The following interview is a conversation we had with Ishita Arora, CEO and Founder Dayslice, on our podcast Category Visionaries. You can view the full episode here: $6 Million Raised to Help Services Businesses Build Modern Digital Storefronts

Ishita Arora
Absolutely, thanks for having me. 

Brett
So, to kick things off, can we start with just a quick summary of who you are and a bit more about your background? 

Ishita Arora
Yeah, definitely. So I would say I think my career path has had a fair number of plot twists, so maybe I’ll just kind of quickly run through the last almost decade now. So came out of college having studied math and thought originally that I’d want to get a PhD and decided to just get a little bit of work experience before taking the plunge and then ended up basically never looking back. So my first job, I joined Dropbox as a part of a rotation program, actually, because I didn’t quite know what I wanted to do in the quote unquote, real world. So essentially it allowed me to try jobs in a couple of different six month stints. And one of those rotations, which was actually the one I didn’t get to pick, was being an SDR. And it’s the one rotation that I actually think was the most meaningful and impactful. 

Ishita Arora
Now, almost ten years later, realizing that so much of my job actually as a Founder is sales, obviously. Recruiting, fundraising, customer acquisition, they’re all sales in some shape or form, but ultimately found my way into product. I found that it aligned with my generalist skill set of both wanting to dig into technical details and the nitty gritty of the user experience while also getting to storytell and position products and work with the business side of the house. So I have spent most of my career in B, two B SaaS product after Dropbox led product at a company called Fleetsmith, a security SaaS company joined pretty early on right as they were raising the Series A and was there up until our acquisition by Apple. So that was a pretty exciting experience to see a company from the early stages to exit. And then now, as I look back, my experiences at both Fleetsmith and Dropbox have deeply shaped how we’ve approached the product experience at Dayslice. 

Ishita Arora
So, like, quick reflections there from Dropbox taking this ethos of bringing the consumer grade user experience to business SaaS, and then from Fleetsmith focusing on workflow automation as a means of generating product value. So, yeah, pretty kind of a lot of twists and turns along the way, but I guess looking back, the story always makes sense. Right. 

Brett
I see on your LinkedIn as well, you’re a board member of a nonprofit that’s focused in, I think it was Nicaragua. 

Ishita Arora
Is that yeah. So one of my close friends started this nonprofit and it’s around teen empowerment through education. And so that’s been a whole other experience. Like, fundraising for nonprofits is like a totally different beast. And obviously the dynamics are very different than venture fundraising. But yeah, that’s been a totally different fun getting to scratch my itch on it in a different context. 

Brett
Nice. That’s awesome. Now, a few other questions that we like to ask really just to better understand what makes you tick as a Founder. First one, what CEO, Founder do you admire the most and what do you admire about them? 

Ishita Arora
Honestly, I think a lot of my day to day learning comes from personal Founder friends who are in similar stages of company building. I’ve built a deep appreciation of the value of learning from peer groups, but I think if I had to pick a Founder that’s more widely known, I’d probably go with Brian Chesky from Know. I think some of the best product designers I’ve worked with through my career, they’ve been incredibly intentional and thoughtful, of course, when it comes to designing the user experience. And then I think to see someone take that ethos and then apply it to the aspects of company building has been really inspiring. And actually, at one of our last company off sites where we all got in person because we’re a remote first company, we took one of Airbnb’s concepts from their early product development process, which is the designing an eleven star experience. 

Ishita Arora
I don’t know if you’re familiar with it. 

Brett
Yes. 

Ishita Arora
So went through that process for our own product and yeah, I think there’s a lot to learn from the Airbnb company culture. 

Brett
Yeah, totally agree on the topic. Know, having peer founders who are in similar stages, how important do you think it is to be in San Francisco and Silicon Valley today? 

