Aaron Ward:
If you are not having good coaching conversations with your teams at work, it doesn't mean that conversation isn't being had. It's being had with a spouse or with Google. Or with ChatGPT. And the answer that they're getting isn't necessarily the one that's going to be best for the person, or best for the company. I think that's a really important feature of Huckleberry is making sure that we can preserve those interests.
Steve Smith:
Hey everyone, welcome back to another episode of Work Tech Weekly. I'm Steve Smith, Managing Director of Growth at Rep Cap.
Coaching has always been one of the most powerful tools for professional development. It's also been almost entirely out of reach for most people. What if that's about to change?
My guest today is Aaron Ward, co-founder and CEO of Huckleberry. Huckleberry is an AI professional coach you can deploy for every single person on your team.
For decades, executive coaching has been reserved for the people at the top who could afford it. Everyone else either figured it out on their own or didn't. AI is changing that calculus fast, and the timing couldn't be more interesting, with managers stretched thinner than ever and HR teams under pressure to do more with less.
In this conversation, Aaron walks me through how Huckleberry works, a voice-based AI coach that knows you, knows your team, and stays with you over time. We talk about why privacy is the foundation of the whole product, why the conversations people most need to have rarely happen at work, and what it means to put a real coaching relationship in the hands of every employee.
We also get into the PLG motion Aaron built intentionally after his last company AskNicely, and why the economics of AI-native coaching are hard for traditional enterprise software to match.
This one was recorded live at Transform 2026 in Las Vegas. Great conversations all around, and this was one of them. Let's get into it.
Welcome to the podcast. We're back with Worktech Weekly. I'm Steve Smith and I'm joined here by Aaron Ward. He is the co-founder and CEO of Huckleberry.
Aaron Ward:
Thanks Steve. Hey, awesome to be here with you. This is so cool.
Steve Smith:
All right. Glad to have you here. I so I wanna start off with the name Huckleberry. Are you just a huge Val Kilmer fan, or what's the origin story on that?
Aaron Ward:
Yeah, so well, thank you for asking. Names are very important and you and I both weren't around, but in the late 1800s there was a saying which Val Kilmer did use in the Tombstone movie, which I think is the one that you and I are both fans of.
And so that phrase is, I'm your Huckleberry. Yeah, and what he's saying and what that was sort of short form for back in the 1800s was, I'm the right person for the job. For what you need. I've got the goods.
Steve Smith:
Okay. And so how does that connect to the company?
Aaron Ward:
Well, I think we were just chatting before this around the, you know, the job market and, you know, how does it work now that AI's come in and you know, and how do we stand apart now that, you know, knowledge and skills is less important?
And I think what the thing that's most important is like, how do we actually show up at work? What am I like to work with? What is the truth of who I am at work? And that's the one question I think when you're going through a job hiring process, or perhaps you're recruiting somebody. It's the one question that's the most important.
It's the one question that's the hardest one to answer. So, one part of the Huckleberry mission is helping people find that language to describe themselves through the eyes and the voices of the people that they work with. Okay.
Steve Smith:
Okay. So what does Huckleberry actually do?
Aaron Ward:
Well, I'm glad that you're asking that and you're asking it today where the answer to that question literally just changed.
30 minutes before I —
Steve Smith:
We have late breaking news. This just changed.
Aaron Ward:
Yeah, I'll just push post on the LinkedIn post. Huckleberry today is the AI professional coach that you can hire for every single person in your team.
Steve Smith:
Okay. And so how does it work?
Aaron Ward:
Well, you know, what shall we, shall I show you?
Steve Smith:
Let's do this.
Aaron Ward:
It sits on your phone. Okay. So let me open up Huckleberry. Maybe we can ask her. So I'm gonna hit a button here to start a coaching conversation.
Huckleberry AI Agent:
Hey, Aaron, what shall we work on today?
Aaron Ward:
Well, good question. I'm sitting here with Steve from Rep Cap and I'm just talking about you, but maybe you can describe like, what are you, how do you work?
Huckleberry AI Agent:
Fair enough. I appreciate the intro. So I'm an AI coach and I work pretty simply. You talk, I listen, ask questions to help you think things through, and we work on whatever's on your mind. Tough conversations, team dynamics, decisions, prep for big meetings, that kind of thing. Okay, sounds good. No typing.
