How AI Orchestration Helps Companies Win Customers | TFOS E20

If every rep had a digital coworker to prep calls, update CRM, and draft perfect follow-ups—what would your team do with the time back? Robert Henderson (Head of Revenue, AskElephant) breaks down AI orchestration for sales & CS, why “proactive AI” beats prompt-and-pray, and how leaders can coach in near-real-time.

What you’ll learn:

• What an AI orchestration platform actually does for sellers, CS, and leaders
• How custom agents (“digital workers”) automate prep, notes, CRM hygiene, and follow-ups
• Building a deal-intervention agent that alerts managers when a call goes sideways
• The future: proactive AI that acts before you ask
• The leadership system Robert uses: a Personal Priority Roadmap aligned to company goals
• Big mistakes teams make rolling out AI—and how to avoid siloed chaos

Key takeaways:

• AI should make humans more human: deepen connection & decision-making.
• Treat agents as digital workers you hire/train to your playbook.
• Move from reactive “prompting” to proactive AI aligned to your customer journey.
• Align leadership with a public personal roadmap to enforce focus.

Resources mentioned:

Multipliers by Liz Wiseman

Designing Your Life by Bill Burnett & Dave Evans

Connect with Robert Henderson https://www.linkedin.com/in/robert-henderson/
Connect with AskElephant: https://www.askelephant.ai/

Connect with Rick Smith https://www.linkedin.com/in/rick-smith-094b29b
Connect with Conquer https://conquer.io/

#Sales #CustomerSuccess #AIinSales #RevenueOperations #SalesLeadership #SalesAI #ProactiveAI #DigitalWorkers #AIAgents #CRMAutomation #RevOps #AskElephant

Creators and Guests

Host

Rick Smith

Chief Customer Officer at Conquer, Host of The Future of Selling Podcast, Eternal Student

What is The Future of Selling?

The Future of Selling is the go-to podcast for sales professionals looking to sharpen their skills and stay ahead in the competitive world of B2B sales. Each episode features expert interviews, real-world case studies, and actionable tips to help you navigate the complex B2B buyer's journey. Whether you're dealing with long sales cycles, multiple decision-makers, or rapidly changing technologies, we’ve got you covered. Tune in to discover the latest trends, best practices, and proven strategies for closing more deals and building lasting relationships in the B2B space. Perfect for sales leaders, account managers, and anyone aiming to master the art of B2B selling.

Future Of Selling (00:01.431)
All right. Hey, welcome to the Future of Selling podcast where we dive into challenges, we dive into trends, we dive into innovations, anything that's impacting the future of sales or the sales landscape. So I'm your host, Rick Smith, and I'm so appreciative you have joined us today. And I want to tell you about our guest, right? So our guest today is Robert Henderson. Robert is the head of revenue at AskElephant.ai. If you've never heard of that company before, I think you're going to hear about them in the future and you're certainly going to hear about them today. Robert leads sales and customer experience and partnerships at Ask Elephant. And prior to joining Ask Elephant, Robert founded, and I'm hoping I'm saying this correctly, but it's spelled with a Q, but Create. And it was an AI powered goal achievement platform. And I'm excited to find out a little bit more about kind of what drove that and why. And so I'm going to dive into that a bit. but also he's held leadership roles in growth and customer success and partnership at another company called Divvy that was eventually acquired. So he's gotten a lot of experience. He's got a great tech background. So, you know, he's just got a lot going on. So I'm really excited for the conversation today and just kind of unpacking where he's been, what he's doing now and where he's really headed. So Robert, welcome to the podcast and thank you for your time today. I appreciate it.

Robert Henderson (01:27.288)
Thanks for having me, Rick. I'm really excited.

Future Of Selling (01:28.965)
Yeah, absolutely, man. We're going to have a great conversation today. You know, before we get started, though, I always like to kind of, you know, we look for fun facts about people just to, you know, give another side of you. Right. If that's if that makes sense. So one of the fun facts that we found out is that you speak Japanese and you actually were in Japan for a while. And you could tell me if this is accurate. Maybe it's all inaccurate. But my understanding is you speak Japanese.

You were in Japan for a while actually serving with a faith based organization that you're that you're a part of. were volunteering there. So I think that's pretty I think that's a pretty cool fun fact. So and how long were you there? What were you doing?

Robert Henderson (02:09.784)
Yeah, so was there for two years, full time, just doing some volunteer work. It was actually right out of high school. So I got to view a whole nother world, really across the world, and learn Japanese. And I also learned that learning a language is a skill that if you don't keep practicing, it goes away. So I used to speak Japanese. It's a little rusty now, but I had an amazing experience just speaking

embracing myself in that culture. It's very different, but learned a lot.

Future Of Selling (02:40.101)
Yeah, yeah, no, that's really cool. So did you get to the point where you were speaking up pretty fluently while you were there, I guess?

Robert Henderson (02:48.396)
Yeah, towards the end, I had some friends there that told me, hey, you actually sound native. And that was the biggest compliment. So it took me a couple of years, but I finally got to where they said I sounded pretty native, which is cool.

Future Of Selling (02:56.752)
Yeah.

Future Of Selling (03:02.609)
Yeah, now that's definitely cool. And so now I assume if they heard you, they would say you no longer sound native at all because you've been away for a few years. know? Yeah. Gotcha. Gotcha. All good. Well, but what a cool experience. It makes sense that you're to lose that after a while. maybe, who knows, maybe you'll get to use it again at some point in the future. So, yeah, got it. Got it. Got it. Okay. Well, thanks for that fun fact.

