Janis Zech: Hello, and welcome to another edition of the RevOps Lab podcast. Our guest today is Stephanie Middaugh, and very glad to have her. Stephanie is a real operator. She worked her way up from the deal desk senior sales operation specialist, various roles up to now being the head of global GTM enablement at a fast growing B2B SaaS company. Stephanie, very warm welcome.

Stephanie Middaugh: Hi. I'm so excited to be here. Thanks for having me out.

Janis Zech: Yeah. Great to have you. For our listeners, could you briefly introduce yourself in two or three sentences?

Stephanie Middaugh: So I'm Stephanie Middaugh, and I have been doing enablement for enablement focus for the past, like, seven or eight years now, but been doing, like, operations and been in tech SaaS, for the past thirteen, fourteen years, I think, which seems a lot longer than it actually has been. And let's see. I'm based in Utah, but originally from Southern California. Grew up with a love of teaching. I wanted to be a teacher when I was growing up, so I think enablement is pretty normal path for me. And, yeah, like, I — what else can I say about myself? I have two cats. I live with my husband. I started playing the drums, which you'll see these in the background. No. That's it. I'm kind of an open book, but that's me in a nutshell, I guess.

Janis Zech: Okay. Great. Yeah. Love it. I also have two cats, so I can connect there. So, yeah, I think you mentioned a lot of interesting companies, WorkRamp, Divvy, Zoom, DataStax, Sage. Currently, at Pinecone. And I think it's just always interesting to understand sort of, like, how you ended up where you currently are. So could you kind of, like, go a bit deeper on your sort of, like, professional journey?

Stephanie Middaugh: Yeah. Of course. So I started out in deal desk sales operations kind of arena way back early days at an ERP software organization at Sage Software. I was there for a good six years. Came across my first enablement role, which, the title was actually sales productivity at the organization. It was my first startup company, and that was a wild ride, but super exciting. Alteryx went IPO, so I got to see them kind of in early stage startup all the way through kind of going public, which was so exciting. I got pulled back into sales operations in that company, as they were, like, kind of revamping or building up the sales ops function. I did that for a couple of years. And while I was good at it, it was one of those things that I just, like, didn't really — I just, like, didn't love it. And I really miss doing enablement and training and supporting the sales team from that perspective. So I ended up moving over to DataStax. And that was, like, ever since then, I've been kind of on the enablement path. I found myself at really small, scrappy startup organizations like Divvy. Found myself at large organizations like Zoom. I was at Zoom in 2021 right after their just enormous, like, crazy ride, in 2020 post COVID pandemic. And then I've really, like, throughout my experience, I've learned that I really enjoy being on small enablement teams at a small scrappy startup building from scratch and everything. So, like, all of my experience has kind of led me to understanding, like, where I personally thrive the best and the most impact that I feel I can have on organizations, which is at small companies. So I love it. It's not for everybody. Startup enablement is definitely not for everybody, but I am a sick sick person, and I love it.

Janis Zech: Yeah. I think, what's the toughest thing about it, do you think?

Stephanie Middaugh: Startup enablement is very, very different, especially if you're, like, a team of one. You're having to do kind of all of it, the strategy and the build execution and the reinforce, like, all of the things. Things change on a pretty regular basis. There can often be a little bit of a sense of whiplash in that you start down, like, one path for one initiative, and then all of a sudden things just shift, whether it's the business, whether it's the market, whether it's a combination of all of the things. So being able to be nimble is challenging, especially when it comes to enablement, because it takes a lot of foresight into, you know, how am I gonna build this training, or how am I gonna support this program or initiative or whatever. So that's the hardest thing about startup enablement is it's scrappy. You don't have a lot of resources. You don't have a lot of time to execute. Priorities change on a pretty frequent basis. It can be a lot, and it's definitely not for the faint of heart. That's for sure.

Janis Zech: Yeah. It's a lot. Things are changing all the time, but that's kind of also the exciting thing. But if you have to rewrite the entire sort of, like, knowledge base and onboarding book for the third time, then —

Stephanie Middaugh: Yes. For sure. Yeah. Yes. It takes a moment too. You know? Just save the weight. Yeah. Just, like, just a moment. It's not a big deal.