Ishita Arora
I feel like I benefit a lot from living in the city know, within a 1 mile radius. I have many friends who are CEOs of Seed Stage and Series A companies, and I think to be able to text someone and say, hey, do you want to get dinner tonight and talk about this topic, that’s top of mind. I think that’s been a big part of my own support system, both strategically and emotionally. That being said, if you are proactive enough, you can form those relationships even if you’re not in the Bay Area. I think it just means probably proactively reaching out to people if you are in their, know, having that in person time where you can get that initial trust. You know, I’ve also had great calls with friends over Zoom, so it’s something that I’ve benefited from personally, but I don’t think that it’s a requirement. 

Brett
Did you ever think about leaving SF? So when everyone was proactively talking about that all the time on Twitter and in the media, the decline of San Francisco and Silicon Valley, everyone moving to Miami, Austin, did you ever consider leaving? 

Ishita Arora
So I grew up in the Bay Area, so I would say yes and no. In know, I have family roots here. My husband’s family is also in Santa Cruz. And so we actually had a big pull to the area even beyond our careers. We did do a bit of a tour of the country, living in different places to vet whether we wanted to move. You know, I think New York City, Denver, Seattle, like, there were a lot of places that were interested in, but after doing that entire tour, we realized we really love the Bay Area, so we kind of I would say we chose the Bay Area post pandemic to really put our roots down. 

Brett
Nice. And what about books? So the way we like to frame this is to ask for a quake book. So a quake book. The term comes from Ryan Holiday, and he defined it as a book that just rocks you to your core and really influences how you think about the world. Do any books like that come to mind? 

Ishita Arora
Yeah, I guess I would probably go with Only the Paranoid survive by Andy Grove. Are you familiar with I am. Okay, yeah. So, you know, like, the high level, I guess, for the listeners who may not be, the context is like intel, navigating all of the shifting competitive landscape of the chip market. And basically, I would say the main concept is it talks about strategic inflection points, so like the big moments of opportunity or risk, for example, a macroeconomic change or a competitive shift. And how it’s your job as a leader to run towards making strategic shifts. That can often be pretty emotionally challenging. Right, because I think as humans, probably both in our personal and professional lives, we tend to instinctively cling to the past behaviors, past priors. And yeah, I mean, when I look at Dayslice’s history so far, I think there are definitely there have been times where we’ve had to reset who our ideal customer persona is. 

Ishita Arora
And I think those are all small examples of really staying vigilant in addressing and looking at what your assumptions are and reupdating as frequently as possible as you get more information, even if it may be uncomfortable. 

Brett
And that’s a perfect segue to dive right into Dayslice. So can you just tell us a bit more about what the platform does? 

Ishita Arora
Yeah, so Dayslice automates workflows for services businesses. So specifically we focus on workflows in three different categories. The first is scheduling, so that includes the transaction piece, so payments, pricing, and packaging for these businesses. The second category is marketing. So tooling that makes it easier for these businesses to reach their customer base. And the third is customer Management and Insights. So our customers tend to be small businesses, often solo owners, and they’re generally selling one to one services to a client list. So our customer base includes dog trainers, math tutors, guitar teachers, and of course there’s this very long tail of niche service providers who are using Dayslice. 

Brett
And take me back to September 2020 when you first formed the company. What were those early conversations like and what was it about this problem and this market that made you say, yes, that’s it, I want to start a company around that right? 

Ishita Arora
So actually in September 2020 I was working on a different problem and company and it was a marketplace sort of adjacent. But through that process I realized I was a lot more interested in building a SaaS product. And building a marketplace has its own challenges and my background didn’t really align with that. And it was sort of an accidental discovery that ultimately led to building and launching Dayslice in later 2021. But I started to notice that people were essentially running full services businesses through these really basic tools like Calendly, sometimes Google Forms. And at first it was just a curiosity as to what was happening here. And so reached out to a handful of folks who I started to observe were running their businesses this way, did these sessions where I was just digging into their stack and where they were spending their time, and started to uncover pain points in essentially the competitive landscape. 

