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Molly Sestak joins Warren Kucker to discuss Sales Enablement from Meeting Rooms to CustomGPTs. Key takeaways include Custom GPTs enable personalized rep onboarding and RevOps and enablement integration creates competitive advantage.

EP. 2 35 min January 8, 2026 Recorded January 8, 2026

Sales Enablement from Meeting Rooms to CustomGPTs

with Molly Sestak

"Using AI to do in 5 minutes what used to take hours"

About This Episode

Molly Sestak discusses leveraging AI and custom GPTs to streamline sales enablement processes. The episode explores how personalized onboarding plans can be created for new representatives beyond standard templates, and examines the strategic value of combining RevOps with enablement functions.

Key Takeaways

  • ✓ Custom GPTs enable personalized rep onboarding
  • ✓ RevOps and enablement integration creates competitive advantage
  • ✓ Future sales teams will be leaner in direct selling, stronger operationally
  • ✓ Sales representatives function as workflow orchestrators using AI tools

Show Notes

Enablement used to be a conference room and a stack of handouts

Molly Sestak leads revenue operations and revenue enablement at Sedna, a Series C shipping communications platform. She started as a BDR at Showpad, a sales enablement platform, at a time when sales enablement was not yet a common term. Training meant sitting reps in a conference room for eight hours with handouts, then calling the job done. Marketing created content and threw it over the wall to sales, with no way to know whether reps used it or whether it resonated with buyers. Sales and marketing ended up blaming each other.

LMS platforms, quizzes and digital sales rooms improved things, but selling those tools meant educating buyers who did not know they had a problem. The real hook, Sestak says, was ROI: did people complete a training, did it affect performance later, and which content actually resonated. Visibility lets a team stop spending hours on a case study for an industry nobody sells into. Kucker notes that the ability to measure drags a buyer into a new process, and that process is what actually gets sold.

AI's first win for enablement is getting off the blank page

The biggest change Sestak sees is how manual the work used to be. She remembers spending hours building something as simple as a call scorecard. She recently built one with AI, using a custom GPT her team loaded with their sales methodologies, including Sandler, and information about the company.

But I would spend so long building it. By the way, I built one of these the other day, and I used AI, and it took me five minutes.

The result matched what she could have built in five or six hours. Many enablement teams are one person supporting as many as 700 people, and Sestak says AI is how they scale.

Kucker asks whether the time saving comes from escaping the blank page or from the model doing the writing. Sestak says both. She still starts by whiteboarding or talking ideas through with someone, then feeds those ideas into the LLM, which surfaces angles she had not considered. Her example is an annual team charter that would take hours by hand. She then edits the output, adding the empathy and human tone that models tend to miss and that she can spot as ChatGPT language. Her point is that the hard part is the high-level thinking about what to do, not producing the document.

Personalized onboarding means training the person, not the persona

Reps' biggest complaint about training, Sestak says, is that it is generic. Most companies respond by making it role-specific, which still does not help much. Sedna recently hired two people at the same time. One had a maritime background but had never used Sedna's tools or methodologies. The other had spent about 20 years in shipping but needed training on the tools. The team hand-built two programs by copying the relevant material, deleting the rest and hoping it made sense. Smaller gaps, such as a rep who knows Gong but not Sedna's way of using it, went unaddressed.

The future she describes is an onboarding or continuous learning program built for one person. Inputs include the company's competency framework, the rep's role, their market, their deal momentum and win-loss analysis, and the seller profile from Objective Management Group (OMG), the assessment every new Sedna hire takes. Selling in Greece differs from selling in Dubai, Singapore or the Nordics. The GPT can produce something like a spider chart of a rep's strengths, covering soft skills plus behaviors such as whether they follow up on emails, their email sentiment and their calling. A second GPT holds the training content, which a team of one does not have to write themselves; Sestak suggests licensing something like LinkedIn Learning. Feed the seller profile into it and it builds a tailored onboarding plan, or a six-month plan with the four things a rep should work on to reach their next promotion.

It sounds like a lot of work. It's actually not that much work once you know what you're looking for.

Done by hand, she estimates, that is a year's worth of work. The bigger cost is maintenance. Hand-built programs get poorly managed and people stop using them, so automating upkeep is what gets them adopted.

