The following interview is a conversation we had with Charlotte Dales, CEO & Co-Founder of Inclusively, on our podcast Category Visionaries. You can view the full episode here: $20M Raised to Transform Workplace Personalization

Brett
Welcome to Category Visionaries, the show dedicated to exploring exciting visions for the future from the founders who are on the front lines building it. In each episode, we’ll speak with a visionary Founder who’s building a new category or reimagining an existing one. We’ll learn about the problem they solve, how their technology works, and unpack their vision for the future. I’m your host, Brett Stapper, CEO of Front Lines Media. Now let’s dive right into today’s episode. Hey, everyone. And welcome back to Category Visionaries. Today we’re speaking with Charlotte Dale, CEO and Co-Founder of Inclusively, a workplace personalization platform that’s raised 20 million in funding. Charlotte, how are you? 

Charlotte Dales
I’m great. How are you doing? 

Brett
I’m doing great, and I’m super excited for this conversation. So I know we’re going to dive into everything that you’re building today, but I want to take a little bit of time to talk about your first company, your previous company that you sold. So let’s go ahead and go back to 2017. You’re sitting there, the deal closes. You know, what are you thinking? What’s going on inside your head? And what is the company that you just sold? 

Charlotte Dales
So the company I sold, we started in 2013. So this is sort of when Uber and all these types of, you know, paying with your phone and digital payments were coming out. But it was not as prevalent as it is today. And we came up with the idea to create an app where you could split and pay the bill from your phone at restaurants and bars. So we grew that to about 200 restaurants and bars in London and ended up selling it to American Express at the end of 2017. And I’d say probably the first thing I thought when we closed it was, I will never, ever, ever do this again. I think it was like an incredibly relieving moment that almost immediately after, you know, a day or two had passed, I immediately had the itch again. 

Charlotte Dales
It’s like, I think, like childbirth, you forget and you go ahead and jump into the next one. But it was a really hard journey to get there. We, you know, it was my first company. I had never done any of this stuff before. I really had probably no business at the time doing what were doing. And we somehow, you know, after many trials and tribulations, pulled off a pretty good sale. And it was just a long road to get there. The buyer pulled the deal right before were going to close, and I ended up flying to New York unannounced and showing up at their offices and really reminding them why it was so important to buy our company and the value that we could add. And so I feel like on that day it was like relief. 

Charlotte Dales
It wasn’t in my mind like the champagne pop in. It was more like, oh my gosh, like we got out of this alive. But very quickly afterwards, after going into corporate and doing our earn out, I knew this was my passion to do it again. 

Brett
So what is that? Like you’re sitting on the plane, you’re flying over and like is the plan literally just to show up at amex and say, hey, like, let’s do this deal? 

Charlotte Dales
Yeah. So we got a call from the person who was leading the deal and she was, you know, very nervous to call me. And she knew how much it meant to us to sell this company. And you know, that we had paid, you know, so much money and lawyers and everything, you know, were basically doing this. We were putting everything into doing this transaction. We had done jump through all the hoops. And she said, you know, we’re not going to be able to do it. And I was just like, that just can’t be true. Like, we’ve done everything. We thought through diligence, we did everything. And so I just called my board and I said, and we had an M and A advisor. 

Charlotte Dales
And I just said, you know, they were kind of like, you know, talking about just going into liquidation and all these options. And I was like, that’s just not happening. I’m going to New York. If someone wants to come with me, they’re welcome to come. And I strategically, this was kind of back when you didn’t really have WI fi on airplanes. And so at 9:00am London time, I was on the plane, sent the text as were taking off to my point of contact there and said, I’m on my way to New York from London and I’ll land at 1pm and I’ll come by the office. Then, you know, took off and had eight hours of no service and landed. And you know, they had all had a lot of time to kind of figure out what to do. 

Charlotte Dales
And they’re like, okay, you please don’t come in today. Like we need to get the right people. And they wanted to do the deal. Like the M and A team wanted to do the deal, this person wanted to do the deal. But you know, in big companies lots of things can just change. People leave and they can just kind of, you know, quickly pivot. And so they were actually very supportive. They got the President of the consumer group at the time, because the person who was trying to pull the deal was out of town in Croatia. And so luckily I actually got to go to the top. And, you know, I went in and the M and A advisor and the woman who was running the deal on the team, we met for an hour before the president came in. 