Janis Zech: Yeah. Yeah. Cool. Okay. Perfect. So, yeah, I think in today's episode, we wanna dive deeper into the relationship between sales enablement and revenue operations. I think it's, like, a fascinating topic, personally, first of all, because I actually don't know that much about it. And so I'm curious to learn from you and with you. And the other thing is I think there's so many things you can sort of, like, break or make with good sales enablement, particularly, like, at a startup where, you know, you kinda, like, really get the first people on board. There's a lot of, like, hidden sort of, like, intangible knowledge often in the heads of the founders or, like, the first people that sort of, like, start there. And then you have these salespeople coming in. You have to onboard them and train them, and that can really break the entire company, I think.

Stephanie Middaugh: Yeah. Or — yep. Ideally. Yes. Ideally.

Janis Zech: Exactly. So I think it's just — you know, it's a great topic to talk about. So, Stephanie, in your own words, how would you describe sales enablement, and what does it mean to you specifically?

Stephanie Middaugh: Oh, such a, like, such a heavy topic, and it's an interesting one because this is actually a point of discussion and contention in some ways at some of the enablement conferences as everybody has a little bit different of a definition of what it can and should be. I'll give you kind of, like, my definition. I also believe very strongly that you should define enablement for the company that you're at and you're supporting because the enablement function at, like, Zoom at a large organization, for example, versus my enablement function at, like, Pinecone right now, world's different, like, vastly different as far as the approach that we were taking and what we were covering. For me, though, like, my brand or my view of enablement is all of the activities that support reps from BDRs through AEs to solutions engineers to customer success to make the most of those interactions with their customers and with prospects — at the end of the day, do they understand the product? Do they understand the internal processes? Do they understand the value proposition? It's all of the things that go into supporting those teams to be effective, productive, efficient members of the go-to-market revenue organization as a whole. That can include training. It can include process documentation. It can include reaching across the aisle and creating consumable content or one pagers or whatever for the teams with product marketing. It can be working with revenue operations really closely to streamline processes and identify, like, gaps and areas for improvement. It's all of those little things that feed into kind of the larger enablement organization. It's actually my favorite interview question when I have been on the market looking for, like, roles and whatever is to ask the leader that I'm speaking to, how do you view or how do you define enablement? Because that's gonna tell me whether or not we're even on the same planet and whether we can be successful together.

Janis Zech: Yeah. Yeah. If you can bridge that gap sort of, like, in whatever their definition is or, yeah, if it's just, like, too far apart — it's not gonna work.

Stephanie Middaugh: Yeah. Yeah. Yeah.

Janis Zech: And curious, like, how does it work at Pinecone at the moment? Do you have revenue operations there at the moment as well? Do you cooperate, or, like, what's the setup there?

Stephanie Middaugh: Yeah. We do. So revenue operations was started before I joined. So I actually report up under revenue operations. My manager is Kyle Himelwright, and he reports kind of under the umbrella of the CRO, which we're currently, like, actively looking for. So this is something that, like, operations came first, and then he hired on kind of the operational team, including myself in enablement.

Janis Zech: Okay. That's great. I mean, that's very modern for sure. And I think that's also probably coming from Pinecone being a relatively young company, I think, is fair to say. So then — I think it's much more common that you actually have that RevOps function, and then you're currently looking for a CRO as I understand it. Yep. So looking to kinda, like, bridge kinda all of those functions together under that main umbrella, which is exciting. And this is — I've reported under a few different types of structures in the past.

Stephanie Middaugh: Revenue operations is the most common. I've also reported directly under a CRO. I've reported under a VP of sales. My favorite structure is usually either operations or a CRO directly. But inevitably, operations and enablement, I usually tie really closely to them either way, whether I report directly under them or I don't.

Janis Zech: Yeah. And and how does that look like? So day to day when you work with your peers in revenue operations, sort of, like, what is the working relationship there?