Robert Henderson (03:12.642)
Yep. Yep.

Robert Henderson (03:21.774)
That's the hope.

Future Of Selling (03:27.141)
You know, we were doing some, as we're doing the research on you, you know, we came across this, you know, one of the facts, you know, that you were the creator or the founder of Create, this AI powered goal achievement platform. And it just kind of piqued my interest. do a lot of reading, do some masterminds around, you know, around performance and just self-improvement and growth and stuff like that. So it just kind of piqued my interest. So tell me a little bit more about Create and kind of why you did that.

Robert Henderson (03:57.965)
Yeah. So, I was at my former company, Divvy, and I really awesome company. got acquired a lot of high performance individuals and at Divvy in my personal life, friends, there was this three month span where so many people in my life were coming and saying, Hey, I don't really know what I want to do with my life. I don't really know how to get where I want to go. And it was just this theme where I'm like, okay, I'm hearing this problem over and over again. And gender day that AI was.

Future Of Selling (04:22.063)
Right?

Robert Henderson (04:27.948)
really just coming onto the scene. And I realized there's this unique opportunity of AI being able to guide people in their life in a different way that we've never been able to experience through technology. So the whole goal was to use AI to help people have really more clarity on how do I come up with goals, how do I achieve goals, and how can I use technology to help with that.

Future Of Selling (04:41.829)
Right.

Future Of Selling (04:50.65)
Right. Yeah. Did you incorporate anything like strength finders or any other type of assessment or was it more just a self evaluative process that people used?

Robert Henderson (05:02.35)
Yeah. So that, uh, it's actually interesting. It's part of my journey to Ask Elephant. ended up, uh, discontinuing that to join Ask Elephant because I saw a little bit better opportunity here, but the whole idea was if you can help people understand their strengths, their values, a little bit more about themselves, the AI can be more fine tuned to them, more personalized to them. So that was the vision originally is, uh, help people discover a little bit more and then AI can translate that into help you achieve your goals.

Future Of Selling (05:21.744)
Yeah.

Future Of Selling (05:30.126)
Yeah, no, that's cool. So which makes perfect sense. What a great use of AI. It sounds like you've kind of put that on the shelf for now, though, now that you're at S S. Elephant. you ever plan on being a just curious, ever plan on being a founder again? I mean, did you did you like the experience that kind of entrepreneurial venture or what's your thought there?

Robert Henderson (05:50.989)
I love it. actually, so I told Woody, our founder here, said, Hey, one of the reasons I want to join Ask Elephant is I actually want to go back to that original idea. one of the great things about Ask Elephant is Woody has a very similar approach to AI for business. So I wanted to come here and learn from experts so then I can go help people apply it their personal lives. So the vision is still very much alive, fully plan on doing it after Ask Elephant.

Future Of Selling (06:00.965)
Yeah.

Future Of Selling (06:16.57)
Got it. Yeah, yeah. So just kind of on the shelf a little bit and get some more experience and jump back. Well, I love it, man. If nothing, if for no other reason, I'd love to stay connected just because of that idea. I think that's an exceptional approach and use of AI. So excited about that. Okay, well, I got my fix on Create and what you were doing. Thank you for allowing me to go there. But tell me about askelephant.ai.

Robert Henderson (06:21.534)
Yep.

Robert Henderson (06:36.248)
Hahaha

Future Of Selling (06:44.026)
You know, did a little, you know, went to the website, did some reading on it stuff like that. You guys are doing some pretty cool stuff. So talk to me about, about that. What are you guys doing?

Robert Henderson (06:53.516)
Yeah. So Ask Elephant is, we call it an AI orchestration platform. And really the idea behind it is the future in our opinion is being able to orchestrate or deploy AI within the workspace. So I'll give you a little bit background of our belief system at Ask Elephant of the future. And maybe that will help a little bit here is we focus specifically on revenue teams. So, you know, sales development.

Future Of Selling (07:14.917)
Yeah, yeah,

Robert Henderson (07:22.03)
account executives, customer success, implementation, the full revenue team. And as we look into the future, there are three fundamental beliefs that we have that are driving our vision. Number one is humans are still gonna be talking to humans in the future throughout the customer journey. If it's just robots to robots, then we're all in trouble, I think. But we fundamentally believe there's the human connection aspect. So that's number one. Number two is,

Future Of Selling (07:48.144)
Okay.

Robert Henderson (07:50.915)
We really believe that people should be empowered to make decisions and AI can help with that. It can bring data, but a core part of our role as revenue people is for the business and for our customers making the right decisions to move everyone forward. And then the last part is beyond those two things, we really believe the future is.

revenue teams learning how to orchestrate AI agents or these digital workers, as we like to call them, that can do human-like tasks. How do we deploy them to take everything else off our plate so we can focus on those two things? So we can focus on connecting with humans and focus on making decisions for our business and for our customers. So Ask Elephant is that platform to deploy, orchestrate, build,

these digital workers that can take really all the other manual tasks that we need to do off of our plate.

Future Of Selling (08:50.554)
Got it, got it. So do you feel like, I mean, is there anybody else in the, know, as film sounds like you guys have kind of coined a term there or a phrase, right? The AI orchestration platform. Anybody else said that, you know, that kind of is in that space at this point, or you guys feel like you're the only one, you know, taking this approach and working on those, you know, those specific three things.

