End-to-end sales plays that drive real revenue growth, with Nicholas Hill

Speaker A: Welcome to the Sales Enablement Innovation Podcast, brought to you by the Sales Enablement Collective. Each episode we sit down with sales enablement and revenue leaders from around the world and invite them to share their expertise and experience with the community. Welcome to the podcast, Nick. Thanks so much for coming on.

Speaker B: Hey Daniel. Uh, yeah, thanks for having me. So excited to be here.

Speaker A: Before we kick off, could you introduce yourself, Explain a little bit about your enablement background, what got you to this point in your career. Let the audience know a bit about who you are.

Speaker B: Uh, yeah, absolutely. So, um, my name is Nick, I'm director, uh, of Enablement at Crunchbase and I've been in, uh, the enablement function, uh, in some form or fashion for about eight plus years now. After college, I started my career in sales. I quickly moved into training and development because I just, I love to teach. Uh, my teaching is a huge passion of mine. I really wanted to do that but, but when I was training and developing, I really missed that rush and impact of sales. You know, I missed being in it, I missed being in the heart of it. And so I was talking to a friend one day and I was like, man, I really wish I could, I could be a seller, but also a teacher. Ah. And he said, you know, there's a job for that, right? It's, it's called sales enablement and that's something that you could do. So I combined the two, I moved into enablement and now I've been at Sprinkler, Miro, now Crunch Base. I've trained over a thousand reps, uh, doing everything from onboarding to everboarding to coaching, um, and never, uh, looked back. It's been an incredibly exciting career.

Speaker A: I love that. Really serendipitous to end up having someone who knew about enablement right at the right time as well. Uh, that's really great. So today we're talking about end to end sales plays and enablement's role in those. Before we sort of get into the nitty gritty of the details and get really into the depth of it, could you explain what you mean when you say an end to end sales play and what, why you felt it was sort of an important topic to share with the community just to get everyone on the same page.

Speaker B: Yeah, definitely. And you know, the term sales play is kind of a loaded term. It means a lot of different things to a lot of different people. So to me a, uh, sales play is a specific outbound strategy that you enable your sales reps with so that they can book more meetings, anything that falls under that category, in my opinion, is a sales play. Um, you're helping reps to go after a specific audience. Um, you know that this audience can benefit from your solution. And the way that you're doing that is you're equipping them, you're giving them the ideal Persona to go after, the messaging to go after them with the outreach assets, the discovery questions, the value prop, and you know, I'll give all the specific steps in a moment. Um, but the reason I think that this is so important, Daniel, is that a lot of times as enablement practitioners, we struggle to prove our impact. We, we know that we're moving the needle in a lot of different ways, but it's really hard to put a number on that. And I've struggled with that my entire career. And, um, you know, I know that we're going to talk about that a little bit later, but I think the biggest impact that I've seen with salesplays, um, for my own career is that you can tie that revenue impact to what you're doing. And that's why I think it's so important.

Speaker A: I love that. And I guess to jump then right in. Could you explain a little bit about sales play process and what that looked like during your time at Miro? I know that's something we spoke about before, uh, recording. What was that sort of sales process? Uh, sales play process. Like what was the sort of experience? What was the. Where did it come to be? And I guess bring us through what that looked like.

