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Scaling Your Social Engagement — How Kate and her team at LatelyAI are helping businesses unlock messages that will soar


Kate Bradley Chernis S2F Podcast Image

How to Be Human While Embracing AI, with Kate Bradley Chernis

Kate Bradley Chernis invited herself onto the Stride to Freedom podcast… And that’s exactly what I love about her. I reached out to Kate on LinkedIn, sharing our podcast with her and looking to start a conversation. Kate flipped the script and said, “So, do you want me as a guest on your podcast?”

Answer: yes. Kate is a force to be reckoned with, living in her zone of genius as the founder of LatelyAI. She’s a well-recognized entrepreneur with many notable talks on marketing and AI.

In Kate’s words, “LatelyAI uses artificial intelligence to generate sales and marketing copy on social media that will not only get you high engagement but get you skyrocketing engagement.” We talk all about LatelyAI and how businesses should use AI properly (spoiler! It’s about keeping the human touch).

What is LatelyAI?

LatelyAI creates social media copy from a company or brand’s pre-existing content. Here’s how it works:

  1.   Text, audio, and video content are run through LatelyAI.
  2.   LatelyAI looks for phrases, one-liners, clips, etc. that represent the brand voice and what the target audience wants.
  3.   LatelyAI creates social posts from that content and then tracks engagement.

LatelyAI can work with both “owned media”—i.e., what the company creates—and “earned media”—i.e., what they are given access to. LatelyAI can work for SMBs looking to generate some quick copy as well as large enterprises who integrate it into a larger strategy.

It also integrates with Google Analytics, Mailchimp, or other social channels, providing a quick snapshot of what’s working and what’s not. LatelyAI is a powerful tool that companies can leverage to increase social engagement, which pushes customers and clients further down the sales funnel towards increased revenue.

AI + Humanity

Kate believes the elevator pitch has taken away the humanity behind ideas. Venture capitalists are looking for entrepreneurs to check a series of boxes and hit the pitch spot-on. But the reality is that it’s hard for an entrepreneur to describe their work, especially if it’s outside of the pre-established boxes. And it’s the space between the boxes where innovation truly lies!

That’s why there must be room for humanity. How?

  • Recognize that it takes a village… or 50,000 villages, as Kate says. No person operates alone, and everyone needs others to help create something.
  • AI can only work with human input. Even though LatelyAI is smart, it still needs the guiding hand of a human to identify what it should focus on.

You’ll enjoy this Podcast episode with Kate—Here are some takeaways: 

  • AI and humans should work together—they have to collaborate.
  • People are looking to check well-established boxes, but the unicorn ideas are in the spaces between the boxes.
  • Use gamification—it’s fun!

And if you want to know more about us at Stride Services, contact us today. We offer back-office accounting and CFO services, including stable and efficient bookkeeping, cash flow management, and actionable analytics for growth.

Listen Now

We are fortunate to have Kate available to spend time with us on this edition of Stride 2 Freedom. If there is a speaker you’d like us to interview, click here and let us know. Stay well. Stay safe. Stay healthy.

Show Notes and Links From Episode:

Kate Bradley Chernis: LinkedIn

LatelyAI: Website/LinkedIn

Kate Bradley Chernis: kate@lately.ai

Episode Transcript:

Russell Benaroya: Welcome back, everybody to another episode of the Stride 2 Freedom podcast. I am your host, Russell Benaroya.

What is the Stride 2 Freedom podcast? It is designed to help business leaders get and stay in their zone of genius. What is your zone of genius? Your zone of genius is that thing that you do where you lose track of time, that feels effortless for you. Where people say, “Oh my gosh, how do you do that?” And you don’t really know because it is so innately your superpower.

We bring guests onto the show that are in the business of helping other business leaders get and stay in their zone. The Stride 2 Freedom podcast is sponsored by Stride Services. Stride Services is an outsource back office, bookkeeping, accounting, and fractional CFO services firm providing services to high-growth companies in the marketing agency arena and IT services space. What is our zone of genius, our zone of genius is helping business leaders get access to data that helps them make better business decisions.

I am thrilled to have on our show today, Kate Bradley Chernis. Hi Kate.

Kate Bradley Chernis: Hi, Russell.

