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Leading a Sales Team Through AI Adoption with Jillian Swenson and Alex Cruz at SentinelOne

Sales Game Changers · 2026-08-06 · 35 min

0:00--:--

Key moments - from our scoring

Substance score

56 / 100

Five dimensions, 20 points each

Insight Density11 / 20
Originality10 / 20
Guest Caliber13 / 20
Specificity & Evidence12 / 20
Conversational Craft10 / 20

SentinelOne is taking a strategic, workflow-first approach to AI adoption across its sales organization, moving beyond simply acquiring tools to fundamentally restructuring how sellers spend their time. Jillian Swenson emphasizes that the real value comes from iteratively working with AI models like Claude rather than treating them as simple search engines, while Alex Cruz highlights how his enablement team is connecting AI to core systems like Salesforce, HighSpot, LinkedIn Navigator, and Demand Base to create a unified intelligence layer. The company has built custom capabilities including a 'humanizer skill' to maintain voice and tone in AI-generated communications, an SE Innovation Center to validate and govern new AI applications, and is leveraging SentinelOne's own Prompt Security solution to prevent shadow AI and data leakage. Key focus areas include account research, proposal generation, RFI/RFP responses, and proactive buyer intent detection through Actively, an agent that crawls LinkedIn and internal systems to identify accounts showing security-related buying signals and automatically alerts teams with customized outreach recommendations.

Key takeaways

  • →Sales reps are experiencing roughly 1000% productivity gains in account planning, research, and proposal preparation by using Claude iteratively rather than as a one-shot tool.
  • →Actively, an AI agent integrated with LinkedIn, Zoom Info, and Demand Base, eliminates manual hunting by automatically identifying and prioritizing accounts with intent signals and delivering pre-written customized emails.
  • →Guardrails through HighSpot brand alignment, business value assessment tools, and voice-matching 'humanizer skills' prevent AI hallucinations, ensure on-brand messaging, and eliminate spam-like communications that damage credibility.
  • →SentinelOne's Prompt Security solution enables safe AI use without stifling innovation by redacting sensitive data when employees attempt to load company information into personal ChatGPT or Gemini instances.
  • →LinkedIn Navigator used alongside hiring signal analysis (watching for AI data scientist and security engineer roles) combines intent data with organizational structure to identify real buying signals beyond passive profile matching.

Guests

Jillian SwensonAlex Cruz

Topics in this episode

GeminiClaudeSalesforceZoom InfoGoogle NotebookLMLinkedIn NavigatorHighspotActivelyDemand BasePrompt Security

Questions this episode answers

What is Actively and how does it help SentinelOne sales teams?

Actively is an AI agent trained on SentinelOne's internal systems and connected to LinkedIn, Zoom Info, and Demand Base that crawls the internet for buying signals, automatically alerts reps and SDRs when accounts show intent, and delivers pre-customized email outreach recommendations - functioning as a 24/7 agent identifying market opportunities without manual hunting.

How is SentinelOne preventing AI from generating inaccurate or off-brand content?

The company uses guardrails including HighSpot integration for brand-aligned content, a business value assessment tool to verify ROI calculations, a 'humanizer skill' to match rep voice and tone, and an SE Innovation Center to validate new AI applications before deployment.

What is shadow AI and why does SentinelOne have a solution for it?

Shadow AI occurs when employees use personal ChatGPT or Gemini instances to process company data, creating compliance and security risks; SentinelOne's Prompt Security tool detects and redacts sensitive information in these instances rather than blocking usage entirely, balancing innovation with governance.

How should sales teams use LinkedIn for AI-powered prospecting?

SentinelOne combines LinkedIn Navigator for contact discovery and relationship mapping with hiring signal analysis (tracking AI security roles being filled) as buying intent indicators, then uses AI to research public profiles and past speaking engagements before crafting highly customized outreach.

What productivity improvements are SentinelOne teams seeing from AI adoption?

Sales reps are achieving approximately 1000% productivity gains in annual planning, account reviews, and proposal generation by moving from treating AI as a search engine to iteratively refining outputs with Claude across multiple rounds.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

11 / 20

The episode covers practical AI tool implementation (Gemini, Claude, Actively, HighSpot integration) and workflow integration, but much of the content rehashes familiar concepts like prompt engineering, guardrails, and verification. Few genuinely novel ideas emerge beyond standard best practices; much discussion focuses on tools themselves rather than unexpected strategic insights. The business value discussion and federal-specific messaging approaches offer some substance, but overall insight density remains moderate with considerable padding around tool features.

