83. AI Series: Sales Craft in the age of AI

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I'm your host, Ashwini. What does a career in sales in the era of AI look like? Now, most technology products are actually built or, you know, at least augmented by AI today. What are the unique challenges and opportunities when it comes to selling these products?

And how can folks at different stages in their career be more successful by leveraging AI? To answer this and much, much more, we have with us Jason Langoni, head of global AI business development at Nutanix. He has over two decades of experience spanning large companies and startups in a variety of roles. And before his current role at Nutanix, he was an early stage growth executive leading a generative AI startup from seed through series A, owning the product market fit, pricing, fundraising, and founder-led selling.

If there's one thing that I'd add to this about Jason, he just has an unlimited amount of energy and mostly very little time. So thank you so much, Jason, for making time for our podcast in your super busy schedule. Oh, thank you so much, Ashwini. I'm very thrilled to be here today.

Awesome. So let's start from the beginning, Jason. I think you have a very unique and amazing background. So you did engineering, architecture, management, sales.

How did you get drawn into the world of sales and business development? Yeah, I mean, it's interesting because I was very much on a technical path. I mean, even from elementary school, middle school, I was always really interested in computers and programming. And through my early career, I got like a Microsoft certification and really was just doing engineering and architecture.

But if I rewind the clock a little bit to like elementary school. So I grew up right outside of Washington, D.C. in the suburbs.

literally in between the landfill and the prison for DC. So, you know, I was modest, loved where I grew up, but I kind of knew this little bubble and, you know, late elementary school, they started knocking down the woods around my house and putting these really big homes, you know, with garages and more than one bathroom. And, you know, so it was kind of that moment. It was like, oh, there's this, there's this world out there of, you know, extravagance or what seemed like extravagance.

And so, you know, as I'm marching through kind of my early stage career as an engineer or a solution architect, I started to take notice of these people, you know, men and women dressed really nice in meetings I wasn't invited to. And, you know, I started to ask those folks questions, like, what's going on? Like, oh, well, we're building this strategy or we're helping this customer through a really complicated challenge. You'll be involved in designing the solution, but we're helping them with their business strategy.

And to me, I wanted to be in those meetings. I wanted to be in the blazer looking sharp. And I started asking questions and started to really start to think through what does it take to be a good stellar? And what does that look like?

Thank you so much for sharing that. It's very interesting because I think many of us don't even observe ourselves enough to realize when that tipping point is. You made some very interesting career decisions, right? I mean, you joined super early on the virtualization ride when it wasn't a super successful choice, I would say.

And then you started really early on the Generative AI journey as well. So what helps these choices? You know, I thought about this a lot because I felt like in the moment I was very fortunate to be in the world of virtualization as it was taking off. I got a high level certification because I do believe in being able to show and articulate your technical expertise, willing to travel.

And it really accelerated everything about my life, career and personal. And from that moment on, I won't say I was always looking for like, what's the next wave of virtualization? But HCI, when I came across Nutanix, I mean, it was literally a no brainer. I was living the pain every day of designing solutions with multiple storage arrays and a SAN and networking and virtual networking.

And it was great as someone paid an hourly rate, but it was wildly complicated and very, very brittle. So for me, it was a no brainer. I've been doing kind of AI on the side, not generative AI, but more traditional AI for a very long time. and once, candidly, ChatGPT came out, I mean, it was another, this is a no-brainer moment.

As long as someone can take this capability, fit it to the needs and the requirements of the enterprise, it's a very easy value, in my opinion, to quantify. So this is going to take off. So again, to me, they were very obvious moments. I recognize that's maybe not the case for everybody, but the value knocked me over the head that everyone's going to need this or want this.

I think that speaks to both your passion and conviction. I see a pattern given that working on the generative AI side now. So I'm curious, are you ever worried about the risk component or do you think the conviction makes it all worthwhile? So I will say, you know, from a risk perspective, let's say you do believe that generative AI is going to take off.

Well, there's risk in where you choose to spend your time from a career perspective. Do you want to be at a very early stage startup, high risk, high reward? Do you want to be someplace maybe it's a little more stable, but maybe it could have larger impact? So to me, that's where I apply my risk analysis.