Voice agents could replace the intake spreadsheet

Kucker adds an idea for the input side. Rather than summarizing conversations into bullet points, teams should feed whole conversations into the GPT. For competencies and industry knowledge, a voice agent could interview the rep. In maritime there are several personas, and ship brokers talk very differently from agents. A rep heading into ship broker territory could have a conversation with an agent that probes their knowledge and scores their competency. Three 30-minute AI conversations before day one would give the training GPT a lot of data, which the rep and manager could then pair with the OMG results to agree on a three-to-18-month progression.

He also suggests a price negotiation voice agent that runs a short mock negotiation, capturing context the OMG test's yes, no and maybe answers cannot. Sestak welcomes anything that replaces a spreadsheet, since many enablement people, herself included, find spreadsheets intimidating.

Enablement and RevOps cover each other's blind spots

Sestak now runs both enablement and RevOps, and she thinks more companies will combine them.

Enablement has a lot of blind spots and rev ops has a lot of blind spots.

RevOps builds data-driven processes and can measure whether they work, but it does not always think about the human side of adoption. Enablement brings change management but often tracks vanity metrics and cannot always pull or analyze the reports. Together they look at the same data and catch each other's blind spots. MEDDPICC is her example: reps hate filling out the CRM, so half the fields stay empty. Enablement designs the process and documentation, and a go-to-market engineer on the RevOps side builds agents that fill in the data so reps do not have to. Her team of six is deliberately built from different skill sets, because a team with identical skills misses things.

She expects sales teams to get very lean while the support teams behind them grow, with go-to-market engineers building agents that draft follow-ups, research accounts and plan territories. Kucker connects this to a conversation about silos: silos usually exist for a reason, but enablement and RevOps share the same goals, to train and to measure, so the wall between them was artificial.

BDRs move upmarket and reps become the conductor

Sestak's hot take is about sales roles. Inbound could probably be fully automated until a buyer enters a deal cycle and needs a human, and Sedna is working out how to do that. Sedna has moved its BDRs off a mix of SMB and mid-market accounts to focus only on enterprise, where deals are complex, stakeholders need mapping and breaking in requires real understanding of the business. In their remaining time, BDRs support the wider go-to-market team. Two recently spent two days training a customer's users, then brought what they learned back to prospecting.

For mid-market and SMB, especially transactional sales, she thinks so much can be automated that those AEs should source their own pipeline without BDRs. Enterprise AEs, meanwhile, will manage resources and automation around a complex deal.

So I'm thinking about it as more like sales reps are gonna be kind of the orchestrator, almost like the conductor of the sales deal with all of these things running behind in the background.

She does not see this as replacing BDRs. Their role becomes more strategic than appointment setting, which she thinks makes it more fun.

Full Transcript Show

00:00 Warren Kucker: Hey there and welcome to an episode of Selling AI. Today we're diving with Molly Sustak in all things revenue enablement. Molly is an absolute dynamite sales leader spending a few years at Showpad before leading enablement for the past three years at Sedna a Series C shipping communications platform. In today's episode, Molly and I are going to talk about how reps should view enablement going forward, training as well as career growth and the age of AI, as well as how the future of sales enablement as a function will be shaped. Really now that we have the ability to extract key insights from every one of our sales conversations. All right, let's get into it. Hey, Molly, thank you so much for being here with us today to talk about the future of sales enablement. Welcome to the show.

00:38 Molly Sestak: Lauren, super excited to be here.

00:40 Warren Kucker: Awesome, awesome. Would you give us a bit about your awesome background and under appreciated but absolutely like fundamental role on the sales team and then tell us about what you're focused on today.

00:50 Molly Sestak: I always said I was not gonna go in sales. My dad works in sales and he was always on his phone, he was always traveling and I'm like, I don't wanna be like that. Turns out, spoiler alert, ended up in sales, loved it. But actually my real passion was teaching people how to sell, so not actually selling myself. So that's kind of how I got my start in enablement. I started on the BDR side, then started building out BDR enablement and now have moved over to full revenue enablement. I know the whole market is shifting now towards revenue enablement. So jumped on that bandwagon and actually most recently jumped on an even bigger bandwagon. So I am now leading our rev ops and revenue enablement team at Sedna. And I think this is really interesting shift where we're seeing a lot of companies starting to team up their enablement and rev ops team. And I think especially in this new AI world, this is going to be even more prevalent across the industry.

