
Rebecca Worsley: Founder and Director at Rainy City
In this episode of Retain. Grow. Thrive., Joe Fox sits down with Rebecca Worsley, founder of Rainy City Agency and owner of DTC Live, to explore her journey from early dropshipping experiments to building a full-funnel Shopify agency and a thriving community for eCommerce brands. Rebecca shares how she grew Rainy City over eight years into a design, development, and CRO powerhouse, why connecting retention, ads, and web is key to driving results, and how she balances agency life with running DTC Live’s conferences, dinners, and retreats across the UK, US, and Europe. She offers tactical advice for early-stage merchants—like focusing on ad spend and customer data before over-investing in a website—and insights for agencies on building community and refining sales processes. From AI-driven QA systems to creating spaces where brands and partners genuinely connect, Rebecca highlights how to stay ahead in a rapidly evolving Shopify ecosystem.
Retain. Grow. Thrive. Season Two
Joe Fox (00:00.918)
Hey everyone. Thank you for tuning into another episode of retain growth thrive. I'm the grow wave president, Joe Fox. Today I'm joined by a very, very special guest who's joining me all the way from the UK. I'm super excited to introduce Rebecca Worsley. She has an incredible agency called Rainy City Agency. And she also runs an event and, almost like a, almost like a partnerships connection program called DTC live. we share a lot of mutual friends and, and we're partners.
in the ecosystem. without further ado, I'd really like to introduce Rebecca. Thanks for coming on board.
Rebecca (00:38.07)
Yeah, thanks so much for having me.
Joe Fox (00:40.126)
Absolutely. Rebecca, you have such a cool agency. I love what you've done at Rainy City. I know that you have a plethora of services and you've got some really, really cool brands that you work with. And every time I sort of look on LinkedIn, it seems you guys are winning more business and doing incredibly well, not to mention everything you're doing with D2C Live. But let's take a step back. Can you tell me how you got here? How'd you get started with Rainy City?
Rebecca (01:07.63)
Yeah, so I I started Brandside, but not in like traditional Brandside where, you know, like I built something from from scratch, like got involved a lot in the early days of drop shipping. So taking product, you know, selling it through Facebook ads. But in the early days where it was really easy, it was easy to launch a Facebook ad, there was no competition, any old products from China tend to work pretty well.
Joe Fox (01:21.75)
Okay.
Rebecca (01:35.038)
and that kind of got me into the world of e-commerce to start with, and particularly into the world of Shopify. but didn't understand like the value or the importance of actually building a brand. And it was very much just kind of acquire, acquire, acquire. And there was nothing else apart from that. and then I was like, I felt like I wanted to have like a physical product brand. and so went through a program and created a skincare brand.
went through all like the formulation process, like the packaging design, got the product shipped, ready to go from the US and was ready to kind of get going with it. But after I'd done all of the, like the fun part of like building the brand and it was then time to kind of start the marketing piece and reaching out to influencers and trying to grow organically, it just really wasn't my thing. And I liked the buildup and the startup phase, but
for me to be able to pay for that. I started designing Shopify sites for the people that were in this group for like $100, $200. And I was like, I think this is what I enjoy doing. And so I got the skincare brand sold and yeah, joined like Upwork, StoreTasca. And that was kind of like the early start for me and getting the experience and.
Yeah, like would definitely Rainy City was a lifestyle brand for me for the first few years. Like I got to travel a lot with it. I, you know, could see the world and take my laptop and live that traditional Nomad digital lifestyle for a while. Yeah, but that was, that was kind of the getting into it.
Joe Fox (03:11.969)
Subway.
Joe Fox (03:16.757)
I love that. mean, one of the, favorite things about this podcast is that whilst every single like agency and partner founder has a different story. I always love that there's some sort of a like unique kind of tipping point that everyone had before they became that the official founder of an agency. And, it's amazing. And I think, you know, to that point, you've obviously got an incredible design, you know, I for design. So.
that really resonates in the work that you do. I know that at Rainy City, you you guys are very, very, very focused on like the entire funnel. So really not just focused on middle of funnel, top of funnel, but how do we create and optimize the entire funnel? And it reflects in the results that you achieve for the brands that you work with. Tell me a little bit more about that process. I mean, we have a lot of...
merchants and our customer base that are watching today. Obviously there's a lot of different changes that are happening in the market. Shopify's, you know, releasing a whole bunch of different features. Obviously, you know, these large language models like chat GPT play a large part in the SEO and search kind of part of that funnel process. But how does that look?
for Rainy City's merchants. What's the funnel sort of look like for you guys?