And I've been right and wrong there many times as well. But from a technology perspective, again, to me, I think we know at this point that it's mainstream. You can't really avoid it. And we're still very, very early days when you think of just enterprise adoption.

I don't think I've taken any wild risks from a technology perspective. I'm constantly dabbling. I'm constantly in forums, reading and learning from others. And I'm just generally very curious about tech in general.

Yeah, I can definitely see that. See you tinkering with a lot of things. Describe a little bit about what business development actually involves and what somebody who is aspiring to get to this position would actually look forward to. To me, business development is great if you view it from the lens that my number one metric is revenue contribution.

I think there a lot of people friends that are in BD roles and other companies and they trying to measure influence and trying to measure things that are kind of difficult to measure which I think ultimately will lead to frustration So coming from a sales background at this point BD to me means developing and continuing to iterate on a go-to-market plan, executing that plan. And then I can see by the numbers, whether that is a successful experiment or route to market or not. That's an extremely important lens.

And I think it's a good lens, honestly, for anyone involved or adjacent to a go-to-market team. At the end of the day, we're not doing this for fun. We're doing this to drive shareholder value. And that's a very easy thing to measure, in my opinion, at least from a revenue perspective.

Yeah, absolutely. So you're thinking of very measurable impact. Given that right now, For example, you're on the generative AI product journey. It's a relatively new space for a lot of conventional enterprises, a lot of customers.

What are the unique challenges you see? Because is there something unique about trying to sell a cutting edge product versus something which is more well understood? I think this is the most common fallacy in this space right now is you have a lot of folks, whether they're in sales or sales engineering or even marketing, who are overly indexed on getting deep on the technology. And I'm not saying you shouldn't understand the technology.

And if you're on the engineering side or the sales engineering side, and you don't find this interesting enough to be dabbling in it on your own time, it's probably time for a new job. but from my perspective, it's a business conversation first. These companies, I mean, grab the latest, grab any economist for the last six months. It's all talking about business value as it relates to AI or Wall Street Journal or Harvard Business Review.

It's all about the business impact of AI. And the great thing about that is anyone in BD, anyone in sales, anyone in marketing can ask really good probing questions on a customer's business. And what are those challenges you're facing? What are the challenges you think you can apply AI to and see value?

Let's score that on a risk spectrum. What are high risk, high reward? What are maybe low risk and moderate reward? But if you frame it with a business conversation, one, I think you're setting not only yourself up, but your customer for success long-term.

not hey we had a high five super great win on this prototype but long term we're building a strategy and we have a north star that is business value or shareholder value or customer value and now we can every time we're making a decision think about it in that context which means we're going to quantify or at least think through how to quantify that value it is a super sexy technology there's a trillion POCs, prototypes, POVs going on all over the planet. But many will stop there because no one thought through, okay, what is the value to this line of business?

It's very cool. It looks cool. It's sexy. But what's the actual value?

And so if you use that as your North Star, anyone can have this conversation if that's, again, how they're rooted and grounded and where to start. Yeah, I think that's a fantastic point. And actually, along the same lines, I'm wondering, is there some kind of enablement? Is there some kind of way for sales engineers or people in general to get up to speed with this, right?

To have these conversations. So I think, you know, if you think of a typical sales team, you've got an account executive, you've got a solution architect or a sales engineer. To me, the most successful teams I've seen at any company, those folks kept each other honest. No one's perfect in every meeting.

But if you understand what the desired outcome is of this meeting, hey, if the account exec forgets to ask a good discovery question and it's a good team, the SE is empowered to ask that question because they have the same goal. So to me, that's important. Understanding from an SE perspective, it's understanding good salescraft. Good salescraft doesn't start with a demo.

It doesn't start with speeds and fees. It doesn't even start with the tech here. It starts with a business conversation and good business discovery. So making sure the SE is read up on Sandler, has some good sales methodology to follow, I think is really important.

And then the ability, I think, to storytell. Again, the most successful teams I see make the sales pitch their own, but they're doing so in a way that is storytelling. And they're walking that customer through something they can visualize themselves in. in.