Robert Henderson (09:13.891)
Yeah, there's some other platforms that are starting to get this similar idea. We, we feel we're unique in the sense of how we envision, envision those three things. And so as other platforms and you know, there'll be more that show up as everyone builds or we're leaning on our, our founding beliefs of those three things. And specifically that human connection is where we're leaning into. And we think it's going to give us a headstart. not just about automation. It's not about.

getting AI in there everywhere. We actually don't believe it should be everywhere. It's where can it make the humans more human?

Future Of Selling (09:48.933)
Yeah, gotcha. Yeah, you're really focusing on the things that humans do best, it sounds like to me. how do you, know, kind of drilling down a little bit, I'd like to talk some about how you believe that Ask.ai actually brings value to your customers, but also to their customers. you know, if I'm a seller,

You know, break it down a bit for me, right? How does Ask Elephant improve my overall experience as a seller? How does it make him or her better in their role?

Robert Henderson (10:23.791)
Yeah, I'll break this down to the two ways we think about it. One is the individual contributor, the seller, the customer success manager, and then number two is their leaders. And we help both think about the true role of a sales rep or customer success manager is to take a prospect or a customer through a journey.

And that's an emotional journey of solving for pain. That is their core job in a way that expands revenue for the business. That is the core job. Now there are so many things that have to get done, but they're really ancillary to that core element of connect to human transfer confidence that your solution is going to get them to a better world. And so when we break that down, it's how do I prep for a meeting to make sure that I connect with that person?

That's a task that someone needs to do in order to have a good human connection, but it takes time away from actually being with that person. So Ask Elephant says, hey, before you get on, we'll go look at all the past interactions with this customer. We'll go search the web. We'll look at all these data sources and present you with everything you need to know before the meeting so that you don't have to spend time doing that. You can just focus on that person and solving their problems.

So that'd be one example of how do we take that task away from them? And then you can expand it to recap emails after updating the CRM, getting coached. There are certain things that just in real time, AI can help do so that you can go be with your prospect, be with your customer more fully engaged.

Future Of Selling (12:06.288)
Gotcha, gotcha. So if I'm a seller, I'll try not to repeat back everything you say, but it helps me understand it better. So I get the front end of on the prep, right? Prepping for a meeting. Yeah, I need all the information I can get about Robert and kind of what do I need to know so I can improve the likelihood of this human connection. So it's gonna search, it's gonna bring me all this info, present it to me probably in a very consumable fashion. And then I get to decide what I wanna use, what I don't wanna use.

Now, or actually, does the platform actually help me decide what to use as well? mean, so it gives me 25 data points. Are they all equally weighted and important? Or does it say, hey, here, based on Robert and what we know about him, here's the five of the 25, the 10 of the 25, they're the most important you should really focus on? How does that work?

Robert Henderson (12:59.907)
Yeah, that's a great question. And it gets me excited because that's also one of the unique parts of Ask Elephant is we like the analogy of an agent being a digital worker because it helps people realize just like you were going to hire someone, you actually get to hire or train your agent specific to your business. So we provide the tools for you to say, hey, as a business, these are the things we care about for our reps to get up and going before a call.

So for example, we have a customer that does shipping returns. And so they trained their agent to say, look for anything, any policy on a public website that helps understand this prospect's shipping policies. So I know exactly how to position it. That's a custom trained agent. And that's really the nuance that we get excited about is everyone can have an agent that's specific to their needs.

Future Of Selling (13:59.867)
Got it, got it. yeah, so and would that agent also help with things like not just retrieving information and presenting a bag? Does it also help put it in format for presentation and things like that? Or does that go back to the sales rep or the CSM to make that transition?

Robert Henderson (14:20.847)
Yeah. So we can pull in data and then we can push out data as well. So one of the biggest nightmares for a sales rep is I get off a call. I have to go spend five, 10 minutes in my CRM, you know, HubSpot or Salesforce. I have to go put in the information, update the deal stage, all of this. Why not go hire an agent to say, Hey, this is how I usually update my CRM after a call. Just go do it for me so I can go to the next call.

and get to that next human connection faster. So we can push, we can pull, we're interacting with your data both ways.

Future Of Selling (14:55.45)
Yeah. So that's kind of, so now that you're kind of transitioning into the post play. So post is going to grab the data. It's going to fill out the, whatever it needs to fill out in the CRM. I think I saw, you know, probably all your looks like you're taking that information, maybe creating emails, follow ups, things like that. Talk a little bit more about how, about how your platform helps a seller or a CSM in a, post meme. So I've now I've had the connection.

with my client or with my prospect, right? I've helped them make some decisions in real time, hopefully. Now what does it do? How does it help me afterwards?

Robert Henderson (15:22.073)
Mm-hmm.

Robert Henderson (15:31.599)
Yep. So one of most common ones, like you said, a follow up email, it's something that the best reps know they should do because it keeps alignment throughout the process. One of the things that's always fun to talk to people about and help, you know, may be younger reps realizes your prospect is not just thinking about your, your product all day, like newsflash, they have their own business. So once they get off, even if they loved it, they're, they might be gone to the next thing.

So how do we make sure that you can keep that human connection? Well, most people know send an email. Well, to send a good email, takes five, 10 minutes. have to remember what they said, action items that you both committed to. So why not train an agent that understands your tone, understands how you like to format emails. So right as the call is done, it says, Hey, Rick, your email is ready to go. Would you like me to send it? You click a button, it sends it off. And now I'm still enhancing that human connection and saving.

an hour a day, not having to send emails after every single call.