We started doing more of that prep and research. But now with the implementation of Actively, we're starting to switch into the more proactive strategic focus on a daily basis.
It is not just, oh, plug in some numbers on some ROI spreadsheet that a lot of people have historically put in front of customers. It is, um, a very structured analysis that shows if you move to this platform, here are the various areas we can bring value back to your business.

Originality

10 / 20

The episode recycles established AI adoption frameworks: guardrails, human-in-the-loop verification, tool integration with CRM/enablement platforms, and the need for AI humanization. While the Actively implementation and federal-sector messaging adaptations show some specificity, the core thinking mirrors mainstream B2B AI conversations from 2024-2026. The strategic deal coach and business value assessment tool are internal builds rather than original methodologies. Few counterintuitive or first-principles arguments challenge conventional wisdom.

It's critical that we connect into Salesforce. Just making sure that all the data is hooked in there.
There's a disclaimer at the bottom of everything. This is AI, it can make mistakes. Guess what? That's true.

Guest Caliber

13 / 20

Jillian Swenson (VP of Federal Sales) and Alex Cruz (Senior Director of Field Enablement) are credible practitioners with relevant operational experience - Jillian previously carried a bag in sales, and Alex has five+ years at SentinelOne managing real field enablement. However, they are not exceptionally senior (not C-suite) and represent a single company's perspective. Their expertise is genuine but somewhat narrow in scope (cybersecurity/federal public sector), limiting broader B2B applicability. Appropriate mid-tier caliber for a specialized episode but not marquee-level.

I'm Jillian Swenson and I have recently joined Sentinel 1 as the vice President of Federal.
Alex Cruz, uh, been with the company for five plus years. I'm the senior of field enablement at Sentinel One.

Specificity & Evidence

12 / 20

The episode names specific tools (Gemini, Claude, NotebookLM, Actively, HighSpot, Salesforce, Demand Base, Zoom Info) and mentions real use cases (RFI/RFP automation, account planning, LinkedIn Navigator for job posting signals). However, concrete data is sparse: one reference to "a thousand percent" productivity gain lacks supporting metrics, no dollar figures, deal sizes, or quantified outcomes. The federal-sector angle and command-of-the-message alignment are noted but not deeply evidenced. Examples tend toward descriptive rather than granular (e.g., "one sales rep uses the business value tool well" versus named metrics or benchmarks).

We're talking about a thousand percent. A thousand percent. So just looking at typical sales cycles, like how to do annual planning, how to prep for, you know, account reviews with a customer, they're leveraging the tools and it's making it better, more effective.
RFI, RFPs, account research, proposal building. How can we help Build out really good, thorough prompts, use cases and provide those for the field to quickly manage.

Conversational Craft

10 / 20

Host Fred Diamond asks decent setup questions and follows up on high-level topics (guardrails, integration, adoption drivers), but rarely pushes for deeper specifics or challenges soft claims. He allows the "thousand percent" productivity claim to pass unchallenged, doesn't probe the gaps between pilot and enterprise rollout, and doesn't dig into failure rates or adoption friction. The guests largely confirm each other's points rather than engage in productive tension. Questions often serve promotional purposes (affirming their innovations) rather than critical inquiry into trade-offs, risks, or limitations. Conversational flow is smooth but lacks intellectual rigor.

Very good, Julian. Bring us home.
That is great. Alex, what are your thoughts on that?

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Share of words spoken

  • Speaker A39%
  • Speaker B34%
  • Speaker C27%

Most-used words

sales37alex37sure24tool21jillian20tools20sentinel19account19team18show15back14making14value14linkedin14first13claude12

Episode notes

This is episode 863. Read the complete transcription on the Sales Game Changers Podcast website . Watch the video of this podcast on YouTube here . The Sales Game Changers Podcast was recognized by YesWare as the top sales podcast. Read the announcement here . FeedSpot named the Sales Game Changers Podcast at a top 20 Sales Podcast and top 8 Sales Leadership Podcast!

Full transcript

35 min

Transcribed and scored by The B2B Podcast Index.

Speaker A: Foreign.

Speaker B: Thank you so much. Welcome to another episode of the award winning Sales Game Changers podcast. My name is Fred diamond with the Institute for Effective Professional Selling. I'm very excited for today's show. We do a lot of shows, Jillian and Alex, on AI and the selling process, but we're going to get very specific in what Sentinel One, uh, and the public sector is dealing with AI tools, how they're using them and uh, we're going to get a great perspective on that. I want to remind people you can read the transcription and listen to today's show at sales game changerspodcast.com salesgamechangerspodcast.com for the complete transcription and audio of over 850 shows. And if you type in Jillian Swenson's name, you'll see her, uh, on occasion. She's been on the show before. And I'm very excited to be talking to you in today's role. If you're watching this on YouTube, give us a thumbs up. Leave a comment, and if you're listening on Apple Podcasts, give us a five star review. All right, I'm very excited. We got Jillian Swenson, Alex Cruz with Sentinel One. Uh, Jillian and Alex, just give us a brief introduction what you do with Sentinel One. And I'm excited that we're going to get very deep into how your, uh, you and your sales organization, uh, are using, uh, AI tools to be more effective. Julian, you get us started.