Russell Benaroya: So good to see you. Kate is the founder of LatelyAI and she’s going to tell us all about it. It is an application that determines, through voice, video and text, what audiences want to hear, and turns that information into engaging social posts. I’m sure I bludgeoned this a bit, but Kate is going to help us understand why it helps businesses and business leaders get scale, breadth, reach, and increasing success.

They serve a lot of companies across a lot of industries and we’ll dig into how she helps owners achieve their highest and best use. She is well-recognized as a powerful female entrepreneur. She has notable recognition for her talks on marketing and AI.

One of her recent testimonials from an individual states the following, “Kate has one of those super duh solutions like Velcro, that will make millions. It’s one of those I-can’t-believe-that’s-not-out-there-already kind of things. You’re pretty outstanding, Kate.

Kate Bradley Chernis: All right. I admit it all.

Russell Benaroya: Now, here’s the thing about Kate. Kate totally flipped the script on me. This is why she’s on the show. She flipped the script on me because I reached out to her through cold outreach. We’re trying to build Stride Services business so we’re reaching out to people and technology, marketing, and IT services.

I sent her a cold message on LinkedIn that referenced this podcast because I wanted to show her that we’re hip and cool, share some episodes, get to know her, warm up, and build a relationship. And her immediate response was, “Oh would you like me to be a guest on your podcast?”

Kate Bradley Chernis: A girl’s gotta ask.

Russell Benaroya: And I was like, “Yeah, awesome.” Kate, what is your favorite flavor of ice cream?

Kate Bradley Chernis: I like chocolate chips. Where I come from, they’re called jimmies, but someone told me you can’t say that anymore. I don’t know why, but chocolate sprinkles are what I like on top.

Russell Benaroya: When you say where you come from…

Kate Bradley Chernis: Vermont, so we call them creamies. It’s the kind that comes out with the twist. So if they have a chocolate chip twist with the sprinkles, and I always get a wafer cone but I never eat the cone. I always ask for a baby’s, which is ridiculous because then they just put a huge large one on anyway.

Russell Benaroya: So you discard the cone after you’ve…?

Kate Bradley Chernis: Isn’t that shameful?

Russell Benaroya: I think we’re going to have to cut this episode short.

Kate Bradley Chernis: It’s because it’s not the same when you eat it out of the bowl. You want this idea of the licking and the twisting and there’s a daring there. What if you push it off the cone and it falls and you lose it forever? It’s a risk.

No one ever asked this, but my very first job was as a frozen yogurt server at a local place in Vermont. I was 13 so I could eat frozen yogurt and all of the toppings all day long. So I always had twists and raspberries and chocolate and whatever we put on there. I ate to my heart’s delight. They also sold beer and we stole a lot of it.

Russell Benaroya: Nice. That sounds like a pretty good business model.

Kate Bradley Chernis: Shame on them. They left us there at night all by ourselves. I feel bad now that I actually did that kind of stuff. It’s probably the worst thing I did as a teenager.

Russell Benaroya: What is the coolest rock band that you’ve ever hung out with? Because I think you’re a rockstar celebrity, which you can talk about. You were also with XM radio for quite a number of years so I think you run in this really interesting crowd.

Kate Bradley Chernis: You’re making me sound so cool. I’m a recovering rock and roll DJ. My last gig was broadcasting to 20 million listeners a day for XM Satellite Radio. My husband is always like, “Why don’t you use the nice voice on me?”

So the coolest, of course, is my husband. He was the lead guitar player for a band called The Damnwells, which was our top pick of the year 2004. I was the music director of XM 50 – The Loft  and my job was to find new music selections for us, which was super fun.

I dated a lot of musicians because there I was, and they’re all assholes, except I found one nice one. I was the asshole to him for a long time and then I was like, “This guy is still here and I’m totally abusing him. He must be quite special.”

But I did get to meet some really wild people. Don Henley, who was really disappointed that I wasn’t going to the dinner with all the VPs, he was a little bit slimy. Colin Hay was a super fun person to hang out with. He’s the lead singer of Men at Work and his voice is incredible. He’s still making records. Those songs stand the test of time.