They can visualize themselves in that experience versus, hey, this is a rinse and repeat story that I'm continuing to give to people. The last thing I'll say that I think an A-plus sales team will do in this space is they will have finance literacy. They will be able to help their champion, their influencer, maybe help their CIO that they're working with build a business case, understand things like net present value, additional free cash flow, not the typical just ROI, TCO. But if you had one slide that your CIO is going to present to the board on why they should invest in this AI project, can you help them articulate that?

Can you be a great peer and a great ally to help them dry run it and workshop it with them or provide feedback or data points, because ultimately the real projects, the significant projects, they're being decided at that level. And if you are not comfortable having a financial CFO grade conversation, you may not be able to help your champion or the folks you're dealing with go actually land the budget for your project or for that project. Oh, I love that. There's a lot to take away just from your conversation.

And I'm not even a sales person. I still got a lot to take away from it. It's also amazing how you articulated. It's about making the customer successful.

And this really reminds me of one of the first conversations we had when we met. I remember you were in a customer conversation and you had this philosophy, only address the customer's need. Like if they don't really have a need for something, walk away, right? and I was really happy to hear that and I felt like it's the opposite of what you normally hear about salescraft in terms of hey sell ice to the esky moors so I really wanted to understand your philosophy in terms of what's the value in maybe optimizing for the long-term gain and the repeat customers how should people think about value I think some of it comes down to good salescraft which is we need to be executing proper discovery.

At the end of the day, the customer that's going to find value in our product or in our offering has a pain point that it addresses. So until we know the pain point, we don't even know if we're a good fit for each other. So that the first thing is really understanding which is why if you got a 30 first call with a customer you may not even need slides It might just be a really in conversation to even explore if we should continue this potential matchmaking journey So for me it just really good sales craft and good qualification You know, to me, it's also ensuring, let's say we do believe there's a fit, a mutual fit.

I see a lot of times people are answering an unasked question. You're just injecting risk into your potential project or opportunity. To me, that's a big no-no. And I will say, I mean, I will agree with you.

I'm hyperactive. This is how I'm wired. I'm high energy. I'm very competitive.

So I view my philosophy forever has been I will not be outworked. There will be people that work as hard as me. I'm not that ridiculous, but I'm not going to get outworked. But what I've gotten much better at as I've gotten older is understanding that time is precious.

And so the better I can be at qualification, the better I can be at having focus on the North Star for go-to-market motion, the easier it is to say no to everything that doesn't align with what we're trying to get done. Because the amount of noise is incredible. Your emails, your slacks, your texts, the, hey, this customer would love to talk to you about X, Y, and Z. But is there a need?

Should we be talking to them yet? And really understanding the value of time and how you apply sales craft to maximize your time to me is, you know, again, it took me two plus decades, I guess, to learn this lesson. It's something I think I've gotten much better at for the last 10 years than I was at the first 10 years of my sales career where I would say yes to everything. Right.

No, and that's an amazing takeaway. And I think it's crossed the board for all roles. I think I'm sure with that. But I think that's a great way to think about it in terms of the value of time as such.

So I think along the same lines, I know you've shared a bunch of these characteristics already. But for someone who's maybe contemplating a career, either a shift or maybe just out of college, do you think there are certain characteristics that make people a benefit for sales and business development that they should vote for? I'll say, I think all of these characteristics can be learned. I think most people, if you were to say, give me the typical characteristics of a salesperson, they'll say outgoing, gregarious, really good presenter.

You know, if my wife was on this podcast, she would tell you I'm awkward in public. Like, you know, I'm awkward at the school events. That's not my cup of tea. So clearly you can work at these things.

And I will never forget kind of my first real presentation in the public space, which was at a VM world like in 2008. It was horrible, like shaky voice, horrible slides. So if you anything, right, if you just put the reps in consistently, you can get good at anything you want to get good at. What I do think is important is that you do have a genuine desire, genuinely, to help that customer overcome the challenge.