Speaker C: Thanks. It's great to be back here again, Fred. I appreciate the time. So I'm Jillian Swenson and I have recently joined Sentinel 1 as the vice President of Federal. And as Fred mentioned, when I did this show before, the closing question for me was, what's your best advice to sales leaders? And I said, if you're not using AI, you've got to embrace it. So when Fred reached out about me doing the show again, I'm like, well, let's go deep on AI and talk about that. So I'm excited to talk to you today, Fred.

Speaker B: That was a great bit of advice. That was close to two years ago. We're doing today's interview. Yeah. And that's. You were, you were ahead of your curve. Good for you. And uh, we're doing today's interview in July of 2026. So it's a different world as it relates to AI and we're going to get deep into how you're directing your, your selling professionals. Alex, Alex, uh, Cruz, give us an introduction.

Speaker A: Thank you and welcome. I appreciate the time on this podcast Definitely checking it out. Definitely a subscriber of it. Um, Alex Cruz, uh, been with the company for five plus years. I'm the senior of field enablement at Sentinel One. So that means onboarding, field enablement, obviously everything on productivity. So AI is close to our heart in making sure that the field has what they need to be successful.

Speaker B: Well, I'm glad to have you on the show because, um, we've done a lot of shows, obviously We've done over 850 sales game changer shows and we actually have a special sub brand called AI and Sales Brief where we get into the ties with AI and sales. And a lot of it's, you know, it's evolved a lot since we've been doing this over the last year. The podcast has been around for nine years, but AI topics and Gillian was one of the first people to get us started. So Alex, once you get us started here, you know, every sales leader of course is talking about AI, thinking about AI. However, many have struggled on how to standardize and manage across the sales process and with the sales organizations. Uh, what made Sentinel One decide this wasn't something to watch, but something that your sales organization needed to embrace and kind of get us started in the conversation here?

Speaker A: Yeah, and honestly I will say this is something that when Julian came on board she said exactly that. She is just firsthand all AI. How can I use it to be a better leader, but also how can I really unlock productivity within the sales work? Um, for us specifically at Enablement, it's all about how can we really enable the teams on the right workflows. What are the repetitive tasks that you're just drowning day in, day out that I can automate. Um, it honestly goes to our DNA as a company. Uh, if you look at something one's history, way back when we were founded, 13 plus years ago, Tomer Weingarten really looked at all these threats coming in and we were a signature based antivirus. How can I use AI in ML to stop attacks at machine speed? And so when we're thinking that and flipping that on the sales productivity side, how can I look at a salesperson's day and see what's taking so much time? There's just so many areas of account research, proposal building, RFIs, RFPs that are just drowning a sales and uh, even account team. When you think about a sales engineer and all the other folks that are involved in that process that are just eating up time. So for us it's how do we really provide the tools necessary that an account team has to automate a lot of those tasks and get some more time back in their day.

Speaker B: So we're going to be talking about the tools in a second here. I'm going to ask you to kind of take us through some of the tools and I'm excited. A follow up question, Jillian, I'm going to have for you is, you know, we talk a lot now about workflow. Right. And how AI needs to complement the selling professionals workflow. And I'm excited to ask you that question. But first, Alex, kind of give us a little bit of an orientation. You mentioned, uh, several different AI platforms. Walk us through some of the different tools your team uses. And more importantly, why would someone use Gemini versus Claude versus uh, maybe a tool like actively, um, which job? I'm sure you've gotten deep into them obviously in the sales process. Which job, uh, performs best? Um, at the various levels.

Speaker A: Yeah. And this is honestly one of the very first questions we got when we were starting to go heavy on productivity for AI. There's so many different tools and a lot of times there's overlap. Um, so we are at Google Shop. So I think definitely on Gemini. NotebookLM is an amazing tool which can do amazing things for account planning and really just building together really good notebooks for all of your accounts. We recently got Claw this year and so that is still a learning journey. I won't say that we are experts in it, but we're making a lot of great strides in it. And then, um, as we're thinking about really the agentic form, because a lot of the enablement that we've had was more of, okay, using these tools to be more efficient. But how can we leverage a tool that is going to go out and be an agent working for you 24 7, where it's looking at signals, buying signals. Looking at a recent podcast like this and saying, hey, there is an account that, that is matching the ICP and matching these buying signals that you should engage and reach out. So this is where we're really taking it to the next level of leveraging AI to be more proactive and more engaged in those early sales cycles.