Stephanie Middaugh: Yeah. Right now my manager is obviously in kind of more of those executive level conversations. He has a lot more visibility into, like, what are the goals and priorities of the business, of our leadership team, and then can bring those back down to us. So now I have more of that north star to be like, okay. This is what the focus is for this quarter, this half, this year, whatever it is. These are the types of enablement initiatives that I can start kind of at least conceptualizing in my mind in order to support those ultimate goals. Typically, like, when I didn't report under operations at other organizations, there was usually, like, a weekly or a biweekly sync just to make sure, like, what are the new things that are coming out? Are we rolling out a new process? Is there new tools? Is there something kind of going on in the business that I need to be aware of? If I need help with, like, reporting or analytics or stuff like that pulling data, usually, they're the first team that I'm gonna go to to kind of leverage that information from. So really close partnership from that perspective, usually on a biweekly or weekly kind of cadence depending on the organization.

Janis Zech: Yeah. Yeah. And are you embedded within — so it doesn't sound like — are you embedded in the RevOps team, or is it more like on the side of the RevOps team, or, like, how does it work?

Stephanie Middaugh: I would say embedded is probably the best description for it, like, right now. So it's myself and then two other of my peers that report directly up to my manager of systems and tools and kind of, like, true, like, operational processes and things like that and then enablement. So I would say, like, embedded is probably the best term for it right now.

Janis Zech: Yeah. Yeah. And then what are some other typical stakeholders? So you mentioned updates to the product. So do you talk directly to product management, or, like, how does that flow of information work?

Stephanie Middaugh: Yeah. Usually, it's coming from product marketing directly. So I have a really close partnership with product marketing. That's pretty common across the organizations that I've been at as well. So staying up to date with kinda what's going on with that. Product marketing is usually a really great kind of translator in between, like, product and, like, the go-to-market function, which is great. Other stakeholders are, like, business development or, like, partnerships for any external kind of, like, ISV or channel partners or however kind of the organization is structured. Marketing as a whole, inclusive of product marketing as another organization. Sales, customer success, field engineering, we've got, like, here at Pinecone currently. So I've got weekly reoccurring, or biweekly reoccurring meetings with all of the stakeholders kind of across the business just to stay up to date with, like, what are you working on? What's going on? Or what are you hearing from the field? What do they need help with? Where are they struggling? What are you noticing? Those kinds of things. So even if there isn't any direct, like, action items or requests, just having that, like, ear to the ground, basically, of, like, what's going on can help me stay on top of or prepare for things that might be coming down the pipeline.

Janis Zech: Got it. Okay. Okay. Great. Yeah. So I think maybe one thing interesting also to understand is you mentioned the term north star earlier, but sort of, like, you know, what is it that you're — what you're thinking about, like, when you have all these conversations? Sort of, like, what is your, like, your inner goal? So you talk to, I don't know, solution engineering. You talk to field sales. Like, what are you thinking about? Like, what is your goal in the company?

Stephanie Middaugh: Ultimately, my goal is to remove roadblocks from my reps and my leaders as much as humanly possible. Sometimes, it might seem like I am adding roadblocks because I'm asking too many questions or trying to, like, answer things that maybe haven't been solved for yet. But at the end of the day, that's what I want. I want my team to feel supported. I want them to have all of the information that they need in order to feel productive. I love being around kind of, like, salespeople in general. Like, I've never been a seller before, but I love the energy and just the overall vibe that you get from kind of, like, sales in particular, but, like, go-to-market in general. So understanding, like, what can I do to support you? I'm not carrying that weight of a quota, but I can definitely carry the weight of, okay, you are running into an issue here. You don't have enough knowledge here, or we need more information, or whatever it is. Let me be the one to kind of advocate for them internally and find the resources or information that they need in order to make them efficient and productive.

Janis Zech: Yeah. Got it. Okay. Okay. Great. I mean, Pinecone itself — maybe I think it would be worth spending, like, one minute explaining what Pinecone does. Maybe you wanna do that first.

Stephanie Middaugh: Of course. So Pinecone is a purpose built vector database, which if you're anything like me, when I first started, I was, like, right over the top of my head. Was like, I have no idea what that is. So essentially, what it is at the end of the day — and all of my new hires that have gone through my class are gonna be grading my elevator pitch on this one now at this point — but essentially, what it is is it's the database layer for most generative AI applications that are being built today. So it makes it so that you can access the information that you've uploaded into the kind of the system at a much faster and more reliable kind of speed. So you would partner with your LLM or your large language model in order to kind of, like, grab that data. Some of our customers are, like, Gong as an example. Notion is a customer of ours. So companies that are really kind of, like, have all of this access to this great information — they need to be able to kinda ping it really quickly. That purpose built kind of vector database layer makes it possible for those companies to be able to do it at that fast speed that their customers are asking for. So boiled way down — like, it's a very technical kind of space and product, but that's kind of the nitty gritty high level overview of kind of what it is.