Rebecca (04:45.75)
Yeah, mean, we was historically have always been design development, CRO focused. And that's, think what we're primarily known for, but more in the past, like 18 months to a year, like the majority of merchants that we were speaking to were looking for recommendations on how we could kind of bring that full funnel piece and look at things more holistically, because, you know, even the brands where we're still just working on like their website of things.
The conversations don't happen enough between the retention agency, the ads agency and the web. And they should be happening. They should be connecting and figuring out what's missing and what pieces of the funnel aren't quite working as they should or where are they not talking together properly. And so that's why we decided to bring that in and offer all of the paid media services, all of the web, all of the CROs, everything that we do.
is all working towards the end goal, which is ultimately increasing metrics across the site.
Joe Fox (05:45.578)
Yeah, no, I love that. think that's really important. And I think, you know, it's interesting to me, I feel you're so right in that the fact that sometimes all of the agencies aren't working together for that sort of common output. But I think, you know, being able to do what you do at Rainy City with the team and really look at things from a top down perspective and a holistic perspective is always going to, you know, result in better results. So that's, that's amazing that you
I've made that pivot and I guess it's not really a quick pivot if it's something you've been focused on for the, for the last 18 months. But I do know Rainy City's been around for, you know, I think it's eight, is it eight years or nine years? That's amazing. That's amazing. Yeah, that's amazing. Congrats. Yeah. Yeah. I, uh, I hear you on that. I feel like, uh, I feel like some days.
Rebecca (06:25.906)
Yeah, eight years and I don't know what she's in the lead for. It makes me feel really old when I say that now though, I'm like, eight years, it's nearly a decade.
Joe Fox (06:41.299)
feel a lot older than others, but no, that's nothing short of amazing. Like congratulations on that. That's no small feat. I think I had an agency in Australia and I only had it for five years and I know what that was like and went right through to sale and exit. And it was such a exciting journey and a big part of what shaped me to be who I am today. So I definitely understand the agency life, but
I think you've got some really, really cool people supporting you and stuff too. Like, know, Molly's amazing. Um, we, we work with her on the partnership side of things. And I know how, how much she respects you and looks up to you as a mentor and you guys have great friends. So you've definitely built a really cool culture over there as well as a good business. So congratulations on that. Um, on that note, I know that Rainy City isn't the only thing you do, you know, uh, D2C live is really cool.
I was lucky enough to go to the New York event last year. I thoroughly enjoyed the format of that. I thought it was super engaging. liked, I liked the panel conversations. I think there was a gentleman from, was it Tommy Hilfiger who was talking? I really enjoyed that, you know, kind of conversational piece and the interaction from the audience. And then, you know, the audience was a great plethora of different people, like a lot of partners, a lot of merchants. I thoroughly enjoyed that. What was the catalyst?
for that because obviously, you know, being an agency founder and owner takes up a lot of time and you're very busy. So it wasn't for a matter of trying to fill your spare time, I'm sure. But what was the main catalyst for starting that and obviously continuing that and growing it into what it is today?
Rebecca (08:16.783)
up.
Rebecca (08:25.743)
Yeah, so I acquired DTC Live last July. And before that, was owned by a lady called Tash. She had built this amazing community of brands that were, you know, going to all these amazing events. And we partnered on a couple together. So we did like a DTC Live Manchester conference and we did a couple of dinners and just got chatting really. And she was, you know, she had other projects that she was interested in pursuing and
you know, we were looking at building a community of our own. then when I was kind of talking to Tash about that, she, she, you know, brought up the idea of selling DTC live and it was just like a perfect fit. was great to go from one female founder to another. We'd been involved together in events before and we'd ran our own events, not at the same like size and scale as what DTC was already doing, but enough to kind of get an understanding and
have that experience on how we should do it. And it just fits so nicely. I think, brands today, especially like, mean, we seem so far out of like post COVID life now, but people really do like getting together. They like connecting with people. They like to be in the same room as them, have that face-to-face conversation. And we just try and like forge as many relationships and connections between people as we can. I'll often get asked.
by a ton of different brands like, do you know anyone that does this or has anyone been in a similar situation or I've seen these guys on LinkedIn, I'd love to get a connection, can you help facilitate that? And it's just amazing to kind of see, like I've met some brands that came to like our first October event in London when we did it. And then since then they've been at everything else and have just become like great fans and great supporters of everything that we're doing.