Future Of Selling (16:32.516)
Yeah, yeah, that's cool. And probably with a greater deal of accuracy as well, which would be a big benefit. so those are some examples of how it helps a seller or a client success manager. How about leadership? You talked about that a minute ago. How does Ask Elephant impact at the leadership level?

Robert Henderson (16:53.997)
Yeah. So leaders are a little bit different. They're not doing the job. Their whole purpose is to empower their reps, their teams to do their job better. And so most of that comes down to how do I have the right data at the right time to help my team move forward? And so there's two ways we think about it. One is how do I help in real time, a leader understand, get a pulse of their business to

help their team with what they need. So for an example here, this is a, one of our customers, they built an agent. call it the deal intervention agent. And the whole purpose is I am a sales manager or CS manager. have eight to 10 people on my team. What happens if a call is going off the rails and I don't know about it. can't really coach off of that. And so what they said is let's build an agent.

that is monitoring every single call. And if something is going wrong or we're going to lose a deal because maybe they brought up that a competitor's pricing is better than ours. The agent is smart enough to say, hey manager, your team member just had this call. Here's all of the context. Maybe go help them overcome the subjections so that we can move that deal forward. So our customer built that. First time he got a notification from Ask Elephant, walks over to the sales rep.

helps them, coaches them, and they ended up selling the deal. And so now that manager feels like Ask Elephant, AI, like this orchestration helps me actually drive revenue for my reps and as a total game changer.

Future Of Selling (18:32.41)
Yeah, yeah, no, that's really cool. So was the manager able to come in in real time during the call or was it after the call that he kind of jumped in on that example?

Robert Henderson (18:45.539)
Yeah, I love the question because it gets me excited of the future. Right now it's right after the call. The future of Ask Elephant is going to be real time. It's going to be as things are happening. You as a leader can know you can intervene, you can help your team and empower them to be better.

Future Of Selling (18:54.554)
Yeah. Yeah.

Future Of Selling (19:02.864)
Got it, got it. Good example too, and I may ask you for one other, but let me pose one more persona to you. We've talked about the seller CSM, individual contributor. We've talked about the leader. And I like the way you phrase that, right? Is how do I as a leader in real time help my team? And that's what the AI agent is doing. That's really cool. How does that help the customer though, of your customers, right?

Robert Henderson (19:10.863)
Sure.

Future Of Selling (19:28.848)
I mean, how does it impact them? Is there a positive impact or is it just now just helps the folks we work with? Talk about that a little bit.

Robert Henderson (19:36.493)
Yeah. So the ideal world that we believe in, that we're shooting for is if we can help our customers be more obsessed with their customers, then the overall experience that they will be able to deliver is going to be exceptional. And so I'll give you another example here of an agent that would help there is customers want to know that

Their feedback is heard. They want to know that they're partnering with a vendor that is going to keep building for their needs. And one of the biggest issues and hardest things to do as a seller and a CSM is getting the right product feedback to your product team. You're busy. You have all these customer requests. You have a quota, but you want to serve your customer. And so that's another thing that we say, let's take that burden off of our

our customers so they can service their customers better. So we have an agent that scans every single call and it stores this data to say, here are all the customer requests issues that are coming through. now internally, they have this repository of customer needs and they can go build a better experience. They can go provide a better service depending on their business. And so that's how we think of it is if we empower our customers,

to give a better customer journey, the natural effect of that is a more delighted customer experience for their customers.

Future Of Selling (21:09.562)
Got it, got it, yeah, that makes sense. Do you have an example maybe where an actual customer of one of your customers has given them feedback on how the experience has improved it or is most of the feedback just simply from the customers you're working with like the example you gave a few minutes ago?

Robert Henderson (21:26.797)
Yeah, most of it is from our own customers, but you've given me a new idea that I want to go start seeing what we can find downstream. So that'll be my homework from this.

Future Of Selling (21:32.304)
Yeah. All right. Well, there we go. It's a good discussion. If you're walking away with an action item, we're good to go, man. We're good to go. But it sounds like you're really excited about what you guys are doing, doing some really cool stuff too. Let me ask you this though. So you kind of led and we can certainly come back to Ask Elephant and maybe this question will kind of dovetail into it actually.

Robert Henderson (21:40.717)
I love it.

Future Of Selling (22:00.624)
You've led a startup, right? You know, a create. You've been in kind of growth stage companies like Divvy and like Ask Elephant. So what lessons have you taken from those previous experiences and how has that shaped you as you as you kind of try to scale at Ask Elephant? I'm assuming you guys, you you guys got an infusion, an investor, you know, I think not very long ago. So clearly you guys are trying to scale this thing at this point.

how those experiences, what lessons learned did you bring from there?

Robert Henderson (22:34.435)
Yeah, probably the biggest lesson that I have to remind myself of every day is that focus and prioritization is what wins. So when you have a big idea, when you're visionary, it's very easy to say, I see this new future. I see this new world that we want to build so that our customers have a 10 X better experience of what they do.

It's so easy to say, let's go build everything. Let's go do everything all at once. And that just doesn't work because you can't be exceptional at one thing. And then you can't do that all at once. so learning from Divvy, learning from building my own startup, you know, it was always, we want to do everything because we, know we can. And where we really found success was when we took a step back and said, what is the number one thing to focus on now?

Future Of Selling (23:00.387)
Yeah.