Janis Zech: No. I love it. I think, like, infrastructure for modern AI in companies like Gong and — yeah. So that's great. I think that is a great business to operate in. And so, I mean, as a sort of, like, a very technical product, I assume, that's also not super easy to explain. Right? And you already mentioned, so you don't only have AEs. You have the sales engineers. You have customer success. I'm sure there's, like, customer support as well and all these other go-to-market functions. So how do you make sure that the people who join Pinecone as new starters actually really understand what Pinecone does and how they should talk about it, how they should sell it, how they should support the customers?

Stephanie Middaugh: Yeah. Onboarding is my favorite thing about enablement overall. It's a big passion project, I would say, of mine or a big passion pillar for enablement overall. When I joined Pinecone, it was typical kind of, like, startup organization. You had, like, a word doc that was just, like, read these articles, like, watch these Gong calls, and then, like, congratulations. There you go. So I built the onboarding kind of structure from scratch. We actually host in person kind of, like, onboarding boot camps for our new hires at our HQ in New York, which I'm very grateful that we're able to do it in person because there's an element that we definitely kinda missed out on during kind of the COVID pandemic when everything was virtual, and you just kinda miss that, you know, human to human contact. But, ultimately, like, usually, what I do is I sit down and I map out what do each of these new hires need to know in the first thirty, sixty, ninety days of their tenure at the company and then work backwards from there. Right? Usually, it falls into a couple of different buckets. It's the market landscape that the company is kind of in. Like, what's the company history? Who are some of the players in the space? What does that look like? What are those conversations gonna be? For Pinecone, especially, one of the things that I've been focusing really heavily on is where do we fit in that generative AI kind of tech stack? That way they can visualize when our prospects or customers are working with us, who are all the other people that they're gonna have to work with as well, and how can we make our experience as seamless and easy as possible for them, not just from obviously a product perspective, but from a sales perspective as well. And then from there, like, what are the processes they need to be aware of? What are our sales stages? What does our customer journey look like? What are some of the, you know, kind of nuances of our business and where we play that they need to be aware of? How do they engage with partners? Like, all of these little things. And then coming back in and organizing all of that into kind of a streamlined flow. It's funny. I'm actually in the midst of preparing for our next onboarding class, which is taking place in May. And this is the fifth class that we're hosting, which is pretty exciting. And every single time I've run this before, like, I gather feedback from the new hires, what worked, what didn't work, what did you like, where are the gaps. And each and every time it's been iterated on, and it's been kind of expanded on. Usually, I've been starting — like, the boot camp is, like, pretty high level in that it's able to cover, like, our account executives and our solutions engineers, like, just at that, like, thirty thousand foot level. This next one, I'm excited. I'm actually taking it to the next level, or the next iteration is going to be, let's start diving into very role specific information. Like, how are you forecasting? What is, you know, the internal Salesforce process opportunity flow look like for our technical people? Like, let's dive deep into the technical aspects of things. How do you run a demo? What does that entail? What does that look like? What are some of the resources that they can have access to? So for me, it's always starting about laying a really solid ground foundation and then building up from there and figuring out what's working, what's not, and consistently kind of iterating on that based on needs of the business, needs of the people that we're hiring too, and then, you know, what levers do we need to pull to make people more productive.

Janis Zech: Yeah. Yeah. Okay. Okay. Wow. I can definitely see your passion. And then, like, there was a lot, but I absolutely love it. I mean, you definitely can see the passion from teaching coming to play here. So, definitely, it sounds like a teacher always trying to improve year over year, the class and the curriculum and just making it really easier to digest and the students more successful. Few things just wanna hone in on. So, like, I really like this thirty, sixty, ninety concept a lot. I think this is also, like, a really good thing to do just generally as a manager. Like, you hire somebody, and then you kinda, like, wanna discuss, hey. After thirty days, these are my expectations. After sixty days, these are my expectations. Ninety days, you should be able to do that — give people some guidance, give people some framework, and what is sort of, like, expected from them organizationally. And so just curious. Like, is this something that is, like, more broadly defined together with leadership, or is this something that you do on the side separately? How's that tied together?