01:52 Warren Kucker: really interesting. We'll dive into that specific topic in a bit because it really is like a fascinating combination where the synergies lie and why it hasn't like it been done before but we'll get into that a little bit later. that's awesome. I appreciate that dive in tons of experience. Molly is a go-to when it comes to revenue enablement along the way. So let's let's dive in. Can you talk about what Sales enablement was like five years ago when you were first doing, let's say BDR enablement, shifting into like rep enablement compared to what it looks like today. What's been like the change in the dynamic that you've seen?

02:25 Molly Sestak: So it's so interesting because I have even been talking about enablement even further along with that. I got, as we talked about, I got my start at Showpad, which is a sales enablement platform. So as a BDR, I was calling into people when by the way, sales enablement wasn't even a word yet. It could have been like commercial excellence or commercial enablement. So they didn't really have the sales enablement word. A lot of times it was like this traditional sales training where you would go sit in a conference room for eight hours in a day with your handouts, right? And that was the training. And then everybody went away and it was like, great job done. And then you had, you know, the marketing folks who were creating content and they were kind of just throwing it over the wall to sales reps, hoping that they were using it. There was no way to get insights. So people really had no idea if that, you know, what they were creating was actually working. Was it resonating with the buyers and what was actually, what was actually happening? So sales and marketing were kind of. just going at each other because it was kind of the blame game there. Then you have like the rise of all of this sales tech and sales enablement tech that started to drill into some of this, change the game a little bit. And, we evolved a bit. You know, we have our LMS systems, right, with, you know, we can do some training online. You know, we can do quizzes and whatnot, maybe gamify it a little bit. And same with the sales enablement tech from the marketing perspective of like understanding what wires are engaging in. if you think about like digital sales rooms, for example. But I actually think the biggest part is that it used to just be incredibly manual. So I remember I used to spend, like I kid you not, hours, Warren, building out something so simple as a call scorecard. And again, this is more like not that older traditional enablement. This is when we were starting to try to do this reinforcement piece. But I would spend so long building it. By the way, I built one of these the other day, and I used AI, and it took me five minutes. And so it's a huge, it's a huge, and it was about as good as I could have created, if not maybe better because I use like a custom GPT that we created with all of our methodologies and information about our company in it. So. Like I could probably do that if I spend five, six hours, but in five minutes, I have the exact same thing with the exact same quality. That allows me to then focus on way more high effort, you know, ROI things versus, you know, creating content and whatnot. so I think this is the biggest shift, especially for like a lot of enablement teams are supporting 700 people as one person or really small teams. Like, how do you scale? And AI is actually that piece that's going to help us scale.

05:14 Warren Kucker: That's like crazy. In the scenario, I talk about this a lot where there are like major shifts that happen and then it doesn't seem like there's been a shift. Like it always seems like it's been that way. I had never even, I wasn't in sales 10 years ago. I never even contemplated a world where most sales training that ever has happened has been bring your sales team into a room, a conference room, maybe once a quarter for eight hours and just do presentations and these types of things. Sales enablement has always been like sales enablement 2.0. that the show pads of the world

05:43 Molly Sestak: Mm-hmm.

05:44 Warren Kucker: kind of showed us. If you get to a good question, like when you were calling in as like a BDR initially into selling sales enablement to teams, how were they talking about it when you were doing this? Like, and how are you trying to shift it? What was the, you're way ahead of this problem to get to sales enablement 2.0 and then we'll talk about sales enablement 3.0 throughout this podcast.

06:04 Molly Sestak: Yeah, that's a really good question. I think most of them didn't even realize they had a challenge. I know you and I have talked about email lot as well where, know... In the business world, we all think about email as, you know, we're just so used to using Gmail or Outlook and that's just how it is. And like, does it annoy us sometimes? Yes. But it's like, whatever, we get on with it and it's fine. But I think it's actually a lot of trying to get them to realize that there is a huge challenge around it. And actually there's a better way of doing things. And so it was a lot of education, to be honest. A lot of time, a lot of education, a lot of discovery to really understand what was going on and I think the biggest thing for them was actually understanding ROI. So really understanding, okay I've created this training but what did it actually achieve? Did people actually complete it? And then what was, know, like how do I measure later down the line? that affect performance later on? and whatnot, and then same with the marketing content. How did it resonate with buyers? Because as soon as you can start to see those things that are resonating, you can start to create more of it, which is a way better time investment than maybe a case study that you created from an industry that nobody's selling into and nobody's looking at. What a waste of time to spend hours upon hours building out this content. So I think it's a lot of education to really get them to realize that they had this challenge because everybody's just been doing it that way. think this happens a lot. It's the same with AI, right? Everybody's a little bit scared to jump on the bandwagon. And the people who are actually using it are starting to build out these business cases of like, if you don't use this, you're gonna fall behind because look at what I'm doing in such a small amount of time. And now I have so much other time to actually focus on the things that are most important.