Robert Henderson (23:30.895)
What, what is the future? We can focus and prioritize other things later, but that has been the biggest theme probably in the last two months here at Ask Elephant is AI makes it 10 X more of that problem of the world is at your fingertips and even Divvy or things in the past. So we have to be ultra focused, prioritize and get good at saying no. Being able to say that's a great idea. Let's table that for three or three to six months.

because we're hyper-focused on what we're doing now. That has been a superpower that I wish I would have learned earlier, but we are applying and growing in that capacity right now.

Future Of Selling (24:09.199)
Yeah, huge lesson learned there because I mean, as a leader, as a visionary, you know, in those kind of roles, that's what happens, right? You just get overwhelmed with with the many and all the things that you could do to be able to shrink that thing back and go, OK, I don't have to do everything right. But but the three or the four things are the one thing that we're focused on. Let's do that exceptionally well. It's kind of how you said it. Did you have a process or a mechanism to help you keep

Priority and keep you know just that that theme that you just talked about that lesson learned you have a way to keep that in front of you is it you know is it just you you bring it up in meetings as or is there something you're like a process or something you use to prioritize

Robert Henderson (24:52.461)
Yeah. So this is something we've been working on and we've been coming up with ideas. the one that's been working really well for me is having a company roadmap, which is pretty common company roadmap of, a product perspective, from just a milestone revenue perspective, where are we trying to get to? So from their work backwards to say, are the priorities as a business? But I think the layer that's really helped us is you should have a personal.

priority roadmap as well. Not just, hey, this is what I'm doing today, but we have public facing personal roadmaps to say, hey, if you're interested in what I'm focusing on, you can look at my roadmap and you'll see for the next quarter, these are my priorities, the projects that I'm prioritizing. And now, especially as a leadership team, we can go discuss, we can argue, we can say, hey, is that really what you should be focusing on? Because there's more visibility and clarity into it.

Future Of Selling (25:23.439)
Okay.

Future Of Selling (25:49.796)
Right.

Robert Henderson (25:50.735)
personal priority roadmap that aligns with the business priority roadmap. And that small addition has been really impactful for us to be able to say, I'm going to say no to that for now, maybe next quarter, because I have my roadmap and I still believe this is more important than those things.

Future Of Selling (26:00.922)
Yeah.

Future Of Selling (26:06.531)
Yeah, no, I love that. I've never heard that phrase, a personal priority roadmap. So is that something that you just share internally with the rest of your executive team or the rest of your company? Is it shared outside your company? How do you guys think about that?

Robert Henderson (26:20.643)
Yeah, right now it's just shared internally. So specifically for the leadership team, I'm okay with even, you know, are anyone at the business to know what I'm working on? So I just have a notion doc. have my quarter planned out to say, Hey, for the next three months in order here, my priorities. And it empowers people to say, Hey, I have something that I think is more important than this. And they can point to my priority roadmap and then we can have that discussion. It's been super helpful.

Future Of Selling (26:22.788)
Yes.

Future Of Selling (26:48.143)
Yeah, do you teach other people to do that or is that something just you guys are doing? You know, you're teaching, I'm sure you've got a team that rolls up to you. Are you trying to teach them to do this as well so that you have more kind of visibility into what they're doing?

Robert Henderson (27:01.773)
Yeah, it's really been honestly the last month or two that it's been a focus. Cause I think everyone knew I need priorities, but there was just this missing part. If I don't know what your priorities are next month, then I don't really know where you're going for additional projects. And so that's just been the teaching of, just like a customer, just like a prospect, the more you can give them clarity on what's to come, the more confidence they have. Let's do that for each other and at least have a quarter planned out.

Future Of Selling (27:16.153)
Yes. Yeah.

Future Of Selling (27:28.239)
Yeah. Yeah. Great, great idea. Love it. Glad to see it's working. Hope to make sure I may try it myself. I like that a lot. Very good. You gave me an action item, is, which is awesome. Good deal. So you've kind of, you you built this, this career that really is kind of at the intersection of sales and customer success and AI. Was there anything in particular that sparked that, that, that, that interest in, how do I bring AI into, I mean,

Robert Henderson (27:36.665)
Try it out.

There we go.

Future Of Selling (27:57.412)
Was it just that everything's going AI and so you jumped on the bandwagon or was there something, some sort of moment that you said, you know, I really want to utilize this, whether, you know, whether it's in the, you know, personal performance and goal setting or otherwise, what got you going?

Robert Henderson (28:14.755)
Yeah, specifically for AI that I think what I got really excited about early on is the ability for it to understand context at a large scale and to be able to personalize that. So I started making connections for, know, for me, it was more personal life until I met Woody, our founder of saying, Hey, everyone has personal context. have experiences, they have things they're good at. have goals and ambitions. What if there was something that could help take that?

Future Of Selling (28:25.199)
Mm-hmm. Yeah.

Robert Henderson (28:44.631)
and then personalize a path forward. And so that's how we think about it. And when I talked to Woody for sales and CS, I was like, my goodness, I've done both of these jobs. The ability for AIDA to facilitate or orchestrate these parts of my job, I could have doubled the revenue I produced for Divvy is what I really feel. I feel like I could have taken on.

More customers generated more revenue. So that's what got me excited is I can do what I do best because it understands me enough that it can be personalized and contextual.

Future Of Selling (29:11.427)
Yeah.

Future Of Selling (29:20.333)
Yeah, yeah, I talk a lot about in just different venues about kind of this idea of friction and flow and how AI can help you reduce the friction or the term, really the term that backs that up is called psychic entropy. You know, it's that thing where you're, I'm worried about doing this, I'm worried about doing all these things, but they're really not aligned with the goals I'm trying to accomplish. So how can I reduce that and really focus in on the things that put me in a

Robert Henderson (29:37.359)
Mm.