Charlotte Dales
And, you know, we spent all this time, like, doing all these perfect decks and making everything perfect. And the end of the day, I was writing a whole pitch onto a whiteboard, waiting and presenting that to the president of the consumer group at Amex. And I think she, you know, like, she wasn’t really part of this was a small deal for Amex, so she wasn’t even really part of it. It’s under 20 million. And so, you know, after, like, getting to hear from me directly what was going on and why I thought this was valuable to the company, they said, you have this one piece of functionality. And I was like, yes, we do. And so they said, okay, we’re going to send someone over for diligence, you know, in a week or two to confirm all of that. 

Charlotte Dales
And then, like, we can start to think about moving forward again. And so went back to London and we built what they needed within a weekend and got through the diligence and closed the deal. 

Brett
Probably a dumb question, but if you hadn’t gotten on that plane, do you. 

Charlotte Dales
Think the deal would have just fallen apart 100,000%? 

Brett
I feel like that’s advice I’ve heard in the past. I can’t remember who gave that advice, but I think the advice was literally like, get on the plane. In those situations where you’re wondering, like, oh, should I do it? Should I not do it? Like, the answer is always, get on the plane. 

Charlotte Dales
Get on the plane. There’s just no reason not to. Like, we had everything to lose. Like, I had nothing to lose besides a plane ticket. And, you know, when the deal closed and when were kind of started working at the company, like, they bring up this story, you know, the woman who ran the whole deal is actually now an advisor of my company now. And I mean, the story just comes up all the time. Even when were there. The president of consumer Group, you know, was like, when I eventually left to start this company three years later, she was just like, that was one of the most amazing things I’ve ever seen. And, like, you got getting on that plane just like says everything about you. 

Charlotte Dales
And so I just feel like as an entrepreneur, you just really have to not, like, you just can’t have any shame. Like, there’s just nothing more important than showing how much you care about, you know, moving your business forward. 

Brett
I can’t imagine the anxiety of, like, not having Wi Fi. You send that text and you just get up. It was actually anxious. 

Charlotte Dales
It was better. I strategically did it because I was like, you know what? They’re going to know I don’t have Wi Fi, so they’re not going to be able to tell me not to come. Like, I didn’t give them enough time to redirect me. And I just knew I was going to land and, you know, they were going to have had a few hours to figure out how they were going to handle me. 

Brett
And let’s talk about lessons that were learned from that journey. I’m sure there were a ton of learnings. Like, what were the top, maybe 1, 2, 3 lessons that really stuck with you. 

Charlotte Dales
From my first company, it was definitely the importance of who you take money from and really understanding how you want your board to behave. I feel like my Co-Founder and I, my first company, we literally felt like it was all on us. Like when were running out of money, we would throw all of our savings in to the company. And, you know, if the board gets used to you always saving the company at your own personal expense. Expense, you’re giving them, like, the best of both worlds. And because they know you’re just leveraging yourself even more, you’re going to work even harder. And I feel like from a sustainability perspective, like, you can’t keep that up forever. And I think that was a huge learning. It’s just, you know, it’s not just me. Like, you are all our investors. 

Charlotte Dales
You are on the board. You have fiduciaries along with me. And like, you really need to find people who want to be on a team with you when it comes to a board and investors and in the trenches. And I think that was not what we had in the first company. And it’s 100% what I have built today. Even though, you know, it took a little while to get there. Still made a few of the same mistakes, but I’ve really realized the importance of that. I’d say the second thing is that I just am a big believer that where there’s a will, there’s a way, and there’s always a way out. Like, you are a smart person. You started a company. If your product isn’t perfectly aligned to what the market needs, you pivot. You just have to go with your instincts. 

Charlotte Dales
And I feel like in Any situation in my first company, and even now, whenever I’ve not listened to my instinct, it’s always, you know, led me really far away from where we need to be. And so I think trusting my instincts is definitely something that’s important. And even if it means, like, I’m going to have a difficult conversation with someone, it’s better to just sort of move forward with your gut reactions a step when you’re in a bind because you don’t have a lot of time. And I’d say, like, on the other end of that is the third thing is around. 