07:51 Warren Kucker: That's a common poll in like shifts in market, right? Where you go to someone you're like you're investing a lot of money in this particular like area Let me give you the ability to measure that but like the ability to measure it comes along with a new way of doing it Right. So like it's that ROI almost drags you to a new process, which is like kind of interesting That's what you have to sell. There's a lot of markets that kind of follow a similar pattern Let's stay on this thread a bit though. You said earlier that It would take you hours to like weeks to develop sales and materials. How do you measure what's happening? How do you and how do you train off of it? And now you're saying it could take five minutes. Like what's what was the difference there? What were you going through as a sales enablement like leader before that now is being taken care of by a GPT that you created?

08:44 Molly Sestak: So I think that there's two things because obviously you have you know the the GPT that can you know, produce content. So I can create a custom GPT that has all the information that I need. So we have one, for example, we use Raskin a little bit, we use Sandler and we kind of put all of that into a GPT. And so when I want a calling scorecard, I just pop in, you know, exactly what I'm, I'm specifically looking for. And then it's like, Hey, build this out in the Sandler way or the Raskin way. we're making sure that the methodologies that we're using are threaded throughout the enablement, you know, trainings and whatnot that we're doing as well, or even the call scorecards. I think previously we didn't really have a way to kind of start this. So it was basically me, myself, and I staring at a blank piece of paper. And so that's why it took so long. So think starting from nothing. is way more difficult than starting from something that's actually like pretty okay. And then I'm just making little tweaks here and there. I've been in the world for a while, so I kind of know when it kind of just looks like Chad GPT language versus a human language. And that's where you can like insert a bit. They're not very good at empathy, let's say. So we can insert a bit of like the human element and the empathy. But then there's this whole other side where I'm getting really excited about, which is the agent side of things. And if we think about from enablement and even I have my rev ops hat on as well even into rev ops I think this is where the two departments working together can be incredibly powerful a lot of enablement people are measuring kind of vanity metrics and I think a lot of them are not as data-driven as our revops folks, right? So actually combining forces, you know, having revops start pulling the data and then having the two departments look together at that data, you get this kind of like diversity of thought, which is incredibly powerful because the way that I would look at something versus somebody with a more financial data background. is incredibly different, right? So we're looking at the same thing and we're seeing each other's blind spots. We might think of something that they didn't think of. And then we can start to figure out solutions. Like here's what the data is saying. Here's where we need to improve. And here's some things that we can do and we can work together on that. So enablement can focus on building out the processes. And instead of like the old, the olden days where you kind of threw that process over the wall to, to sales reps, hoping the hell that they adopt it. You don't know if they're adopted. And then usually it's not think about things like med pic, right? Half the time people aren't filling out the CRM. hate it. So how can we then leverage agents to start helping us to fill these things out, right? Get better data, actually drive these pieces of the sales process that are incredibly important and build the foundation for the rest. And so I think that's where we can really partner with the folks in rev ops to have like, you know, enablement builds out the process and they end the doctor documentation and then rev ops aids almost like a go to market engineer role. I know some of these are popping up here and there. We actually are very lucky that we have one in our team who are then thinking about this from an AI perspective, right? Like how do we how do we enable them with with the agents so that they don't have to do it themselves and it just gets embedded into the process automatically.

12:09 Warren Kucker: These are two phenomenal threads and so I want to stick on the sales enablement thread and then come back to this data revops combination thread. So let's go down this path. You said that one of the biggest pickups in saving, condensing, challenging strategic work, let's say creating scorecards that are actually valuable for your team, that give you data and then feedback, right? The time to do these really shrunk. Do you feel like it was more around me getting off the blank page that like, really kind of condense that time space? Or do you feel like it was actually that the LLMs were doing like, what is the, like hours of actual like writing and typing and thinking that was happening?

