Enable salespeople with AI like an Optiversal PMM

0:02Hi friends, welcome to Product Marketing Adventures, the only show that takes you beyond theory and into the real execution of product marketing. My name is Elle Grossenbacher, your trusted guide and host of this show. In each episode, I bring in expert product marketers to co-host two segments of this show. First, a case study example of their work, followed by a messaging critique for companies we admire. So if you're a PMM looking for practical guidance and inspiration, you're in the right place. Are you ready? Let's go. If you're a millennial like me, you probably grew up watching Scooby-Doo on Saturday mornings.

0:42Every episode followed the exact same formula. There was always a terrifying monster, a ghost, a swamp creature, a skeleton, right? Chasing the gang, quote unquote, around some haunted mansion. Doors are slamming, hallways are spinning, everyone's running around in different directions. It's total chaos. But at the end of every single episode, they'd pull the mask off and it was never a ghost. It was the janitor, the shop owner, right? It was some guy trying to cover up something much more boring and much more human. I think that that is what sales enablement looks like when revenue starts slipping.

1:17The quarter gets shaky, deals start stalling, forecast gets really tense, and suddenly the monsters appear, right? We need more sales enablement. We need more messaging. You get the idea. Enablement becomes the thing chasing everyone down the hallways. But before we sprint into panic and spin out new messaging or crank out another battle card, maybe we should pause and ask, is this actually the monster? That's what we're talking about today. How to fix sales enablement when it's not working and make it truly impactful. And I'm so excited to welcome someone who has lived this transformation. With that, it is my pleasure to have Michelle Nieberding on the show.

1:56Michelle is one of the most thoughtful and execution-driven PMMs in the business. Let me tell you why. She's currently the Senior Director of Product Marketing at Optiversal. Before that, she led product marketing and sales enablement efforts at Treasure Data, building go-to-market strategy, messaging, and positioning for the new AI products and suites. Michelle has also driven product marketing initiatives at MetaRouter, Iterable, and Qualtrics, giving her a broad and battle-tested perspective across tech stacks and sales motions. But here's what really sets Michelle apart. She's one of the top product marketing voices on LinkedIn with thousands of followers who look to her for sharp, practical thinking on AI, messaging, enablement, and real business impact.

2:39She's known for relentlessly asking, is this actually working? And for using customer insight and experimentation to build enablement that actually drives revenue, not just decks and trainings.

3:00Michele Nieberding:Michelle, welcome to the show. Oh, thank you so much for having me. I'm so excited. I know you're currently at Optiversal, but the case study that we're referring back to today is really about your time at Treasure Data. So we will come back to Optiversal and talk about how you're applying some of the same lessons, some of those lessons now in your current role. But just to prepare us and get us set up well for the case study, tell us a little bit about what is Treasure Data for those of you or those of the listeners out there who may not know. So Treasure Data is a customer data platform. So when you think about anything you do online or things you do in a store, all the shopping that you might be doing, one of the things that Treasure Data does really well is stitches all that together and says, hey, Elle, that this is you doing all these cool activities so that it makes how they market to better, hopefully more relevant and more interesting.

3:50Michele Nieberding:So we do a lot of that unification, but now we're layering on AI to, you know, act out all the things that you hopefully want to do because you can't use AI if you don't know who you're using AI for. And that's where treasure data really comes in. So I'm a MarTech queen through and through. I've been in that industry, in that space and customer data, maybe more specifically for a very long time and super interesting to kind of see how that's evolving. Awesome. Okay. So that's going to be super helpful as we think about the context for the case study today. So with that, let's dive into the case study segment of the show.

4:23So this is where you'll walk through the case study example of your work, and then together we'll talk about what a playbook looks like. So the topic specifically for today is around sales enablement, maybe a little bit of voice of customer sprinkled in there. So take us back to treasure data. What was happening when you realized something needed to change?

4:41Michele Nieberding:I guess good news is there was a regular cadence for sales enablement. And when I say sales enablement, I mean a every single week, one hour dedicated to sales enablement. So it was blocked on everyone's calendar. Like that time was set. We come up with topics, the deck kind of your standard, you know, enablement things, but host that every single week for an hour. But with that, But sometimes we got the topics last minute. We're like throwing decks together. So like we weren't always fully prepared or sales didn't know what was coming. They started maybe not showing up because they're like, we can just listen to the recording or it's not relevant or they weren't, you know, prepared to attend that specifically.