Charlotte Dales
You can be more patient, especially at the beginning, about who you partner with, because you don’t have this huge burn, you don’t have all these employees yet, but you’re so excited to start your business that you feel like you’re in this big rush. But you’re actually, that’s like, the best time to take your time and get the right people involved. And I think that is definitely something I’ve learned not only in my first, but in my second. I just was so excited to start my second company that I dove headfirst into sort of the wrong situation because it was the situation I felt like would get me to, like, start the business faster. And I think you have to really understand, like, when do I need to rush? Like, when is this so urgent? And then when do I not? 

Charlotte Dales
Because you need those time. Like, you need to take advantage of the times where you actually can sleep on it. And so I think it’s just knowing the difference, the whole, you know, while you’re running the company and making sure that you’re taking your time when you can so you don’t fall into mistakes and then trusting your instinct when you’re in more of a urgent situation. 

Brett
You mentioned the second company there, so let’s dive into the second company. What does the company do? 

Charlotte Dales
So my company now, Inclusively, I actually came up with the idea while I was selling my first company. My cousin became the first licensed facialist in the state of Florida with Down syndrome. And I went to go see her work for the first time. And I just noticed how easy it was for her employer to make some slight adjustments to her working environment. And so wanted to figure out how can we leverage technology to make it really, really easy for large enterprises to do this at scale without disrupting their operations and, you know, without the perception that it’s going to be so hard. How can we use technology to make this, like, very easy to support employees for all the different reasons why they might need support. So our company today is called Inclusively, and we have a product that we call Retain. 

Charlotte Dales
What it does is it allows anyone at our partner organizations to sign in and type in anything about themselves anonymously. So you can say, I have ADHD and trouble concentrating in meetings. You can say, I’m a caregiver of someone with a disability. You can say, I’m a single parent, I’m going through a divorce, whatever it is that you’re kind of going through from a personal situation. And we can deduce what pain points have we identified. And then we serve up all the company’s existing products, benefits, services, technologies, policies, everything that usually is spread across a million different platforms at a company, and it’s hard to access. And we serve that up to people based on their unique needs. And then we collect data on what needs are coming in that they don’t have resources for. 

Charlotte Dales
So companies can better predict what investments they should be making to have the biggest impact over time. 

Brett
At the category level, what is the category? When I did the intro, I think I called you a workplace personalization platform. I stole that from somewhere on your website, maybe your LinkedIn. Is that the market category or how do you think about the category you’re in? 

Charlotte Dales
I think we’re creating a new category, and maybe that’s the name of it. So we started as a hiring platform and we created this technology, which is very similar to what I said. We could deduce what pain points people had and then serve up what accommodations they could be asking both for the interview on the job to be more successful and productive. And what we realized when we quickly started working with companies, that actually this technology solved an even larger problem for companies, which is a very new problem. There’s, you know, a skills gap that is growing. There is a workforce shortage. And we really need this next generation of the workforce to plug those gaps. And they’re just very different than historic workforce generations. 

Charlotte Dales
You know, over 50% of people from Gen Z identify with having at least one learning difference, mental health or some sort of disability. And we’re already seeing the ramifications that companies processes aren’t set up. There’s 30% of people who are Gen Z get fired or leave within the first 90 days. So as it stands today, they’re not really plugging the gap. And so what the problem is companies need to kind of update their existing processes and better needs of this next generation of the workforce. And so, you know, it’d be really easy if were disrupting an existing category in my mind, because you can say, oh, we’re just like workday, we’re just better and cheaper. But this is really a new category. 

Charlotte Dales
It’s around how do you customize and make your employee experience personalized to the same level that you care about it for your customers? And I think that it’s a very new way of thinking about employee experience. And I think it’s been accelerated by the fact that this next generation kind of demands this. And we really need to figure out how to access on talent pool now with sort of, you know, this talent crisis that’s, you know, within the next five to 10 years when you’re giving. 

Brett
The pitch, what’s like the aha? Is there a common aha that you see with prospects? 

