How Real-World Coaching Helps Scale Productivity

According to research from Sales Enablement PRO’s State of Sales Enablement Report 2023, when reps understand the winning behaviors that will help them improve performance, they are 74% more likely to effectively replicate them with buyers. So what role does effective training and coaching play in an overall enablement strategy?

Shawnna Sumaoang: Hi and welcome to the Win Win Podcast. I’m your host, Shawnna Sumaoang. Join us as we dive into changing trends in the workplace and how to navigate them successfully. Here to discuss this topic is Malia Di Salvo, senior manager of training effectiveness at Upwork. Thanks for joining, Malia! I’d love for you to tell us about yourself, your background, and your role. 

Malia Di Salvo: I am super excited to be here. A little about myself, as you mentioned, I lead the training and effectiveness team here at Upwork. Under my purview, we have sales coaches, we have onboarding that is part of my scope, as well as a leader enablement program called lead up.

A little bit about me, I am in Seattle, Washington so I am just getting in to enjoy the fall weather. I have a master’s in teaching. I’ve been a salesperson, a sales leader, in enablement, leading onboarding, coaching, and all those fun things. This has just been really the opportunity to marry a lot of my passions into one role and be able to play a part in the strategic vision and helping our sales teams and go-to-market teams really become effective. Marrying all my favorite things together now. 

SS: I love that. As you mentioned, you specialize in both training effectiveness and sales coaching at Upwork. Tell us about Upwork’s approach to training and coaching what are the key components of your enablement strategy and how do training and coaching both play a role in this?

MD: One of the things that really drew me to Upwork was the fact that they had a sales coach team and we’re looking at expanding it and building it. Having been a sales coach in the past, I recognize the impact that coaches can really have when it comes to not just driving rep behavior and skill change, but ultimately revenue.

One of the things that drew me was the fact that they had a portion on this team. Training and effectiveness to me, when it comes to our overall enablement strategy is really about effectiveness, like exactly what the team is. With enablement, we partner closely with our marketing team. We have a content enablement team that we really work closely with when they build playbooks or talk tracks, and then we launch the training and the pull-through. 

Training and effectiveness, to me, are one of the most paramount parts to pulling that enablement strategy forward and through all the way to application to competency to mastery. We’re integrally tied to our enablement as well as our overall strategy when it comes to driving revenue and impact.

SS: I love that. We have this theme here at Highspot to help others understand what good looks like. What does good look like for sales training? In other words, what makes for an effective training program? 

MD: Sure, I think the overall best look for training is if it’s tied into larger strategic initiatives for the org. What are the overarching OKRs? Our OKRs should align back up into the go-to-market organizations and all the way up and through. Good looks like being able to tie your initiatives to those larger-scale initiatives and start showing the impact you’re having on those initiatives.

I like to say that with enablement and with training and coaching, it’s really hard to say we’ve caused those success metrics, but have we correlated with them? What part of the equation were we when it came to attaining those overall strategic initiatives? Were we part of the equation? Anyone who’s in enablement knows it’s really hard. There’s a lot of squishiness in enablement when it’s like, did we make an impact or not? I think it’d be if you tie it into those larger initiatives, so you can show correlation to having achieved those, and that’s where it really shows the impact.

I feel like when it comes to some of the programs that we’re doing to achieve these OKRs and these larger-scale programs, you start looking at progressive metrics along the way. For example, if we have a certain large-scale OKR from the CRO or Sales VP or whoever that might be. What are some of the programs we tie in place to tie back into them? If they’re looking to achieve X amount of revenue by the end of the year or by the end of the quarter, we can look at some programs to start increasing some of the leading indicators to tie into those ultimate goals. 