And yeah, so we run like a host of different style events. We do four conferences a year across London, Manchester and New York. We do like intimate dinners that are usually like niche to specific. So focusing on like beauty or health and wellness or subscriptions. And then we do our retreat as well, which is a pretty amazing experience for people. Brands are very lucky, I've got to tell you.
Joe Fox (10:36.092)
Yeah.
Rebecca (10:41.289)
And that's like an all expenses trip paid for to Gran Canaria, three days of connections and with 20 other brands. And honestly, like the people that came, came from that have all stayed in touch. Like they're in a WhatsApp group together. They're like helping each other. do weekly calls to hold each other accountable. And it's amazing to say, and it's amazing to think that we're like a small part and kind of bringing that together.
And it's nice that we can include like the brands that we work with on the agency into that side as well and kind of give them a little thank you and treat for working with us. So yeah, it's been like, it's crazy busy, like managing the two, but it's exciting and I like to be at the peak of busyness at all times. So it suits me.
Joe Fox (11:27.078)
Yeah, absolutely. I mean, I think there's obviously a huge rewarding, you know, factor with agencies seeing success and seeing all of those sorts of things. But I heard it several times there. And I know this from like meeting you in person is like the community component is obviously a huge factor of what you consider success. And you obviously enjoy doing that and connecting people. So that's amazing. I think.
I think, you know, to that point, those events are incredible. And I think being able to connect in this post COVID world can often be difficult with so many people working remotely, like on the brand side, the tech side, the agency side, but being able to bring everyone together and just connect is amazing. So thank you for doing that for the community. think it's awesome. And, you know, to that point.
Yes, brands are incredibly lucky getting to go to a lot of these things. Sometimes I sit there and think, my goodness, it would be cool to get all of the free swag and all of the invites to these incredible dinners and trips. But at the same time, think, you know, it's not just about the flashy events, it's about the community behind it. And I think when people come together in those environments,
They've got their guard down a little bit more. They're more likely to be open. Everyone knows someone who knows someone in this community. So everyone feels this kind of sense of community and sense of trust, which is awesome. So that's very cool that you're fostering that. Obviously, you know, there's a lot of changes that's happening in the Shopify ecosystem at the moment. We touched on a little bit, you know, some of the things like,
What's happening with chat GPT and there's this shift of, you know, sometimes shifting, shifting where people will be shopping. There's talk of sometimes the fact that people won't be necessarily shopping within the, within the website anymore, but they may be, you know, shopping actually through some of these platforms like chat GPT. Google is seeing, you know, some of their traffic being shifted across to these LLMs.
Joe Fox (13:48.227)
I keep referring to chat GPT because I think it's just the one that everyone knows, even though it might not be the one that everyone uses. But in that kind of realm and environment at Rainy City, how are you shifting to adjust for these market changes? And what are some of the things that you feel that merchants need to be wary of with all of these changes?
Rebecca (14:12.079)
Yeah, I we, listened to a really interesting talk the other week. I mean, we're not SEO experts, but around like how like the percentage is still so small and like everyone's, know, quick, like, oh, let's pivot. We need to change and we need to, you know, focus on like AI and making sure that the site is readable. And I think things like it's important, but we need to not lose track on where the majority of the traffic is coming from on site. And, know, it's even things like, you know, the new features that Shopify have created for.
the section builders and things on Shopify inside the themes like in reality when they're actually looked at and used like is the quality fully there yet? No. Is it going to be something that's you know they're able to kind of lean on support from Shopify from? No, not at all. So it's kind of like I think it's about looking at the tools that can be used to assist and move things a little bit faster but I think there is still going to be a reliance and a need to work with.
an expert that helps you understand the why on doing things as well. Like, you know, it's all well and good building a website, but are you really understanding like the user journey? Are you understanding like the key conversion rate points where people will be dropping off? Like why they would be dropping off if we do things in a certain way. And so I think there's like definitely a need for like the understanding on using the tools and the why before like agencies become redundant, I guess.