Speaker B: I love that because there's so many tools. And what a lot of people get wrong, we think is that they focus on the tool. Right? As like, you know, let's just get, especially in enablement, you know, there's thousands of tools at this point, if not tens of thousands. You know, you could spend all the time working on tools and it's really about the workflow. So Jillian, good to have you again on the podcast. Thank you so much. Um, why don't you walk us through the typical day, typical sales day with AI? Uh, where does AI show up for the first customer interaction until the opportunity closes?

Speaker C: Well, uh, we're actually seeing a big shift there. So even just you know, five, six months ago, when I joined got with Alex's team, started looking at it, and my team had not embraced AI much and I was a power user, really experienced on Claude. So my first thought was, well, how do we start doing that basic research? And that is where we started. And then we started to get more, uh, focused on what Alex touched on, which is how do you take the work out of like, routine activities? So if you're putting together a presentation, you can leverage Gemini to create your Google PowerPoint, for example. Or, um, if you're putting together communication, what does that look like? And then I had my team doing things like their account planning using a tool that Alex's team built that's like our account plan is going to look like this, going to leverage everything underneath. So we started doing more of that prep and research. But now with the implementation of Actively, we're starting to switch into the more proactive strategic focus on a daily basis. And my team is just getting up to speed on that. It's a new implementation for us, so we'll have to do this again in a year because I'm sure it's going to have completely changed at that point. But it really is about starting to just look at your workflow and figure out where it is not a high value, high experience task and shift that work over to an AI tool.

Speaker B: So, uh, most people probably know about Gemini and Claude and chatgpt, of course. Can you tell us a little more specifically about Actively, uh, either one of you, about what actually it does, how it's used. To be frank with you, it's not a tool that I'm particularly familiar with.

Speaker A: Yeah, sure, I can take that one. So Actively is it's really, uh, an agent, right, that's, that's trained on the vast majority of our systems internally and that's also hooked into LinkedIn, into Zoom info, into Demand Base, which is our buyer intent tool. And so what it'll do is crawl the Internet, right? It crawls basically all of the signals on LinkedIn, um, and then basically compares it against all of our internal systems that will essentially slack a rep, an sdr, an account team. As soon as there's intent, as soon as it identifies, there's some signals going on. With this account, that marks an engagement. And that's not just a signal of hey, go, reach out. It provides buyer from LinkedIn. It also will provide a customized email. So it's basically doing a lot of this guesswork of, okay, which accounts do I need to really start engaging with? And I think this is the one thing that gets me most excited about AI. It's like when you have this account base and you were hunting and we all were there before when we didn't have AI and you were looking for something, you were looking for some diamonds in the rough. A tool like Actively will literally eliminate a lot of that. Just that time space of here's someone in the market that right now is searching for security tools that we can, uh, as a problem that we can solve. So that at a high level it does a lot more. But that's really the intent behind it. A 247 agent that's working for you, um, to find those, those ripe accounts.

Speaker B: Very good. Julian, I'm going to ask you in a second about some of the biggest promises with AI and what some of the things are that you're seeing from an improvement perspective. I'm going to ask a very basic question. Alex, you just mentioned LinkedIn. Uh, maybe Jillian, you can chime in. How are, how are you? Um, again, most basic tool that there is right now, probably one of the biggest tools in B2B and B2G, et cetera. How are you instructing your sales organizations to use LinkedIn? Very, um, basic question, very basic tool. But I'm kind of curious. We're getting deep into the AI. What's your advice and strategy for them on using LinkedIn? Whoever wants to take that first? Dillian, why don't you go first?

Speaker C: You start, Alex, and I'll close this out.

Speaker A: LinkedIn for us, it's, it's critical. Um, we have LinkedIn Navigator and that's something that we use to, to really understand where the contacts are. Again, just understanding their profile matching up honestly with us, understanding who we have relationships with within Sentinel One that could actually broker a meeting. That's something that we use very heavily here within Sentinel 1. And then just understanding that profile of do we have really good buying intent. Also with, um, openings of job boards, AI security is top of mind. So if they're actually going and hiring a lot of AI data scientists, a lot of web developers, AI. Right now we're looking for those job roles on LinkedIn, which are mostly posted and using that as buyer signals. Jillian, go ahead and share more.