If people find me, you can see the banner on my LinkedIn page and Twitter pages of the Rolling Stones. David, my husband, is right next to me. Now he has short hair and he wears chinos, and he’s in sales, sadly. But when we met The Stones, that picture is so funny because you can tell the radio guy because he’s got his arms around the musicians and you never do that. You never put your arm around a celebrity. It’s super uncool. But radio guys are kind of uncool for the most part.

Then there’s this one guy in the middle who’s got a weird face on. He’s a surgeon and he went out till four in the morning with us and then flew home in his little jet plane to do surgery at six in the morning. I don’t know who the victim was there. The best thing you can see Mick is out front and he’s wearing a silk red shirt.

When he walked through to say hello to us, he held his hand out like loyalty and made it clear that he wasn’t interested in us. Then Charlie Watts, rest his soul, you can see him standing there stiff as a board, which is his personality. That’s how he was.

And then Ron wood is in a striped shirt, and he saunters in all happy and he finds the 116-year-old with a large chest and he’s right on her. Then Keith Richards comes in and this is  right around Pirates of the Caribbean. Everybody, except for Charlie, doesn’t have gray hair. Keith has all those coins tied in his hair and he comes into the room and he grabs my husband, David, the only guitar player in the room, who’s also 5’4”. And he says, “Come here, shorty,” and the picture is snapped right then.

Russell Benaroya: Love it. We’ll be throwing that picture in the show notes. That’s classic. We don’t get that good background very often. What is the biggest risk you’ve ever taken? Don’t overthink it. What comes to mind for you?

Kate Bradley Chernis: I climbed an 80-foot rock wall with no ropes outside in San Francisco. I was with a boyfriend and I wanted to impress him. I can’t believe I didn’t die and I thank God. There’s a lot of dumbass things I’ve done, but that’s pretty top of the list. I have a picture of it too and I look so hot. My arms are really pumped in.

Russell Benaroya: Holy smokes. That is freaky. Have you seen Alex Honnold’s Free Solo documentary?

Kate Bradley Chernis: I haven’t because I know the story.

Russell Benaroya: That might make you pee your pants 

Kate Bradley Chernis: Yeah, it makes me pee my pants. I was a gym rat so I would go climbing in the gym. I’m happy to fall on a rope all day because, who cares? Then I didn’t do a lot of outdoor climbing. I don’t know what possessed me in that moment to do it. And I was wearing jeans and I think sneakers even, not even my climbing shoes. I had a jogging bra on and nothing else. Those were the days where I could bear the midriff. What a dumbass! Don’t do this at home.

Russell Benaroya: Glad we’re kicking off the podcast establishing that because I think that might set the tone. What is something that scares you?

Kate Bradley Chernis: Failing. I have this sense of deep shame that it’s my fault. I know that I should shut it. Most women I know share this kind of feeling where when something goes wrong, the first thing we do is run through that tape recorder in our minds of all the things we did to cause it. I’m like that too.

I get failure and I fail all the time. And it’s part of my charm and I know this. That’s not what I mean about failure. What I mean, with LatelyAI specifically, I want it so badly, and the reason I want it is super childish. I want to rub it in. That’s what I want.

All the people that have said, “You can’t do this, you’re wasting your time,” or have wasted my time, which is a lot of people and I hate that, or have been dismissive of me. It’s funny. The derogatoriness never comes out directly. It’s always some roundabout way. Oftentimes, you don’t even realize it’s happening until afterwards and you’re like, “That was awful. I just got beat up and I didn’t even know it.”

So, for those reasons, and that’s the competitor in me. Again, failure is not about winning. It’s about beating the machine. I know I’ll win. I’m already winning, no doubt about that. I always win. I get lucky a lot. I know I’m a good bet but I just want to kill it so that there is no doubt.

Russell Benaroya: I hear that. That is a long episode but it’s relevant. As people on the show probably know, I published a book about four months ago called One Life to Lead: Business Success Through Better Life Design. It’s both my journey as well as the journey of many entrepreneurs that have traversed many of the same drivers and beliefs and had to and wanted to be introspective on that story they’re telling themselves about what is it that they want and why do they want what they want as a way to self-reflect on the difference between the stories that they tell themselves and the facts as they are.

And facts and stories are different things. We live in a world of stories; we tell ourselves a lot of stories. Some of them serve us, like your story or around a competitive drive and why you want it. That might be in service to you. There’s an equal story that may not be in service to you and that’s the work of entrepreneurship and probably a great segue into LatelyAI.