If we focus on setting more net new meetings or better qualifications or things like that, do we see an increase in some of these leading indicators knowing that they will impact the lagging indicators? That’s where the correlation starts to come in, and that’s where the enablement program happens. You need to be able to show that pull through that you were able to do, not just launching something, but the reinforcement, and then the ultimate indicator is like, oh, we saw an uplift in those new meetings and new opportunities I’m covering, knowing that that will ultimately lead to some of the larger scale programs and initiatives. 

SS: I love how you guys are able to draw that correlation. I have a similar question about sales coaching. What, from your perspective, does good look like for sales coaching, and what are maybe some of the core components of an effective coaching program?

MD: I mean, there are anecdotal and empirical ways to say what good looks like with coaching. My coaches both come from sales, so they’re very empirical. They’re like, how do I know I’ve been successful? How do I know what I’m doing is making an impact on these teams? Since they come from very black-and-white situations where it’s like, you were successful today, you’re successful this month, or you weren’t, there’s that anecdotal and empirical type of way. 

Let’s start with the empirical. Do we see an uplift in any metrics? If you started coaching a rep and you’ve had them on your roster for X amount of time, did you see an uplift in some of the behavior and the indicators you were trying to impact? It’s really case by case because you might have one rep and this is very situational as well. You might have one rep who is really struggling with getting to the power in the deal. They’re having trouble gaining executive alignment. The coaching strategy is on that. We look at, did we get an increase in the VP plus opportunity or personas added onto these opportunities. Someone might have been struggling to close deals, so the coach comes in and really focuses on why aren’t you closing deals as strongly. Oh, well, they’re not creating urgency enough earlier in the sales process. We can start looking at the deal to move from stage one to stage two faster. 

On the empirical side, there are multiple ways you can look at that correlation. Again, I’m going to say correlation because the coaches are working tightly with the sales leadership as well. There are multiple things coming at them to help drive this particular behavior set. You can see the correlation on the empirical side. Anecdotally, it’s really like, do the reps get excited to meet with them? Are they like, hey, can I be on your roster this next month, or are the leaders like, hey, can so and so be on your roster this next month? They get a great Slack message at the end of the session like this was really great and impactful. You really helped me close this deal. 

When it comes to what good looks like, it really is twofold. There’s empirical and anecdotal, and you can look at it and I feel like you have to take both of them into account because. As a coach, people have to want to meet with you for you to be impactful. That’s where the anecdotal comes in before the empirical can even happen. 

SS: Absolutely. Now, I know, especially this year, a lot of organizations are hyper-focused on how they can improve productivity, especially amongst their revenue-generating teams. How can real-world coaching help to scale the productivity of a sales team? 

MD: That’s a great question. I think right now in this day and age, everyone is being asked to do more with less. We are off the teams that are impacted by rifts and layoffs. You have the sales teams that were cut drastically and are still having to drive revenue. How do you really focus on the most impactful part of your revenue team to do that? One of the things that I talk about and that we’re really looking to focus on as well here at Upwork is moving the middle. How do you identify the most robust group of people where the marginal benefit of them increasing their quota attainment by 1% will exponentially increase your revenue and productivity goals?

The A players and the non-A players, we’ll say, the D and F players, that’s where the leaders can really lean into that. That’s where you’d be that the sales coach side of the house can really lean into the middle and focus on their productivity. How do we, again, get more with less, but not just necessarily more, but better conversations, better quality conversations, more power in the deal, and more effective ways to create urgency? We really try to focus on the middle portion, because again, that’s where we find if we see the increase in productivity, the increase in deals, the increase in quota attainment, that’s really going to drive our revenue goals in a whole, in a whole new direction.

The coaching team can really help the leaders focus on and double down on that as well. To be able to help achieve some of that productivity and those revenue goals that we still have to hit. Every company still has to hit. 

SS: Absolutely. How do you guys leverage Highspot to help bring your coaching strategy to life?

MD: Our company, our org is set up a little differently than other companies. Our enablement function and our sales enablement function focus on our content enablement. They live in our marketing department, and so my team lives in the ops department. We work really closely with our content enablement team to be able to develop playbooks, develop plays, develop talk tracks, and all these things to be able to double down and reinforce. We partner closely with them to build that content out, and then we launch the live training. We launch any e-learns you might need to have as well. 