We all know salespeople, I'm sure, you know, the phrase coin operated. And there's very successful salespeople out there that are, that's how they're thinking, and they've got their own methodology. But I do think if you're going to build a personal relationship, because at the end of the day, especially the largest of projects are done on a personal level, you really have to understand and emphasize with the customer from their perspective. What are they going through?

What are they trying to accomplish? What is their boss breathing down their neck about? What do they worry about? And if you have those innate characteristics, or you work on being a good listener and asking good questions, at least in your work environment, I think those are fundamental capabilities.

You need to have to be successful and to enjoy the role long-term. Yeah, that's great. So I guess the 100 hour of practice rule. I think this also goes back to some of what you were saying about limited time.

I know you're a power user of AI, Jason, and everything that you do, right? So do you have any tips for folks who are in a similar role, who are juggling things? How can they leverage AI? Any tips?

I mean, at this point, I use it constantly. I won't even say I use it every day. I won't say I use it every hour. I literally use it constantly.

For me, I've got everything from researching customers to giving me an outline for a proposal I'm working on or, hey, look through this QBR deck and view it from a CEO's perspective, what's missing. So you've got that basic stuff, but I'm also using it to afford me more time at my job. I've got agents running that will go out and pull information from my kid's school and understand where grades are at. And hey, there's a French exam coming up on Thursday.

Go ahead and build flashcards. I can quiz my middle kid on French on the way to school. Ultimately, if it does come back to time, you're going to use AI partly in making your work better, your productivity exponentially better, but you're also going to use it to free up time to apply probably to work, but maybe it's an 80-20 split, that additional free time, 80% of it's worked 20%. Now I can get into the gym today, or now I go on a walk, an extra walk with my dogs and think through the challenge.

So to me, that's really important. And I'll say, I mean, completely on a tangent, really interesting trend for me. I was a heavy chat GPT user this time last year. I've almost fully shifted to Gemini's like my default artificial intelligence at this.

But I don't know if you're similar, but I'm still using ChatGPT and a bunch of other tools and N8N and all this other stuff. But Gemini's become my default AI. I don't know if it's the same for you. Yeah, I think the integration into the entire Google suite really helps, right?

It's like you don't have to go to a different interface to use it. So it's become pretty seamless. So yeah, I agree. I think my usage has also shifted.

Yeah, I mean, which means it's probably going to shift again. It just is another indicator how fast the space moves. I'll say one thing when I'm talking to folks like, yeah, you're right. I got to use this every day.

I got to get better at using it. One, just use it in your personal life. Just start there, right? It's low risk.

You're not going to expose any data. You're asking, how do I optimize my schedule for whatever it is? And then I will say, operate under the assumption you're bad at writing prompts. So ask AI to write your problem.

Hey, this is what I'm trying to do. Give me a good prompt for this. I find that the output there, and again, we're talking like basic usage of these tools. I find just those couple of things alone, people will see success, which means they'll want to use it more, which means they'll start to use it in a more sophisticated fashion.

And then they'll start looking at things beyond just typing into a chat window to workflows. But you have to start, you have to start using it. Have to, if you're not already. Yeah, absolutely.

Completely agree. And I think you brought this up as well. I think a little bit of agility is something that you need because you're probably going to keep shifting tools. You going to experiment in different ways but that great how you integrated it to really make more time and blurring the boundaries between the tasks right So you like optimizing across the board Ashwin, I'll give you one more real world example.

My first stint at Nutanix, the primary social platform people were using to have tech discussions was Twitter, right? And so you're manually hand crafting each tweet and you're having little spats or discussions or whatever. And in my opinion, and again, maybe from a demographic perspective, people will disagree, but in my opinion, LinkedIn is that space now, at least from my perspective. And so how do I maximize conversation and engagement?

I had AI build me an engagement plan. I gave it a bunch of articles. I find interesting, my commentary on articles and Instagram posts and podcasts. and align it with my content plan.

And now I'm waking up to, or at night I'm getting drafts in my voice from all my works for tomorrow's posts and I'm editing it. And so now I'm able to not spend a ton of time putting what I think is good content or good enough content and thought-provoking content out. Whereas if I wasn't using AI1, I probably wouldn't have the plan. I wouldn't take the time to put the plan together.