Aaron Ward:
No, but like, what makes you different from like ChatGPT? Surely we just got a ChatGPT now that we need some therapy and advice, don't we? Like, are you different from that?
Huckleberry AI Agent:
Good question. Three things really. First, more natural for coaching than typing, especially when you're thinking out loud or practicing a tough conversation. Second, I remember you and your team over time, so I'm not starting from scratch every conversation. I build real context about what's actually going on in your world. And third, I'm connected to your work tools, your calendar, your team data, feedback from colleagues. So the coaching is grounded in reality, not generic advice.
Aaron Ward:
Awesome. Well, let's come back to that in a minute. So, so yeah. So Huckleberry knows you and knows who you are and knows about your Strengths Finder, your DISC profile, your Enneagram. Also knows how you show up to your teammates. So Huckleberry will go and get 360 feedback from your team. So, she knows your strengths, she knows your blind spots, and she knows all the context about your company as well.
So all of that is what you'd typically go to an exec coach for. Except instead of spending $500 an hour, you're spending 20 bucks a month.
Steve Smith:
Okay. That sounds interesting. So, I mean, what do I have to go through an employer to get it? Or if I think, hey, that sounds pretty good, I want to go to the app store and just click and buy. Is that something I can do?
Aaron Ward:
Yeah, just go to huckleberry.com. You can sign up, it's free. Everybody gets 30 minutes of coaching a month for free. It resets at the start of every month. But then you can upgrade for additional coaching, or your company can, you know, buy it on your behalf.
Just like a Headspace subscription.
Steve Smith:
Okay. Wow. Okay. That's interesting. So how did this come about? How did you get to this point? What's the origin story that led you to, we're sitting here in Las Vegas in a very quiet room having this conversation.
Aaron Ward:
Well, it's a, you know, I have a dark and scattered past.
I think, you know, you ask people like, how did you get to this? How did you get into this role? And people typically say, well, I sort of just stumbled into it, you know, like, none of us come at our career with a plan. It's more like a sort of a drunkard's walk. Right. We zig and we zag.
And I think that's a big part of the Huckleberry philosophy, is if we can find the truth of like, who you are, what your strengths are, what is it that you're pulled by and motivated by, then as a coach, we can help you find, you know, the place where you can really play to your strengths and pursue a mission that's true to you.
Sadly, that wasn't my path. You know, I started life in finance. I'm a recovering accountant. You know, it turns out that I was a very average accountant. And then, if I fast forward a little bit, my previous startup was a customer feedback business called AskNicely, which we started in a garden shed in New Zealand, which is where my accent came from.
And that went really well. It was a very fast growing business and I found that the business was actually outgrowing me. Mm-hmm. So I needed to upgrade myself almost every year, you know, fire the last CEO and sort of upgrade myself to be able to hold onto my seat. And about seven years ago, I got my own executive coach, which was transformational for me. I became a far better leader, a far better colleague, but also a better husband. And a better father to my children. It totally changed everything for me.
But the thing is that, you know, to get access to that coaching, which was so important to me and all the people that I worked with and lived with every day, all I needed to do was be a 40-something-year-old CEO of a venture-backed SaaS startup. Right? Because that's who gets coaching, right?
Steve Smith:
Right?
Aaron Ward:
You know, so what about everybody else? What about, you know, where was this in my twenties?
Steve Smith:
Right?
Aaron Ward:
So essentially Huckleberry is everything that I've learned through that coaching process and figuring out how do we democratize that, make it available to everybody at the start of their career rather than the end when they're, you know, broken.
Steve Smith:
Well, it's funny 'cause it's always like, what would you tell your 20-year-old self? And you know, you think about, or what would you tell somebody who is 25 and breaking into the workforce for the first time? And, you know, being a man of a certain age, it's just like, yeah, there's a lot of shit that I know now that I didn't know then.
And there's things that I wish I had known and could have done differently. And, you know, I also know from being in this industry, it's just like there's been a lot of talk about democratizing coaching. And at the end of the day, coaching still has remained pretty rarefied, in sort of the exclusive, for the exclusive benefit of primarily senior executives and people who could pay for a coach.
And then it was limited by, there's a certain number of coaches. This looks very different and interesting for a lot of reasons. I mean, you have the ability to have a natural conversation. But I think that one of the questions that comes up for me is, you know, why should I trust this?