Future Of Selling (29:50.23)
know, a flow state, the goals, the energy, all those things. So, you know, it sounds pretty similar. So, everybody, so I'll shift gears just a little bit. Everyone in sales and kind of customer success now, you know, they've access to pretty similar tools. What in your view actually separates top performers from everybody else as they're kind of leaning into AI and sales and CS?

Robert Henderson (29:54.253)
Absolutely.

Robert Henderson (30:19.599)
Yeah, I think a couple of things for me is one is, you really understand the customer journey? And I'd say that very specifically because that's one of the things I think we're going to see in the next few years of AI is it's going to make a more cohesive journey because it can bring teams together, can break down silos. And so if you're a sales rep, I think just saying, Hey, what pain do you have as a customer? What do I need to solve?

Future Of Selling (30:26.681)
Okay.

Robert Henderson (30:49.589)
is good, but to go from good to great, it's what is the journey that this customer is on? Because I know our customer very well, you know, they might be a little bit different, but in general, I know the struggles they've had before. I know that in order for them to have a great experience with AI, they need to go through this mindset shift. And so I think it's a little bit deeper of those who are standing out and are going to stand out more, understand that journey.

And then can leverage what they do best into that and tell AI to do the rest. And that kind of goes back to that focus is now as a rep, can focus on those things. What is the journey? What is my part in transferring them along that journey? And then I'm going to get, be the best at facilitating AI to do everything else.

Future Of Selling (31:37.082)
Got it, got it. Okay, that makes sense. That was actually probably my next question was just kind of talk about that human element, what aspects of it are the most important to keep in the sales process or the client experience, but it comes probably comes back right back to what you're saying, right? Just, you know, the connection piece, the pieces that only humans can do, you know, the humans do the best. So any, any additional thoughts around that, that kind of question, what, what human elements are the most important to maintain in this AI?

human balance.

Robert Henderson (32:08.461)
Yeah, for me, the biggest one is when you talk about understanding that journey, it's being proactive and prescriptive as the expert in that domain. And I think a lot of reps, especially maybe newer sales reps, they're taught like discovery, discovery, like you got to go discover. But it's a much more powerful experience in my opinion for Prospect that the discovery is meshed with, they already understand me.

Future Of Selling (32:37.284)
Yeah.

Robert Henderson (32:37.453)
So it's not just, hey, know, Mr. Prospect or Ms. Prospect, what are your biggest pains? It's, hey, I've worked with five other CROs just like you. They tend to struggle with X, Y, and Z. I'm curious, which one of those is the biggest pain point for you that we could really hone in on? That human connection of either consciously or subconsciously, they think, this person understands. They've been here. They've done this.

Future Of Selling (32:55.257)
Yeah.

Robert Henderson (33:04.749)
I think that's where we need to get to just every single time because AI can bring all that data. It should make you the expert. So let's, let's make Rick feel good, feel special that every interaction is, this person already knows my journey. Let's just keep moving forward. That's going to be a big differentiator in my opinion, the future.

Future Of Selling (33:25.049)
Yeah, I agree with you. I've got this kind of this bias, right? That when I'm coming into a customer or prospect discussion that, you know, I kind of owe it to them to a degree to come in consultative, right? Not just again, discovery. Yes, of course, we're doing discovery. But also to come into that conversation with a well, just exactly what you said. I've got a point of view.

right, a recommendation based on what I understand about you so far. That doesn't mean that it's not a demand. It doesn't mean we have to do it this way. But to come in with an educated and informed recommendation, I think that puts you at such a stronger place as the seller or the CSM. But I think it also puts the customer in a better place because, you know, when I'm the customer of someone else, what I'm looking for, again, is expertise. You know, I mean,

You know, what's the best practice? you know what? Yes, I see what the data says, but what does the data mean and what should I do about that? That's the kind of things I'm looking for. So I think that's what you're referencing is be that person that can come in with a recommendation, be proactive, be prescriptive. Is that kind of what I'm hearing?

Robert Henderson (34:43.275)
Absolutely. If you're talking to a CS leader and you say, Hey, like, do you care about churn? It's like, well, duh, obviously you should know that I care about it versus, I already know you care about this thing. I've worked with three other e-commerce companies or whatever they are. This is kind of a nuance I've learned. How can we help you with that? Like those are the things where now it's, this person's a partner with me. Let's go solve problems versus.

Do I need to educate them on some of the basic things that they should already know? So that's, yeah, that's exactly if you're consultative, that discovery is much more of a discussion versus sometimes prospects feel interrogated of, me go find all of the discovery points. And I just don't think that's the way to connect with them.

Future Of Selling (35:14.201)
Yeah.

Future Of Selling (35:28.697)
Yeah. Well, and it kind of comes back to your, you you threw out two things, right? You know, AI can help you as a human better connect and also better decision making. Part of that better decision making is bringing recommendations and as opposed to just, you know, hey, here's an empty whiteboard. What do you want that seldom ends up well for anybody, really, when you take that approach. So, OK, good deal.

Robert Henderson (35:50.093)
Yep.

Future Of Selling (35:56.27)
So talk about this as leaders are trying to kind of lean into AI and infuse AI into their sales process, their sales teams, their client teams and processes. What are some of the biggest mistakes that you've seen leaders tend to make? We'll start there. mean, any mistakes that you're seeing people make?

