Sales Pipeline Radio, Episode 325: Q & A with Justin Clifford


By Matt Heinz, President of Heinz Marketing

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This week’s show is entitled, How to Hire, Onboard and Coach World-Class Sales Talent and my guest is Justin Clifford, Head of Sales at Demandwell.

Tune in to hear more about:

  • Hiring in a remote and hybrid environment
  • Strategies for better onboarding
  • Training with more empathy for the entire team

Listen in now for this and MORE, watch the video or read the transcript below:

Matt: All right, welcome everyone to another episode of Sales Pipeline Radio. My name is Matt Heinz, I’m your host. Thank you so much for joining us. If you are listening or watching on demand via our podcast or via LinkedIn, thank you very much for finding time for us, for subscribing, for downloading every episode of Sales Pipeline Radio, past, present, future. Always available at

Every week we’re trying to feature some of the best and brightest minds in sales and marketing, especially in B2B. And we get a lot of PR pitches for this show. We get a lot of folks reaching out saying, “I’ve got a topic, I’ve got a presenter, I’ve got a client I want to get on.” A lot of stuff that definitely looks pitchy. When I heard from Justin and the Demandwell team, it caught my interest because it’s a topic we’re talking a lot to clients about and just our community at large. And it’s the idea of, how are we effectively finding onboarding and training and making successful sales and marketing people and professionals in a largely remote and hybrid work environment? It’s always been hard in person, but now it’s infinitely hard in more of a remote environment. So Justin Clifford, head of sales at Demandwell, joining us for this conversation. Justin, thanks so much for being part of this today.

Justin: Yeah, Matt, thanks for having me and thanks for the opportunity to talk about this topic, one that I’m super passionate about. Wish I was better at it than I am, but super passionate about it.

Matt: Well, we are all learning as we go. We had a physical office for 10 years before COVID hit and it forced us to go remote, and we have now decided to stay remote and hybrid, meaning we still get together in person, we’re largely a western Washington based company, but very, very different from where it was before on a lot of fronts. And as someone who’s been leading sales organizations for a long time, talk a little bit about that transition that we were forced into, what that was like as a sales leader and how that’s evolved into your thinking around onboarding and making salespeople successful today.

Justin: Yeah, the interesting thing is that I was working, when we transitioned to a fully remote organization, I was working for a company called Lessonly, and we sold online training software. So we were already selling the purpose of learning almost asynchronously in a lot of ways. And it forced us to get really, really good at leaning into it and making sure that we were making adjustments that took some of the in-person learning that occurs in an office of and move them into either our platform or live events like this followed up with online lessons. We call them lessons.

But it’s been interesting, and if anybody went from a local office and only onboarding locally and had never hired remotely before or outside of that local area, it has to be incredibly difficult. The first time I did it was really hard. Had all these people that we were used to having in the office, and then we started hiring somebody in Denver and then we’d hire in Austin, Texas, and now we start to become more of a national sales organization. So almost by default you have to figure it out. And it becomes exponentially hard when the entire team is never getting together. For us for me it’s really been about, number one, listening to what people need and making sure that you’re hiring people that are equipped and feel comfortable raising their hand and tell you.

Matt: So let’s break this down, because we want to talk about hiring, onboarding, ongoing training. So let’s talk a little about each individually. From a hiring standpoint you have the advantage now of technically being able to hire someone from anywhere. If they’re going to work remotely, it could be across the street from me here outside of Seattle, you could be in Africa, I don’t know and I don’t care, because we’re able to still have this conversation effectively. The downside is, sometimes when you don’t have that in-person hire, don’t have that, there’s the EQ component of hiring that has always been important. How do you replace that? What are some of the components that are even more important now as you evaluate and hire people remotely?

Justin: Yeah, I think a big part of this, and I have the luxury of going through and hiring people and interview processes for the past six, seven years anyway. But the thing that I have really leaned into is making sure that I don’t underestimate the role play that we do. The role play as part of the interview process is a discovery call. And we used to do it at the end, it was the last step almost of an interview process. And what we found is that we’d fall in love with candidates, we’d get to the role play, and it wasn’t quite what we were hoping for. So moved it to the front, and make sure first and foremost that we’re not wasting people’s time. They can be interviewing a lot of places. Make sure we’re not wasting our own time, but making sure that we’re aligned from at least that discovery call, and then after that we can make adjustments as we go.

But I think it’s really important to meet part of the team. I think it’s really important to do proper sales interviews and look for some of the behaviors that you want to see, and making sure that you have those things at least documented for yourself or your hiring team. So that you can, even if you don’t have a specific scorecard, have those conversations and all be aligned across the board on it. And that alignment I think is really what has helped us be successful in hiring remotely.

