In keeping with analysis from Gallup, 21% of staff who voluntarily left their group stated their departure might have been prevented by extra constructive private interactions with their supervisor. So how will you create a training tradition that retains groups motivated and drives gross sales success?

Riley Rogers: Hello, and welcome to the Win-Win podcast. I’m your host, Riley Rogers. Be a part of us as we dive into altering developments within the office and the right way to navigate them efficiently.

Right here to debate this matter is Robin Handley, Senior VP of Gross sales Enablement at Direct Journey. Thanks a lot for becoming a member of us, Robin. We’re actually excited to have you ever right here. To kick us off, I’d love should you might begin simply by telling us a bit bit about your self, your background, and your function.

Robin Handley: Yeah, I’d like to, and thanks a lot for having me. I’m completely thrilled to be right here. I’ve really been within the journey business for 30-plus years, so I suppose you might say I grew up right here. I’m the SVP of Gross sales Enablement at Direct Journey, such as you talked about. Below my present remit, you realize, I’m chargeable for gross sales enablement, managing additionally what we name the inbound and outbound lead era with our gross sales growth reps and the proposal writing staff.
So I’ve obtained fairly, you realize, three completely different distinct traces of enterprise inside my remit. After which I believe it’s vital to share that in my prior roles, along with gross sales enablement, I additionally led groups associated to reporting, knowledge analytics, CRM platforms, in addition to change and transformation.

RR: Great. Thanks for sharing. It looks like you may have a wealth of information acquired over plenty of completely different roles, and I’m so excited to sort of dig into it and steal a few of your finest practices. Excited about your expertise—possibly in knowledge analytics, product, buyer success, all of this stuff that you simply alluded to—I’d be curious to know the way this various background sort of comes collectively to affect your strategy to gross sales enablement at Direct Journey.

RH: You realize, I believe having expertise spanning throughout, you realize, many areas, it offers a broad perspective round how issues intersect, how they affect, and, you realize, how they help one another. So, for instance, leveraging knowledge factors comparable to why we win, explanation why we lose, in addition to listening to buyer suggestions, you actually begin to see developments and begin to perceive the client and business ache factors.
So from there, you’ll be able to actually begin to work with key enterprise companions—I might say in advertising and marketing, product, buyer expertise, you realize, these completely different areas—to just remember to develop content material and belongings which are gonna arm your gross sales reps to beat objections, to spotlight key differentiators, and to align options to buyer ache factors.
And when, you realize, you’re main in enablement, I all the time say it’s like vitally vital to make sure that the precise content material and collateral and coaching and training is offered to allow these gross sales reps to rapidly advance by way of these gross sales cycles and shut, win that enterprise.

RR: Great. I’d like to possibly double-click a bit bit deeper into that enablement strategy and philosophy, particularly targeted on teaching, as a result of I do know on LinkedIn you’ve highlighted the significance of people-centric management, particularly in gross sales teaching and suggestions.
I’m curious to know possibly the way you carry this philosophy to life in your enablement efforts, after which how that impacts your overarching teaching tradition.

RH: Yeah, so people-centric management, you realize, it actually isn’t simply being caring, empathetic, dedicated. I believe, you realize, that’s all extremely vital, nevertheless it’s additionally about being intentional in how we develop our groups.
So growing people by way of teaching, suggestions, and recognition is so crucial. So one factor I do is I run pitch workout routines the place reps report themselves, and I all the time inform them, that is your playground. You realize, you’ll be able to mess up right here, not in entrance of a buyer. And it seems like a secure house. In order that mindset shift makes an enormous distinction.
And this strategy not solely helps people develop, nevertheless it additionally fosters a tradition the place, you realize, suggestions turns into normalized and valued. So over time, this creates, like, that ripple impact as effectively. And so what I begin to see is reps begin to coach one another. They really feel snug sharing suggestions or tips or suggestions. Even, you realize, it’s not a lot then from that top-down directive. It feels prefer it’s extra of a collaborative neighborhood. And because of this, I believe it’s additionally vital simply to name out that we begin to see reps develop into extra assured and collaborative simply basically. So because of that, I might say, you realize, it even helps improve or enhance our win charges and, you realize, helps individuals be higher ready and hopefully, once more, win that enterprise.

RR: Yeah, I like to listen to that. I believe the thought of like making a secure house for observe is so vital. Folks want to have the ability to make errors. That’s the place you study. In order that’s nice to listen to. I’d like to modify gears possibly a bit. I do know that along with making a wholesome teaching tradition, bettering gross sales effectivity is a key focus for you at Direct Journey.
I’d be curious—possibly a few of the challenges to GTM effectivity that you simply’re seeing your groups face at present.