Speaker C: Yeah, so we're doing all the typical things, social amplification, driving people to our events that you've historically seen. But where I've personally used it and seen my team using it more recently is having that outreach very customized. So, um, having the research done across their public profiles, not just LinkedIn, but where they've spoken publicly, articles someone might have published, and really getting a sense of what that person is trying to drive at their organization before you do the outreach. So doing the background research and then actually customizing it. So I was sharing with Alex recently, I was doing a cold outreach to three different C levels at the same company and I wanted to make sure that the messaging was consistent but was completely customized to their particular role. So, you know, having Claude just rapidly do that, it would have taken me, I don't know, maybe two hours to craft a great response. And I was able to take that, do it pretty quickly. But the only thing I changed was the first responses didn't sound like me. They were flowery, they were long. I'm like, oh no, that's not me. Let's just get to the point, make the ask, use the data and go. So, um, I was able to work with Claude and send it some of my previously written emails so they could have more of my voice and tone. I think that's important. We talked a lot about AI slop and not wanting. I mean, I get, I get stuff in LinkedIn every day. It's just delete, delete, delete. Because it's just spam at this point and I don't want to show up that way to our customers.

Speaker B: That's great. So, Julian, let's get back to some of the biggest promises of AI and of course one of them is speed. And hopefully speed being more productive. Um, what are you seeing as some of the biggest gains with your sales organization? Um, you know, you mentioned prospect research, account planning, writing emails, you know, writing LinkedIn requests. You just talked about, uh, collaboration amongst groups. Um, are your reps getting, Are your sales getting. Sales reps getting faster? Are they, Are you seeing improvements, uh, from them by better utilization of all the tools?

Speaker C: We're talking about a thousand percent. A thousand percent. So just looking at typical sales cycles, like how to do annual planning, how to prep for, you know, account reviews with a customer, they're leveraging the tools and it's making it better, more effective. And what I will say, particularly with Claude, is that, um, as you move up the maturity level in working with AI and you stop using it just as like a super Google and you really start refining things and having it as a conversation with Claude, you get a much, much higher quality product out of it. And I've had results come back initially that aren't quite right. And my experience allows me to say, oh, that's not quite right. Let's tweak it a little bit. And we found that if you are, um, working iteratively with Claude in particular, that it gets very good at actually recommending approaches to take. It will often give you three options based on the research that you provided it and things like that, and help you really hone your messaging.

Speaker B: That's amazing, Alex. So here we're talking with, um, Gillian Swenson and Alex Cruz with Sentinel One. We're talking about usage of AI. So of course AI, Alex, becomes more powerful, uh, when it's connected. And you've already begun to talk about some of the ways that it gets connected here to various other applications, but talk about how you're integrating AI with platforms, uh, such as Salesforce and maybe HighSpot. Um, how does that change the seller experience? Because everything we're talking about here is designed to make your sellers more effective. And again, I run the Institute for Effective Professional Selling. And the reason In May of 2025, we changed our name from M. The Institute from Institute for Excellence in Sales to the Institute for Effective Professional Selling. Because, Jillian, we talked to 200 people like you, senior sales leaders who said coming out of the pandemic, our people just need to be more effective at 30 different things. So, Alex. And by the way, Alex, I'm getting from you that you really enjoy this. You know, that you really enjoy.

Speaker A: You gotta be passionate about it. Yes, exactly.

Speaker B: I do.

Speaker A: I love what I do. And I mean, as any good enabler, I definitely held a bag for many years, had a passion for mentoring, and here I am. So that's what I love. And seeing other people really get successful is something that I crave. Um, for the integration piece, I think this is what's critical. And it might parlay into another question you have or just around areas of that we've seen as concerns or issues that we're seeing across the Salesforce. Um, but it's critical that we connect into Salesforce. Just making sure that all the data is hooked in there. If you want to query your account base, if you want to query an account, the next steps to win have to be. We're really diligent on having that, that, that deal and the opportunity at the next step level. So getting into those areas, um, high spot for Us is our, really our source of truth when it comes to content, when it comes to sales plays. And so leveraging that content when we're querying Claude and making sure that there's guardrails in place and this is something that we see is, I mean AI is amazing and you can definitely spend just inord amount of times building great content. But if you don't have guard rails that are really making sure that we're staying on brand, that we've got really our, our key value messaging, then it's going to have a tendency to hallucinate. There's no way that you can just, you know, eliminate hallucinations unless you put some guardrails in place. Um, another example is really big on value, quantifying value. Right? So we're solving a lot of big pain points a lot of time back into these security teams. If we just trust AI without any checks and balances, who's to know that that calculation is right? So we do have a business value assessment tool which we're now working on integrating within all of our AI stack. So that when you say, hey, I want to create a value assessment, a cost ROI analysis, it actually is using guardrails to eliminate a lot of the kind of hopeful calculations and content that's built without some guardrails. So that's a little bit of things that we're dealing with now, which I think the folks on the call would appreciate.