It’s a double-down approach. We can use Highspot as well for reinforcement and to ensure we can get the insights we need. Anyone in enablement has heard of the Kirkpatrick model for measuring success. I think we use Highspot and recognize that Highspot is a great asset to us as we look to measure that impact. For level one for reaction, we can get the training survey and maybe do a quick pull to see if it was impactful, but for level two and level three, you start seeing the behavior, the learning, input, and impact. You can do the role plays and have them uploaded in Highspot. We have the reinforcement material. Who’s accessed it? Who’s been in the playbook that we created? Did it help drive a deal forward? 

It’s a real way to get that empirical data where it’s really hard to enablement, a way to continue that progressive measurement of success by utilizing the tool properly you can really start getting those insights. You can also see who hasn’t utilized it and get some feedback on why you aren’t there. Why haven’t you used it? We can pivot quickly as well to ensure that the material is as used as possible if you will. 

SS: Do you have any wins or best practices you can share about the outcomes of leveraging Highspot for sales coaching?

MD: It’s all wins to me. Anytime we can utilize a tool to see what’s working, and what’s not. This is the beginning of the year we launched a program called Gaining Executive Alignment. As with every other company out there, as we’re all trying to get our people as equipped and enabled as possible, having power on the deal is really important.

We partnered with our enablement team to build out the content and playbook for gaining executive alignment series. We were able to have a progressive series program where we did three different live sessions. We did some content and playbooks associated with it. We were able to not just use our live training, but also our content team to be able to measure who’s utilizing it. How is it working? We continue to still use it. We saw that when we focused on it, it really helped you, but we saw a pretty decent increase in actually getting power on deals and setting up new meetings with the right people as well.

We’re able to back that into insights we use from it. If the person’s getting good, getting more deals or they’re getting more power on deals, of course, even in the Highspot, a lot utilizing some of the talk tracks and the playbooks that we have. There’s an easy correlation to make. If you use it it actually works.

SS: Now, we’ve talked a lot about ongoing training and coaching, but I know that you guys are also using Highspot to help with your onboarding process. Tell us a little bit more about that and how you leverage Highspot in your onboarding program. 

MD: We’re actually in a revamp of it too right now, and I was just speaking with Nikki, who is our owner of Highspot over here at Upwork. Historically, we’ve used it for e-learnings and getting them on the path for that, but as we look to revamp our onboarding program and make it a more, I won’t say progressive, but for lack of a better word, progressive approach towards a true ramping experience versus this kind of like exponential curve and then fall off.

We’re looking at how we’re going to be utilizing Highspot to have that experience be even more interactive with our new hires. Can we have a new hire landing page where every new hire goes to the page, they knows exactly what their journey is, where they are on the journey, what e-learnings are going on that week, what milestones we call them, and what assessments are coming down. We’re actually revamping it and going to be doubling down on our Highspot usage for our new hire training to really make it a much more singular source of truth for our new hires to come in. 

It’s not so, go to the search bar and find it, and here’s e-learning. It’s going to be a one-stop shop. I’m excited for what we’re going to be doing. I know that it’s going to be a lot more impactful to our new hires. It’s a new way that we’ll be utilizing Highspot. One of the other things we’re going to be looking at doing with our new hire experience is as we’re building out this content or revamping this content, what I think we’ve found is that governance is really hard as we like having people leaving the business or moving into new roles. We have to go in and update any e-learning or any videos where they were in. 

We’re also looking at making sure we have facilitator guides so that anyone who does come in can take over quickly. We’re going to start utilizing AI. You know, ding, ding, ding, the term of the quarter of the term of the year. How do we bring AI into some of our e-learnings and things too, to really make it a much more general approach versus a specific sales leader or person speaking to it? We’re also going to look at how we have a gated way within Highspot to have all of these facilitators, like kind of the backend, like with that leaders can access specifically where it holds all the facilitator guides, holds all the depth.