LatelyAI is a super cool company that I want to hear about. It’s also a company that you’ve been involved with for quite a while. You’ve been on a journey. You’ve been through the ups and downs. You’ve probably told yourself a bunch of stories. I want to hear more about it. Give us some lens into LatelyAI and what you’re trying to accomplish.

Kate Bradley Chernis: You’re hitting on the button, which I think is so smart, the wisdom to know which of those stories serve you or not is what makes a great leader. Believe me, I have my faults and I fuck up sometimes. But I know I’m pretty good at this.

LatelyAI uses artificial intelligence to generate sales and marketing copy on social media that will not only get you high engagement, but get you skyrocketing engagement. That’s the high-level, salesy elevator pitch. If you asked me that a year ago, I would have said something totally different. You learn to evolve the conversation.

By the way, the last two months is the first time I feel really confident in saying that. People have some understanding of what we do. They don’t look at me with crazy eyes now. And that took some doing, by the way, Russell. We used to be like, “LatelyAI is a marketing resource management platform that…” You’re like, “WTF, what is she saying?”

Russell Benaroya: “It uses intelligent automation to activate the relevant language.” Blah, blah, blah.  What’s the fifth-grade level explanation of the business, whether you’re talking to investors, or to employees or to yourself? Simplify, simplify, simplify. That is the hardest thing to do.

Kate Bradley Chernis: It really is and everybody is on you about it all the time. So the pitch is the thing. What really frustrates me is we’ve scienced the idea of so many things to the death, Shark Tank being a big cause in my industry. This has caused venture capitalists and investors to sort of dismiss the human in the process and not have the patience to take a moment and listen beyond the “elevator pitch.”

Every entrepreneur I know is terrible at talking about themselves. It is hard to describe what you’re doing, especially when you’re doing something that doesn’t exist. So you’re looking to find familiar touchpoints to give you any idea and make a metaphor to understand what I’m doing. And sometimes it’s hard. The shoemaker often has no shoes.

What they’re looking for is for you to check these boxes that have been established. Now, what’s happening is that there’s space in between the boxes, and that’s where the unicorns are. It’s these things that don’t quite fit the mold.

At LatelyAI, we’ve not fit the mold in multiple ways. I’ll give you an example. We don’t do any paid ads at LatelyAI because I know the value of organic marketing. My Uber power is making listeners into fans or customers into evangelists. I did it for XM and I did it for other radio stations. I was a fiction writing major and I wrote lots of commercials. So I really understand not only the strategy around getting people to listen and engage and convert with you but also getting them to work for free on your behalf, indefinitely.

And that’s about the long tail, which was part of the whole music business. I know all about this. The payoff of the long tail is infinitely more than the immediacy and in the moment. So if you go into marketing a business with this mentality, you’re investing in your customers, you’re investing in your network, your friends, your family, and all the people around you, and giving them the ability and permission to fly the plane with you.

That’s so important because I can’t do this on my own. It takes like 50,000 villages, especially because I’m a woman. Female founders only get 2% of all venture capital funding. So I have to work much harder than you to do this. So I have to rely upon the help of others.

I didn’t follow this path of an SDR bank where you just get a bunch of dudes usually to smile and dial and call a day. And eventually somebody is going to pick up the phone and you can sell them. The other way is to throw money at paid ads. Just forget the problem and let someone else figure it out or let SEO figure it out. We do none of those things.

I’m going to ask you for the file of this show. We’re going to run it through LatelyAI. Lately’s AI is going to first use the model that it’s created for my voice specifically. And it’s looking for the phrases and one liners you and I say today that it knows our target customers are going to share, comment, and like. Then it’s going to automatically clip up this video into all those video clips with the quotes of what we’ve said, and turn them into social posts.

We’re going to watch who likes, comments, and shares and move them into a demo. We have a 98% sales conversion because the AI is so smart at knowing what our targets want to watch, read, or hear. Now, I tell you all that because that’s not the way you’re supposed to do it.