12:53 Molly Sestak: Really good question. I actually think it's both. So there's that piece, least from my perspective, I know, Warren, we've worked together, you know I love a whiteboard. I have to be in a, I think for me it's really helpful if I'm talking things out with somebody or whiteboarding something, and that's because you get off that blank piece of paper, and it's a really safe way of getting off that blank piece of paper. And that's how I would historically do it. I still do it like that today, but then I take those ideas and then put it into the LLM. which again gives you something that's not blank and probably then perpetuates that brainstorm where you're like, I actually didn't think about that or I didn't think about that. And then once you have the more solid idea, you're right. It is so time consuming. for example, I'm, I'm doing annual planning at the moment and I'm thinking about, you know, what am I, what am I working on with my team? What's our team charter look like? All of this stuff that, I mean, I could write it out. It's going to take me hours to write out. And it's not that difficult. I know what it needs to say more or less, but again, if I can plug that into an LLM that, you know, I've trained and knows what our business looks like. and what I'm trying to achieve, it can spit out something that's pretty much good and save me hours on handwriting something like we wouldn't used to do that would take so long. And it's just not necessary, right? Like I can then focus on tweaking it to make it even better and exactly what I'm looking for versus spending the time on actually building the thing out. So it's more than, I think you're then more focused on the actual strategic part versus the executing part that actually is the hard bit. I think the hard bit is thinking about that, you know, that blue sky thinking high level and trying to figure out, you know, what exactly you want to do versus doing the thing.

14:44 Warren Kucker: get tactical in this space and see if we can leave something helpful. Let's picture we're speaking to a sales enable manager, usually a one-man band and sales enablement, unfortunately, for you guys. It's generally not a team of eight that are constantly brainstorming in what enablement could be like. So one person wants to get off the white page with using AI. And I was like, listen, how can I use this better? Can you describe a specific? like thing that you've had to do in the past. Give me the three, four, five steps behind what you used to have to do. And then give us the three, four, five steps on what you can do now, including like the baseline setup and option B. Like how do you get a GPT up, for example, in this case, what did you pump into it? How did you pump, like create what you pumped into it? Can you give us the A and the B?

15:31 Molly Sestak: Yeah, I'm actually, I'm actually gonna do a slightly different example. So one that, I actually talked about it at a conference the other day. So one of the things that we want to look into next year, one of the challenges that we have is if you think about traditional enablement and, and reps, right? One of their biggest gripes is training and training being generalized and how do you make it so it's personalized for them? Well, most companies, what they do is they're like, Oh, I'm going to make it personalized. I'm going to make it role specific. And it's like, cool. That's still not helpful. And so actually the other day we had two new joiners. One had a maritime background and one didn't. And in our industry, in maritime, like if you're selling into maritime, you have to be an absolute expert. And it's not just an overnight thing to get involved. It's incredibly deep. We have to do quite a lot of training around that. So those onboarding programs have to actually be incredibly different. So one of them needed tons of maritime experience, but actually had used all of our tools, all of our methodologies. Other one. hadn't used any of our tools and methodologies, but he's been working in shipping for about 20 years. So this is like opposite. And I was trying to train them at the exact same time and that is incredibly difficult. So we kind of fudged it together and what we did was we just removed, we basically just hand built these onboarding programs by the way. So copy paste of all the things that were important and then deleted all the things that weren't important and kind of prayed that it would make sense. It still wasn't 100 % perfect because there's slight variances in it so maybe one of them you know has used let's say Gong for example before but they haven't used Gong in our way so how do you how do you account for those kind of like really small niche things? And we didn't, by the way. So we just kind of ignored it and we're like, I hope this is gonna be okay. Probably what's gonna happen is it's gonna come back and bite us later on and we're gonna have to do like a personalized session for this person at some point when it comes up. Now here's what I think the... future looks like because again, I think there's a lot of just spray and pray there and we're just hoping that it it lands or it does a good enough job what I think the future looks like is a incredibly personalized onboarding program or even continuous learning program, so The other thing we haven't talked about is competency frameworks. But competency frameworks are incredibly lengthy to build out. A lot of times, it's literally having to either you steal something that somebody's already done and kind of make it work for your company, or you build it completely from scratch. Some people already have this, but they don't really know what to do with it. So they're manually measuring this and whatnot. So one of the things I want to look into is how can we actually plug this in to a GPT and have our competency framework in there. We also use a company called OMG, so that's Objective Management Group, and every time someone joins our company, they take a test and that gives us their affinity for selling. And this pops out an entire seller profile, incredibly personalized, of everything that we need to know about their strengths, their weaknesses, and how we can actually help them. You plug that into the GPT. How about their role? Maybe their market, for example, and we can train the model to understand what the different markets are for us. In Greece, the selling is very different than if we're selling in Dubai, for example, or in Singapore, or in the Nordics. So how can we then train it to understand that piece and whatnot? We can also then put in their deal momentum and their win-loss analysis and whatnot. And you put all these things in a GPT, and by the way, It sounds like a lot of work. It's actually not that much work once you know what you're looking for. And what it can pop out is actually almost like one of those spider charts where you understand you get a really strong picture from not only like the soft skills piece, because that's what we think about competencies a lot of not just the soft skills, but also some of these other skills, which is like deal momentum. You know, do they actually follow up on emails? What's their email sentiment? You know, are they good at calling or do they need help with that? We can actually get real life examples of what those are doing rather than kind of finger in the air. I think this person is good at this because right so you get that and then you have a separate GPT where you have all of your Sales trainings in and by the way, you don't even have to have sales trainings You can purchase like LinkedIn learning and hook it up with something like that So you don't even have to create these so for teams of one there's like really creative ways around this where you don't have to build out everything yourself and you you put that seller profile into that and it's now created an onboarding program for you specific towards that person. Or it creates a six month program of like, we want to get this person to this next level. Here are the four things that they should be focused on between this performance cycle and the next performance cycle to get that promotion that they're looking for. So it's a really interesting way of like, you can do this with a person of one and that takes I mean, probably a year's worth of work for yourself in having to like build out all of these and maintain them because it's the maintenance that takes so long. So that was a very long-winded answer. But I think it was it was so exciting to think about that because those are the things that like I love to build. But it's the maintenance that's absolutely terrible Warren. takes it takes up all it's a time suck and it's it's not actually helping anybody because it ends up getting poorly managed and then people to stop using them at some point. So this is a great way of using AI to actually enhance the stuff that you're building and actually get it adopted as well.