5:16Michele Nieberding:And then I don't know what made it even more interesting, I guess, is the following day. There was also an hour for product office hour. So a little more technical, a little in the product, but same thing. One hour weekly cadence. You had your kind of I don't want to say random sales enablement. there was a regular cadence, which was good, but then you had office hours. It was just kind of like we were, you know, on that hamster wheel of sales enablement. It wasn't like, why are we doing this? It's like, we're going to do this every week and we're going to put the deck together and do it and send out the recording and check the box.

5:44Michele Nieberding:I guess what we'll get into today was like, was it really that effective? It seems like it's well intended, right? It's good to have a regular check-in with sales, but I could see how that very easily starts to turn into something that doesn't exactly align well with the end goal. So I guess like, take us back to what was the goal in, you know, meeting with every week and talk about how like, you know, maybe you were really busy, but not necessarily effective. I think that's the biggest thing, right? Like, again, it's one thing to say you've done sales enablement and the company was moving fast.

6:19Michele Nieberding:I think so many are right now in the world of AI, where you can build things more quickly, or you're trying to catch up to the competition because you can because you can build more quickly, right? There's more pivots and messaging, right? I've seen a lot of companies go through what I call an identity crisis. Like, there's a lot of reasons to do enablement, especially when you're moving that quickly. But like, to your point, what is the effectiveness of it? So we weren't really having good feedback loops, like we weren't hearing back from sales, what was working, what wasn't working, we weren't really getting to the root cause of like, why the sales enablement was needed.

6:51Michele Nieberding:It was everyone's talking about like let's enable on it but we weren't really even like putting a number to that like what what are we trying to influence what are we trying to impact is it revenue is it sales cycle whatever like we weren't really tracking anything like that and i think so we don't know the effectiveness we don't know the impact it's kind of like okay we did it cool but sales we don't know what you think and we don't know how it was impacting them and then what we found is even though we're putting all this time into it like we still weren't hitting revenue goals. And, you know, people that know me know if we're not hitting revenue, like I think product marketing needs to do something about obviously this is one of the many things we do.

7:29Michele Nieberding:So what's wrong? We're doing this, but it's not clearly not working because we're, you know, well below revenue goals. So we knew something had to change. Yeah. So you mentioned a ton of different signals where you know that like sales maybe isn't working as well as different tactics, right? when you realized that, okay, revenue is kind of the shared metric for the whole company. And it makes perfect sense that that would be, and I agree, product marketers should absolutely be tracking that as one of the metrics. And when you realize like, okay, this isn't working. We all agree stakeholders that were not satisfied with, you know, where we want to be.

8:12where did you do from there you know i guess like what was your what was your task at hand

8:16Michele Nieberding:yeah so again i think it's like take a step back and go back to basics i think it's so maybe common and easy almost like ptsd about why this happens in the first place like i don't know a cro a coo is like obviously this is a messaging problem right and that's kind of what sparks maybe this like hamster wheel of enablement like throw spaghetti at a wall see what sticks kind of situation like you started of course it's messaging and positioning and that's how product markets fall into that trap. So to your point, like, okay, so then what do you do back to kind of any problem you want to solve, right?

8:48Michele Nieberding:You really need to dig into like, what is the root cause of this not working? Okay. We know we're not hitting revenue goals, but we're doing this every single week. So like, what is, what is that gap? And so for me, step one, and maybe seems obvious, it's like, go, go talk to the reps, like actually have conversations with them. How are they feeling? What are they getting? What are they not getting? Yeah. You can go through customer calls, you can go through your gong recordings, whatever, nothing beats actually talking to the reps and like getting a real feel for like, what are they struggling with?

9:17Michele Nieberding:What assets are they using? What feedback are they getting from customers? Like the very human to human back to basics is having that conversation with, I think we talked about this before, like your best reps and maybe you're not so great reps, right? Like what are the best ones doing really, really well that we need to replicate? And then why are the ones that are struggling? Why are they struggling? And how do you, again, bridge that gap is a really interesting concept. But back to basics, talk to your reps. Okay, so you realize like, okay, we're not hitting revenue targets. You had different ideas around why that wasn't happening.