And part of this, by the way, it’s not just the AI on its own. We talked about humans having to be in the mix. At LatelyAI, we know that humans have to be part of the equation. It’s AI and humans together. And that’s not 1+1= 3; it’s 1+1=33. They have to be collaborating. So that part is hard. You have to do work. The hard way is the way. When you know that and you put that effort in, you’re not just trying to throw money and a numbers game at the problem. That’s when you’re seeing an exponential growth, conversions, all the things

Russell Benaroya: If you’re on the client side of LatelyAI, let’s say we used LatelyAI at Stride Services. We operate a professional services firm, like many professional service firms, one of the challenges is scale. Scaling professional services is obviously hard. So many professional service firms are built on the single reputation of the owner that can’t get out of their own way and everything revolves around them and it’s all their network.

But if you really want to build value, figuring out how to create a machine of customer acquisition in your target segment that transcends you as the individual is really important especially if you’re a business owner that wants to spend more time working on your business and not in your business. If you are the machine, you will never create the equity value that you probably aspire to.

So I’m curious how LatelyAI helps firms like ours. We use technology. We’re not on the cutting edge of technology. We’re a services firm. How could we use it to help us achieve our goals?

Kate Bradley Chernis: We are armies of one or that’s what we’re aspiring to be. And it’s almost impossible to be everywhere all the time. So you have to use automation in some way to help you do that. Now, automation is great but AI is not automation. It’s more than automation.

Automation would be perhaps simply clipping up the content, but AI knows which parts to clip up specifically. That’s the difference. My job is to give you the power to scale yourself like Gary Vaynerchuk without the army that he has.

Speaking of Gary, we did a project with them where Gary’s team created an entire Twitter channel. It’s called @garyveetv, fueled only by LatelyAI and nothing else. We wanted to do a test to see how well it worked and to also compare the AI to the humans.

The parallel of the content that LatelyAI chose versus the content that his human team chose, there was an 80% correlation. Then it also got him a 12,000% increase in engagement. Number one, it’s smart. And number two, Gary has so much content and AI has to learn from something. So the more you feed LatelyAI, the smarter it gets.

Russell Benaroya: What kind of content gets fed into the system?  Number two, how do you know that it’s working? You used the term in engagement and that could be a tricky metric, I suppose. It depends on what engagement is defined as for your organization. So give me some examples.

Kate Bradley Chernis: LatelyAI works with earned or owned media. Owned media is stuff you create. This podcast is yours; you can run it through LatelyAI. And we do this with text, audio, or video. So owned media could also be a blog that you write. It could be a newsletter you create. It could be just audio from a podcast. It could be a keynote that you’re giving at a conference that your company is sponsoring.

It could also be earned media, which I just have to ask you for the file. I have to have the actual file to upload it to LatelyAI.

Russell Benaroya: It’s super expensive, but it’s fine.

Kate Bradley Chernis: Here’s the win: I’m going to use all the clips that LatelyAI gives me and drive traffic back to the link of the full version of this. So you get the win; I get the lead gen. But you do too so it’s a double. Why wouldn’t you help me?

Russell Benaroya: Consider it done.

Kate Bradley Chernis: The other thing we do is a lot of companies don’t even have either of those things. They’re just getting started. So we integrate with an amazing company called UpContent, where if you type in a couple of words, they’ll go out and find thought leadership blogs in your industry. Then LatelyAI will automatically generate those blogs into social posts for you so you can look smart on LinkedIn or Twitter.

The second question was, how do you know it’s working? In the analytics that we created, we thought a lot about how hard it is for people to understand this question. Is it working? How do I know? What do the numbers mean?

Marketing has been bogged down by analytics for a long time. Even marketers don’t even know what they mean. I know this because they used to hire me and my agency to tell them. So what we did is a couple of things. Number one, we look at all of your social channels and we allow you to upload your Google Analytics to the same page inside LatelyAI. You can also upload, let’s say, your analytics from MailChimp. So you can look at all the analytics from your different sources in one view, and you can quickly see if the peaks and valleys are lining up.

For example, we put a lot of effort into Twitter and all I have to do is look at the page. I can see my Twitter peaks and valleys lining up with my Google Analytics. So I know, just by a quick look, that what I’m doing is working. I can also click any spike and LatelyAI will pull together everything that I posted on Twitter that day to cause that spike. So you can literally see the messages that worked for you.