Speaker B: Yeah, sure. So, you know, when I was at Miro, I was in charge originally of the onboarding function. I was not thinking about sales plays, I was not thinking about long term kind of ever boarding revenue enablement. And, um, I had a PMM partner and a strategy partner approach me and say, we want to try something, we want to test something out. We're going to create a specific Persona and we're going to give it to our reps and enable them to go after it. So if you haven't heard of Miro very, very quickly, it's an AI powered collaboration platform. It helps teams kind of build products and ideas. It does that through like online whiteboarding, deep integrations with collaborative tools. Um, that's important because I'm about to explain how we used it. So we looked at our platform, we looked at what Miro did and we asked ourselves, okay, what is a specific use case that Miro can help with? One that we know is successful, we know that it's brought in money before and we settled on, uh, what is called product planning or PI planning. It's something that a lot of product and engineering teams do and they spend a ton of money on this event. And we knew that if they moved that event to be virtual with Miro, they could save a lot of money. That was a specific title that we knew we could go after and a specific use case we know would benefit them. And that became our first sales play. So we now wanted to go to our teams and enable them to uh, go after this in the right way. So the first thing we did was we picked a target list of titles, six specific titles that we knew would benefit from this use case. Um, so think like product team leaders, scrum masters, agile practitioners, et cetera. We went to our team and we said, this is our sales play. These are the titles we're going to go after. Here's exactly who they are, here's what keeps them up at night, here's what they care about. So the first step in enablement was let's train the titles. The second thing we did was we trained on outreach and we made it super easy for them. We gave them specific outreach materials that they could work with. So we pulled together case studies of all the companies we were already doing this with. Um, we had our PMM team create one pagers, customer facing assets that they could use to run these rituals better. And we built one outreach sequence and yeah, we did some A B testing and stuff too. But ultimately we created a very simple kind of six step sequence. A couple of phone calls, couple of LinkedIn steps, very value driven. And we, we kind of spoon fed it to our reps, which, if you're in enablement, you know how important it is to make things easy for reps, otherwise they're not going to adopt it. Um, and so now we've given them the contacts, what to do with those contacts and the outreach sequence. Then we move to. All right, the last thing that you need to be successful is a quick discovery guide and a value prop. So we gave them about four to six discovery questions that we knew would be incredibly impactful for this specific group. And then we gave them a value prop of how our product Miro could specifically solve that challenge for them. So I realized as I'm talking to you about this, Daniel, I know that this sounds like sales 101, right? You're listening to this and you're like, yeah, okay, yeah, you got an audience, you got some messaging, you got discovery questions. The thing that makes it so impactful as a sales Play is the specificity. It's the fact that we are saying, no, no, no, we're not going after a bunch of audiences here, we're going after one. We're going after one specific type of person that we know can benefit. And so we set up the metrics, we set up the feedback mechanisms to track the success of it. We assigned everybody a list of contacts to go after and we were off to the races. We basically let the AES loose on this group of contacts, knowing that they were equipped to handle it. Um, and we generated over 100 meetings, uh, within 90 days. And so we saw a, ah, huge amount of success from this.

Speaker A: That's really impressive and I love the fact that, yeah, I also stress the sort of cross collaborative aspect of that. You were talking about working with product marketing on the content and how it was a sort of meeting of the minds sort of came together with that. It's really interesting. Sort of see how that came to be, I guess. Um, you spent a lot of time working on this. You've seen what works, what doesn't. If our listeners are thinking about sort of installing this, or thinking, yes, this sort of specificity is sort of what we're lacking. Let's start with the do's. What do they need to do to sort of get it right? Because I'm sure there's a lot of ways that can go wrong as well.

Speaker B: Yeah, definitely. And I think, um, you know, if I'm being honest with you, Daniel, at Miro it wasn't like an instant success right off the bat, right? We, we struggled a bit to figure it out, we over complicated it. So, you know, one of the first things I would say is you need to get very specific. That's what makes this so successful. So choose one problem so that your platform solves to start with. So if I'm at Zoom, I might say, okay, Zoom obviously does a lot of different things for a lot of different people. So one problem that Zoom solves is that it helps sales trainers like us run virtual workshops that don't suck. Right. So I come in and I say, cool. Zoom does this one thing for this one title, sales trainers and that's who I'm going to go after. So get very, very specific. That's the first one. The second one is make it incredibly easy for your reps to follow. If you can pull a list of the job titles in LinkedIn, sales NAV or Zoom Info or whatever you use, pull that list first. I would start with like new hires in that title in the last 90 days. Get a list going. Make sure that you're specifically assigning this out to reps. I know it sounds a little like hand holding, but you kind of have to handhold a little bit at the beginning, at least for the first one. The third one that I would recommend. And I'm sure you've talked about this a lot on your show. I think I've heard a few episodes on it. Use AI, right? Use AI to help you automate everything that you can. When I was creating these sales plays with my counterparts Jamie and Lindsay, I was using Chat GPT to help me build the sequences, the discovery guides, the value prop. I used Chat GPT and Perplexity as thought partners to kind of uh, to hone in on, on what we were doing there. Um, and, and give it context, case studies, assets, quotes that it can use to build you outreach sequences. Um, the next one is keep your value prop simple. So you want to make sure that, you know, your goal isn't to overwhelm the reps. I told you, you know, to make sure you're keeping it specific. Same thing with the value prop. You want to go to your prospects saying one thing, not 50 things. So give them one specific point of view, a quick elevator pitch, one paragraph tailored to that Persona. The next one is don't stop with just one. Right. Once we saw the success of that sales play, we immediately started doing sales plays for our security add on for different Personas. Um, and so I would encourage you to say, okay, we've tried it for this use case. Now let's try, you know, and don't do it all at once, but maybe the next two weeks or the next month or the next quarter, we're going to focus on this sales play over here. And then you start to see which ones are getting traction, which ones aren't, and you can, um, you know, pivot from there. Which leads me to my next one, which is track everything before you launch this sales play, before you enable it. Remember I said this is a way that, that we as practitioners can tie success to what we're doing. So track the entire funnel. How many contacts did you provide them? How many of those contacts did they reach out to? How many, um, clicks did you get? How many of those emails led to meetings and how many of those meetings led to closed one revenue. And if you do that, you're going to be able to double down on what works and see the success from there. The last two I would mention are you, uh, need to celebrate every single win from this play in enablement, we don't celebrate our wins enough. We go in, we enable something and then we walk away. So what I would recommend doing is go in, enable it, but then stick around and wait for those wins to come in. And the second a win comes in, evangelize it across the business and say, this is what we did, we dissected it, we understand what works and we're going to continue to do that. And then the very last one and uh, I know I've said a ton of them, but you need to include your reps and your managers throughout the process. And Daniel, I know we're going to talk about including the managers here in just a bit, but for the reps, give them feedback mechanisms, let them in on, you know, uh, coming up with the discovery guide and the outreach messaging, uh, have them come to you maybe once every two weeks in a meeting to talk about what's working and what's not working out there and show that you're listening, um, and pivoting so that they'll continue to buy into the process. So those were all the steps that I think we learned along the way. All of the important lessons that Lindsey and Jamie and I were kind of taking down as we went through this.