So if I'm 25, you know, if I'm 25, it may be, oh, it's tech, it's cool, I'll trust it, the end. But what's the real difference or benefit versus just like queuing up ChatGPT or Claude and just start talking to that?
Aaron Ward:
Yeah, I think the first thing that's really important is that it's a hundred percent private, so every conversation is fully encrypted. Mm-hmm. So even if you're using it for work, this is something your manager can't see or hear what you talk about, neither can anybody else in the organization.
And that's really important to make sure that people are able to be open and honest and vulnerable.
Steve Smith:
Mm-hmm.
Aaron Ward:
And what we're hearing in a bunch of, you know, other AI apps like therapy and stuff, like, people are able to have much more open conversations in an AI context than they are with another human. Right.
Which is kind of ironic, right?
Steve Smith:
That is very ironic.
Aaron Ward:
Really important. You know, in terms of distinguishing from ChatGPT.
The important thing about Huckleberry is it knows you deeply. It knows you better than your better half, right? 'Cause it has all of the context of who you are at work, from your 360 feedback, from your personality assessments and also all the context of the conversations that you've had with Huckleberry over time.
So, you know, if you're talking about an issue that you've had, an ongoing issue with a person, you know, it will say, well, did you have that conversation that we last talked about with that person? How did that go? And so it takes a lot of context about you as a person, but then it can fold in the context about your company.
So if your company is using Huckleberry, now we connect with your HRIS, so we know your whole team structure, your teammates. Mm-hmm. Huckleberry also notes the feedback that they are receiving, so it can help you build better relationships with your colleagues over time. And then it has things like your employee handbook.
And so when you think about the guardrails that are important here, about when are the times when you actually do need to go and speak to the HR function, Huckleberry's able to make that bridge, which again is something that ChatGPT or Claude won't be able to do for you.
Steve Smith:
Well, and what's interesting that you just brought up is that when you think about, I guess there was an old joke, it's just like the only, you know, two entities in the entire universe who know everything about you are Google and God, and, you know, people would type things into a Google search that they wouldn't tell the closest person to them.
And it seems like that has been turned up by a hundred. With AI, people will now ask, you know, questions in AI and not think twice about it. And then you bring in the conversation elements, and they know, okay, this is an algorithm, this is a robot. It's a human voice. But I can bring up things and not fear.
Is it judgment? I mean, what's the dynamic there? Do you think, in an odd way, it increases the human connection?
Aaron Ward:
Yeah. I'd say, you know, people spending their time on Google or, you know, ChatGPT is quite scary for HR, right?
'Cause that conversation's being had off the platform. They've got no visibility. They've got no control around that. But, and it just reflects the idea that if you are not having good coaching conversations with your teams at work, it doesn't mean that conversation isn't being had. It's being had with a spouse or with Google.
Yeah. Or with ChatGPT, and the answer that they're getting isn't necessarily the one that's going to be best for the person, or best for the company. Right. You know, and that's, I think that's, yeah, that's a really important feature of Huckleberry, is making sure that we can preserve those interests.
Steve Smith:
Okay. That's interesting. So, how did, I mean, you know, obviously AskNicely was a company that it seems like did pretty well. What was the thing, you know, that made you say, you know what, this idea could also kind of work for employees.
Was it just your own personal, the transformation that came from working with a coach and you're like, hey, we need to make this available to everybody? Where did this go from, wow, this is a cool idea to, no, I'm gonna turn this into a business?
Aaron Ward:
Yeah, there is a lot of connective tissue and there are a lot of philosophies that were really important to AskNicely that port over into Huckleberry.
So, AskNicely was all about helping service businesses deliver better experiences to their customers. And the insight that we built that business around was that the difference between an experience that's awesome or awful is the frontline worker. Right. And so if we wanna deliver great experiences, we need to be able to elevate, motivate, and celebrate the frontline worker for serving the customer, right?
And so what AskNicely did is we'd get feedback from the customers and then we'd deliver that directly to the frontline worker on a little mobile app, which effectively drove recognition and reward for serving the customer. Right? We were catching people in the act of doing things right. Right. And so the big aha for me, and you know, that I took away from that was the power that feedback had on the human condition. 'Cause frontline workers typically don't get a lot of feedback. And if they do, it's typically because something's gone wrong. And we saw with AskNicely, by being able to share all of that evidence of people that appreciate the experience that they were getting, that changed the way that people felt about themselves and their roles, and they turned up more motivated every day to, you know, to serve the customer. Right?