Speaker B: I want to follow up on the guardrails. Um, so how do you encourage, I don't know, experimentation while making sure that customer data messaging compliance and quality stay protected and ah, I think also I know that Sentinel 1 has a tool uh, related to that. Would you mind addressing that now? Uh, the whole concept of guardrails for sure.

Speaker A: Um, so the guardrail piece and this is something that when we rolled out Claude, we saw just a lot of amazing innovation where uh, specifically the ses, the engineers were first at bat of creating these amazing skills and just these things that other people could use. Um, so what we did is very quickly establish an SE innovation center to just go and make sure and see, okay, is this something that we can leverage internally? Is it customer facing? It needs definitely a lot more checks and balances and governance. So we have a good process of in or you know, organically trying to surface up some really good talent and just, you know, skills that an SE may be using in Vancouver that could be something that could be applied globally. So that's, that's something that we've, we've had really good success in, um, also as a company for engineering and, and support. We also have an area of review for skills and then making those publicly available. Um, speaking about the human, the human piece that Jillian was saying, we've all seen those AI generated emails. We actually have a humanizer skill that will go in and crawl your emails and look to see your voice of tone, your inflection, how are you speaking on zoom and making sure that your AI generated communications out to the customer are at a human nature and they're not AI with all the hyphens everywhere. Right. Um, but going back to essentially the, the solution, I think this is something that's really, um, one of the fastest growing lines within S1 is prompt security. So shadow AI is rampant everywhere. Before we had a lot of these guardrails in place. You can imagine employees just want to leverage AI so they'll go on to their own personal instance of ChatGPT, of Gemini, of Perplexity, and start loading up, you know, possibly some, some sensitive data like account information. You want to build an account deck, but you're using your personal, your personal, uh, information or uh, actually account information on these personal websites. And so this is a severe risk, which obviously is a lot of companies are grappling with. We have one of the best solutions here that can not eliminate the use of shadow AI, but enable safe use of it. And this is imperative that companies shouldn't stifle innovation. But you have to have some guardrails in place. So if there's sensitive information, we can either redact it, stop it, and then actually give a bit of information, um, back to that employee of. This is why we, we can't have you loading this, this instance of information and then also making sure that we're staying within separate governance and guardrails, um, for obviously data compliance is massive as well when you think of the act.

Speaker B: Yeah, exactly. Alex, I have one more question for you, Gillian. I'm sorry if you feel left out in the last couple of questions here, but, you know, you know, one of the things we've talked about is, uh, social media got big, was how do your people represent the company on places like we alluded to LinkedIn and Facebook and other Instagram or other type of social media. And that may or may not, you know, have been a huge challenge. But you also mentioned Alex developing sentinel 1 specific AI skills. So what does that mean? And you know, again, your employees represent Sentinel One.

Speaker C: Right, right.

Speaker B: You know, yes, they're human beings. Yes. They have hobbies, hopefully, and maybe Kids in little league and maybe political views and, you know, whatever it is that they want to get out there. But they're representing Sentinel 1, you know, in the work environment, it's gotten a little bit blurry. So. So how do you make sure that their usage of the AI, you know, reflects Sentinel 1? Messaging, positioning, competitive differentiation, um, and best practices. It's tell me if that's a big challenge or. And how do you do that?

Speaker A: So internally, for sure, like hooking into high spot number one enables us to make sure they're on brand. And this, these are things. When they're developing custom content, we want them to tailor content. You don't want boilerplate decks going over and just assuming these are the challenges you're dealing with. We want them to customize until the content, but we also want the main narrative to be involved there. Going back to social media, we have a really good social brand team which will build out LinkedIn posts on key announcements on key thought leadership pieces. So ensuring that they've got a good baseline, we encourage a little bit of flexibility. And to Gillian's point, we want to make sure that it's supporting her federal DOD and civ teams. Um, but at the minimum, as a company, we should be supplying that, that overarching narrative, that key areas of differentiation and then from there we'll tailor it. But yes, that's the key thing of hooking into a lot of our systems and also working closely with our social and brand team. So the sales teams are leveraging the approved content, um, that should be going up.

Speaker C: We actually have a resource spread that specifically focuses on taking that core messaging and then making it appropriate for public sector, particularly federal customers. Because some of the words are different, some of the way you talk to those kinds of customers are different. So we want to make sure that we have the appropriate wording, uh, approach with our federal customers that are slightly different than what you're going to see in the commercial space.

Speaker B: Yeah, absolutely. So, Julian, you told me that adoption happens when leaders, of course, model their behavior. Um, talk a little bit more about that. What are your, what are you directing your management level people, your sales managers, what are you directing them to do differently that encourages sellers to embrace all these great tools. So obviously we're doing a show today. You know, we're bringing on Alex. He's obviously doing a lot of things. The company's investing a lot. You know, you wanted to come on the show to talk about some of these great things. So how are you directing your leaders to, to make sure that it happens.