Thank
Joe Fox (15:41.062)
Yeah, no, no, definitely. mean, I certainly, I concur to that. I don't think there's ever a world where, you know, I don't, I'm, I can somewhat be a realist. I can somewhat be a pessimist and I can somewhat be an optimist. It really just depends on the day. And so for me, I look at AI like anything. It's like a computer as a tool.
And all AI is really is a software being ran through a computer and it's a tool. still requires and still will require a massive amount of input from someone that is human and understands nuances and everything like that. And I think people need to sharpen their skills around using these tools, but we've had to do that for so long with all sorts of tools, whether it be in e-commerce or
different forms of commercial industry. So I mean, I don't see it as that. I'm kind of more saying, are you finding like, I think it's a really good piece of advice for merchants. And I always say this, it's like work with experts. Don't try and, you know, handle all of this yourself. And I think, you know, most mature merchants understand that. I'm also kind of referring to like,
Are you experimenting with these kind of new technologies and tools at Rainy City? And I guess you are. And to that point, are you finding that they are still a little bit redundant?
Rebecca (17:18.935)
definitely like, I'd say that we're using things much more internally. Like I was speaking to like our head of web and you know, he says that he's really glad that he learned how to code prior to AI coming out because now like developers that coming in are solely relying on it and they're never going to be able to fully diagnose and understand the problems. But we're using it for things like so internally, and we've created a
Joe Fox (17:35.961)
Mm.
Rebecca (17:45.551)
QA checker so that when a developer is submitting a piece of work, the AI will cross-reference it against the Figma design and highlight them any issues there with their work before they submit it for a proper QA. So that should...
Joe Fox (17:47.565)
Nice.
Joe Fox (18:01.613)
Wow, that's really cool. That's very forward thinking.
Rebecca (18:05.281)
Yeah, that should like, because I mean, QA, I'm sure it's like a problem for most agencies in making sure the work they're submitting is to the highest quality. And it's human error, isn't it? Sometimes like not not spotting absolutely everything. So we're hoping this will alleviate a lot of like styling and things. And so then QA really should just come down to like the functionality and the cross browser. I think once we've got
you know, the styling and everything nailed and it's alleviating pressure on the QA team for going through rounds of QA with the development team. And that should be a really good like first step on things that we can do. And then we're looking at things like agents around like advertising and, you know, managing multiple meta accounts and just trying to stay as honest as possible. Like every time that we have like a management meeting or a team meeting, like we try and
come up with some ideas that haven't necessarily been thought of because I do think like we have to move pretty quickly in terms of thinking of these things and trying to stay a little bit ahead of the curve. So yeah, like I mean, the new like Shopify AI assistant is pretty cool for merchants as well. I think that's definitely improving and how it's working and how it can help and support them for little things that they need. And I think...
that will help them with the smaller tasks that they might be leaning on agencies for. And then the agencies can kind of focus on those bigger pieces, more impactful things and utilize their hours that way instead of on smaller data tasks that they could be doing themselves.
Joe Fox (19:41.282)
Yeah, I love that. think that's true. It's kind of, it really, it really is a tool that can be used by merchants to free up the agency's time, right? Like it's like, you guys are absolute experts and you should be putting that time to the highest important tasks, driving revenue, improving all of those metrics that you mentioned earlier. So that's awesome. I think those sort of things are really cool. And I also think the thing that excites me,
with those tools is it helps very small kind of like entrepreneurs coming into this who are new, who unfortunately aren't at a stage where they can hire an amazing agency such as yourselves to get to that next level where they can. I think that's what excites me the most. think that that's where I see these tools can be very much applied as like smaller merchants under a million GMV.
who are really sort of getting into the space and looking to grow as quick as possible, but don't have the know-how. They now have these tools that can support them get to there. And then they can have, you know, as I said, an amazing agency such as yourself, you know, come through and really help them get that whole funnel in place and continue to grow to a really, really big level. So that's awesome. So, okay.
Couple more questions, because I know we're sort of getting to time. Obviously, as I mentioned, we've got a lot of customers and everything who watch this. If you could give, so two questions here. If you could give merchants one piece of really quick advice that are on that smaller side who are not quite ready to work with an agency such as yourselves, what would you recommend to them?