Ishita Arora
And coming out of those conversations found that when you look at the product ecosystem serving these folks, you’re basically looking at one of two buckets. Bucket number one is either really narrow utility tooling that’s fragmented, so for example, you have the payment bucket which is like Venmo, PayPal, Zelle, Stripe. Then they might also be using a narrow utility scheduling tool. Let’s just say Calendly is one of the more popular ones. Then they’re probably using a spreadsheet for tracking the session packs that they’re selling. And they probably have a tab in there that’s like customer list. They’re using a Word doc to collect the testimonials they’re asking for. And so as I really dug into the tool stack of these service providers, you end up with like twelve different things that don’t really talk well together. And so there was something that lacked the connective tissue in this ecosystem of utility tools. 

Ishita Arora
So that’s like bucket number one. The second bucket is software that’s built for much larger organizations. So if you look at a CRM, traditional CRMs on the market are far too heavyweight for our target customer. A traditional CRM, a lot of times they’re built in a way that assumes you have a sales ops team that’s going to set it up and even the number of steps you have to take to get value from that product are way too many. So you have to know what are the right questions to ask, how to run reports, and then you get that data, and then you have to actually take that and act on it in your business. So if you look at the customer functionality in Dayslice, it’s a very streamlined CRM that’s reimagined for our customer base where we surface, hey, this person hasn’t booked with you recently. 

Ishita Arora
You probably want to follow up, or you have consistent bookings with this person, but they’ve never given you a testimonial. This is like the right moment to ask. And so it’s taking these concepts that exist for much larger businesses and rethinking what they look like for the smaller. 

Brett
Service provider and for that ideal customer. How do you define that in terms of size? Is it someone that’s doing a service business that’s less than one hundred k? Or how do you define that? What’s your criteria? 

Ishita Arora
Yeah, most of our customers are solo business providers, and some are making that much a year. Some are making less, some are making more. It’s less about how much revenue per year. But we have found that most of them tend to sell one to one services. They have repeat customers. That’s a big indicator of they are starting to need that functionality around the CRM piece. They care about things like session packs. But the number one thing we’ve actually found is just like a great qualifier for a lead is, do you have a customer list? Right. And kind of going back to what I’d mentioned with that Andy Grove, kind of like shifts you make in your business once you learn new things about an ideal customer persona. Early on, when we launched, when the product went out in the market early last year, we had this wide array of people signing up. 

Ishita Arora
And so we had these service providers who we ultimately decided to focus on. But we also had creators signing up, people who had huge audiences, and they were trying to monetize these audiences and services was one tactic they were using to monetize their audiences. And within a couple of months, it became clear to us that creators were not the audience we wanted to go after. And when you ask them that question of, do you have a customer list? The answer is no. That’s not how they think about their audience. That’s not how they’re thinking about their business. They want the Swiss Army knife of monetization of like 15 different ways that you could pay a creator. And that’s very different from the behavior of, let’s say, a dog trainer who probably has a list of like 25 customers. They have clearly defined services, and they have the sense of repeat interactions with their customers a lot more than a different type of persona. 

Brett
Can you give us an idea of the growth, adoption and traction that you’re seeing today? 

Ishita Arora
Yeah, so 2023 has been a really exciting year of growth for us just being a little bit over halfway. We’ve already four extra user base from last year with revenue scaling pretty similarly and I would say one of the more exciting things for me in this growth is we are starting to see our percentage of growth from organic and word of mouth sources particularly shift higher and higher. And so it’s a bit of the network effects of Dayslice and if you’re using Dayslice to run your company there’s like product visibility in the market. Because of that. I’d say the other kind of exciting thing we’re starting to see this year versus last year is we had a lot of folks who tried us out early last year when we launched. And I think if you’re using a tool to run your business, a lot of them felt, this is a new company, it’s a new product. 