If it’s like, oh shoot, this leader’s out this week, in the Highspot link, here’s the facilitator guide, here’s the deck you’re going to be presenting to the person who might be filling in for them. We’re going to be looking to expand over how we use Highspot for our new hire instance. We’re working on the plan this quarter with a potential launch in Q1, or Q2. I am excited to see how that turns out and how that’s going to impact our new hires coming in. 

SS: Amazing. Well, I’m excited about those plans as well. You guys are doing amazing already. You guys have incorporated Highspot training and coaching into day to day workflows of your reps, and you guys are already seeing an 83 percent recurring usage, which is amazing. I think adoption and usage are really critical in order to ensure that you’re seeing that intended behavior change. My last question for you, sales leaders obviously play a very critical role in reinforcing behavior from the top. How do you enable sales leaders to effectively support their teams and reinforce the value of training and coaching?

MS: Great question. I got to give huge props again to Nikki, who is our manager over at Enablement. She owns, runs, and really drives that adoption for Highspot. She’s an incredible partner. I couldn’t do this without her. Reinforcement is the key when it comes to any enablement programs. I think we have all been at companies that had training rollouts, whatever that might be, new programs, new products, new pricing, new methodology, and it’s like, oh, great. We’re going to be sitting in this training and let’s check the box and get it done and then the next shiny thing happens and that’s all fizzled out and forgotten. 

Reinforcement is a huge part of success for any program or anything you’re trying to launch as we all know, but it’s also the hardest thing to do. What we’ve been looking to do, especially knowing that leaders have so much on their plate, is enablement teams are often a team of one or two. How do you scale that reinforcement? How do you enable and provide the leaders with the tools that they need to help you reinforce that? How we use Highspot is after we have training for some of our larger scale programs, we create what’s called a meeting in a box. It’s simple, but it’s a one-sheet that ties out just some decks that can provide some additional team huddle materials, and one-on-one questions to help continue that conversation.

With leaders, we try to make it as simple as possible, knowing that their days are insane and slammed. I’ve said it before and I’ll say it again, I think frontline leaders have the hardest job in any organization. That middle manager, you’re really managing up, down, across in so many different ways. In enablement and training, our job, when it comes to making sure that we get behavior and skill change and that these training are impactful, is on that reinforcement and that sustained motion. While we depend on the leaders a lot, how do we make it as easy as possible? 

We create this meeting in the box, we share it with the leaders afterward, and then we can, using Highspot, look at who’s actually going in and utilizing that resource and that tool. It does a few things. It’s like, okay, they’re utilizing it, it’s being adopted like that’s that level two of Kirkpatrick, we’re starting to see it. We can see who’s not using it. Again, it’s a great way to go and see if someone’s not utilizing it, why not? Our goal is to get 100% of our leaders utilizing our content and at least getting in there to assess it and be able to pull through to the application.

It’s a way to also get feedback and really identify the not, the non-adopters, which is to me the key. Who’s not utilizing it and why not? We can quickly iterate quickly, by seeing who’s not actually going in there and getting some insights from Highspot. We can go in really quickly and be like, Hey, Mr. Sales leader, let’s have a quick conversation, a couple of questions. My customers are the sales leaders, so I want to know what’s not working so that we can make it right so that they’re utilizing it and their teams are impacted as well.

SS: I love what you guys are doing. It helped to enable your sales leader. You guys are doing a fantastic job there at Upwork. Thank you so much for joining us today. 

MD: This was awesome. Thanks for having me. Thanks for having such a great tool too. We are huge Highspot fans over here.

SS: To our audience, thank you for listening to this episode of the Win Win podcast. Be sure to tune in next time for more insights on how you can maximize enablement success with Highspot.