Now, getting more granular, LatelyAI surfaces word clouds of the ideas and words inside those messages as well. It’ll ask you, “Hey, Russell, the idea is getting a lot of engagement, meaning clicks, shares or comments, from your target audience. Would you like the AI to look for more of that or consider it a noise word to look for less of that?” This is where the human comes in and tells the AI what to focus on. It needs that guidance here.

And I’ll give you an example of the word clouds. One thing that we discovered is we do them for words, we do them for mentions so you can see when you tag people, who’s actually getting you the most bang for your buck. We also do them with hashtags.

Here’s a myth I’m going to bust about marketing, which is, forever marketers have used hashtags as an indexer, hoping to glom on if someone’s searching for content. Now, people don’t actually use hashtags as search content almost at all anymore unless there’s some super in-the-moment event like Elon Musk buying Twitter.  They don’t use it for general purposes.

Russell Benaroya: Like Super Bowl Sunday or something.

Kate Bradley Chernis: They’re not looking up like weight loss, for example. Instead, when you use hashtags as a way to augment the message you just put out there, or to enhance it, or to add personality, that’s when we see the engagement skyrocket. I’ll give you an example: my personal highest performing #peeingmypants because that’s what I said when Gary Vaynerchuk was tweeting about us.

You can see my voice there. That’s some human element. That’s the reason why. It wasn’t just, “Hey, Gary posted about me.” Who gives a fuck? What’s my reaction? That’s interesting.

Russell Benaroya: So if a company uses LatelyAI, what do they need to be prepared for on their side to make the most of the service today? Is this something that a marketing manager is overseeing? Is this something that integrates into their CRM for their SDR? How do we work that through the funnel in a process?

Kate Bradley Chernis: I totally slipped Russell 100 bucks, by the way, folks to ask me all these great questions.

Russell Benaroya: You didn’t but it’s probably your wizardry and your DJ genius that you say things in such a way that trigger me to ask the next logical question. I’m basically being brainwashed. Keep going.

Kate Bradley Chernis: By the way, that’s one thing I learned in venture capital pitching is to force them to ask the questions you want them to ask. Then have slides that answer the questions before they’ve even asked them. I would do the pitch and then before I would let them ask, I’d be like, “Listen, I know you guys have some questions. I’m going to kick them off for you. First question, how do you do XYZ?” And then I’d have a slide for that. You look like such smarty pants because then you can control the conversation.

So we serve small, medium, and large customers. On the small side, you can walk it to LatelyAI, essentially have hardly any marketing background except for you having a couple of social channels and you’re trying to figure out, push a few buttons, and we’re going to give you content that will be appropriate for you. You can publish it right away and walk away and feel like you didn’t have to guess what to say or take the time to wrestle with the fear of the blank page.

At the higher end, we work with enterprise companies where we’ve built in a syndication feature. So one CRO, for example, can auto-generate content from the company blog and instantly publish it on the personal sales social media accounts of his/her entire team. Or a CMO who is in charge of thought leadership for her C-suite, she can also auto-generate content from the CEO’s latest interview with you and broadcast it across all the employee channels who are participating in employee advocacy for the company.

There’s a way where the employees, for example, if they didn’t like that content, they can choose not to use it, or they can collaborate with it. There are a lot of different ideas there. So it can be robust, where you need a marketing team to really benefit from the AI. In the enterprise package, there’s so much more you can do with editing the video and curating the AI. It’s advanced; that’s why we charge more for it.

On the small medium business side, what we found those customers want the most is just to eliminate the fear of the blank page and/or unlock something they’ve busted their ass doing, like writing a blog for four hours.

What’s interesting to us is what we discovered last year: while those products are different, the way customers want to use them are the same. So we’ve learned to kind of gamify the act of using the auto-generator because it’s fun. You push the button and you’re like, what’s it gonna pick? It’s like a jukebox. That’s one of the things I’m doing now. I’m raising money to take those learnings from both sides and merge them.

Russell Benaroya: So if I were to simplify it down, as the owner of a small professional services firm, I might think of this as a pretty efficient way for me to scale my content in a way that’s not going to add very much marginal cost at all. So I get scale and reach to content in places that I might not otherwise be present or not staffed or I don’t have the expertise there, but I feel this desire to have presence as part of my overall brand strategy. Is that right?

Kate Bradley Chernis: It’s not just the presence; it’s the results.