Stephanie Middaugh: Yeah. It's kind of a combination of both, actually. So I definitely, obviously, have my own kind of opinions, best practices, things that I've seen work really well. I actually had a meeting with our leadership team, like our sales leaders, our head of field engineering, and a couple of the other leadership were kind of in attendance. But we had an entire kind of, like, couple of days workshop where we sat down and we're like, okay, what does success look like for your specific team, for enterprise sales, for commercial sales, for, like, EMEA sales, that kind of stuff? How do we define success? What does good look like? Do we see it being exhibited right now in our reps? If we do, what are the specific skills and behaviors that they are doing that we should and can replicate throughout the entire team? So it's a combination of making sure that I bring my own ideas to the table and best practices, but then also being flexible enough to mold whatever the business needs or whatever. And it could just be for, like, for this year or for this, like, six month stretch. This is what the business needs. Okay. Great. Like, how can I be flexible enough to support that while still building for kind of scale in the future? And I think this is where kind of that it's applicable to everybody information, like, at boot camp kinda comes into play, and then I'm gonna start, like, really narrowing it down. If I started with the narrow piece first, I'm gonna be spinning my wheels and working really hard. I'm all about the work smarter, not harder kind of scenario. So making sure that I can, like, start broad and then, like, scope down as needed based on the roles that are coming into play.

Janis Zech: Okay. Okay. Yeah. That's really great. So what are some of the most common mistakes that you're seeing when running — or, like, that you've encountered yourself — when doing onboardings? One thing you mentioned in the beginning was also differentiation, like, how you talk about, like, sort of, like, a Pinecone, how it fits into the Gen AI stack. I think that was, like, a really important one. I think, like, a lot of companies are not really good at explaining what makes them different to, like, their ten thousand competitors. So I'm assuming this is one, but curious, like, what else you think are pretty common mistakes.

Stephanie Middaugh: Yeah. Mistakes are an interesting one because, like, you won't know it until you, like, step right in it. It's like a pile of poop. You're just like, oh, there it is. Look. It's just right there, and I just stepped right in it. It's one of those things where I've definitely started too specific. I've started, like, too narrow, and then I have to, like, oh, that was, like, we need to, like, pop it out a little bit, or it's not as applicable to whomever. One of the things too that I think often gets missed, and I know I've missed it in a lot of my previous kind of roles — the further in that I've gotten into kind of, like, enablement, I've actually been on, like, the buyer side. So I can relate to all of the different things that, you know, buyers kind of go through of, like, I don't wanna sit through another discovery. And, when you're evaluating a bunch of vendors, for me, like, I actually started bringing that into my onboarding experience of instead of, like, a checklist of you have to make sure that you ask these questions on BANT. Like, you have to fill out your BANT checklist spreadsheet or whatever to make sure that the opportunity is qualified. Instead, it's all about kind of, like, giving a crap about the prospect themselves. Like, what are they struggling with? What are they trying to solve for? If they had a magic wand, what would this kind of solution look like? Why are they even talking to me right now? Who else are they talking to? Like, understanding, like, the buyer on a very, like, human kind of level, I think will — for me at least, like, this is where I've started kind of, like, changing my approach, especially in onboarding. I tell my new hires all the time, just, like, lean into genuine curiosity. Like, I'm gonna give you a list of discovery questions. I'm gonna give you a list of qualifiers that we need you to kind of, like, fill out for whatever framework methodology we want. But at the end of the day, like, as a buyer, I'm gonna know when you're checking off your list versus, like, actually wanting to engage with me on a human personal kind of level. There's an art to it, but you can do the two things at the exact same time. Right? So I would say, like, that's one thing that I've definitely seen mistakes, and I've made those mistakes myself — is making sure that the team that you're training isn't just seeming like a robot. They actually are selling on a humanistic kind of level. Even if you're in transactional sales, you can still develop a relationship with the customers that you're working with. So I think that's an important thing, I think, for me is, like, methodology, process, whatever. All of that rigor is important, but make sure that the team that you're supporting at the end of the day doesn't come out sounding and interacting with your customers like robots.