Speaker C: Yeah. Ah, my poor team. They probably hate me at this point. But I found Alex's team in my first week at sentinel1 and just started asking them all kinds of questions and using all the tools and probably asking them for things like we hadn't thought about that and really leaning in. That's why Alex and I are both still excited to be here today. And um, I started with just kind of getting an evaluation. Where was the team using any of the tools? I honestly did not see that much adoption. So I started to kind of make it non negotiable. So we said, oh, we've got this meeting coming up and we're going to talk about this topic. I want you to use this tool. So one of the things Alex's team created was a, um, strategic deal coach almost. And it would say, uh, I've got this opportunity. You could actually put in very little about it. It was surprising how much you could get out of the tool. I've got this customer. Here's what I'm trying to talk to them about. Fairly minimal requirements to enter and it would come back with an entire play. And we use, uh, Command of the Message as our sales training. So it was completely aligned with Command of the Message and it would give you a way. So we're in the process of adopting AI and adopting Command of the Message. And this tool really brought it together and made it impossible for the account executive to not comply with both requests. And it made it much more productive and it got the adoption level up very quickly. And then I went to the second phase where it was like, oh, I'm asking you a question and if you come back to me with an answer and I can't tell that there was some deep AI work in here, I would go ask the question. I'd say, oh, what you gave me was okay, but look what I was able to get in 30 seconds, you know, and then they're like, oh no, now we need to get serious. She's going to check. So then it was more, um, proactive on their part. And now I think we've come out with the, with Claude in particular, it's a much stronger tool. And with the investment and actively now I'm seeing my reps starting to, across the board, just embrace it.

Speaker B: So Jillian, I want to ask you a general sales leadership question. So we talk about the fact now, again, we're doing today's interview in July of 2026 with Jillian Swenson and Alex Cruz from Sentinel one more, uh, sales professionals have Always had to bring value, right now more so than ever. And one of the great things about the AI tool that you've touched on, it can do a lot of research into what your customer's direction is. Right. Especially with public sector, there's never been a problem with knowing where government agencies are going because it's public information. Of course you had to read a lot of things and you had a research. Now at the, the flick of a button you could figure those things out. How are you leading your teams to help them bring or at least show the customer value? Right. You know, the customers don't need to be talking to salespeople because they could go on, they can go on AI as well and type in what is sentinel one's direction or what are, you know, what's the tools that you fit in with your competition's direction so they don't need you to sit for a day and go through a product roadmap. How are you instructing your, your reps and Alex, if you want to talk about, you know, non public sector, uh, or what your thoughts, how are you helping them use AI not just for the productivity stuff which we touched on, but to bring more value to the customer.

Speaker C: So one of the things that Alex mentioned earlier on was our business value analysis tool. And I have one, uh, sales rep that has just been all in on that tool from day one and we actually kind of hold her up as the model for how that tool works. And it is not just, oh, plug in some numbers on some ROI spreadsheet that a lot of people have historically put in front of customers. It is, um, a very structured analysis that shows if you move to this platform, here are the various areas we can bring value back to your business. And to have that business based discussion I think is one of the primary areas. So it's unacceptable to show up not prepared with AI. There's no reason for that. That was last year's problem. This year's problem is then how do you translate it into business value? And it's particularly challenging in the federal space where you're not looking at an annual report and going in and saying how I can uh, increase your earnings per share. It's a very different discussion. So being able to not just take that business value analysis from a financial perspective, but then being able to translate that into mission impact is something where I still think the experience and the human touch is highly additive to AI.

Speaker B: That is great. Alex, what are your thoughts on that?

Speaker A: I couldn't agree more. Um, I think everyone right now is selling an AI powered solution. So how do you separate yourself from all the noise? It's literally quantifying what we can actually drive and providing a proof point of how we've done it. Going back to command of the message, it's all about business outcomes. Here's what we've seen. Here is an example of hypothesized value and then helping your champion actually provide this and sell it internally to the economic buyer. These economic buyers need to see clear line of impact to their business. Same on the enterprise and commercial space. You need to show how we're attaching to business problems and how we can actually influence the business. So AI is tremendous there. And latching on to regulations if they don't adhere to the AI EU act is huge in Europe. Even for US Companies that are doing business in Europe, you have to adhere to it or else you're at risk for 7% of revenues. So quantifying that and making sure that they can build the case internally, paramount to getting these six figure deals across the finish line.