Robert Henderson (36:16.345)
Yeah, I think one is thinking of it in silos, especially across the revenue team. So we are an orchestration platform for revenue, not for sales. It's for the revenue team. Cause we believe that the revenue team coming together and having that experience is what is going to make them get into swing or get aligned moving forward. And so, you know, when it's just a sales.

manager or as VP of sales that is just thinking of this in a silo. I think they're missing an opportunity of, we are still at the beginning of AI. Evan always says this is the worst it's going to be, which is awesome to think about. It's just going to get better. But that means now is the time to think of a strategy as a business, as an organization. How do we make this cohesive rather than CS, sales?

implementation, whoever you guys go do your own thing, get your own tools that still going to, you know, expound on some of the problems we've already had of data siloed experience differences. Like let's bring it together. And that's the teams that have had the most success with us personally is they brought all their teams on and all their teams are loving it together. And that's more of that orchestration that we see is don't get too caught up in your sales quota that you forget.

Hey, we need to set this up for the longterm for our whole org, not just our team.

Future Of Selling (37:43.983)
Yeah, it's a good point. the mistake would be siloed, that the cure to that or the best in class approach would be, let's think about this holistically. And you could almost see that being, and I'm assuming you work with CS, sales, marketing's probably a part of that as well. And so your solution could be something that helps actually unite those teams.

areas where maybe they're not as united and working together as they should. That's what I would see. Yeah. Okay. Good deal. All right. Well, we're getting a little close to time, but I did want to ask you one last question around AI. What do you think's next? What do you see in the future of sales podcasts? So what do you see in the next year to maybe three years? Maybe three years too far to predict with AI, but what do you see coming down the pipeline?

Robert Henderson (38:18.775)
Absolutely. Yep.

Robert Henderson (38:27.535)
Okay.

Robert Henderson (38:32.847)
Hahaha.

Robert Henderson (38:40.257)
Yeah, I think the biggest shift, and this is when you talked about mistakes, I think it actually is a current mistake that people are making that they can quickly change is the future. Like we're starting to get there, but the future is truly a proactive AI experience. And that's where agents get really exciting is because you can train them. can. You know, put them into place where they are proactive, not reactive right now. Everyone's used to.

I use AI, I go and ask chat GPT something. Well, that's incredibly reactive. That means you have to go, you have to prompt, you have to know what to do in the next situation. If you have a system that understands your customer journey, it understands your goals, it understands your business. Why should it not be orchestrating in the background and then being proactive with you? Kind like that deal intervention we talked about, that's a proactive experience of as a sales manager, I don't have to worry about that.

AI is going to come to me when I need to, because I've trained it that way. I think that's more of the future is these systems that know here's what sales should be doing. Here's what CS should be doing. Let's take that burden off of them to be reactive and let's be proactive. That's what I'm really excited about to build, to see how other companies build as well. Cause there'll be a lot of great, you know, other tools for different teams. Let's be proactive.

And I think that's a guiding principle that AI is starting to get more to.

Future Of Selling (40:08.834)
Yeah, fascinating. Yeah. So true, a truly pro you think it'll be a truly proactive AI experience as we move forward. yeah, it's incredible. Well, cool. Let me ask you, I always like to ask a few kind of questions as we, know, just about you, right? Again, just to let, you know, people know a little bit more about you. So, so who's been kind of the biggest influence in your life?

Robert Henderson (40:17.177)
Yep.

Robert Henderson (40:23.695)
Sure.

Robert Henderson (40:30.991)
that's, a good question. I, I've had a lot of really key influences. This is, this might be the, cop out cliche answer, but, you know, my, my parents were, have always been the biggest influence. And I'll tell you why is, from a, and this might, this might've been a, know, if you want to get deep ricks sometime on the create journey, it's maybe why I wanted to go down that route is, they've been huge in helping me understand how do I apply the right principles to.

to make decisions throughout my life. So a lot of the reason I've gotten to where I am with Divvy and then Create and then Ask Elephant is I don't look at life as this linear path with all of these rules that you have to follow to be successful. It's a fluid, experiential journey that you need the right tools to know how to make decisions when you come to crossroads. When you come to forks in the road, no one has ever been in your shoes. No one ever can be.

So how can they, how can they always know the right decisions? You have to have the right tools to say, Ooh, what are the different principles, priorities, goals that are coming together here? How do I make a decision? I think from a young age, having a parents that helped me understand that has been huge for my professional career. Uh, and it's, you know, it's the reason why I connect with people like Woody, our founder, because he sees the world very similarly. And that foundation has gotten me where I.

Future Of Selling (41:57.017)
Right. Yeah, yeah, no, that's good. That was not a cop out answer. That was a very good answer. what are you reading or watching or listening to right now that you feel like is stretching you and that you'd kind of recommend to someone else to read or watch or listen to?

Robert Henderson (42:17.798)
Yeah. Um, this is one I'm going to answer the question by not answering it. I'm not reading it right now, but I'm going to bring it up because I've brought it up to like four or five people recently is, uh, the, the book multipliers, if you've ever heard of it by a pretty common book. The reason I bring that up is I have been talking to a lot of people of this, that concept of your efforts, multiplying others around you and

Future Of Selling (42:28.11)
Okay, I like.

Yeah. Yeah.