Like to me, that's a real demonstration of how technology and feedback specifically can really make a difference to the human condition.
And that was very much focused around frontline service workers. And so I came away from the AskNicely experience saying, okay, how could we repeat that exercise, but not just for frontline workers? How could we do that for everybody? And that's where Huckleberry came from.
Steve Smith:
Well, you know, and it's an interesting time to be, you know, essentially getting into like, you know, the coaching and talent space because I think that, you know, broadly it's having a bit of a crisis. Because of AI. It's just like, or it's also because, not just, you know, AI can do this better than humans can, but also this sense in the workforce of, oh, we don't need performance reviews or coaching anymore because we're not gonna need employees, 'cause we can just turn it all over to AI.
And then of course, the existential dread that comes along with knowing that in the back of your head, you know, and at a very point in the market where everything's in flux and there are no shortage of very well capitalized, established brands that kind of do this. Why Huckleberry?
Aaron Ward:
Yeah, absolutely. I think you should look at the core of the Huckleberry product, which you've just seen, wasn't possible a year ago. So what we're bringing to market is only just becoming enabled. If we think about the types of people that are really going to succeed and flourish in an AI world, and in turn the companies that are gonna be able to win off the back of that, are those that are able to really lean into their own personal career development, continually getting feedback, continually building mastery, staying in their roles, you know, getting promoted through the ranks. That's essentially what Huckleberry is enabling.
Steve Smith:
So what about the trust issue? I think that we're seeing this broadly about, you know, can I trust that AI is working in my best interest? And I mean, I think that it really comes into play with the conversation element. We were talking about this earlier. It's just like, great, I'm more than happy to type something in.
But I know people who walk around and they're talking to their AI all day. And I just think that there's an element to that I know that I am not comfortable with personally. It is, it's in some ways unsettling and scary. And I don't know if that's just part of the journey of like, you know, great, in six months I'll be talking to it all the time. But, you know, how, where do you think this fits in that trust conversation, kind of the way that you're approaching this?
Aaron Ward:
Yeah, it's funny that, isn't it? I mean, you and I have been through a number of different waves of technology. Yeah. You know, and you find that everything feels, you know, each new wave feels a bit odd.
Yeah. It feels a bit scary. Yeah. It feels a bit confronting. Then we get to the other side of it and we look back and we think, oh, isn't it odd we used to do it that old way? You know. Today typing things, pushing buttons to communicate through a computer feels natural, right?
But we all learned how to talk before we could type. And so I think we'll look back at the not too distant future. We'll probably measure it in months rather than years and say that, you know, typing is, talking is the most natural and obvious way to interact and to communicate.
Steve Smith:
Well, and I mean, what's interesting is like there's been a lot of conversation here at the Transform Conference about the role of the line manager, and it seems like, you know, we're in an environment where companies are cutting head count.
You have, you know, an average manager, I forgot where I saw this, it's like the number of direct reports went from like 12 to 15, just in the last two or three years. And so then there's, you know, you're responsible for more people, for more throughput. You're responsible for AI, you know, and then on top of it, the conversation is, oh, and then the manager also needs to give feedback to his or her team and employees and things like that.
How do we do that? And I mean, your approach is, well, maybe we just take that out of the hands of the manager almost altogether. Is that, am I getting that right?
Aaron Ward:
That's exactly right. Yeah. I mean, I'm sitting here with a t-shirt that's got "We need to talk" on it.
Yeah. As I'm walking down the hallways in this conference, I'm seeing, you know, dozens of HR leaders look at the t-shirt, smile and nod because they know what that means, right? They know what it means when somebody comes up to them saying, we need to talk.
Steve Smith:
It's never anything good.
Aaron Ward:
Well, I think this is what, you know, people in those roles, this is what we're paying for as leaders.
This is when you need to step up and help somebody who's like really struggling. Or help resolve some sort of team conflict or help talk somebody off the ledge who's thinking about quitting.
Steve Smith:
Mm-hmm.
Aaron Ward:
This is the value of great coaching. And if you're an HR business partner, an HR leader, you know your value when you're having that conversation.