21:46 Warren Kucker: a phenomenal process and what it of begets to is like, so then let's, let's pull that out. Something that gets under talked about is like voice AI in this space, right? So like we, we, and you talk, we talk about conversational intelligence. I think that gets under talked about as well, but it gets talked about enough, right? Where it's like, great. And that scenario in a perfect world, you're pumping all of the conversation that your teams are having internal and external into their GPT. And you're leveraging all of that context because why are we translating what was said into like just bullet points, why don't we just push in the conversation? But if you think about it, right, like, and that OMG test is phenomenal, and I couldn't find myself replacing it. But for like, the other things, say competencies, industry knowledge, these types of things, we should really be pushing the bounds on what the intake data there is. And like a voice agent would be great at this, right? So like, have a conversation about Maritime to tell me how much you truly know about Maritime. And let's get really specific there. Even within maritime, I know that there's four or five different personas. agents talk a lot different than ship brokers, right? Cool, you're gonna be in a ship brokers like territory, right? Like you walk into a room of ship brokers, they'll laugh at you if you don't speak the speak to speak. Let's use a voice agent, have the conversation to actually do the competency scoring. Now you've had like an agent pressing into answers and questions given by a rep. And all that becomes the framework. You could do this in like three or four different areas, pre-onboarding, pre-first day, maybe three 30 minute conversations with an AI agent, and it would give you a ton of data to launch that training GPT. And then you take the OMG test and you come to a common understanding with the rep of what does that like three, six, nine, 12, 18 month progression look like for them. So I think there's an opportunity to do data capture, especially in the beginning there with a voice agent rather than a spreadsheet. They're really fascinating kind of process there.

23:42 Molly Sestak: I love it. And it's music to enablement people's ears because I'm not speaking for everybody in enablement, but I know a lot of enablement people who are scared of spreadsheets, including myself, although I'm in the rebob side of things, I've had to get better at it. So something that's not a spreadsheet and it's taken out of that is a massive win for us and definitely speaks our language.

24:03 Warren Kucker: You could also take that scenario, right? Like you're trying to figure out, is this rep strong in price negotiation? Maybe you create a price negotiation voice agent, right? How does that work now? ONG's secret sauce is they're really good at asking several questions in a way that you can't game the system. They're going to figure out if you're good at it or not. You have to be a psychopath to game that system, right? But if you had a voice agent that was asking you questions, asking about past examples, looking for key items, maybe running a mini. negotiation here. If I said this, what would your response be? You get a lot of like a lot of the OMG answers are like, would you do this? Yes, no, maybe, right? Like, so like, let's get out of the yes, no, maybe. And let's take the context from a discussion would be really fascinating way to kind of run like an enablement voice agents might be a really cool spot to insert in this.