Russell Benaroya: That’s a good point. Yes, I want engagement and then the bridge is how do I map that back to the conversion funnel of what I ultimately measure my success by, which is, am I growing revenue?

Kate Bradley Chernis: The map is so important. I hate to say it, but we live in spreadsheets. So I know that I need to do a minimum of three public speaking engagements a week, or writing a blog or being on a conference or webinars. Three a week will roughly drive 160 demo requests or  in the self-service space, it’ll drive 200 visits to the homepage, let’s say okay. Of those 200 to 400, as we watch them convert from the homepage to the pricing page, then from pricing to sign up, sign up to trial, trial to conversion.

In the self-service, it’s been live for 85 days. We have a 74% trial to sale conversion, which is very high. The industry average is like 45%. Then on the enterprise side, we’re going from homepage to demo request, then they’re having a demo with an actual human, then in a trial and then conversion, and that’s the 98% conversion. This is what you do. You just map out these things in the spreadsheet.

We look at these numbers, daily, weekly, monthly. And what we’re looking for is a pattern. For example, we’re partnered with HubSpot and Hootsuite and I’m looking specifically to see what customers are using LatelyAI to integrate with those products. We can spy on them. We can actually see what you do in the account. We can watch to see if you’re clicking a button that’s not working for you.

So I can see the installs from HubSpot or Hootsuite, and then I can see what percentage those particular people are staying around or not staying around. I noticed that a bunch converted one week and then a bunch canceled another week of these particular groups of people. And we didn’t know why. I said, “Go in and watch and look for the patterns.” There’s going to be something that happened three or more times.

Maybe somebody went first to this and then to that. Obviously, we can see if something’s broken and it’s not working for them. Sometimes it’s less than that. Did they only see three posts before they were like, “These all suck, I’m out.”

And the patterns are the thing and it’s hard because you don’t know what you’re looking for. It’s a needle in a haystack. But they’re always there, which is what I learned from Mark Roberge, former CRO of HubSpot. Patterns are everything and you can’t for a moment take your foot off that gas. For a second, you can be like, “Whoa, everything’s great. Everything’s going up.” But shit is happening in there that you’re not seeing.

Russell Benaroya: That comment about continuous improvement of the customer experience and the customer journey is equally applicable in the conversion funnel of a SaaS piece of software like yours, or in professional services. That maniacal focus on the customer experience in the customer journey and root-causing—where the problem resides—and systemically solving the problem so it doesn’t happen again is a discipline that we want all companies to embrace.

Two more questions: one is the customer segment. We focus a lot on what’s our customer segment? Who do we want to serve? Where do we think we can uniquely add value? And for LatelyAI, it sounds like you serve across a spectrum of client sizes—SMB to enterprise—but their needs, goals, and wants are very different. And there’s a cost associated with service enterprise with a level of features and support that’s different from SMB.

Why not just say, “Our expertise is serving this client psychographic or demographic, this segment, and just maniacally focus on them?

Kate Bradley Chernis: Because we are consistently proving that we don’t have to, and I will back that up. I can market to these customers exactly the same way I described it to you. So I reach SMB customers and enterprise customers dogfooding my own product for free.

What I learned early on is that, at very large companies, individuals are passing us around because they want it for themselves. So if I can make them my champions, then I can sell to the person that I need to sell to across the enterprise. That’s part of the key thing. And that was the opposite of what we thought. We thought we would have to sell to a CMO who would then make everybody use it. But it’s not that way for us.

So making a product that sneakily serves SMBs actually also serves the humans inside an enterprise. So I can align product and marketing to do the same things. That’s cost efficient for me. Now, the lift as you noted is on the customer service side. So for enterprise, there’s more training that needs to be happening but not really. LatelyAI is really easy to use.

I was on stage giving a demo once and for some reason, my PC wouldn’t connect to the damn screen. So I had to use somebody’s Mac and I don’t know how to use a Mac. So the tech person got up and did the demo for me, which is so funny because I’m always asking my tech team to make it easier to use. And they’re like, “You know it is pretty easy to use.”

The other course, as you also mentioned, is sales and sales cycle. Now, we were able to take the sales cycle from enterprise down from around 28 months to two months recently, and we’ve seen that a couple of times. So, I know that we’re improving on that. I know that it’s possible. Stuff is just getting easier.