RH: Oh yeah. I say, you realize, fairly a couple of come to thoughts, and I believe that’s regular, proper? I imply, in any firm there’s all the time these issues. I might say, you realize, sellers utilizing outdated, outdated collateral, typically looking for the place are these belongings saved, as a result of they could possibly be saved in a number of completely different areas.
I might say one other huge factor that we’re challenged with is said to lengthy gross sales cycles, and so, you realize, for me it’s all the time prime of thoughts: how can we proceed to shorten and shrink these gross sales cycles? After which I believe plenty of occasions you’re not getting full visibility into purchaser engagement. So with out that knowledge, plenty of occasions the gross sales reps are utilizing their intestine.
There’s only some knowledge factors that they’ve, like, oh, can we have one other assembly? Are they responding? However you’re not likely getting that purchaser engagement. After which, along with that, you realize, actually cumbersome and handbook methods to teach the gross sales reps. Simply—I can inform you—doing a pitch session a 12 months in the past with out Highspot, it was so cumbersome. Simply having to construct out what’s the discuss monitor, sharing that video by way of e-mail that we recorded of the pitch, after which coming along with a rubric after which making an attempt to do all of the scoring. It was very labor-intensive.

RR: Yeah, I believe you’re spot on with these challenges. There are issues that we’re actually listening to from our clients, we really feel ourselves, and different organizations are speaking about. And I believe the large factor is that everyone is making an attempt to resolve for them. And so, as you sort of talked about just a bit bit, you may have discovered a platform that will help you with that. So I’d be curious should you might inform me a bit bit concerning the strategic benefit of an enablement platform and the way it’s serving to you sort of overcome a few of these challenges that you simply’re seeing.

RH: Completely. So utilizing Highspot is a dream come true, to be sincere. Primary, you realize, having one central hub for gross sales content material is so crucial and so vital. So I really feel like our gross sales reps which are within the Highspot surroundings now not really feel like they’re digging by way of e-mail or SharePoints or occurring a staff website looking for that collateral.
So that could be a large effectivity acquire, but in addition consider job satisfaction. These sellers really feel like, wow, that is a lot simpler for me to navigate. I might additionally say, once more, going again to the real-time insights and analytics from purchaser engagement—so now we’re capable of see what content material is being seen, and it’s additionally serving to us tailor our follow-up in addition to having the ability to shut offers sooner.
The opposite I might say is constant teaching and coaching. So going again to the instance I simply used—very handbook course of traditionally—however having the ability now to leverage AI to offer suggestions immediately is unimaginable.

RR: Great. That’s completely what I like to listen to, and I’m tremendous excited that you simply’re discovering these wins already so early.
Excited about platforms and enablement expertise, I’d wish to possibly name out a win that we’ve heard by way of the grapevine, which is that though you’re early in your journey with the platform, you’ve already achieved a extremely spectacular 96% recurring utilization fee. So I’d actually love to listen to what a few of your finest practices for driving that adoption are and the way you’ve achieved that.

RH: Yeah, completely. So proper out of the gate, timing-wise, this labored completely as a result of we had been having our gross sales kickoff assembly in particular person, and so we used that as our launch, proper? So we had been capable of get the hype going, and we had periods the place we did a whistle-stop tour of all of the instruments, key capabilities, and actually obtained individuals enthusiastic about what was coming across the nook.
So after our SKO, we then did what we referred to as necessary kickoff implementation calls to get everybody arrange. And what we actually wished to make it possible for we didn’t do was one huge bang as a result of we all know there are such a lot of options and capabilities within the platform that we wished to be actually intentional about phasing that out.
So the very first thing that we did is we targeted on content material administration. Once more, you heard that was certainly one of our challenges. So we wished to make it possible for we had one cease store for all of our content material and make it tremendous simple for individuals to navigate and discover something that they want for his or her gross sales cycle.
Along with that, the following factor we wished to do was roll out digital gross sales rooms as a result of, once more, you heard that was a problem. We wished to begin to see purchaser engagement. In order that was very well acquired by your entire group. So it was very simple for us to get them excited and into the software and the repeat utilization. In order that was the place to begin.
Along with that, we began and proceed to host each Friday an optionally available drop-in workplace hours name. And that is actually nice as a result of individuals which are out there, they’ll leap in, they’ll hear in the event that they don’t have questions, or others will really ask questions, which then drives dialog and likewise highlights successes. As a result of in these moments, you realize, individuals are beginning to speak about, oh, you realize, that is how we did it, or this labored for me. You actually begin to see a few of these true successes come to life.
I believe the opposite vital piece is ensuring that we had our govt management staff and different leaders be advocates for Highspot—so ensuring that they’re speaking about it of their conferences, that they’re highlighting it on the town halls.
And in addition, as we’re beginning to see a few of the knowledge and the proof factors, I, together with different leaders, are sharing these out by way of e-mail or on requires recognition. So issues like recognizing prime customers of Highspot, people who constructed probably the most digital gross sales rooms, people who had probably the most content material seen, or individuals viewing their digital gross sales room.
After which I might sort of wrap that up with additionally—we’ve had some individuals create some actually artistic intro movies that they’ve included within the digital gross sales room. We’re ensuring that we’re sharing these broadly so individuals can spark new concepts on how they need to present up of their digital gross sales rooms.