24:52 Molly Sestak: bit. I'm gonna I'm gonna go off.

24:53 Warren Kucker: Yeah, easy to spin up too. Yeah.

24:55 Molly Sestak: Yeah, I'm gonna go off and talk to my team member for maybe put it on the roadmap for H2.

24:59 Warren Kucker: I know, well, I say like, wanna hop off this and just start a piece of software that does all of this

25:04 Molly Sestak: Thank

25:04 Warren Kucker: for enablement reps. All right, cool, so we're coming up on time. I'm glad we really focused on this. I don't wanna leave, I wanna leave with two topics. I don't wanna leave this thread on pull that. Tell me about the combination of sales enablement and rev ops. I'll be specific. Why do you think it works so well now? But why didn't we do it in the past if it works so well?

25:25 Molly Sestak: think that realistically, and maybe some people would disagree with me, but I think we're entering a new world here where we're going to operate incredibly lean on the sales side. And we're going to probably have more inflated teams on the enablement and the rebop side. And the reason I'm saying this is because of the roles of things like go to market engineers who are going to be tasked with building out these agents and all of the ways that they can support sales. So that actually sellers can do so much more with their time because they're not focused on, Hey, did I follow up with that email? No, actually. an agent just told me to follow up on it, have already drafted the email and tell me exactly what I should put in that based off of past conversations, right? So all of these really just simple tasks are automated for us. Same with prospecting, account research, account prioritization, territory planning, all of this stuff can be automated. So all the sales rep needs to do is a highly strategic human kind of intervention things, right? Negotiation, know, empathy, building the relationships and almost acting as kind of like the puppeteer and managing that whole process. So I'm thinking about it as more like sales reps are gonna be kind of the orchestrator, almost like the conductor of the sales deal with all of these things running behind in the background. And that support team is going to need to be quite large to be able to support that, to be able to have. incredible data to make sure that any of the AI stuff that we're working on is actually functioning correctly to build out, you know, any of these like specialized GPTs to manage the tech stacks, make sure that they're all talking together and the agents are working well with them. So it's a really different world, but I also think it works so well together because Enablement has a lot of blind spots and rev ops has a lot of blind spots. So. RevOps is incredible at creating these really data-driven processes. So understanding like, okay, cool. Here's the issue. Here's the process we need to do based off of the data. And then I'm going to follow up and be able to measure that whether or not that process works. Right. What they're not good at is thinking about the human interface of how do people actually adopt it. And so that's where the change management piece comes in and people with more of that, like enablement profile can really support RevOps in these, in these processes and vice versa, because enablement doesn't always have that data driven background to understand where it's coming from. They don't know how to pull the reports or analyze that data. So I think it's, it's such a perfect marriage of skills and that kind of thought diversity that I talked about earlier. And that's where we're starting to see huge strides in our team. And I'm starting to hire on this as well. So making sure that, you know, we're, we're about a team of six and all of us have a really different skillset, but they compliment each other really well. So every time we're something out, I might be rolling something out and all of them can notice what my blind spots are and vice versa. And I think that's so important because we all have them, right? We all have biases, we all have blind spots and getting someone to be able to call them out versus an enablement team with all identical skills, we might miss those and we might miss the mark. And I've been there before and I've missed the mark before because nobody caught them. yeah, I think this is the way that we're gonna move in the future. future.

29:06 Warren Kucker: That's awesome. I had a recent conversation where someone talked about how we have been for decades talking about breaking down silos and crossing functions. The thing is that I never thought of it this way. It's a of a misdemeanor. Silos exist for a reason. There's different functions that have different skill sets and different goals. So breaking down silos, it's like, all right, let's meld everything together. Well, that's not really the right approach. Finding the right operators to cross silos along the way. is the way to push it, right? Like the silos exist for a reason. But in this scenario, there seems like there's a lot of synergy between the two roles that maybe there was an artificial silo, right? Like the goals are the same, right? Like train and measure, right? So like let's combine the two and put it together. Great. Well, one last question. What's like a hot take or unpopular opinion you have about AI and sales just in general?