Charlotte Dales
Yeah. So like we kind of, you know, lay the groundwork of sort of, here’s the macro problems which I kind of just described, and here’s how we fit into that. But I think the real aha is when we actually pull up the demo and we’re like, so like, what do you want to say in here? It’s like they can literally say anything. They can say, I have a child with something, I have a coworker I’m trying to support. You literally can type in anything. And then they see everything that starts getting popped up. And like, it’s very immediate. It’s like, here’s what it is. Here’s how to access, here’s where you go, here’s who’s eligible. That’s really the aha. They’re like, oh my gosh, we actually have all this stuff and no one uses it. 

Charlotte Dales
And we don’t know if it’s because they don’t know about it or they don’t connect it to their needs, or maybe they don’t need it and we just bought it. And this is sort of like the answer to all of those questions. I think it really is sort of that initial, just tell me what you want me to put in here. And when they See, sort of the fact that we’re pulling up everything that they’ve already invested in, they realize really what the value is and how, you know, I think a lot of companies are struggling with like this generation is so needy, et cetera. But they didn’t just wake up this way. They grew up in an education system where they were diagnosed way earlier and way more frequently. And they grew accustomed to advocating for accommodations in the education system. 

Charlotte Dales
And they’re just placing those demands on the workforce. And I think when they see our product, they realize actually it’s not going to be that hard to solve for this if we can connect people’s needs to what we already have and then build from there. 

Brett
What about the icp? Who is the ICP today? And is that the ICP you started out with? What was that journey to figure that out? 

Charlotte Dales
We started as a hiring platform, so the ICP was actually much easier. It was like a VP of Talent Acquisition and then we started at the end of 2020. So that was like in a very good moment for DEI and where a lot of investments were getting made. So it was usually the VP of Talent Acquisition and the Chief Diversity Officer. But as we entered into early 2023, we started to see, okay, the hiring market is turbulent, the DEI market is turbulent. And we need to figure out how we can actually make a sustainable impact over time that’s not reliant on strategies that will ebb and flow. And so that’s how we came up with the idea for our product retain. 

Charlotte Dales
And that has actually completely changed our icp, which in some ways is very good because it actually creates a more senior buyer, which helps with a lot of, you know, just sort of like the sales cycle. But it one meant that it wasn’t. So we grew to about 50 enterprise companies. We worked with Salesforce, Accenture, all different, mostly large enterprises, but all different industries. It meant that it was really hard. We couldn’t just jump from our, you know, contract we had with them today to selling our new product. Cause it was a totally different buyer. And underneath the Chro, our product touches, you know, hr, technology, benefits, product services, their accommodations team. So we’ve actually kind of moved into like a more senior buyer set. But also there’s just a lot more people now that need to be involved. 

Charlotte Dales
So it’s like, you know, a catch 22. But I think that the problem that we’re solving now actually has a lot more bottom line impact in a positive way for organizations. It solves an even bigger problem. It’s expanding Expanded our market size. And for the sake of, you know, accelerating our mission, we’re actually leveling the playing field for people with disabilities by normalizing this process for everyone. But we definitely have a completely different ICP than we started out with. We still have DEI involved where, you know, these companies still have their chief diversity officer and they really, I think a lot of the work we do helps, the data that we’re collecting actually helps inform their initiatives and get more buy in from the company. But we completely had to change icps from one product to the next. 

Brett
I’ve been hearing about that. So is that confirmed true that a lot of these large enterprises are getting rid of like the DEI head or getting rid of DEI entirely? Is that what you’re seeing? 

Charlotte Dales
Yeah. So we’re seeing it in some instances more so with prospects than with our existing clients. Today we’re seeing it more with, you know, prospects that have been in pipeline and then that person is no longer there. I do think that there’s some people that are doing it from the perspective of we don’t need to do this anymore. I think the majority of people are actually trying to make it more of ingrained in their workforce planning strategy and not have this separate siloed group because ultimately this is a part of a larger problem of not only including people, but ensuring that we have the right talent, you know, to sustain us for the next few decades. And you know, this next generation is coming into the workforce very quickly and we have to solve for it. 

Charlotte Dales
So I think, you know, I’m a Founder and I’m usually on the optimistic side, but I really have, in talking to lots of different companies, I feel like it’s the majority of people, if it is transitioning, they’re actually trying to transition it to be ingrained in the fabric of the organization instead of this siloed group just really trying to push a number of initiatives across the line that other people aren’t viewing as a priority because it feels very separate to them.