9:49But before you immediately just kind of like follow instruction on like, oh, go redo the messaging. You're like, hold on here. We're going to investigate a little further. You talk to some reps. I guess like what happened next as you're talking to reps? Did you discover anything interesting? Was there any other data that you looked at?

10:07Michele Nieberding:And this is kind of where you said, like, voice a customer kind of sprinkled in. And maybe two nuances that I think are important to call out here. One is, like, the questions that you're asking the reps. I think that's really important. Not just, like, what do you like? What don't you like? It's, like, why are you not hitting goals? Like, you don't want to put your reps on the defense, right? You don't want to say something is wrong necessarily that, you know, start off the conversation. So, like, I guess maybe one step back is the questions that you ask your reps are super important here. not just to like build rapport and trust which is obviously so important for our role but like to actually get to that root cause because you can say broad stroke like what's working what's not working but that doesn't get down to what you actually need to do good enablement so things like you know i love the ptsd element because we all have it but like what deals have you lost that you like keep up and i went we talked like what you know the bad ex-wife and you're still thinking about years later like there's always something that sticks in your mind that like you know i like I didn't you know know my competitors or we think we lost on price but I don't really know and like my gut tells me that it's not price even though the CRM says you lost on price right my opinion it's never price but you know back to like how are the refs feeling so that's you know something to think about and then step two is how do they want to learn everyone does this differently right so it's it's kind of getting to the root cause of how they're feeling but then how do they want to learn now what's tricky about that is you know again we all learn differently so is it something written?

11:32Michele Nieberding:Is it audio? Is it role playing, like speaking back and forth? There's all these different ways that you can do sales enablement. So when you know why you're doing it and how to do it better, it's like, okay, now what do we do? There's so many different tools and ways to do this, but it's kind of like you have to go through this experimentation process to one, see what your reps respond to well, to what they enjoy, what they're actually using. Of course, you can get stats on that. And then three, like what is coming off as actually effective? Like how are they remembering things we call this like recall or retellability what can they really grasp onto that when they finally have those conversations whether it's a new product new messaging whatever that they can actually like retell that story or that you know that thing that they need to do in that moment how to overcome that objection whatever it is that they have that recall to be able to do that quickly as you have to experiment with a lot of different like tools and ways of doing it for us, you know, the weekly call sales name meeting just wasn't wasn't doing it.

12:30Michele Nieberding:I'm not saying don't do that. It could be then that and something else. Right. But there's like so many other ways to engage the reps that you have to like reinforce what they're learning. I could see definitely having office hours. I think we have multiple places I've worked. We've had office hours for sales, of course. But it's one thing when you're like, as you pointed out, like just checking a box or just making a stakeholder happy versus actually putting very logical thought into what your enablement goals are and how you're going to achieve those goals. Okay, so what happened at the end of the day, right?

13:05Michele Nieberding:Like you ran some experiments. So ChargerData was really an enterprise solution, which of course, we all know, means long sales cycles, like tons of conversations, lots of shareholders, stakeholders, all the people are involved. And one of the trends that we were seeing, if we're really looking at like deal analysis was kind of like two things. One, we had a new pipeline problem. So we weren't getting as many prospects in the door as we wanted. So like the hook was wrong or the initial outreach wasn't right. So that was like the very, very start of the funnel. And then at the end of the funnel, we were like kind of losing in the last mile to like one of our biggest competitors.

13:43Michele Nieberding:So there were like, I don't know, gaps in the funnel. and we'll talk about that more in depth of like, here's clear areas that we're struggling within the sales cycle. What do we need to do to make sure our reps can like start off well and end really well, right? Can actually close the deal. So when we kind of re, I don't know, rejuvenated, whatever, fixed our enablement in terms of how we did it and what we were doing, we were seeing some really, really fast sales cycles happening. So we were getting better prospects in the door, like really, really great enterprise brands in the door more quickly, but we were getting from like initial conversation to POC within like a month.

14:20Michele Nieberding:And that was unheard of. So the speed at which not only were we getting more people in the door, like qualified enterprise deals that everyone's fighting for, but to get from that to like true POC in a month was just like unheard of. And we were seeing that more and more, which was really exciting. Yeah, that's awesome. Okay. So you actually fixed the like leaky bucket, but the leaky bucket was enablement, not like, you know, messaging or, you know, some kind of tool that you needed and didn't have. Okay. So in this story, what we heard was that you had the hamster wheel effect of sales enablement that was well-intended, but started to feel like a checkbox rather than, you know, being goal-oriented.