Ishita Arora
And some folks went out into the market, tried a bunch of the incumbents and competitors. And at the beginning of last year, we saw a lot of folks come back and basically say, hey, we tried a lot of other things in the market. And I’m most excited about these slice. It was the easiest to use and so that’s just been like another exciting thing we’ve seen now that we’ve been in the market for 18 months. 

Brett
And you have to be in a pretty unique position too compared to a lot of other startups right? Because you’re not selling to other tech startups. So a lot of the tech companies I talk to, their customers are larger tech companies. Obviously tech companies have been crushed in the last year and a half so everyone’s been impacted that way. But because you’re targeting services businesses I’m guessing you’re not seeing that happen. Is that fair to say? 

Ishita Arora
Yeah, definitely. I mean I think not selling to tech, there’s so many advantages and disadvantages exactly. Spot on in terms of the market impact. I mean our service businesses and a lot of the services we sell to, they’re more critical businesses like their business is not being significantly impacted by sort of tech bubble and public markets situation that we’ve seen in the last twelve months. On the flip side, I think the playbooks on how to reach tech B to B leads and companies are definitely more evolved and refined because I think a lot of tech companies will sell to other tech companies. And so yeah, from a go to market perspective we’re at a very interesting spot of we are selling to businesses but a lot of our customers also have consumer like tendencies. So we have one of our customer acquisition streams is from TikTok, right? 

Ishita Arora
And I think that’s obviously a less traditional B, two B channel than a tech company selling to other tech companies would be using. 

Brett
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Ishita Arora
Yes and no. In the sense that even though there’s a lot of different niches that use Dayslice, because if you were to describe their business, you can describe their businesses in two very similar ways. Like, they have repeat customers, their customers often will purchase session paths. Their ways of engaging with their customers is often through loyalty discounts. They care about getting testimonials, so if you distill their pain points, they’re actually pretty similar. That being said, obviously more custom and bespoke messaging is always better. And so we have landing pages that speak to all types of niches, right? And a personal trainer may care more about tracking session packs than a different niche. And so, yeah, I think positioning is a part of it. But we have found that even our generic landing page, when we have done user tests, people understand the concept pretty quickly and can kind of self serve that like, oh, this feature would solve my pain point x, Y and Z. 

Brett
And as I was preparing for this interview earlier this week, I spent some time on your website and I was just thinking to myself, wow, you guys did such a great job. From a branding perspective, it’s very memorable, it’s very approachable, it’s very fun. Talk us through that branding process and why you ended up going the route that you did. And of course, we’ll make sure to link to it in the show notes so listeners can see what we’re seeing, so they can see how cool it is. 

Ishita Arora
Yeah, I think this is where my experiences from Dropbox and Fleetsmith, which was a security staff company, but had a very playful brand, like there was a cartoon dog as the logo. So coming from having spent considerable time at two companies where playfulness was very much a part of the brand and a reason why customers would remember our brand, it felt very natural to bring that to Dayslice. And so having the watermelon logo, it’s something that leads and customers will bring up all the time because it’s just memorable. Right? And I think there are a lot of, like I said, fragmented point solutions in the space. And so we wanted to go with something that felt very friendly and playful because even if you’re running a business, I mean, ultimately it’s like an individual with consumer preferences running that business. And so, yeah, we wanted to go with a playful and bright, friendly brand to differentiate ourselves in the space. 

Brett
I also saw on the site that you have comparisons with some of the competitors or alternative competitors that companies may go with or your target customers may go with. Talk to us about that decision because I think I hear like 50% of founders love that approach and 50% of founders don’t want to go down that path of being compared to anything at all in the market. So talk to us about that decision. 