Speaker A: I love that. That was an amazing run through loads to sort of pick away at. Ah, ah there. And we'll do that in a little bit as well. But I guess the natural follow up to the do's is the don'ts that listeners should be aware of. Where did you maybe stumble? Where were sort of lessons that you took away from maybe the less successful elements before we dive into the successes a little bit more there.

Speaker B: You know, I think one of the big things, and if, if my counterparts are listening, they'll laugh at this. But one of the biggest things we did was that, that we did wrong, I would say is we over orchestrated the entire sales cycle from beginning to end. We basically tried to turn the sales play into a min sales cycle and we shouldn't have done that. We, you need to remember that the idea, the goal, the objective of a sales play is to get meetings. So once you get to that meeting, allow your AES to run their natural strengths, to use their natural talents. Right. Don't try to over orchestrate all the way to a closed one deal. We were coming in, we were trying to tell them exactly what steps to take from every single meeting all the way through the demo, the evaluation, the pocket, um, and that was a mistake. So I think, you know, give them the materials to get to the meeting and allow them to use their strengths from there. Um, don't give up too early. That was a big mistake where we came in and we said, oh, we haven't seen any traction. It's been two weeks, you know, I don't know what's going on. And luckily we had good sales leaders that were like, yeah, these things take time. You know, it's not something that's going to see traction. Remember that it takes a lot of touches to get a meeting. So when you're enabling these reps, I would encourage them, you know, mentally, psychologically, you need to tell them, hey, this is going to take some time to see traction. So don't give up on it too early. Um, the next one, I would say this is a big mistake that we made at first. Don't be afraid to pivot if something isn't working. So if you are running this play and you see that the emails aren't being opened, it's been like a month now, you know, you're not getting to meetings or, or a, uh, rep raises a red flag and says, hey, I was in a meeting and I got laughed out of the room when I gave them this value prop. I don't think this value prop is the right thing to go to market with. Listen, don't be afraid to pivot. Um, because the benefit of a sales play is that it's meant to be agile. It's meant to be something that you can change on the fly to meet the needs of your reps and ultimately your prospects. Um, and the last one, I think every one of my enablement counterparts will laugh at this. But don't assume the managers are going to take it from here. Right? Don't assume that the managers are just going to take your sales play and say, great job, you enabled it, I'll take it from here. I'm going to go run with it. Um, the managers need handholding too. Not because they're bad managers, because they're busy. They are so busy, they're being pulled in so many different directions. They want to be able to own this sales play with their team, but you need to be able to make it easy for them. And so don't assume that the managers are going to own everything. You need to be involved through every step of this sales play enablement, um, from beginning until, uh, you would consider the play to have been run. And I think those are, those are the big don'ts that we discovered.

Speaker A: Amazing. Really interesting. Also because it's easy to sing about the successes, but sometimes you can learn just as much from, from the failures as well. So really interesting, especially the points about being agile, because I think it's very easy to get set in your ways. Bogged down. We've decided we're going to do it like this. Let's stick it through. But you raise a really good point there. I think that's a really good springboard actually, to go into the topic about managers. Let's look at that a little bit deeper. What did that sort of relationship with the managers, uh, and enablement look like? Uh, you touched the challenges a little bit. Um, how did you sell it to them? I guess in the beginning, just overall, that sort of manager enablement piece, when it came to Salesforce, what did that look like?