15:04Once you realized your signal of revenue started to drop, stakeholders got around, and you took the initiative to do some digging. You looked at win-loss data, you talked to salespeople, and then you ran a bunch of experiments to fix what you felt like was the enablement problem. And it turned out that you were right. And you're able to get and kind of close some of the gaps that you saw in the sales process. So what I want to do now is to take your story and to turn it into a playbook. So, and you kind of mentioned us a few steps already, which is great. It kind of gets us an early start in what this playbook could look like.

15:44But imagine if, you know, you're coaching me, I'm a PMM and I am trying to do the same thing. I have the same signals, right? Like I'm working on sales enablement and we're not hitting our revenue goals. And, you know, we've identified or I have I have a suspicion that sales enablement is the thing, the reason for that. So coach me and tell me what to do. Like, what is the step one that I need to take in order to try to achieve the same success that you saw?

16:13Michele Nieberding:Yeah. So I think kind of one, like you mentioned, like, what is that signal? Like, when should you even evaluate? So for us, it was revenue, right? So that is, you know, obviously a broad stroke thing, right? Just because we're not hitting goals doesn't mean like that sales enablement is the reason. And in our case, it was one of the big ones. But that is just one like kind of macro thing to look at. I think other things to consider, like, and this goes back, you know, we love a good PMM math problem, right? PMM math. But are you getting enough people in the doorway? Is there enough pipeline to hit goals anyway?

16:46Michele Nieberding:It's one thing to like, you know, have a certain pipeline and certain close rate. And like, you know, you do all the backwards math to say you need this amount in the pipeline. but especially again for us we are pivoting from like the cdb cdp category into this more like ai focused ai forward ai suites like this ai world which in the market can be a little confusing of the story that we're telling so there's like what is the pipeline being generated as well like just the market understand who we are what we're doing and what we're trying to solve in that market in that category so that that identity crisis too so it could be like it's pipeline plateauing it's you know that's beyond just revenue goals because that can include like retention and upsell things like that for us again like where where are you losing stages i worked for a company where i mean 90 of our deals were lost at the very end when it was us and one other person you know that was something to consider as well um and again like how many how can you get all the reps to be doing like are there 10 good reps are there two good reps is there one good rep like a veteran that's been there forever and everyone else is failing like yeah is that gap so there's all these things or signals to consider when you're evaluating like, hey, do I need to take a look at sales enablement?

17:55There could be any number of signals that tells you that you need to look at sales enablement. And one of those could be revenue, but it could, there could also be a number of different things that are happening in the actual, well, I guess ultimately it wouldn't be revenue, but, or maybe like the initial signal, but you dig deeper and then to know, okay, well, is it sales enablement or is it messaging? And for you, you dug really deep into like the sales cycle and you know where deals were starting to fall off and are you the PMM math that you mentioned like are you getting enough people through the door to begin with and I'm so glad that you looked at that just like standing up for the PMMs out there right rather than like your CRO no offense to him but like or her rather than like jumping into like oh I got to redo our messaging again then you're like hang on is that really the monster here like so if I'm trying to mimic your playbook.

18:44Here I'm digging deeper. I'm looking at the sales cycle. It's a lot of data analysis, right? Or not even Nesca analysis, just like gathering your information and, you know, looking at all of the signals right in front of you that tell you that it could be, that it could be a sales deployment problem. Okay. So number one, I guess, like diagnose that, like, you know, the revenue pipeline signals, as you said, then what's step two?

19:06Michele Nieberding:Yeah. Diagnose, I would say, build your hypothesis, right? Like what do I do? this is my favorite part is like the experimentation, right? Like, so you kind of know how reps are feeling and like what the gaps are. It's like now what, like what's going to work? Like what's going to be good? So for this, yeah, we tried a lot of things, some good, some bad, some like in between. So one of the things we did was an internal podcast. So I would go interview, you know, CS reps or the technical team, account management, you know, everyone in between the product team. I would do like one-on-one interviews about a topic and, you know, we would build a similar to this, right?