Speaker B: So we have time for one more question before I ask you for your final thoughts. You guys have implemented a ton of things. There had to have been some mistakes, some lessons learned along the way. Uh, especially Jillian, you leading such a, such an important organization. Um, Julian, why don't you go first? Like what's a mistake that you learned that, uh, you know, in retrospect, uh, you know, you wish you didn't go, uh, through. And then, Alex, your thought as well.

Speaker C: Um, I, I edit everything. I actually read it. So, uh, fortunately I didn't get too far down the path with some slop that came out that wasn't usable. But I have seen people present things to me that have obvious errors. So it's a very basic mistake. But I mean, there's a disclaimer at the bottom of everything. This is AI, it can make mistakes. Guess what? That's true. And also not just the glaringly obvious errors, but things that are just not strategically where you want to go. You can't just rely on AI to do your job.

Speaker B: Yeah, I mean, that's something that we all hate is when we see something that's obviously AI generated and it didn't give any thought to me. And I like what you said before, Jillian. You talked about how you had to train it to be humanized to you. And we, uh, constantly know that needs to happen. Alex, ah, what's a mistake that you'd like to focus on?

Speaker A: I'll piggyback on Jillian's comment Just putting guardrails in place so that we can minimize the amount of inaccuracies. Um, AI is amazing and it does just crazy things on just reducing time as a rep. But without guardrails in place, it can get you in some hot water. If you send something over that's generated and you don't do, you know, trust but verify. We've all came through that, that, that, that frame of thought. So we have to verify AI, we've got to make sure that before we send out anything to a customer, we're reviewing it with a subject matter expert. Is this in fact legit? Are, ah, there things here that we don't know? We need to make sure that we're validating before we send out to a customer.

Speaker B: Absolutely. I want to thank Alex Cruz and Julian Swenson with Sentinel 1. This has been great. As a matter of fact, uh, we've done over 850 shows. I think this might be the first one I ever did with a in the field VP and a sales enablement leader. So I'm going to be doing more of these. So I love the, uh, way that you both worked on each other. I worked, you know, bouncing ideas and getting the key message across. So I want to thank you both with that. Um, as a wrap up, uh, final thoughts. So, uh, if you want to uh, talk to something, maybe give some advice. Jillian, to a peer who's maybe six months to a year behind you and want to get going. And Alex, maybe the same thing with enablement, uh, leader. You know, one of the great things about you were doing, Alex, and what you're talking about is you're literally helping the field, you know, become more effective. And Jillian's. One of her challenges of course, is making her selling professionals more effective. So I love to see the, the synergy and, and the working together. Um, Alex, why don't you go first? Why don't you give us advice, maybe for your peers on what they should be doing and then Jillian, you'll bring us home?

Speaker A: Sure. I'll, um, I'll say there's, there's nothing more than really, um, spending time with the field to understand what the problems and where the time savings could be. And I think this is where we, we got it right was as soon as AI came out and we had, you know, just like, we've got to get this jump on board. We very quickly spanned the field globally and said, what are the major use cases that are spending the most time? RFI, RFPs, account research, proposal building. How can we help Build out really good, thorough prompts, use cases and provide those for the field to quickly manage. I think that's one thing staying close. And then honestly, for me, speaking with Gillian and understanding what she's dealing with and constantly iterating because as AI is moving at lightning speed, space, those use cases have now changed. So I think the constant iteration, making sure that the field has what they need for us is the number one thing for us as enablement M Org ensuring that we're close to the field.

Speaker B: Very good, Julian. Bring us home.

Speaker C: Well, you stole my answer because my answer was going to be, go out and find your Alex. Having that partnership between sales leadership and sales enablement is completely game changer. To steal from your title, um, that's important. And also you have to do the work so your people will only do what they see you doing. I think one of the reasons I have credibility with my team is I was in sales for a long time, carried a bag. I carried a bag well. Now I'm using the tools. I'm not asking them to do anything that I'm not willing to do myself. And I make time for myself every week, even if it's just one small thing to do that I haven't done with AI before. And I'm actually surprised myself. It's like, oh, I wonder if Claude can do this. And I just ask it like, this is amazing. So, um, just challenging yourself every week to just get a little bit better. That way you don't get so far behind. Back on a catch up, I will

Speaker A: piggyback also on that. The leaders have to lead from the front. The lead, you can't go and say, learn AI and you as a leader, don't know it yourself. And this is something that Jillian, when she came on, just was passionate about. Show me what we can do with AI. Show me the stack and I'm going to really get my team to the next level. You have to lead from the front.

Speaker B: Absolutely. And you have to be doing it all right. Once again, I want to thanks. I want to thank Julian Swenson, Alex Cruz with Sentinel One for sharing this great insight today. My name is Fred Diamond. This is the sales Game Changers podcast.

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