Brett
I see that makes a lot of sense. So it’s not going away. It’s just more being deeply integrated into everything they do. 

Charlotte Dales
Instead of being isolated, it’s getting streamlined. And I think, you know, one of the chief diversity Officers we spoke to at a really large company said it’s just now really important to show the ROI of these initiatives, which in my point of view was always important because nothing is sustainable in a capitalist economy and at for profit enterprises if it’s not driving roi. So I think that there’s just like more attention on the metrics. But I think in the long run I hope that this is actually a positive move, a net positive move, at least for the majority of enterprises. 

Brett
Let’s talk a little bit about marketing. So sounds like you’ve really locked into your icp. What’s the marketing strategy? What’s the marketing playbook to reach and find and connect that icp? 

Charlotte Dales
Okay, well we have tried everything under the sun. We have done demand gen, we have done webinars, we’ve done all the things BDRs, tried to do, cold calling, all the stuff. And I think that especially in the past two years for enterprise sales in particular, a lot of those doors have shut. Like there are spam filters on every enterprise account. If you’re like attaching HubSpot tracking and stuff, it’ll just automatically decline. And also we’re just all inundated with emails all the time from randoms and strangers that like you don’t read them anymore and I don’t read them anymore. And so I think that a lot has changed in the past two years. Whereas, you know, when we first started, like I almost got a response on every cold email I sent. 

Charlotte Dales
And I was sending emails to CEOs of these companies just like, hey, I want to tell you what I’m doing. We get a response. But now that everyone’s sort of able to flood people’s inboxes, at the beginning of this year were like, this isn’t working. Like we’re not getting any type of conversion. We’re spinning our wheels. We’ve set up this whole cold calling and all this different stuff and none of it’s really yielding anything. And you know, demand gen is amazing, but it really needs to come once you’re kind of foot like off the ground a bit more where you can have that wait for like, you know, pieces of content dripping out and waiting for those leads to come through. And you’ve built up enough pipeline that it kind of services you. 

Charlotte Dales
So what we started doing is I actually went to all of my investors and we have about 60 investors. But that’s because we have a lot of angels at the beginning. And I essentially put all of them. I got LinkedIn sales navigator and I essentially Put in all of my investors, and then I would curate their connections to my icp. And then I would say, hey, can I have a quick 15 minutes with you? Because obviously you don’t know everyone that you’re connected to on LinkedIn. And I said, who of this list of 100 people do you actually know and will you make an intro to. They’ll quickly give that to me. 

Charlotte Dales
And then we have people who write the personalized emails for each person, send them all separately, send the investor the email addresses, and then they just forwarded on with a cover letter that we’ve written. And we tripled our weekly meeting rates within starting that. And actually to turn it off for a while because we didn’t have enough to time to take all the meetings. And we’re getting higher quality introductions with way more senior people. And I think that strategy, alongside the fact that we are just showing up in person to our events, to other people’s events, and really making connections and hosting like dinners before a big conference the next day where we know a lot of people will be there, those two things have completely driven our top of funnel strategy. And honestly, we’ve pretty much turned off everything else. 

Brett
And it’s a good problem to have. If you have to turn it off because you have so many leads coming in, that’s a great problem to have that I think any Founder listening and dreams of that being there, they’re probably. 

Charlotte Dales
Very passionate about this approach. Like, your investors want to help, but you do have to make it easy for them to do so. And so we used to send out emails being like, how you can help make introductions to these ICPs. But I made it even easier by being like, it’s these people that I know, you know, per LinkedIn. And I’m going to write the email and I’m going to send it to you. And we’ve streamlined it so much on our end that it’s as effective as sort of the old way of sort of blasting out emails and getting a 2% conversion rate because we’re getting a way higher conversion rate on a lot more quality leads. And I even get like my clients to do it. 

Charlotte Dales
Like once we’re close with sort of a client or, you know, I’ll say like, hey, do you have any other chros that you know that would be interested in this? So we kind of just keep spreading it outside of just our investor group. I may ask you, Brett, I’ll see who you know through this podcast. 