29:59 Molly Sestak: That's a really good question. I feel like it might be a bit of a controversial one, but I think there's going to be some pretty big shifts. So I've talked about the rev ops and enablement shift, but I think on the sales side, I think there's going to be a pretty big shift when we think about roles like BDR, SCRs. MDRs, so they're doing inbound, and mid-market SMB account executives and enterprise account executives. So inbound, by the way, could probably be completely automated. We're actually looking into trying to figure out how to do this ourselves. Up until the time where they enter a deal cycle and they need to speak with human. SDR, BDR, there's so much of their role that actually can be automated, that we're actually at our company starting to think about BDRs in a different way. So we're actually moving them from, they were working historically on SMB and mid market, also a little bit of enterprise, but it was a mix. And we're actually having them exclusively focus on enterprise. There's really complex deals that are hard to get into. You need to map stakeholders. You really need to understand their business in order to break into that account. And so we're moving them and using their brains for that and training them how to do the more strategic stuff. In their free time, we're actually using them, I say their free time, in their other time, we're actually using them across the go-to-market team in areas where we might need different additional support. So for example, two of our BDRs actually recently went to a customer. So they've been trained up on how to train a trainer and teach people how to use our platform. And they've gone to a customer. and spent two days at the customer. So not only do they sit with the customer, they're now training them, they're understanding what their challenges are, they're seeing it in real life, and now they can bring all of that back to their BDR life. So it's like this really great circle, I think, in how we're leveraging them in a different way. So that's the MDR BDR side. Now, if you look at AES as a whole, I think that mid-market SMB, I think so much of it could be autumn. to be honest. It's a lot of more, especially if you think about transactional sales, so much of it can be automated that you probably don't need mid-market BDRs. Those mid-market AEs or SMB AEs, they should just be driving their own pipeline, because again, so much of it can be automated. So it's a completely different skillset than we've ever seen before. And then you look at enterprise, who, again, we talked about the BDRs, how we're changing those a little bit. They might have BDR support, and they're just thinking about you know, how do we go to market in a more strategic way? How am I managing all of the resources that we have? So again, being that almost like conductor at the front of the room, conducting all of the people that you need to get an enterprise deal over the line with some elements of automation and AI along the way, right? Because there has to be some stuff that we can automate even at an enterprise level. But I think those two roles are going to be completely different skill sets. that we're going to look at with completely different support and different uses of AI. So that's my hot take. I think some people would disagree with me. And it's not that we're replacing BDR's jobs. I think it just is going to change slightly what those look like. And they're actually going to become even more strategic than those kind of appointment setters that we see in some companies today, which I personally think is good thing, because I think it makes the role a lot more fun.

33:39 Warren Kucker: Yeah, talk about breaking down silos and then really the like, crystallization of selling as a team sport there. That's great. Molly, fantastic conversation. Tell us, have you done any like roundtables recently that we should look out for any content? you got anything scheduled coming up?

33:58 Molly Sestak: So I actually just was at a conference the past two days. So I actually did a round table. It was on change management, which was really interesting. think sadly not recorded, but I'm definitely looking into doing some other podcasts and whatnot in the future. This is so fun. And I think it gives you just some time to reflect and think about some of the trends that are going on and take it back to your own team and your own thinking, especially at the end of the year when I'm starting to plan and I just think it pulls you out of that every day. I just keep doing what I'm doing, right? And it helps us innovate a little bit. So I love doing these things and looking forward to whatever's next.

34:41 Warren Kucker: I really appreciate you taking the time, phenomenal conversation specifically around how you've like set up, let's say a GPT infrastructure, absent of like, I didn't hear all the software you bought to do these types of things. Get off a blank page, load your information into a GPT, make it personalized truly rather than persona-based outcomes are like exponentially better. So a phenomenal advice for sales and movement teams out there. Appreciate you taking the time, Molly.

35:07 Molly Sestak: Thanks for having me, Warren.

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About the Host

Selling AI is hosted by Warren Kucker, founder of Topiq. Each week he sits down with revenue leaders, founders, and operators to unpack the strategies, tools, and stories behind selling AI products and using AI to sell smarter.

Warren Kucker — Host of Selling AI

Warren Kucker

A revenue leader and entrepreneur who founded Basiq.work, focusing on conversational AI for sales teams. Previously served as VP of Sales and CRO at Series B companies, scaling revenue to $2M+ quarterly bookings. His exits include Shelly.ai (ML email automation) and Boxton (digital freight platform). Started his career at Apple managing a $100M shipping efficiency program.