Janis Zech: Yeah. Yeah. No. Of course. I mean, that's — yeah. That's terrible, and I totally can relate to your point of the checklist part. Definitely been there as a buyer.

Stephanie Middaugh: Oh, yes. Right?

Janis Zech: Yeah. And probably also as a seller, if I'm honest. Like — yeah. It's easy to fall into.

Stephanie Middaugh: It's a hundred percent easy to fall into. Yeah. Yeah. And sometimes you are in these conversations where you're like, I just don't know how to make that transition now. So I'm just gonna ask —

Janis Zech: Yep. Like, really bluntly and stupidly and, like, we'll be okay. One thing I'm curious about in that regard is — so, you know, sometimes you have these, like, really, really good sellers, and they're just like — they bring in all the quota. They bring in all the deals. And how do you deal with these people? Like, are they less engaged in onboarding, or are they super engaged in onboarding or just like the others, and it's just, you know, you find out later that they're, like, actually, like, really, really, like, top one percent sellers, president's club sort of, like, style?

Stephanie Middaugh: It very much depends on the person. I would say, like, I've met those really experienced kind of mature sellers who have been doing — I've been doing this for twenty years, you know, like, longer than you've been alive kind of a situation. Yeah. Sometimes those folks, like — I've had those conversations with other enablement professionals where they're like, I've got these, like, really tenured sellers, and they don't give a crap about enablement or, like, whatever. And sometimes the best response is, like, fine. Like, then I'm not gonna waste my breath, my time on trying to convince you that you need to do the things that I think that you should do. So it's, like, one approach is, like, sometimes you just have to, like, cut them off and just be, like, have at it. Like, just go live your best life, and I'm not gonna worry about you. But there are other sellers that actually — if you run into those really tenured experienced, like, A player sellers that aren't maybe as necessarily engaged with your training content, but they like to give back. They like to, like, you know, kind of pay it forward to the team. Leverage those people all day every day. Like, I don't need to be the one that's always talking to the team. I don't need to be the one that's always training the team. If I've got an internal subject matter expert, if I've got a rep that is crushing quota, doing the things that we want them to do — and it's also an important thing that they're not like a maverick kind of rogue agent that are doing weird things that we don't want them to do, but they're doing all of the right things. They're hitting their quota. Like, let me highlight them. Let me put them in front of their peers because their peers are gonna wanna hear from the person that's going to president's club every year and crushing quota and, like, blowing it out of the water. Like, let me shine a big old spotlight on them and engage with their peers and make sure that they understand that, like, this is what we should be doing. Like, this person can do it. You can do it too. Here's, like, breaking down all of the things. For me, though, from, like, an enablement perspective, a lot of times if you go to those really great sellers and you're like, what are you doing? How are you doing this? And they're like, I don't know. I'm just doing it. And, like, it just comes naturally to them. So for me, that's like on me — or from an enablement standpoint, it's up to enablement to be like, okay. I'm gonna shadow you. I'm gonna observe what you're doing, and I'm gonna figure out what makes you so awesome at your job and kinda, like, pull that out of them because sometimes they genuinely don't know. So all day, every day, I would, like, put those folks in front of their peers if they're able and willing and if they're doing the right things. Sometimes you have to, like, just let the other rogue agents go off on their own and be like, okay. Fine. And then you'll have the other ones that are like sponges that just wanna, like, absorb all of the stuff, and those are always really, really fun too.

Janis Zech: And and how do you go about — so, I think there's, like, you know, product company specific sales enablement, and then there's more like this, hey. These are, like, the fundamentals, these are the things that you absolutely need to know, like MEDDIC, right, for example, or BANT or, you know, things like this or sales stages. I would assume — I mean, of course, they can be specific to the sort of, like, process that you're — the style that you're selling, but, you know, overall, it feels more like, okay. This is some fundamental sales knowledge I'm gonna teach you now. Sort of, like, what is sort of, like, the ratio there? Or maybe you completely disagree with what I just said, which is also fine.

Stephanie Middaugh: So I would say it's probably like — at least initially, it's a fifty fifty kind of split as far as like, you know, you should run, like,