Jake Spear's guest appearances

Jake Spear

Predictable Prospecting's Podcast

Level Up w/Jacques Spitzer

Sales Enablement PRO Podcast

Sean Campbell

Andy Paul

Viveka von Rosen

Liston Witherill

Jessica Mehring

John Jantsch

Scott Lewis

Joanna Wiebe

Max Altschuler

Steve Maxwell

Brad WIlliams

Andy Conduit-Turner

Matt Johnson

Mark Roberge

Peter Lang

OwlTail

Jake Spear is the founder and CEO of Digital Selling Machine. He and Jacques discuss Black Friday strategy, the power of edutainment, and what to look out for in 2020. 

Jake Spear is the founder and CEO of Digital Selling Machine. He and Jacques discuss Black Friday strategy, the power of edutainment, and what to look out for in 2020.

Edutainment is Key | Guest: Jake Spear

Shawnna Sumaoang: Hi, and welcome to the Sales Enablement PRO podcast. I am Shawnna Sumaoang. Sales enablement is a constantly evolving space, and we’re here to help professionals stay up to date on the latest trends and best practices so they can be more effective in their jobs. Today I’m excited to have Jake Spear join us from ringDNA. Jake, thank you so much for joining us. I would love for you to tell our audience a little bit about yourself, your role, and your organization. Jake Spear: Yeah, absolutely. And thank you, Shawnna, as well and also to the whole Sales Enablement PRO team for having me on. It really is an honor. So, about myself. As Shawnna said, my name is Jake Spear. I joined ringDNA back in February of this year as the senior manager of sales operations. For a growing startup like we are, what that means is that I kind of do a little bit of everything. So, everything from working with the sales reps on onboarding, training, and deal strategy to all the stuff that is behind the scenes. Everything from Salesforce reporting and dashboards, analysis of our numbers, a little bit of all of that. SS: Yeah, absolutely. And operations is often one of the close partners to sales enablement within slightly larger organizations, so I think as you guys grow and scale that will definitely become a need within your organization. Now, I want to talk to you a little bit about sales training specifically because as you mentioned, you guys are a fast-growing organization. So, in your opinion, what are some of the core elements of a sales training program for new hires? JS: I think onboarding is probably one of the most important times in a reps’ career at any given company, and so getting them off to a fast start is really critical. And I think what that comes down to is you focus on the core competencies that all sales reps have to have. So, everything from general business acumen, to objection handling, to reflective listening, and then furthermore to your own personal elevator pitch that needs to be the standard across your sales reps. Getting all that down in the first few weeks makes for a much more effective sales rep down the line. SS: Absolutely. What are some of the strategies that you’ve implemented, either in your current organization or previous ones, to actively train new hires? Particularly maybe even elaborate a little bit more on new hires that may be earlier on in their career. JS: Yeah. I think one of the most effective tools that I have used is best practice call libraries. So, once you start building up a library of good calls from your current reps, you can then use that and truly have a baseline of what you want your calls to sound like. That allows your newer reps to hear that and start to emulate the things that they see in those that they like and that fit into their voice. I think that’s probably the biggest key. So, having some sort of call recording functionality and capability to group those is absolutely key to that. Furthermore, I think roleplaying is one of those time-tested and never-gets-old strategies that we make heavy use of here. And I don’t think that that’s just the new hire thing. Roleplays for experienced reps are just as important. I think call coaching down the line is also probably the best thing to do. And that can be an extension of the best practice call library. But I think it’s important that when you have some managers that are managing 10 or 20 or 50-plus reps depending on where you work, you’ve got to make sure that you know what’s happening on those phone calls and how to coach them. SS: So, you had mentioned frontline sales managers, and obviously they are a core component to ensuring that coaching is done successfully. What are some examples of ways that you have empowered frontline managers to do coaching? I think you mentioned that some of those managers have several reps that report into them, so what are some tools or tips that you have used in the past to make sure that they’re providing the best coaching for their reps? JS: Yeah, I think one of the things that a lot of companies struggle with, especially as they get bigger, is that the sales training or coaching starts to become very different and break down among different teams. I think that the biggest tip I give to this is to make sure that your coaches or your frontline managers are following basically the same sales methodology or strategy that they’re giving to the reps, because reps talk. So, if one rep hears from their manager, “handle a call this way” or “talk about a product this way”, and another rep hears something completely different from their manager, it causes friction. So I think it’s really important for leadership to develop a clear-cut, concise message that all sales managers know and know how to coach to. SS: Absolutely. How much do you think coaching has an impact on sales culture or even maybe with a specific rep for their morale? JS: I think it’s quite possibly one of the most important things when it comes to morale. I’ve seen companies where reps will either quit or consider quitting purely because they weren’t getting the kind of coaching that they had signed up for. I know as a hiring manager myself, one of the questions that I get asked almost every single interview — when I give the candidate time to ask questions about us — is, “tell me