I wouldn't be measuring myself against the plan. And I know I would fall adrift of the plan because I wouldn't have enough time to actually go create the content and iterate and get creative. And so to me, again, it's just a tremendous productivity tool applied however you would like. Yeah, absolutely.

And shout out to your newsletter, by the way, I will show notes as well. But one other angle to this entire conversation, Jason, is you're absolutely right that everybody needs to evolve their way of operating and thinking with AI. But I think it's also more so for the leaders in this space, right? Because the leaders' way of making these decisions or incorporating AI, that impacts the entire team.

What are your thoughts on the leadership in the AI space? if leaders aren't mandating the use of AI approved AI within their corporate environment they are going to get left behind they will be replaced in a number of years you can't avoid it and I'm not saying be irresponsible but have a framework where you're prototyping new AI tools you're testing them and then you're ensuring they they are compliant and you're rolling them out and then you're mandating their usage. Do you have a dashboard to understand generative AI usage across your HR, across your accounting, across your finance, your engineering, your sales teams?

If you don't, you're not measuring anything. And if you're not measuring it, then you have no idea if you're being successful, if you're investing correctly, if your teams have the right tools, what gaps could be filled by AI, but you'd have no idea. I've seen companies get really smart on mining prompts to uncover process gaps and going to fix those process gaps. If you're putting it out there and hoping people go to the AI watering hole, you're doing it all backwards, in my opinion.

You have to mandate, otherwise your company is going to get left behind. It's the nudge needed for everybody to lean in and start actually participating in the AI conversation. It is. And I think you can make it fun.

The leaders have to be using it. And if they need an intern or an assistant or they need some AI person attached to the HIP for three months to get them AI provision, that's a great investment. Because if the leader isn't using it, then it's not really going to flow down. They're not going to really understand the value, in my opinion.

But again, if you just put the tools out there and make it optional and you don't spend the time to teach the users how to use this effectively, they'll steer away from it. Because there are plenty of people who still either are intimidated by AI, they think AI is going to take their job, or they're using AI like Google search. And okay, that's step one. But you don't use it like Google search.

I don't use it like any, I don't even say power user. Anyone who has a step beyond basic user is doing things slightly more sophisticated than just asking a question and getting an answer. Any parting thoughts, Jason, for our listeners? I would add, and I was saying about this last week until writing on this as well.

No matter where you're at, even if you're self-employed, actually you've got a budget allocated for your team, right? and that budget's allocated primarily for people. You can have this whole additional org chart under you that is AI. And again, you may not have them doing the most sophisticated tasks, but there are plenty of things that everyone has to do every day or every week or every end of quarter that AI could at least take the first step, at least create a really good draft of what you then need to review.

So to me, it's thinking through what is my digital or what is my AI org chart look like? How am I being smart with, hey, the things I know I have to do, not a good use of my time, not going to add shareholder value, but I know I need to do it because I have to go report this to my chain of command. Can you start using AI for some of those things? It's going to be very low cost or very low cost to the company, high value, and you freed yourself up to spend time on the things that really do drive value.

Yeah, that's a brilliant point, Jason. And I most definitely will link that particular post of yours as well. In this show. And I think that's actually, so I had done a course in Stanford with AI driven leadership, right?

Like, and this is one of the pieces that came up. There's a lot of research on what's called flash teams now, which is exactly how it is in terms of like these teams of agents being recruited into your org chart. But then your organizational dynamics and rules now have to change to make sure that they actually become a functional part. And so I'll also link Flash Teams by Professor Valentine for people.

Oh, please. Yeah. Yes, that's great. Thank you so much, Jason.

This was a fantastic conversation. And I was feeling very guilty about stealing your non-existent time for the podcast. But you had so much to say. People had to hear it.

So thank you so much for being here. Thank you so much, Ashwini. I tell you this every time I see you're one of my favorite people that I'm very fortunate enough to be able to work with every day. So I very much appreciate the opportunity.

And thank you for the time, Ashwini. Thank you so much. Thank you for listening. If you enjoyed this episode, please like and subscribe to our channel on YouTube or on any podcast platform.

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