Matt: Well, something you just mentioned that I want to double-click on a little bit as well is the remote interviewing and evaluation and creating some consistency around how you’re doing that. Anything new that you’ve seen work particularly in the last couple years to help create improved quality and consistency of how that’s done?

Justin: Yeah. Matt, I have always talked about documenting this, and at one point I did, and then I went back to my old ways. But I really think if you’re working with a team, making sure that everybody’s aligned. And like I said, you don’t have to have a scorecard built out. It’s super helpful if you do and a great practice if you do, but at least alignment in what you’re looking for from the phone screen perspective, from a role play or a presentation, so that there is some scoring methodology that everybody is aligned on. And then everybody throughout that hiring team knows their role. Because the sales manager and the AE, call it the culture-add side of things, those are different roles. And it has to be really clearly defined on who’s doing what, why, and how to ultimately go do those things and then how to report back. And making sure that those things are all not just aligned, but they are all succinct in one place is super helpful.

Matt: Yeah. And I would agree with you, we talked to Steve Richard last week from Mediafly, and when I asked him about, what are some of the biggest challenges in driving productivity with sales teams, actually I thought he was going to say CRM or sales processes. He said no, it’s lack of culture and cohesiveness in the way that companies operate. And so goes your point about creating something that is documented, some standards and questions and evaluation criteria. When we were in person together some of that happened just naturally through osmosis. We have to be more intentional now at ensuring those things are done. And yeah, does that take a little more documentation? Yes. Is there still room for creativity and wiggle room? Yes. But creativity and wiggle room comes on top of having a consistent process that is delivering consistent, repeatable results.

Justin: Yeah, totally. And I do remember, and you probably remember this, you go through an interview, you’ve got the interview team, everybody meets at a little bit of a different time. And then a lot of times that interview team would go and they would meet together and they would walk through, just give their feedback, same time, specific time. That can still happen, but it’s a lot harder to do right now, I feel like. So making sure that if you can do it, especially if speed is important, that everybody can be aligned and can do it asynchronously is super, super helpful and beneficial to both the candidate and the hiring team, the hiring company, just for speed purposes and quick feedback.

Matt: So let’s talk about onboarding and training, and I want to separate those. Because clearly training is part of onboarding, but another part of onboarding is welcoming someone to your team, to your culture, to your employee community. Again, doing that in person we’re going to take you out to lunch, we’re going to put balloons on your desk. There’s a lot of in person things that no longer exist. What are some best practices you’re seeing for onboarding, specifically around helping people feel welcomed and warmly engaged with a new team of peers?

Justin: This is a great question, and I will precede the answer with the fact that having worked for Lessonly, I know what world class onboarding and world class sales enablement looks like. Because I got to work with world class practitioners, enablement practitioners. I would love to be as good as they are one day myself. I am not. But I think one of the things that, when you’re thinking about that culture, one of the things that at least I have felt is making sure that I’ve got time set aside for meaningful conversation across the company. Not just with the sales manager, not just with your specific manager, that you’re talking with people from product, that you’re getting introductions to the executive team, that you’re meeting people on the people and talent side even more so than you did in the interview process, that you have the opportunity to come together with your teammates.

And that’s really hard right now. We are a remote-first company, and although we do have a small office here in Indianapolis, I think nine or 10 of our 16 account executives are outside of Indianapolis. So making sure that there is intentional, meaningful time to connect with those people is probably the biggest way that I’ve seen a fast track to feeling part of a team. And I’m not talking about the first month and first four to six weeks, I’m talking in the first week to 10 days that needs to start happening. Or else you’ve got somebody sitting at home going, “I don’t even really understand who I work for right now and who my teammates are.” The faster you can get there it feels, at least it felt to me when I onboarded at Demandwell, that that was pretty critical to making me feel welcome.

Matt: Yeah, I would agree. And just to reiterate what you said, I think face time is so, so important. And you can replicate that by doing stuff like this. It’s not just get on the phone, but let them see you, get to know each other a little better. “Hey, is that really a Husky football helmet behind you? Are you a college football fan?” These are the connected moments to help you feel connected to a new team and help you as an employer feel connected to new people and vice versa. And that could be done in a live environment, especially amongst your immediate team if you’re a manager, but even having a CEO or a VP of sales who may be one or two or three degrees away from a new hire just record a quick video and say, “John, welcome to the team. I’m so excited to have you here. The team has told me a lot of great things about you, including the fact that you’re a Husky.”

Whatever it is, it can take you 20, 30 seconds to record it and going to mean so much to a new person to feel like they’re being seen and noticed by someone else on the team as well.