what you’re coaching is like.” How often do I get access or time with my frontline manager? Are we doing one-on-ones every week, is it every month, how much time do I get with a coach or a mentor? That’s becoming one of the key things that I think people even consider a benefit in their jobs, like they expect it the same way someone expects health insurance or time off. They expect a full-time coach. SS: Yeah, absolutely. I wouldn’t disagree at all. In fact, I would think that it definitely helps retain sales talent, for sure. I would love to understand though if you see any nuances in generational gaps between certain sales reps and their preference for sales coaching. JS: That’s an interesting question. I think sometimes that seems like the stereotype, that you have the older reps who, for whatever reason, they feel more experienced and less in need of a coach. But I feel like I’ve heard that more as a possible danger than I’ve actually seen. I think if you are hiring for the right person with the right sort of qualities, looking for someone to help them and someone that’s going to be a resource to them, you can find that in an SDR that’s fresh out of college or you can find that with a 20-year-plus veteran. It really just depends on the personality of the person. SS: I love that and I think you hit the nail on the head. When you’re talking about making sure that you’re looking for the right hiring criteria, how much do you think sales operations or sales enablement should be playing a role in deciding the right criteria that perhaps the talent or hiring team should be looking for when they’re out there recruiting for new sales reps for an organization? JS: It’s an interesting question. Here, I play a pretty big role in it because we’re still, as I said before, in start-up mode. So, I’m wearing a lot of hats. I think that sales enablement or operations should play some role. If they’re not the actual interviewer themselves, I think they should be there to structure maybe how the interview is set up. So, I know for instance it’s a bad candidate experience if I walk in and ask the same questions that the previous two people asked as well, so structuring the interview of maybe this person takes the behavioral interview, this person takes the situational type interview, this person digs into the background. That can be at least structured in a way that sales ops probably would do even better than just a regular sales trainer would. SS: Now being on the operations side of the house, obviously measuring efficiency and effectiveness is really critical to that particular type of role. When you take that lens and you apply it to things that you guys are doing particularly on the onboarding, training, and coaching side of the house, what are some ways in which you’re measuring whether or not those programs are successful in the eyes of the business? JS: It’s a great question. I think when it comes to onboarding, I’m really focused on the ramp quotas that we’ve set in place. Not only how we’re trending toward those, so is our rep hitting the ramp goals that they’re supposed to. But as I add in new training or new coaching or anything new to that process, are we doing that process quicker than we were doing before? Are reps getting ramped faster than they were previously? So, I really look at their attainment to goal for the first three months and having a really fair ramp quota is very important to that, because if you set something too high, then it demoralizes reps and it looks like none of your programs are working. As it comes to the success of future training, I think the most important thing is twofold. One, do I see sustained continuous improvement for reps? And obviously sales reps have a little bit of an up and down nature to their performance and that’s just natural for them. But is it up into the right over time? And then the second part of that is those who have been in the position for some time, maybe six months-plus, are they confident to be a part of that training process with me and train the newer reps? Because those who are not only confident to do it but can start training them in the way that I would be training the reps and lend a hand that way, that shows me that our training really sunk in. SS: I’d just like to close and understand some of the upcoming initiatives that you may be working on. Are there any that you’re excited about and want to share with our audience? JS: Yeah. I think one thing that I’m really excited about, and excited about for two reasons, is a training that we’re running called reflective listening. The first reason I’m excited about it is that one of our account executives actually came up with this training on their own and was so excited about it that they wanted to run the training. That to me is quite possibly the best-case scenario, not just because I don’t have to do the work, but because I think it really fosters a different type of collaboration when one of the reps bring something to the team. As long as it’s on message with what myself and our chief sales officers would feel comfortable with, I’m all for that. The second reason I love it is I think the content is great. It’s basically making sure that when you’re on the phone with the prospect that you’re truly listening to what that person is saying and responding in an inappropriate way that allows the person to say a little bit more. And it’s a great sales technique. I love that our rep is running it and has actually gotten really excited and created additional training for it. So, I think to end on that note, I would say the other thing I’m actually really excited about is having more rep involvement in our training sessions where they’re running things. SS: Thank you so much, Jake. I really appreciate you taking the time to talk to us today. And thank you to our audience for listening! For more insights, tips, and expertise from sales enablement leaders, please visit salesenablement.pro. If there’s something you’d like to share or a topic you want to learn more about, please let us know. We’d love to hear from you.