Ishita Arora
So for us, that has served us very well in that the traffic that comes to Dslice specifically through those product comparison pages, actually converts the best to paid users. And so early on, we tried it and we saw that it was working. And now we’re very much like leaning into that strategy. And I think it works for a couple of reasons. I think. One, I mean, as an early stage company, people default don’t know your brand, but they do know who Calendly is and Shopify is and Acuity is, and so know if someone is looking for those tools for their services business, they may search Calendly and then a couple of keywords. And so one, I think it just naturally helps us with organic rankings. I think, two, we compare ourselves to products that somewhat solve the pain points of our target audience, however, are not built for them. 

Ishita Arora
So, for example, just taking Calendly as the example, if you go to Calendly’s landing page, you will see that they’re very much targeted towards customer success, recruiting sales teams. And then you go to Dayslice, and if you’re a service provider, you automatically start to see that, okay, Dayslice is built specifically for my workflows, but they don’t know to search for Dayslice. Right? So the way they find us is through that Calendly search term, and then they end up finding content that is actually more personalized to them than Calendly. So I’m a big believer in mentioning your competitors because those competitors are probably already in the headspace of your target customer. I don’t think we’re introducing people to Calendly because it’s listed on our site. 

Brett
And what about not requiring a credit card to sign up? That’s something else that I see debated a lot with companies that are pursuing a PLG motion. 

Ishita Arora
Yeah. So we’ve decided not to do that because I think also it goes back to being an early stage company where we haven’t been in the market for many years and there isn’t built in trust that, okay, I’ve been hearing about this company for five years. I feel very comfortable just trying it out. We’re asking people to take a bit of time and to take the energy to check Dayslice out. And so when I think about, okay, do I want to put one more step in between them actually first witnessing the product value before getting them to put in their credit card. For me, the easy answer right now is no. That being said, I think decisions like that, you continue to iterate on as you grow and you move from one stage to the next. I also think that we could put a paywall when someone signs up. 

Ishita Arora
And do I think our revenue would get another bounce up? I would say probably yes. But then I also think that model of getting people to put in their credit card first and then charging them as soon as the trial ends, I think a lot of times you end up getting a segment of customers who just forgot to cancel. We saw that a lot at Dropbox. There was a surprisingly large number of people where there was no activity in their accounts for months and then they would remember we’d send a marketing email and then we’d see a spike in churn. And I think right now that feels a little bit like tricking someone to pay you for a couple of months. But when I think about I want to build an enduring company, I’m not interested right now in that artificial increase for a bit and then having people who just forgot to remove their credit card churn off like six months later. 

Brett
And it probably leads to a certain portion of them hating you. Right, I know whenever I end up in that situation, I kind of feel like they got me. 

Ishita Arora
Yeah, exactly. Yeah. It definitely feels a little bit of like a trick and I feel very confident. And when we look at the percentage of people who end up buying their first customer through Dayslice and testing the booking experience in the trial, a very large percentage of those people convert to pro. And so right now, I don’t feel like we need to trick people early on by getting them to put in their credit card. 

Brett
Makes a lot of sense and it’s super helpful, I think, for founders listening in because that is something that I do see just debated a lot and a lot of the growth hackers really push hard for it so very useful to hear your perspective. 

Ishita Arora
I would also say one more thing there. It really depends what you’re optimizing for at a given stage. And right now we are still early enough that I want more people to use our product because it will help us understand more signal on. These are the indicators in a trial that correlate with a paid upgrade or a user deciding not to use the product and adding another step that paywall just reduces the qualitative product learning that happens in that world. 

Brett
And do you feel like you have product market fit yet? 

Ishita Arora
I think the way I’ve heard it described is if you’re asking yourself that question, you probably don’t. And I’d say that we have a lot of exciting early signal that we’re moving in that direction. But I think it’s about really scaling that positive feedback and monetization we’ve seen in our earlier segments to a much bigger base. Before, I would feel like saying, yes, we have product market fit. I think it’s a spectrum, and it feels like in the last three to six months, we’ve made a lot of progress in that spectrum, but there’s still a lot of growth I want to see before saying that we have product market fit. 