RR: That is all actually nice recommendation, and I believe very useful suggestions. I like the thought of tapping into that aggressive intuition in your salespeople—who has probably the most pitches, who has probably the most views. That’s one thing that’s gonna ignite exercise for positive.
So now, considering that you simply’ve achieved this adoption and you’ve got your sellers purchased in, I’d like to dig a bit bit additional into possibly what’s subsequent for you. I’ve heard that you simply’re planning to leverage Highspot AI capabilities to drive scalability and effectivity. So are you able to share a bit bit about the way you’re constructing AI options—issues like assembly intelligence—into your enablement technique going ahead?

RH: Yeah, completely. So we’re actually enthusiastic about leveraging the AI options and assembly intelligence. The truth is, that was one of many promoting factors once we had been going by way of the gross sales cycle with Highspot.
Primary is we love the truth that you’ll be able to ingest assembly recordings into the platform and straight away, utilizing AI, get some suggestions on what I might say is like efficiency suggestions.
So I like having the ability to see stats on how a lot share of time a vendor spoke versus a prospect—as a result of we would like that to be 20%, roughly, proper? And we actually need to do all of these high-gain inquiries to have our prospects open up and converse to us, particularly, you realize, throughout discovery.
The opposite factor that I actually love is utilizing supply insights. So there’s the pitch variation, tempo, and filler phrases, and that’s actually useful for those who have by no means used a software—to share that with them. They possibly do not know what number of occasions they are saying “proper,” “um,” “you realize,” all these completely different filler phrases. And so it’s actually nice to provide them that consciousness and to additionally present the tempo as a result of some individuals are quick talkers and a few possibly are a bit bit slower, so it offers them some intel on the right way to enhance.
The opposite factor that we’ve actively began utilizing is the follow-up function. So you will get fast seize or, you realize, a transcript that then reveals you subsequent steps and actions. So it’s a time saver, and also you don’t really feel like it is advisable take notes. You may simply let your self give attention to the dialog and be an energetic listener.

RR: Superior. I like the worth that you simply’re seeing in a few of these options. I actually like to listen to concerning the imaginative and prescient, so I might like to possibly hear a bit bit about the way you’re bringing that imaginative and prescient to life and what that technique is.
In Could, you really joined us right here in Seattle for a workshop on our real-world teaching capabilities, and also you shared with us that you simply’re at present testing them with a pilot group.
So I’d love should you might sort of lay out the way you’re rolling out these capabilities, how the pilot’s going, and the way you’re sort of empowering customers to begin leveraging this software.

RH: Yeah, so that you’re proper. I did attend the assembly in Seattle and it was unbelievable. It was such a terrific alternative to study extra concerning the capabilities and begin framing up, you realize, our go-forward imaginative and prescient of the place we need to go together with this.
And I might say you’re proper—we’re nonetheless very a lot within the early phases of leveraging this, particularly, you realize, the teaching capabilities. So what’s within the works is, you realize, we’re beginning to construct out pitching workout routines for various business nuances and purchaser personas, and I believe that’s gonna be tremendous useful to actually get our sellers snug with completely different discuss tracks primarily based on completely different people that they’re chatting with.
So to me, that is likely one of the first issues that we actually need to give attention to, and we’ll be popping out of the gate quickly.

RR: Superior. Effectively, I can’t wait to listen to about the way it’s getting into a couple of months. I do know plenty of work to be finished, however I’m positive plenty of wins sooner or later.
Talking sort of of down the road, I’d wish to possibly flip to your measurement technique, particularly, you realize, as we talked about, figuring out that you simply’re a frontrunner with a powerful analytics background.
I’d be curious—in the case of enablement applications like this new teaching initiative, what key metrics you’re monitoring to measure their influence, after which possibly what success seems to be like within the subsequent 12 months or so.