Shawnna Sumaoang: Hi, and welcome to the Sales Enablement PRO podcast. I am Shawnna Sumaoang. Sales enablement is a constantly evolving space, and we’re here to help professionals stay up to date on the latest trends and best practices so they can be more effective in their jobs. Today I’m excited to have Jake Spear join us from ringDNA. Jake, thank you so much for joining us. I would love for you to tell our audience a little bit about yourself, your role, and your organization. Jake Spear: Yeah, absolutely. And thank you, Shawnna, as well and also to the whole Sales Enablement PRO team for having me on. It really is an honor. So, about myself. As Shawnna said, my name is Jake Spear. I joined ringDNA back in February of this year as the senior manager of sales operations. For a growing startup like we are, what that means is that I kind of do a little bit of everything. So, everything from working with the sales reps on onboarding, training, and deal strategy to all the stuff that is behind the scenes. Everything from Salesforce reporting and dashboards, analysis of our numbers, a little bit of all of that. SS: Yeah, absolutely. And operations is often one of the close partners to sales enablement within slightly larger organizations, so I think as you guys grow and scale that will definitely become a need within your organization. Now, I want to talk to you a little bit about sales training specifically because as you mentioned, you guys are a fast-growing organization. So, in your opinion, what are some of the core elements of a sales training program for new hires? JS: I think onboarding is probably one of the most important times in a reps’ career at any given company, and so getting them off to a fast start is really critical. And I think what that comes down to is you focus on the core competencies that all sales reps have to have. So, everything from general business acumen, to objection handling, to reflective listening, and then furthermore to your own personal elevator pitch that needs to be the standard across your sales reps. Getting all that down in the first few weeks makes for a much more effective sales rep down the line. SS: Absolutely. What are some of the strategies that you’ve implemented, either in your current organization or previous ones, to actively train new hires? Particularly maybe even elaborate a little bit more on new hires that may be earlier on in their career. JS: Yeah. I think one of the most effective tools that I have used is best practice call libraries. So, once you start building up a library of good calls from your current reps, you can then use that and truly have a baseline of what you want your calls to sound like. That allows your newer reps to hear that and start to emulate the things that they see in those that they like and that fit into their voice. I think that’s probably the biggest key. So, having some sort of call recording functionality and capability to group those is absolutely key to that. Furthermore, I think roleplaying is one of those time-tested and never-gets-old strategies that we make heavy use of here. And I don’t think that that’s just the new hire thing. Roleplays for experienced reps are just as important. I think call coaching down the line is also probably the best thing to do. And that can be an extension of the best practice call library. But I think it’s important that when you have some managers that are managing 10 or 20 or 50-plus reps depending on where you work, you’ve got to make sure that you know what’s happening on those phone calls and how to coach them. SS: So, you had mentioned frontline sales managers, and obviously they are a core component to ensuring that coaching is done successfully. What are some examples of ways that you have empowered frontline managers to do coaching? I think you mentioned that some of those managers have several reps that report into them, so what are some tools or tips that you have used in the past to make sure that they’re providing the best coaching for their reps? JS: Yeah, I think one of the things that a lot of companies struggle with, especially as they get bigger, is that the sales training or coaching starts to become very different and break down among different teams. I think that the biggest tip I give to this is to make sure that your coaches or your frontline managers are following basically the same sales methodology or strategy that they’re giving to the reps, because reps talk. So, if one rep hears from their manager, “handle a call this way” or “talk about a product this way”, and another rep hears something completely different from their manager, it causes friction. So I think it’s really important for leadership to develop a clear-cut, concise message that all sales managers know and know how to coach to. SS: Absolutely. How much do you think coaching has an impact on sales culture or even maybe with a specific rep for their morale? JS: I think it’s quite possibly one of the most important things when it comes to morale. I’ve seen companies where reps will either quit or consider quitting purely because they weren’t getting the kind of coaching that they had signed up for. I know as a hiring manager myself, one of the questions that I get asked almost every single interview — when I give the candidate time to ask questions about us — is, “tell me what you’re coaching is like.” How often do I get access or time with my frontline manager? Are we doing one-on-ones every week, is it every month, how much time do I get with a coach or a mentor? That’s becoming one of the key things that I think people even consider a benefit in their jobs, like they expect it the same way someone expects health insurance or time off. They expect a full-time coach. SS: Yeah, absolutely. I wouldn’t disagree at all. In fact, I would think that it definitely helps retain sales talent, for sure. I would love to understand though if you see any nuances in generational gaps between certain sales reps and their preference for sales coaching. JS: That’s an interesting question. I think sometimes that seems like the stereotype, that you have the older reps who, for whatever reason, they feel more experienced and less in need of a coach. But I feel like I’ve heard that more as a possible danger than I’ve actually seen. I think if you are hiring for the right person with the right sort of qualities, looking for someone to help them and someone that’s going to be a resource to them, you can find that in an SDR that’s fresh out of college or you can find that with a 20-year-plus veteran. It really just depends on the personality of the person. SS: I love that and I think you hit the nail on the head. When you’re talking about making sure that you’re looking for the right hiring criteria, how much do you think sales operations or sales enablement should be playing a role in deciding the right criteria that perhaps the talent or hiring team should be looking for when they’re out there recruiting for new sales reps for an organization? JS: It’s an interesting question. Here, I play a pretty big role in it because we’re still, as I said before, in start-up mode. So, I’m wearing a lot of hats. I think that sales enablement or operations should play some role. If they’re not the actual interviewer themselves, I think they should be there to structure maybe how the interview is set up. So, I know for instance it’s a bad candidate experience if I walk in and ask the same questions that the previous two people asked as well, so structuring the interview of maybe this person takes the behavioral interview, this person takes the situational type interview, this person digs into the background. That can be at least structured in a way that sales ops probably would do even better than just a regular sales trainer would. SS: Now being on the operations side of the house, obviously measuring efficiency and effectiveness is really critical to that particular type of role. When you take that lens and you apply it to things that you guys are doing particularly on the onboarding, training, and coaching side of the house, what are some ways in which you’re measuring whether or not those programs are successful in the eyes of the business? JS: It’s a great question. I think when it comes to onboarding, I’m really focused on the ramp quotas that we’ve set in place. Not only how we’re trending toward those, so is our rep hitting the ramp goals that they’re supposed to. But as I add in new training or new coaching or anything new to that process, are we doing that process quicker than we were doing before? Are reps getting ramped faster than they were previously? So, I really look at their attainment to goal for the first three months and having a really fair ramp quota is very important to that, because if you set something too high, then it demoralizes reps and it looks like none of your programs are working. As it comes to the success of future training, I think the most important thing is twofold. One, do I see sustained continuous improvement for reps? And obviously sales reps have a little bit of an up and down nature to their performance and that’s just natural for them. But is it up into the right over time? And then the second part of that is those who have been in the position for some time, maybe six months-plus, are they confident to be a part of that training process with me and train the newer reps? Because those who are not only confident to do it but can start training them in the way that I would be training the reps and lend a hand that way, that shows me that our training really sunk in. SS: I’d just like to close and understand some of the upcoming initiatives that you may be working on. Are there any that you’re excited about and want to share with our audience? JS: Yeah. I think one thing that I’m really excited about, and excited about for two reasons, is a training that we’re running called reflective listening. The first reason I’m excited about it is that one of our account executives actually came up with this training on their own and was so excited about it that they wanted to run the training. That to me is quite possibly the best-case scenario, not just because I don’t have to do the work, but because I think it really fosters a different type of collaboration when one of the reps bring something to the team. As long as it’s on message with what myself and our chief sales officers would feel comfortable with, I’m all for that. The second reason I love it is I think the content is great. It’s basically making sure that when you’re on the phone with the prospect that you’re truly listening to what that person is saying and responding in an inappropriate way that allows the person to say a little bit more. And it’s a great sales technique. I love that our rep is running it and has actually gotten really excited and created additional training for it. So, I think to end on that note, I would say the other thing I’m actually really excited about is having more rep involvement in our training sessions where they’re running things. SS: Thank you so much, Jake. I really appreciate you taking the time to talk to us today. And thank you to our audience for listening! For more insights, tips, and expertise from sales enablement leaders, please visit <a href="http://salesenablement.pro" rel="nofollow" target="_blank">salesenablement.pro</a>. If there’s something you’d like to share or a topic you want to learn more about, please let us know. We’d love to hear from you.