Robert Henderson (42:45.711)
being aware of that in the book, talks about like the accidental diminisher, the person who's well intentioned, but actually isn't helping others grow. When you talk about AI, when you talk about just business with sales, helping people get to hitting their quota, being promoted, the things they care about, you have to be able to multiply your efforts. And I actually think AI ties into that perfectly is let's multiply. Let's understand the principles of

How do you and I multiply ourselves across our teams, across our customers? And so that's a concept in a book, if people haven't read, think has been really on my mind is how do I multiply myself and then also help my leaders under me and multiply themselves. And it's just this compounding effect. That's really fun to try to figure out the exact way to do that.

Future Of Selling (43:37.869)
No, I love that. Yeah, it's a great recommendation. I've actually not read that book yet or listened to it. So I'm always looking for the next great read. So I'll definitely pick that one up. What's the last question? I want to kind of jump into some key takeaways. But what's the biggest lesson learned that made a difference in your kind of your journey, your success in your life? You you're a pretty young man to be where you're at. So, you know, what's the biggest lesson learned?

Robert Henderson (43:47.203)
Ha ha ha.

Robert Henderson (43:51.983)
Sure.

Robert Henderson (44:06.319)
For me, the biggest lesson is being in control of your life is a decision that you get to make. There's a lot of circumstances that affect life and I'm not someone who pretends those don't affect us. They don't change things. But there's a book also, there's another book I love, it's called Design Your Life. It came out of Stanford. It was a big inspiration for CREATE as well of...

We each of us have the ability to design what we do, whether that's designing the type of life we want to live, designing the career that we want to have in sales and something else. And the more intentional we are, we're going to get to where we want to get. I don't, I didn't just choose Divvy just because it was a job. said no to actually a lot of other jobs because it just didn't feel like it was the growth trajectory I wanted. And then Divvy came along. I'm like, these people are kind of crazy actually. They're incredibly ambitious. This is something I choose for my career because it's going to impact where I go. And so there's countless examples, but my big takeaway is be intentional. Design your life, design your career, be the designer of what you want to do and leverage the tools like AI to get there, but be in the driver's seat and good things will happen.

Future Of Selling (45:05.96)
Yeah.

Future Of Selling (45:30.67)
Yeah, love that. Love it. Cool. Well, man, great discussion today. Let's kind of end it with maybe some takeaways. So if I'm a sales leader, a CS leader, executive leader in a company, right, and I'm wanting to lean more into, man, this AI thing that's happening all over the place, right, what would be two or three key takeaways that you would tell them? Hey, you got to do this, you got to do that. And man, don't forget the other. What would those be?

Robert Henderson (46:01.209)
Yeah, I think number one is start now. Like key takeaways should be if you haven't talked about AI internally, if you haven't looked into it, if you don't have a strategy, and I don't think it has to be a super crazy, like we've talked about it for months strategy, but just something to get started. If you haven't done that, like start this week, like start today. A quick 30 seconds I think will be helpful for the audience, Rick, is why Combinator came out with a...

Future Of Selling (46:21.422)
Yes. Yeah.

Robert Henderson (46:29.731)
this research from OpenAI, think it was, you know, showing the curve of what AI can do. And right now it's like AI can take a task that someone might take 30 minutes to do and it can do it well. Well, next year they're anticipating that to go to something that would take you and I four months to do. AI can actually do accurately. That's a crazy jump. If we're not thinking about it right now, others are, your competitors are, like we're going to fall behind. So I think number one is.

Future Of Selling (46:52.93)
right? Yeah. Yeah. Yeah.

Robert Henderson (46:59.855)
Don't fall behind. Like let's do it now before that crazy curve of what AI can do is probably my first takeaway.

Future Of Selling (47:05.038)
Yeah. Yeah. And then what I kind of add onto that, what I hear is don't wait for perfection, right? Perfection is a figment of your imagination, right? Just get, get, get some, the information maybe, but get started soon. Start experimenting, start doing some stuff. So, okay. Got it. Okay. Anything else?

Robert Henderson (47:12.047)
You

Robert Henderson (47:21.261)
Yep. number and then number two, think is the big takeaway we talked about earlier is don't think about this in a silo. No one's an expert. go to LinkedIn, go to your friends, talk about it with your, if you're in sales, talk about with your CS leaders, talk about it with your SDR managers. How do we bring it together? And I'm a little biased cause that's just, you know, an ethos here, ask elephant is bringing the revenue team together. And I would just say,

Start today, start now and start with other people that can help you start crafting that journey, help you start iterating on it. And if you can get do those two things, everything else will fall into place. But I just, I want to see people not fall behind. I want to see great companies come because they were at the forefront. so bring others and involve them because we're all learning together.

Future Of Selling (48:14.658)
Yeah, gotcha, gotcha. Well, man, been a fantastic conversation today. I appreciate I appreciate just kind of what you guys are doing at Ask Elephant and kind of your vision and for that and just your excitement around it. Appreciate you telling us a little bit about more about you. I find your points of view on kind of, you know, books you're reading and things like that be really interesting. We need to maybe we connect some more later on that, because I'd like to kind of dig into some of that with you and appreciate the key takeaways. That's perfect. So.

Robert Henderson (48:40.61)
I it.

Future Of Selling (48:43.182)
Well, sir, thank you for the time today and I hope you have a great rest of the week and we'll stay connected

Robert Henderson (48:50.137)
Thank you, Rick. This has been awesome. And thanks for everything you're doing on this podcast. Appreciate it.

Future Of Selling (48:53.92)
Absolutely. Good to see you. Talk to you later. Bye bye.

Robert Henderson (48:56.143)
You too.