Brett
What about fundraising? So I believe this was the first time you’ve fundraised, is that correct? 

Ishita Arora
No, we’ve actually raised two rounds. 

Brett
Okay, two rounds. So from those two rounds, what would you say you’ve learned? What was some of those actionable takeaways that you maybe didn’t know when you were first starting your fundraising journey? 

Ishita Arora
Yeah, I mean, I think fundraising is a little bit of a black box before you’ve done it. And I remember talking to a lot of my friends who had previously raised and it’s like someone can describe it to you, but until you’ve done it doesn’t quite fully make all the pieces don’t quite make sense. It’s like reading a book on how to swim versus actually swimming. And for me, it’s a sales process, and you are connecting with people who are going to be partners on your journey, hopefully for a very long time. And so I thinking about it through that lens and also, yes, you want to get funded, but you are picking your partners over the long term made me rethink it’s, not asking for money. It’s like, who do I want to partner with? And so I think that was like the biggest shift that I made partway through my fundraising journey, and that also totally up leveled and increased the quality of conversations I was having. 

Brett
Makes a lot of sense. Now we’re into the final couple of questions here. So if you were just starting the company again today from scratch, what would be the number one piece of advice you’d give to yourself? 

Ishita Arora
I think the skill that has served me probably the most over the last few years and also has been the reason why, all things considered, I would say I’m pretty like low anxiety is if you can identify the one or two things that either are going to move the business forward or derisk a major open question. Just think about those problems and don’t worry about anything else. There’s a lot of problems that are like medium term problems that I think people can get caught up on and then they start worrying about. And that’s a distraction from the one thing you need to be focusing on today and early on when you start a company, when it’s either just you or maybe a Co-Founder, I think the challenging part of that phase is like, you could focus on anything, right? And so having that skill of being like. 

Ishita Arora
Actually, the one thing we’re going to focus on this week is, like, ads. And nothing else really matters. If by the end of the week we’ve answered this question, and then as your team grows, that’s like a very helpful mindset to also give your team focus, which they’ll also appreciate because you’re never going to have enough resources to do everything you want to do as an early stage company. And so I think being able to answer that question is very important and final question. 

Brett
Let’s zoom out. Three to five years from today, what’s that vision that you’re hoping to build? 

Ishita Arora
Yeah, I mean, I think if you look at the labor market, the exciting thing about our target audience is like increasingly more and more people are going solo as they sell their services. And so what I’m really excited about building is a product where you don’t have to worry about anything else if you are good at doing your service, whatever that may be. Dayslice can be that really like personal assistant that makes everything else a very small part of your business overhead and enables you to do what you do best. And there’s a lot of tactical ways that we’re going to achieve that. But I think zooming out, it’s like enabling people to go solo, spin off of those medium services, businesses and orgs they may be a part of and really achieve more of that independent career that they may have been hoping to do that historically there hasn’t just been like, infrastructure to support. 

Brett
Amazing. I love it and I really love everything that you guys are doing now. We are up on time, so we’ll have to wrap here before we do. If people want to follow along with your journey as you continue to build and execute on this vision, where should they go? 

Ishita Arora
Yeah, if you want to check out the product directly, you can go to Dslice.com and then you can follow us on pretty much every social platform by following Dayslice HQ. 

Brett
Amazing. Well, thank you so much for taking the time to come on and talk about what you’re building and share some of the lessons that you’ve learned along the way. I’ve really enjoyed the conversation. I know the audience is going to as well. So thanks so much for taking the time. 

Ishita Arora
Thank you so much, Brett. 

Brett
All right, keep in touch. It. This episode of Category Visionaries is brought to you by Front Lines Media, silicon Valley’s leading podcast production studio. If you’re a B, two B Founder looking for help launching and growing your own podcast, visit frontlines.io podcast. And for the latest episode, search for Category Visionaries on your podcast platform of choice. Thanks for listening and we’ll catch you on the next episode. Our don’t.