RH: Yeah, I believe we’re monitoring a mix proper now of adoption, engagement, and efficiency metrics, which I believe is basically vital as a result of we’re nonetheless within the early phases of rolling this out.
So we need to make it possible for individuals are adopting it, after which we need to be sure that from an engagement perspective, we’re beginning to see individuals leveraging suggestions and issues of that nature—and efficiency metrics. So I’ll dive a bit bit deeper into that.
So positively we’re taking a look at, you realize, the p.c of reps who’ve accomplished teaching modules and periods, p.c who accomplished teaching duties, and suggestions rankings for gross sales reps.
Along with that, we’re taking a look at issues like leveraging conferences intelligence metrics, comparable to, you realize, these discuss ratios and the objection dealing with—as a result of the opposite cool factor is on the backside of the recording, it reveals some key, I might say, like competencies. And I’m undecided the right way to phrase that, nevertheless it’s actually useful for a vendor to say, okay, this was an space the place I ought to have been specializing in objection dealing with, and possibly I didn’t, proper? So a few of these issues are actually vital proper now.
After which efficiency metrics as effectively. So we’re taking a look at quota attainment, pipeline development, conversion charges, gross sales cycle size. And for me, you realize, these appear to be the largest indicator of success. You realize, since you actually need to see that ROI.
You realize, we’re beginning to see a few of our DSRs that, within the early phases right here, we’re profitable enterprise. And we do really feel like this can be a sport changer for us as a result of we’re displaying up in another way.

RR: Superior. I like to listen to that. And as I stated, I can’t wait to listen to extra about how the momentum grows over time at Direct Journey.
Possibly returning to the current, I do know you’re nonetheless early, however I believe it’s vital to speak about your wins, proper? So I’d like to know—possibly key wins or issues that you simply’re happy with that you simply’ve achieved up to now. Something you’ll be able to share with us?

RH: Yeah, completely. So I might say, you realize, by way of this pilot and launch that we’ve finished, now we have had gross sales reps simply completely elated once they ship out a digital gross sales room, and the very first time somebody takes a take a look at the room, proper, they usually take a look at the content material, they’re sending messages in chat like, oh my gosh, it’s working! And that in and of itself is a testomony as to why, you realize, we rolled this out.
Along with that, like I used to be simply mentioning, now we have already some sellers which have created and used digital gross sales rooms for your entire gross sales course of, and it has shortened the gross sales cycle.
Now we have a couple of people the place they began at discovery utilizing an intro video, updating some content material and collateral about our tech stack and companies, after which used all of it the way in which to beginning to put up the proposal and pricing.
After which there we’re—we received the enterprise proper after that. So it’s fairly spectacular. So I believe these are the large wins. Simply once more, you noticed the utilization, you realize, within the excessive nineties. We’ve obtained many digital gross sales rooms which have been created, and we’re profitable enterprise because of it.

RR: Great. I believe that rep suggestions says rather a lot. If you will get your reps excited, you’re getting exclamation factors by way of Slack—you realize you’re doing one thing proper. It looks like you and your staff are doing actually nice work.
And I simply need to shut with one final query. I do know you’re deeply concerned in mentoring, and also you’re a mentor within the GBTA WINiT group.
So to shut, I’d love should you might share with us one or two items of recommendation that you’d give to different ladies seeking to develop as leaders and drive influence for his or her group.

RH: Yeah, completely. I believe the primary factor that I might say to individuals is: say sure. There are such a lot of occasions the place a possibility comes up—whether or not it’s a stretch objective, a possibility to take part in a venture, or to even apply for a place.
So many occasions I’ve talked to ladies the place they really feel like, I don’t have the talent, I don’t have the data, I don’t really feel snug taking that subsequent step. And I all the time problem them to say: what’s holding you again and why?
Proper. One of many issues I all the time share with them is a number of examples in my profession path the place I’ve stated sure. I used to be nervous. I actually didn’t have the expertise or possibly even the talent. However I didn’t need that to carry me again, as a result of if somebody is keen to spend money on you, that’s the testomony in and of itself, proper? That’s the reply.
So take that leap and have faith in your self and provides it a whirl.
And the opposite factor that I’ve had lots of people say many occasions is: oh, now’s not a great time. And there’s all the time causes to carry again. And I all the time reply: if not now, when?
There’s all the time going to be one thing. So recover from that one thing and simply go for it.

RR: That’s nice recommendation. I like the thought of simply, you realize, spend money on your self. There’s by no means a greater time than now. I do know I’ll actually be taking that to coronary heart.
However that’s all I need to say—thanks a lot for becoming a member of us at present. It was unbelievable to study a bit bit extra about you, your work, and the unimaginable trajectory that Direct Journey is on.

RH: Superior. Thanks a lot. I actually recognize the chance.

RR: To our listeners, thanks for listening to this episode of the Win-Win podcast. Make sure to tune in subsequent time for extra insights on how one can maximize enablement success with Highspot.