The problem though, and to the point that you raise, is that you can't be there for every conversation. No. Nor can you be aware of every issue that needs that type of conversation, and you don't wanna find out after somebody resigns or when it appears on Glassdoor. Yeah. So how can you enable that level, that grade of coaching conversation for every person in your business, at the moment that conversation needs to be had, especially when you're under pressure to, you know, reduce the footprint of your HR organization? And then you've got managers who are often, you know, not all as skilled at having those conversations and then being able to do that with more people.
So, all of the levers are against you in that, and that's where AI needs to come to the rescue and help enable that type of coaching conversation for more people, and then free up the capacity of your HR people and your managers to be able to, you know, do the stuff that really makes a difference.
Steve Smith:
Well, and I think you're very diplomatic about it. I think that, you know, I guess the saying is most managers are not well equipped to have difficult conversations, which is a very polite way of saying, most managers suck at it.
And I know when I think back at my, when I started my career as a young manager and having difficult conversations, I was fucking terrible at it. And I look back and I'm just like, God, how? And it's just like, but that's the reality. You know? And so maybe it is better that we're taking that out of the hands of managers.
But if we do that, are we losing something? Are we losing the human element? Or are we actually creating a better, more human outcome? And that's, I don't know the answer to that. I mean, what do you think about that?
Aaron Ward:
Well, I think the truth of it is that there are managers out there that, you know, are good coaches, but the truth of it is that actual results do vary.
Yeah. And for each person that you're not there for, or you perhaps do a poor job on that conversation, then that's bringing risk into your business.
Steve Smith:
Right? Well, yeah. I mean, I can absolutely see the risk, and I can see where this could potentially eliminate the risk from it, because it's just like, you're having a difficult conversation, but it's armed with facts and it's also armed with best practices.
And just like, you know, you're a lot less likely to get the stupid things that a manager or anyone might say when it is not an informed point of view, or it is informed primarily by emotion and not facts or rational thought.
Aaron Ward:
Yeah, totally. Totally. And I think the practical reality of when these conversations actually do come up, it's not during work hours, right? It's when you're getting home, when you're sitting down with the spouse, right? And so one of the fun pieces of feedback that we've had over the past month, whether about years, is like, oh, my spouse is so happy now that I've got Huckleberry to talk to, that I'm not unloading on him or her.
Steve Smith:
Well, isn't that the reality?
It's just like, you know, when you come home and she's like, oh, how's your day honey? And the first 15 minutes is just like, here is something shitty that happened at work that I'm pissed off about. Yeah. You know? And it's just like, you know what? Your spouse had a bunch of things that they were dealing with.
Why should, you know? And it's just like I can see some immediate benefit by turning this into an AI conversation.
Aaron Ward:
Yeah, totally. Totally. I mean, we are here to help people, you know, be more successful at work, but it turns out we're actually helping marriages along the way as well, which is kind of nice.
We don't charge for that.
Steve Smith:
Oh, wow. Okay. So free counseling is what I'm hearing. Well, well, tell me this. So it's just like, so obviously you're early stage. How many, I mean, and this is just an announcement that happened today, it's just like, what's the actual experience with customers? Where are you at in terms of deployment and adoption?
Aaron Ward:
Yeah, so we've been beta testing over the past few months and the results have just been phenomenal. So, we know we've got something that really fills the gap for people and, you know, that's the 98% of people that, you know, don't have coaching. So you know, that's super fun.
And we are here at Transform to find out how HR leaders respond to it and whether this is something that we can, you know, deploy across organizations. And you know, so far the feedback has just been phenomenal. One of the things I really enjoy here is that we're talking to HR leaders that really want to lean into exploring practical solutions for AI.
They have no patience for the narrative around how fast everything is changing and how it's smarter than all of us and gonna take all of our jobs. They're looking for ways to actually deploy practical solutions today that are gonna make a difference for their business tomorrow. And that's where Huckleberry is super fun.
'Cause you can literally install it on your phone, be up and running, having a coaching conversation within 30 seconds. And so from a software deployment perspective, you know within a minute whether this is something that's gonna make a difference for the people inside your business or not.
So it really de-risks the whole solution and the whole process for businesses, you know, compared to, you know, perhaps the old days when enterprise software was a six plus month decision and we all sort of held our breath and hoped that it delivered upon the promise.