Speaker B: Yeah, you know, I've had a lot of trial and error in my career when it comes to working with managers and I, I have met some truly great managers in my career and none of this works. If your managers aren't bought into the idea, period, it's all going to die on the vine. So you have to be very, very considerate of what your manager's priorities are, how they want this slotted into their team's workflows and how they're going to coach it and enable it on their side. Manager is first enablement, right? In my opinion, they're one of the most important enablement practitioners out there. So the first thing that you should do is ask for their input on what sales play to run first. So when I, when I, you know, we maybe made this mistake is we came to them and said, you're going to run the product planning, PI planning, sales play. And a lot of our SMB, our corporate managers, they came in and said, that doesn't really work for our size of business, so we need something else. We didn't think of that. And if we had brought in the managers earlier, we would have. So the first thing you should do is ask for their input on, um, what sales plays to start with. Ask them what, uh, titles are being underutilized, what use cases are bringing in big money that they're seeing out there. Um, the second thing is have managers review every asset that you create. It doesn't have to be every manager, but bring in a few of the popular managers, right? The ones that are kind of culture setters and have them review the outreach sequence that you come up with. Do the kind of BS sniff test, right? Like, is this something that would actually pass muster out there in the market? Um, have them look at the Discovery questions. Is this something you would actually say on a call with a customer or prospect, have them look at the value prop, um, make sure that you're not giving them, I hate to call it this, but kind of like marketing fluff, you know, we don't want to give them marketing fluff. We want to give them something that's really tactical. So bring the managers in earlier. Uh, it's only going to help you in the process. The next thing I would say is meet with your managers regularly while the sales play is going on to understand what they're hearing from their reps. Reps are going to talk to them in their one on ones about the sales play and they're either going to say, wow, this has been really great, it's getting me a lot of meetings or they're going to say dude, this sucks. I don't like this. This is not, it's not working, it's not getting traction. So meet with the managers regularly while that sales play is running to get their feedback. Um, give them dashboards, let the managers see how their reps are doing. Give them a manager specific dashboard so they know where their gaps are, what to coach, what not to and create some healthy competition with it. You know, put the managers up against each other. In sales, we like to have some healthy competition. So make sure that you're uh, you're putting up. If one manager is executing a play better than the other, kind of riff on that a little bit. Also if you see a manager that's succeeding more than others, maybe their team's doing a bit better at running the sales play. Meet with that manager, ask them what are you doing differently, what are you coaching? How are you doing this with your teams? Because you want to evangelize that with the rest of them. And I think if you do those things, your managers are going to have fun with this. They're going to use their natural strengths as managers to coach and enable this and you'll see way better traction.

Speaker A: That makes a lot of sense and I guess it's, it's related to something you touched on earlier as well. You uh, mentioned how the sales leaders, uh, we're actually sort of encouraging you to give it a bit of time. How, how was that sort of relationship with the sales leaders as well? They were sort of bought into it as well because we hear, you know, enablement, buy in is, is can be hard to come by. Um, I guess with the managers that, that was all really, really interesting. With the sales leaders they were just as keen. How did that sort of develop, I guess.

Speaker B: Yeah, you know, we got very lucky because this was something that was actually driven by the sales leaders. So we had, um, you know, our, our VP of, of sales, Ammer, he came in and he said, this is something I've seen work at other organizations. I would love for your team to take this on and run a sales play with ours. Um, but what I would do, what I would say is you want to go to your sales leadership with an. An open mind and a mind towards experimentation. You want to let them know, hey, this is something that I think is going to drive specific numbered meetings with prospects that care about a value prop. Can we test this out? Is this something that you'd be willing to have us test with your managers? And it's a form of outbound that we've seen work. Um, you know, and, and we can set up dashboards so that you'll be able to see early wins as they come in. So really approach it with an open mind. Let them know that it's something that's worked at other orgs. You know, just like when you're selling, you bring in case studies. Right. So let them know at other orgs they've seen success running sales plays. And I want to try to run one here. And I think that. I think they'll be more open to it than you would think, because a lot of sales leaders, they are desperate for pipeline mechanisms. Um, so make sure that you kind of, uh, that you push this forward as a pipeline generation mechanism.