19:41Michele Nieberding:Podcast style interview, we would put it into a whole, you know, library that reps could listen on their way to work or I love a good podcast. And it like, and from a, like effectiveness standpoints, reps really listened to it and they would be 30 to 60 minutes. But, you know, for a small product marketing team, about five of us, maybe three of us could like consistently doing these interviews. And then also doing those weekly enablement sessions, It took a ton of time. It was like really, really hard to scale. So yes, it was valuable, but we tried to spin it out every week along with our weekly enablement.

20:15Michele Nieberding:And it was just very, very hard to scale. So to supplement that, we tried the notebook LM, like Google's notebook LM podcast style interviews. So the AI generated, you know, podcast style question and answer type of thing. So you could put in like a messaging doc or a recording where, I don't know, your product team was talking about a new product or customer calls that are talking about a new product, whatever it is and then notebook lm can turn that back podcast style audio so we would then pepper that in to our our library of podcasts which was obviously easier to scale but you do miss that like human interaction connection yeah or like the i don't know the war stories right you have a cs yeah person who's who has a really good story to tell maybe a customer like absolutely loves a new product or you know has certain pain points and they're excited for the like that kind of realness that can come through in like a podcast like this, which is kind of lost.

21:09Michele Nieberding:So we were like, okay, it scales, but maybe the effectiveness or the value that our internal stakeholders were getting out of it wasn't quite as strong. So we tried that. I think one of the most impactful things that we did was like AI role playing. So at a QBR, we were playing around with targeting a new persona, like someone in this case, it was paid media. So someone our sales reps had never really spoken to, never really targeted, didn't know a lot about. And so at QBR, we did like an AI role playing session where there would be a question, hey, I'm a paid media manager. And like, here's my problem.

21:44Michele Nieberding:How would your solution solve my problem? And the reps actually recorded their own audio responding to these questions. And of course, as sales reps love in real time, you see a leaderboard with a score. So how did, you know, Bob rank and then Kelly did test. And it's like, as a product marketer, fun to see right in real time, like, who's doing well, what their scores are. The engagement rate, yeah. And then, of course, you could see the best performing scores, like what did they say, how did they say it, maybe same with the lowest performing, and then you could go back to those reps and do one-on-one coaching, or you also could see what are reps struggling with for this persona that I would need to cover in an enablement session.

22:22Michele Nieberding:Then you can go into that enablement session and say, hey, I have data to say that this is what we need to talk about. And that practice, I mean, nothing beats saying it out loud. pitches and you know responses like nothing beats that kind of practice of verbally communicating it so that was really effective not only for engagement to actually get the reps to do it but the best performing reps did win money so if you can tie yeah what they care about right to to that it only makes it better and then that can again tee up like future enablement sessions because you have data to say this is what is working not working i also tried one of my favorite new ai tools.

22:58Michele Nieberding:It's called Eddie. It'll take, you know, your internal, again, messaging doc, FQ doc, if you have a product requirement doc, whatever, like maybe the team needs to know about, again, a product launch and messaging change, whatever you've thrown into Eddie, it builds out milestone, like learning points. It'll build out a survey, like questionnaire. So sales actually has to answer the questions. And, you know, it's like a survey that you don't have to create and I'll serve all that straight into Slack. So like where, you know, your sales reps are spending all their time anyway, or CS teams or whatever.

23:29Michele Nieberding:And you can change the questions based on team. If it is it, you know, pre-sales versus post-sales or the technical account team, whatever. And then similar to like the role-playing, you can see, are there questions that all the reps are getting right or wrong? Is there something you double down on? If there's again, a certain rep that's struggling to do one-on-one coaching, like the data that can, you can get from that, but also serve any, I'm a sucker for a Slack integration. So like anything that can come straight into Slack, like automated. Heck yeah. It's that reinforcement learning that you could take, that enablement session, the hour-long recording, transcript, whatever, put it into Eddie, have the automatic follow-up, and then see how reps are remembering the information or telling that story again.

24:09Michele Nieberding:And then one of the last things we tried that I think was maybe by far one of the most successful was having a customer join the enablement call. So we would tell reps ahead of time, so-and-so customer is joining to talk about their experience in the beta program for this new product launch. And so you kind of, it's the best, right? You let them do the talking and they can say, here's what we loved about it. Here's what we're excited for. And then it makes it so easy for a sale to retell it. Totally, so much more memorable. And again, if it's not coming from you, it's one less slide, one less, you know, less content you have to worry about.