Steve Smith:
Well, and so what I'm kind of curious about is like, if I am, you know, head of HR in a thousand employee company, and I'm talking to you, say, hey Aaron, that sounds great. Let's get started. What? I mean, what does that look like from signature to deployment to actually seeing some results and getting some indication that this is actually working?
Aaron Ward:
Well, well, first and foremost, we don't have any signatures.
You'd literally just sign up on the website. We had a guy come to our booth, you know, 45 minutes ago, had a five-minute coaching conversation about one of his teams that was really struggling with comp. Mm-hmm. On the booth. And you know, he was live immediately. So I think that's the opportunity for HR leaders, is you can test and find confidence with Huckleberry, you know, immediately.
And then it's something that you can, you know, deploy through your organization, you know, in a day.
Steve Smith:
What are the indications that it's working other than employees aren't walking around pissed off?
Aaron Ward:
Well, totally. I think that first and foremost people are having those tough conversations.
They're having those more often. Those conversations are going better. People are starting to grow in their role. Ultimately it's about people that are staying in their role and getting promoted over time.
Steve Smith:
And as a, you know, if I'm looking for, you know, data points, what does that look like to an HR leader? Is it just, oh, we're seeing, what are the indications they can point to? And they can go to their boss and say, here's the return on investment on my spend, which is always a conversation that's gonna be had.
Aaron Ward:
Yeah. I mean, I think the simplest one of those is just, how many people are having, how many conversations on Huckleberry?
Steve Smith:
Yeah.
Aaron Ward:
Each, every single conversation is essentially two hours of productive time recovered in the organization that would otherwise be a, you know, a meeting between somebody and their manager. Okay?
Steve Smith:
Okay.
Aaron Ward:
So, the more coaching conversations, the more productivity, and that's helping drive more coverage of your HR business partners across the organization.
Steve Smith:
Well, and I think that, you know, if you, I guess then you're looking at, you know, there's cost savings around, you're not having to spend as much time in these conversations.
There is risk mitigation in that you don't have to worry about a manager saying something stupid, which never really will. And then, I guess there is also usage, and it's just like, if you're looking at the data, it's just like, okay, the average employee is getting two hours in a month, then it seems like that's probably two hours more coaching conversation than they're getting ordinarily.
Aaron Ward:
Yep. Yeah, absolutely. Yep. So, time savings from those coaching conversations, avoided cost from the person that didn't leave, who, you know, who doesn't go to Glassdoor.
Yeah. Who doesn't, you know, bring the case against the company, right? So, yeah, there's a lot of flow and benefits, but I think from a positive perspective, it's about people staying in their role longer, building mastery, building stronger relationships, enjoying their relationship with their colleagues and their manager longer.
And, you know, all of that translates through to the bottom line for the company.
Steve Smith:
Well, I think another thing I'm kind of keen to talk about is sort of like the go-to-market motion on this. 'Cause obviously what I'm hearing is a very strong product-led growth opportunity. You know, I'm assuming that was intentional and kind of, I mean, is that just drawing on your previous playbook or what kind of led you to that point?
Aaron Ward:
Yeah, it's by design. I think, you know, when you think about AI-native businesses now, we obviously know that we can move far faster and deliver far more ambitious products with far less. But I think the same is true also from a go-to-market motion.
You know, we don't need the weight of, you know, huge sales and marketing teams, with a really well designed product and really good quality partnerships. So from a go-to-market standpoint, it's definitely a PLG motion. This is probably akin to like Headspace, you know? Yeah.
If you wanna meditate, you go download Headspace, you can start for free. You can upgrade to the paid plan, or maybe you join a business where they offer Headspace to everybody in the business. That's what Huckleberry is. Interesting. So we're working, yeah, we're working on exactly that same model.
Steve Smith:
Well, and I guess I'm kind of curious because, you know, as they say, not your first rodeo. You've been a founder previously. You've grown a company to, you know, good size and success.
You know, what are you doing now that you learned from that initial experience? And what would you tell, you know, that Aaron who was going through that at the time, if you had a time machine, what would you tell that guy?
Aaron Ward:
Yeah, well, there's probably too much to tell that guy in the time we have left on this podcast. You know, I am a work in progress. The good news is I now have Huckleberry and I'm literally talking to her on a daily basis on real challenges that I'm having with this business.
