can make it a deeper level training. In short, it’s deciding how serious the training needs to be and what priority level it is and then just doing a quick preview with the managers and getting just like in sales verbal, yes or no, can you commit to doing this thing after we launch it?

Gina Stracuzzi: And what about the follow up and reinforcement? Because as we talked about earlier, quite often, nothing really changes. How do you make sure this sticks and it’s reinforced?

Brooke Bachesta: Most of the work in creating a training happens before it even goes live. Making sure that if there’s an outcome that you want to measure, do you have the data architecture in place? Have you worked with revenue operations to run automated reporting? I can do some kind of dashboard to check, are we having the business impact there?

Making sure that you have those in place. Then after the training is done, I think this is where enablement can play a huge role, because I know how short sales leaders are on time. They’ve got a number to hit, they’re in a million meetings today. They don’t have a ton of time to be creative when it comes to reinforcement. Giving them a point blank -I called it a meeting in a box or like a manager toolkit- here’s three bullet points I need you to ask your reps that are not yes or no questions, open ended questions to ask in a one on one, in a huddle and here’s a worksheet to run them through or rubric for roleplay. Giving it to them so all go up to those meetings and read off the sheet and then they’ll be like, “Okay, yeah, I can grade whether or not my rep did the things that I was supposed to ask him to do.” Making it easy.

Gina Stracuzzi: Tell us a little bit about JLLT. How did you happen to get with them and what is it about that company that attracted you?

Brooke Bachesta: JLL stands for Jones Lang LaSalle. We’ve been around for, I think it’s over 250 years, which is bananas. It’s a commercial real estate company that started in London and now it’s a global company. But in short, they’re buying and selling commercial real estate. So, offices, apartment buildings, restaurants, what have you.

The JLLT side of the organization is relatively new. It’s I think, maybe three or four years old and maybe 3,000 employees out of the larger 100,000-person organization. What we focus on is specifically proptech or property technology and workforce management solution. All of the SAS that has to run all these buildings, things like if I’m an employee, and I want to book my desk or order lunch from my phone, there’s an app for that. JLL probably created it or partnered with somebody who sells it. If I’m the workplace management person, and I have to make sure that the HVAC is going on at the right time, that I’m using energy efficiently, that I’m capacity planning for company growth. All that gets done via software, and our team sells that.

I got in touch with JLL -They had actually reached out to me when I was still at Outreach, and I was approaching about five years in Outreach and it had been a really good run, but I think such is the nature of joining high growth, fast paced startups. When I joined, we had 250 employees, when I left, I think they have 1,300 employees now. The company changed quite a bit, which is totally understandable and fine, but it’s just a different company than what I had joined, and I was ready for my next chapter. When JLLT had reached out saying “Hey, it is a startup and a much larger organization”, it seemed like a great opportunity for me to leverage the skill set that I had in SAS high growth companies, and how I apply SAS metrics and frameworks to this organization while also getting to learn how to work in a mega company, because this is by far the largest company I’ve ever worked in. It seemed like a perfect marriage of things that I wanted to do, skills that I got to leverage, and it gave me an opportunity to really refine my skill set in commercial learning design, as prior I was a Jane of all trades.

Gina Stracuzzi: Sometimes that helps, because until you find the one that really energizes you, you get to try a lot of things. Let me ask you, if someone was interested in sales training as a career, what advice would you give them?

Brooke Bachesta: I think tech in general, there’s no singular path. I would say, find opportunities. If you’re in sales, you’re probably doing aspects of sales training already, whether you’re a manager onboarding your new hires, whether you’re the top performing rep who constantly gets paired with people to share your best practices. Start jotting down what it is that you’re doing because chances are, you have created frameworks or you’re leveraging a standard process of doing things without even knowing it. Start to jot those down so that if you’re interested in applying for a sales training job, even if you don’t have the title on your resume, you can speak to the programs that you’ve rolled out, the results that you’ve driven for the company as part of your day-to-day job.

Quite honestly, that’s how it happened for me. I was a frontline BDR manager, I was really enjoying my job, but I had an opportunity to chat with a lot of customers on a regular basis. I was doing a lot of new hire onboarding. I just told my boss at the time, “Steve, I really like my job, I’m not going to leave, but I just want you to know that I don’t see myself pursuing like a VP of BDR land. I think I want to get into training. I really like this. We just kept that on the back burner for a couple years, and then when a position opened up, specifically for the BDR team, it was kind of serendipitous, like, “Hey, you’ve been doing all the stuff on the side. We need somebody to do this for BDRs, why don’t you give it a shot?” I guess just like speaking it into existence, and finding opportunities to add those side projects to your resume.

Gina Stracuzzi: I always advise women that come through the forum to keep up a sheet anyway. Call it whatever you want, but just keep track of everything that you’re doing because when it comes time for promotions or raises or something, it’s really hard for managers to keep track of everyone and everything they’ve done. That’s great advice too. If there’s things that really light you up, make sure you’re talking about those so that you can use that language in the future.

We’re at that part in the conversation where I will ask you to share with our listeners one piece of advice that they can put in place today to help take their sales career or their sales in general or their sales training in this case, to the next level.

Brooke Bachesta: I think just a general tidbit of advice, I’m stealing this from an old boss that I had, who he taught us this, but it’s to run towards the fire. There is always something going wrong. Whether it’s a process that’s busted, a team that’s not performing, a product that needs help. There’s always something wrong in a business and if you can just identify that and instead of avoiding it, say, “Hey, I think I can help out with this.”

Proposing those ideas, before you know it, you’re going to label yourself amongst the organization as “Hey, she’s somebody who gets things done. She’s somebody who doesn’t have a problem getting their hands dirty and making an impact”. The opportunities that tend to come from those, it’s pretty mind blowing when you think about. Even if the project fails, just the fact that you were willing to throw yourself out there and throw an idea can really position you well. When in doubt, just find something that’s busted in your role and say, I think I can help with this.

Transcribed by Mariana Badillo

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