Brett
I know a lot of people. I just did the math we crossed a thousand episodes in the last three years, so we know a lot of people through that. Yeah, I appreciate the tactical and actionable advice there. You know, normally when we ask about marketing strategy, people are like, super fluffy. They’re, yeah, we’re creating some content and the content works. But you took it to another level there. I like to always ask about decisions and important go to market decisions for you. What’s been the most important go to market decision you’ve made to date? 

Charlotte Dales
Pivoting to our retained platform, knowing that we needed a better way to accelerate our mission. I think we did that really quickly. We got Salesforce to be the first pilot and it sort of, you know, started taking off from there. And I think had we not been honest with ourselves and you know, there’s times where you can have like Founder Kool Aid and you’re not really seeing what is actually going on in the market and you’re laser focused on your product. And I think the best go to market decision that my Co-Founder and I made was how do we accelerate and expand the application of this platform so that it’s a must have and not a nice to have. And we’re fortunate enough that we had built enough enterprise clients like Salesforce that we could leverage. Like, we just weren’t shy. 

Charlotte Dales
We interviewed them, we had them help us build this product. And I think that’s probably, you know, when I talk to investor today about how the business is doing, you know, I’m like, you know, we saw this coming, built a product, got Salesforce to launch it, like all within 12 months. And we’re like, very proud of that. 

Brett
Definitely something to be very proud of. What about your marketing team? What does that marketing team look like and what are some of the lessons that you’ve learned building out the marketing team? 

Charlotte Dales
Our team now we have one VP of marketing, and then she reports into like our service and delivery person who manages both like marketing, but also all the content that goes out to our existing clients and the employees that we are attracting to come on to our platform. I think tying marketing in the early stages, this is not a forever thing, but I think tying marketing in the early stages to part of the organization that’s actually delivering value for clients has been really helpful because those messages get so synced up. Anything we learn from a customer perspective is like going into marketing within the same day. 

Charlotte Dales
I mean, I remember we kind of came up with some of this new messaging around, you know, tying the macro trends to what we’re doing and really seeing like, oh my gosh, that’s like really helping people to understand what we do, the problems we solve. And you know, within a month that whole story was covered by Forbes and I was like, guys, we got to take a moment here. That was really fast. Like we came up with this, we brainstormed, we tested on a few clients and it was in Forbes within, you know, four weeks. So I think lessons learned for us and I don’t know if this is for everyone. I think if you’re doing non enterprise sales and it’s more volumes play, smaller ticket sizes and faster sales cycles, some of the traditional techniques work a lot more. 

Charlotte Dales
My old Co-Founder for my first company has a business that’s like completely inbound because of the marketing they’re doing. I just think at enterprise it’s complex. And so I think for us right now having the marketing org so tightly knit with like the servicing side of our business is making sure that those messages get blasted out as we even get tiny kernels of, you know, feedback from customers and understanding what’s resonating with them. 

Brett
Final question for you. I’m realizing that we’re almost over on time here. So let’s zoom out three to five years into the future. What’s the big picture vision look like? 

Charlotte Dales
Our big focus for this coming year is around channel partnerships and strategic partnerships. As I said, the enterprise sales cycle can be a slog. It’s slow, it’s complex, there’s lots of people involved. And so I think next three to five years I want to have two to three really strong partners that are way bigger than us in the industry that we’ve aligned to and are sort of co selling together. I think our platform fortunately is very synergetic with a lot of different types of organizations. So I hope in the next three to five years we’ve really honed in to like what is the ICP of our strategic partnerships because those can sell so much faster for us than our sort of one off, one to one sales. 

Brett
Amazing. I love the vision. I really love this conversation. We’re up on time so we’ll wrap here. Before we do, if there’s any founders that are listening in that want to follow along with your journey, where should we send them? 

Charlotte Dales
My LinkedIn is Charlotte Dales and you can send them to me charlotteclusively. Com. I love talking to founders. I think having support when you feel like no one else understands what you’re going through is really important. It’s gotten me through a lot of stuff and so however I can help. I’m always here to listen to whatever shit the world’s throwing at you guys. 

Brett
I just hope you don’t get spammed endlessly for sharing your email, but like these days, possible. Thank you again. 

Charlotte Dales
Thank you. 

Brett
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