But you're right though. I think, as we're starting Huckleberry after AskNicely, I get to recycle a lot of the lessons of the things that we did well, but probably have a lot more value from, you know, the potholes that I drove directly into with AskNicely. We can steer around them here with this business.
And part of that is about creating a product that relies less on, you know, sales armies to be able to go and sell it. That's a big part of it, but also because we are able to operate far more efficiently, we're able to do it at a price point that is very hard for your traditional enterprise software company to match.
So, you know, Huckleberry is $20 a month, yeah, per employee. You know, we're replacing a $500 an hour executive coach. And we're enabling that for every single person in the business. To me that's an exciting idea for companies to be able to enable that for all of their employees.
And it's an exciting business to be able to run as well.
Steve Smith:
Well, and I think that if, you know, looking at it from like a SaaS perspective, if I can look at $20 per employee per month, those numbers are pretty compelling, especially if the cost economics on the go-to-market side are as favorable as they probably are.
So that doesn't hurt either. I imagine.
Aaron Ward:
Yeah. I, as a recovering accountant, I'm excited by the economics of this. But you know, it all comes back to the customer, and the customer is the human who's on the other side of it. So if they can have a conversation with Huckleberry and then go back into their workplace and be more productive and build stronger relationships, that's what underpins the, you know, the potential for this business.
Steve Smith:
I really appreciate you making some time for us. I mean, it's been a really good conversation.
I mean, I'm glad that we got a little bit of a product demo here too. I'm gonna give you the last word. Is there any question I should have asked and didn't, or anything else you want to add about kind of, you know, either where we're at at the conference or where we're at as an industry?
Aaron Ward:
Well, I'm excited to hear what you take out of this as well. Okay. Having seen the, you know, the mini revolutions that we've seen in technology, you know, what's your hope for this next phase that we're coming into? If we're sitting here a year from now and we're recapping this conversation, what is it you're gonna look back and be excited about, you know, for the 12 months that we have here?
Steve Smith:
Well, you know, I think what's, for me, what has been heartening over the last couple of days is the fact that, one thing I've always liked about this industry is you have people who are trying to build solutions that will make things better, not just for people at work, but just make things better for people. If you have a good experience at work, you're gonna go home, you're gonna be nicer to your kids, you're gonna be nicer to your spouse, you're going to pet the dog. I mean, good things are going to come out of that.
And so I think that I've always believed that at its best, solutions in this space could change the world for the better. And I guess over the last few years it's easy to kinda look at technology and AI and feel like, no, we're changing things for the worse. Things are not getting better. But the conversations I've been having with, you know, founders and entrepreneurs like you have left me feeling no, that fire's still very much alive and the potential still very much exists. I mean, because of where we're at with the technology to do things even better if we do it the right way.
Aaron Ward:
Yeah. I fundamentally, I'm totally in your camp here. I think that is the big opportunity with AI, is to literally make work better for people. Yeah.
We're excited to be part of it.
Steve Smith:
Yeah. Well, thank you for making some time. I hope you have a great rest of the conference and I hope you have a chance to have a conversation again soon.
Aaron Ward:
Let's do it. Yeah, we need to talk.
Steve Smith:
Yeah. Ah, nice. Nicely done. You didn't even have to “AskNicely”. Thanks, Aaron.
Aaron Ward:
Oh, so good.
Steve Smith:
Coaching has always been available to the people at the top. What about everybody else?
That's not a new observation. People in this industry have been talking about democratizing coaching for years. But talking about it and actually doing it are different things. What's changed is the technology. Voice-based AI that knows you, remembers you, and has context about your team and your company. That didn't exist a year ago. Now it does.
What I found interesting is where Aaron locates the real value. Not in the performance review. Not in the feedback cycle. In the conversation that happens at 9pm when someone gets home frustrated and either vents to their spouse or figures it out with an AI coach that actually knows their situation. That's where the coaching gap lives.
The question of whether AI can replace the human element in coaching is real. But if the alternative is no coaching at all, and for most people it is, that's a different conversation.
If you enjoyed this episode, make sure to subscribe to Work Tech Weekly on Apple Podcasts, Spotify, or YouTube Music. And I'll see you next time.