Normally, a legal process with one of our customers would take a year. They made it take 45 days with us because there was so much pressure from inside and outside to just get the damn thing in there. In part, that was because of the cost of not doing it. We know that there are smaller companies that might spend $3,000 a month to have an outside source writing content and clipping up their videos for them, where they can now do it themselves. So that saves $3k minus the cost of LatelyAI, and maybe they have to spend an hour with each video to guide it along. That’s a lot of time saved. 

The other thing that we’re seeing with our enterprise customers is that less and less people need to understand how to use the product that they’re teaching their employees on our behalf. We have one customer who gives a seminar every quarter to all of her franchisees on LatelyAI, and we’ve offered to do it  a million times and she’s like, “No, I got it.”

Russell Benaroya: What is the next chapter of LatelyAI for you? Where are you on this journey?

Kate Bradley Chernis: I need to take a nap.

Russell Benaroya: Sometimes a breather can be a great idea.

Kate Bradley Chernis: The honest answer is we have a version 2 of AI. Right now, LatelyAI is designed to start you 75% of the way there, to start you on third base. I can take like six innings just to get there. With the new version of AI, we’re going to get you almost a home plate so about 90% of the way there.

That’s really around learning that brand voice and being able to not just parse up the things with the ideas we know, but parse and then also write as well. We did a test with Anheuser-Busch InBev to prove that this could work with 10,000 pieces of content from one of their brand voices and their content because the AI has to learn from something. So the content came in the versions of social media posts, radio scripts, press releases, anything we can find around the single brand.

And the idea, in combination with our friends from UpContent, was to type in a couple of ideas. UpContent went to find blogs based on these ideas, LatelyAI applied the new writing model, parsed up components, then rewrote those components so they were not quotations, and then added brand-isms to them and they’re awesome. That’s what’s being implemented, hopefully, starting next week. I parked it for a little while because I didn’t have the resources. We built it and then I couldn’t put it in the product.

Also, we’re really interested in watching what you guys want. We’ve been asked for paid advertising to use LatelyAI. That’s been our number one request for our customers for years now but that might change. I think that’s probably the next place we’re going. I just need to listen a little bit more. 

One of the things that we’re seeing is, on a smaller business side, less scheduling. They want one-off content to publish right now. So we altered our roadmap to address that. And I think that’s the gift you need. One we already noted is to see the glass half empty. Find the problems. That’s my state of being, much to my husband’s dismay. But also to know when not to stay the course. 

Russell Benaroya: What is something people don’t usually ask you that you wish they did?

Kate Bradley Chernis: I was Googling in the background and I was talking because I wanted to read this to you today. I’m just in love with it. The question would be, what piece of writing has made an effect on you lately?

It doesn’t sound like a very exciting question. But when I read this to you, it will. So I heard this on a podcast recently. The author’s name is Kyle Carrero Lopez and it’s a poem. It’s called Ode to the Crop Top

O sliced crêpe;

dress code break;

half-set Sun, 

slut symbol

cracked window

short story

a whole summer carnival, shrunk

How I adore your spunk

your sincere open call for air 

on my belly hair

The little Target® boy

groaning eww as I pass 

isn’t worth any ire.

He’s playing with fire, 

but his parents lit the torch.

To think such small cloth

sparks grown brains a flame.

Why you in a girl’s top,

the man yells in DC.

I could have cut him one too

so we’d both feel the breeze.

Isn’t it delicious? 

Russell Benaroya: I love it. Kate Bradley Chernis, thank you so much for flipping the script on me to be a guest on the show. As much as you identify with AI and have built a company on AI, you are so human. I do appreciate your authentic approach to this conversation, a willingness to teach me, a willingness to teach our listeners, and a willingness to acknowledge that doing things the way people think you should is not the best path for everyone. I appreciate you forging a journey on your own. It’s been such a pleasure to spend time with you.

Kate Bradley Chernis:  It’s been mine. It’s like a man wearing a crop top, right?

Russell Benaroya: Like I am right now although you can’t see below my midriff. All right everybody, thank you so much. Another great episode of Stride 2 Freedom podcast. Look forward to the next show in the next couple of weeks. Have a great day everyone. Take care. Bye

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