Justin: Yeah. And Matt, I use video a lot to communicate with our specific team. I’ve never done it to communicate with a new hire that’s not on the sales team. So I am stealing that today and I’m going to start using it. So thank you for that. That’s a great idea.

Matt: Yeah, no, do it. There’s a lot of formats to do that, obviously. You can use a bunch of places, Vidyard, BombBomb, depending on what version of Slack you have you can record videos and send them to individuals or groups. So yeah, it takes this much time and it has this much effort.

Justin: Totally. Love it.

Matt: So, we’ve just got a few minutes left. And let’s get into a little bit of the concept of training. And so I wanted to separate it from onboarding, both to talk about the non-training components of onboarding, but also to talk about training as an ongoing component. Some companies will train you at onboarding and then off you go and there isn’t continuous training. And I want to talk about the continuous training component of making sellers successful. What are you seeing working right now in that area?

Justin: Yeah, I think the first thing, there’s so much change going on in everybody’s job. Products might change, services might change, pricing, packaging, the list just goes on and on and on. So from where I sit, working with our enablement manager, who is amazing at what she does, really helping prioritize the most important things to impact. Because we could be training nonstop on stuff, whether it’s those things that I mentioned or soft skills, sales skills. We could do it nonstop. And it’s really making sure that you’re balancing the load, especially for sellers, who are really the hub of the entire company. They have to know more than anybody else in the company, I believe, about that company. They have to know the services side and the marketing side and they’ve got to know how to handle leads and know about the product and all of those things.

They’re busy people. And so when you overwhelm them with training, they can get behind really quickly. So the prioritization of that training and making sure that you’re hitting the things with the most impact and you’ve got that scheduled out probably four to six weeks in advance with some wiggle room to throw something new in there if the environment calls for it, I think is really, really important. So having that schedule that is prioritized based on need, and overall need versus just maybe one or two individuals, I think it’s the stepping stone to getting really, really good at training in an ongoing fashion.

Matt: Yeah, love it. How do you think about the mix of topics? Because I think too often people focus training on, “Well, let’s make sure you understand these new features. Let’s make sure you understand how to talk about our product.” I don’t see enough selling skills. I don’t see enough understanding and teaching people to be more empathetic, to be active listeners. Talk about the mix of topics in a training program that you think are important.

Justin: Yeah, I think this is great, because I think this is where some of that wiggle room comes in too, because sales leaders can get together and they can often have similar observations and realize, “Hey, this isn’t just a one person or a two person coaching topic for their individual coaching plan. This needs to be a team topic.” We saw it, for instance, pandemic hits, you automatically have to start with more empathy. And even though you’re dealing with empathetic people by nature hopefully, it’s a good time to come back and to do a refresher together on it. So I think that wiggle room really helps. And really I think it comes back to just that prioritization. What is going to help our team be the best that they can be in their job in the next four to six weeks?

And just do that on a rolling basis and make sure that you’ve got multiple inputs. You’ve got your enablement, you’ve got your product team, your marketing team, they all want to train AEs on something. But really letting the sales management, even the frontline sales management, be a filter for that. And if you’re not getting feedback from AEs on a regular basis, there’s some room for improvement there. Because they have a whole host of things that they want to get better at for sure.

Matt: I love what you just said around thinking about what your sales team needs in the next four to six weeks. Because I imagine some people may hear that and say, “Oh my gosh, that’s such a short time period. I want to be thinking about training people for the next year. I can’t be doing that quick of cycles in terms of turning around training topics.” I’m like, how can you afford not to? Your market is moving incredibly fast. Your competitors are moving fast.

Justin: I love that.

Matt: The selling conditions you had in Q1 of this year are very different than the selling conditions companies have right now in late summer of 2022. And so you have to adjust to that. And it doesn’t mean you have to reinvent your training content or your curriculum every four to six weeks, but to have a more frequent touch base with your team to ensure that they are armed with the best hard and soft selling skills in this environment, in the current environment that may be different than what it was a couple months ago and it will be different again in two months. I love that increased speed of cadence. So thank you. I know we’ve got to run, we’re running out of time here. Justin, thanks so much for joining us today and for sharing your insight. Where can people learn more about you and learn more about Demandwell?

Justin: Oh, if it’s Demandwell, if it’s me, LinkedIn is the best place. Would love to connect if anybody so chooses.

Matt: Awesome. Well, thanks so much for being here with us today. Thanks everyone for listening and watching. We’ll be back next week for another episode of Sales Pipeline Radio. In the meantime, have a great rest of your week. We’ll see you all soon. Bye-bye.

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