Speaker A: That makes a lot of sense. And I think the last sort of the piece that's missing is, and you mentioned it earlier, the, um, tying it back to revenue and tying that sort of enablement, revenue, sales play sort of trifecta together. That's a difficult thing to do. Like you mentioned. What was that like? Uh, you mentioned sort of some of the metrics and the dashboards overall, that sort of big picture. How did you actually manage to say, hey, this was enablement? We did really good here. Look how great we did, I guess. What did that look like?

Speaker B: I know. It's such a nice moment when you can say that. And let's kind of, you know, if we take a step back and we think about how difficult it is to prove metrics and enablement. A lot of it is qualitative. You're sending out surveys, you're doing certifications, you. You're showing maybe recorded clips of things that they've done that implemented from your workshops. And those are all great things. We should continue to do those things. Um, but a lot of the metrics we do, when you think about, like, ramp time, time to first deal, a lot of those, A lot of people can take credit for those. You know, the recruiting team can take credit, the sales leadership, the manager, the rep themselves, they can all come in and say, well, actually, that was me that did that. Through natural talent or natural recruitment, recruiting or adoption. The benefit of a sales play is that it didn't exist until you got there. So you can come in and say, from the very beginning, I'm setting up the assets. And of course you're doing it with partners, PMM and sales leadership and managers. But you can come in and say, this is my baby. I am going to create a sales play from scratch. This Persona, this messaging, this discovery, this pov, it was all built by me. Um, so I feel comfortable taking, uh, a large portion of credit for what comes out of it. And it goes back to what I said earlier about tracking the entire funnel. You need to be able to come to them at the end of this, your leadership team and your managers, and say, I provided, um, 756 contacts. From those 756 contacts, we sent 14, uh, hundred emails. From those 1400 emails, we had 97 meetings. From those 97 meetings, we closed $192,000 in revenue. That's the North Star. That's what you're going after. Um, and without that dashboard, without working closely with your RevOps team to set it up before you enable the play, um, you won't be able to tie revenue, uh, tie revenue to your success. So make sure you're including the RevOps team. Make sure you tell them exactly what you're looking to track. Get the dashboard set up with the contacts that you've pulled before you start any of this, and then go enable the teams so that you're able to see that success at the end. Um, and when you do that, I, I truly hope for each of you that you have that same aha. Moment that I did where you're like, wow, this was really impactful and I'm so proud of this.

Speaker A: That's amazing. That's the, the everything you're waiting for at the very end, right? If you can, if you can pull that together. So I love you. Sort of the deep dive into that before we wrap up. I'm looking at the time as well in terms of putting, uh, yourself in the shoes of a listener who's thinking, yes, this is great. Um, I want to get sort of started on this. What's the sort of golden nugget of advice that they need to sort of take away from this episode. What's the one sort of key to the sales play? If you can sort of distill it down into a little short takeaway, uh, for anyone who's listening, I.

Speaker B: You know, I think. I think my biggest piece of advice for this is it is not going to be perfect right off the bat. And don't let, uh. What is that? What do they say? Don't let perfect be the enemy of good. Right? I want you to get started. I want you to just try it. I want you to get in the mud and say, let's try and figure this stuff out together. Pull in your PMM partner, your strategy partner, your rev ops partner. Just book a meeting. Just book a meeting with them and say, hey, I was thinking about trying this thing and I don't know what it's going to look like, and it's going to be a little messy and we might make mistakes along the way, but I think it's going to get us some meetings, I think it's going to generate some revenue, and at the worst, worst possible case, it's going to teach us something about discovery, about value, props about our ability to enable, outbound about our manager's ability to enable and coach. You will always learn something from running a play like this. So my last piece of advice is just get in there, start making moves, try it out. Um, you're definitely going to learn things and have some success along the way.

Speaker A: That's a brilliant takeaway. I think that is. We're up to time, unfortunately, but, Nick, thank you so much for coming on and sharing that. That was an amazing episode. I've learned so much. We really went into the nitty gritty of some of those details. So thank you so much for coming on. I can't wait to get this out to the audience and be awesome.

Speaker B: Absolutely. Thank you so much, Daniel. I'm a huge fan and I love listening to all of your guests. So very excited and honored to be here.

Speaker A: Thanks for tuning in to the Sales Enablement Innovation podcast. Be sure to follow us on your podcast platform of choice so you don't miss a thing. And if you're hungry for more sales enablement content, Visit our website, sales enablementcollective.com for articles, events, and an easy way to join our Slack community, home to thousands of your sales enablement peers.