Episode 43: Jake Spear on Building a Successful Sales Training Program

For the 21st century professional, an insatiable desire to learn is crucial for staying afloat in an ever-changing market. The face of sales and marketing has seen big changes due to technology, but the constant introduction of new apps and tools can make some sales teams feel overwhelmed by the sheer mass of new information. So how do you build your skillset and education without getting lost? Companies like Sales Hacker Inc. make it easy for sales reps and developers to learn about and take advantage of these tools and techniques by hosting conferences, facilitating workshops, and compiling information for companies big and small. Jake Spear is a leading sales executive with Sales Hacker Inc. After beginning his career as a management trainee for a semi-trailer leasing company, Jake Spear used his skills in cold calling and prospecting to move into tech sales and bring his experiences to Sales Hacker’s conferences and consulting.  Episode Highlights:    Jake Spear’s sales journey   Importance of continuing your education   Putting the right person in the right sales role   Know your audience: non-tech vs tech sales   Sales Hacker June 2016 and November 2016 conferences     Resources: Sales Hacker Read Sales Hacker Blog Posts &amp; Educational Resources Request to join the Sales Hacker Linkedin Group Contact Jake Spear: jake@saleshacker.com Podcast Listener Discount Code

For the 21st century professional, an insatiable desire to learn is crucial for staying afloat in an ever-changing market. The face of sales and marketing has seen big changes due to technology, but the constant introduction of new apps and tools can make some sales teams feel overwhelmed by the sheer mass of new information. So how do you build your skillset and education without getting lost? Companies like Sales Hacker Inc. make it easy for sales reps and developers to learn about and take advantage of these tools and techniques by hosting conferences, facilitating workshops, and compiling information for companies big and small. Jake Spear is a leading sales executive with Sales Hacker Inc. After beginning his career as a management trainee for a semi-trailer leasing company, Jake Spear used his skills in cold calling and prospecting to move into tech sales and bring his experiences to Sales Hacker’s conferences and consulting. Episode Highlights: <ul> <li>Jake Spear’s sales journey</li> </ul> <ul> <li>Importance of continuing your education</li> </ul> <ul> <li>Putting the right person in the right sales role</li> </ul> <ul> <li>Know your audience: non-tech vs tech sales</li> </ul> <ul> <li>Sales Hacker June 2016 and November 2016 conferences</li> </ul> Resources: <a href="http://www.saleshacker.com/" rel="nofollow" target="_blank">Sales Hacker</a> Read <a href="http://www.saleshacker.com/library/" rel="nofollow" target="_blank">Sales Hacker Blog Posts &amp; Educational Resources</a> Request to join the <a href="https://www.linkedin.com/groups/6932016/profile" rel="nofollow" target="_blank">Sales Hacker Linkedin Group</a> Contact Jake Spear: <a href="mailto:jake@saleshacker.com">jake@saleshacker.com</a> Podcast Listener Discount Code

Episode 22: Building Skillset and Education in an Ever-changing Market - Jake Spear