Rebecca (21:32.331)
I would say focus your money on advertising first. Like don't think you need to be going spending a fortune on building and all singing or dancing site. Like the templates that are in Shopify are a really great starting point. And I think if you're on limited budgets, build as much of it as you can by yourself first and then use that money and add spend because that's the fastest way to kind of like test the market and.
gather the data that you're going to need to make those more informed decisions a little bit later on. And as soon as you've got the traffic coming through to the site, like make sure that you've got heat mapping on there and using something like Clarityware, it's free to have, like it just allows you to really understand and know who your customer is straight off the bat.
Joe Fox (22:19.799)
Amazing, amazing. That's great advice. I'll make sure that's sorry. It was clarity. I'll make sure that's linked in the in the show notes as well. And then second second question to all of the obviously there's a lot of agencies and a lot of agencies who haven't had the success that you have had Rebecca and aren't as big as Rainy City and are looking to, you know, kind of grow and everything like that.
what advice would you give yourself if you were back early on on that agency journey?
Rebecca (22:57.499)
gosh, so much. I think the community aspect is really important. It's building that tribe of people around you, not just from the merchant point of view, but creating a group or being around other people in the same position. It's honestly invaluable, the amount of support that I get from...
other agency founders is unbelievable. Those that are like my direct competitors, like we all talk, we all know each other, we all help each other out. And I think without that, it can be quite lonely, especially as a solo founder. And so the more that you can kind of like lean on and get advice from others that are in the same space, I think is great. nail down like your sales process as early as possible. So like just think like outflow equals inflow.
Joe Fox (23:48.33)
Yeah, I love that. Yeah, that's awesome. I love that. It's probably a good way for us to give our mutual friend Rachel a really good plug here. So like, you know, being a part of the e-commerce partners network, I think to your point is a really good way to connect with other agency owners, big, small, in between, and everyone can kind of connect and share there. So I'll make sure I connect. I put that in the show notes too.
Rebecca, two things lastly, where can everyone connect with you and Rainy City? What is the best way for people to stay in touch with you? If there's merchants who are interested in working with you, how can they get in touch?
Rebecca (24:29.837)
Yeah, LinkedIn is, I'm incredibly active on there as I'm sure most of us are. But yeah, LinkedIn for all like the updates and things and then obviously like our website as well which has got a bit more information about us and some case studies and things like that.
Joe Fox (24:34.581)
I know that. Yeah.
Joe Fox (24:47.615)
Amazing, I'll make sure those are all connected below. And lastly, we've spoken about this in a few different formats is the travel piece, because I feel like in our industry, know, particularly yourself, you know, running two very successful companies, one of them is very, very focused on travel and events and locations. We all travel a lot. And I always paraphrase this with
You know, you cannot choose a person, but what is one thing that you cannot travel without? I always explained all the last few episodes I've been explaining to everyone that it's this, I had to go to Europe for a work trip for grow wave recently. And I've always had these rechargeable batteries that are great for charging your phone on the go, your laptop as well. But this one, which I've linked in the show notes as well is like 10 times better than any other one I've had. It weighs a ton.
But at like, get about five, I think it's five phone charges and it may even be, it's like three laptop charges. So one or the other, I don't get both out of that, but it's very, very powerful. So that's, that's my recommendation.
Rebecca (25:48.44)
Wow.
That's amazing.
Rebecca (25:58.031)
Mine's more personal than that. I love Coke Zero. I need a Coke Zero at 12 o'clock every single day, so I always have to make sure that I've got a Coke Zero handy.
Joe Fox (26:10.701)
I love that. My wife is an attorney and part of that is a caffeine addiction and she's a diet coke fiend. So I relate to that a lot. We have a fridge that has a whole shelf of that. I only have like one or two a week, but yeah, she demolishes those. So I know how that feels. Awesome. Well, look, Rebecca, thank you so much for coming on board. Thank you for our partnership. think
Joe Fox (26:37.788)
You've given the audience here some incredible insights, whether they're a merchant, a growing agency, even a tech partner. So thank you so much. Hopefully we can do this again. look forward to catching up in person, but thank you. Appreciate it.
Rebecca (26:52.719)
Thank you so much for having me, it's been amazing.
Joe Fox (26:55.322)
Awesome. Thank you. Audience. Thank you so much for tuning into another episode. Obviously there were some incredible insights, incredible suggestions that Rebecca was able to provide. All of those will be linked in the show notes below, no matter where you get your podcasts and where you're listening to this. If you have any future guests that you feel would be a good fit for the show, please comment below or feel free to reach out to me on LinkedIn.
And thank you for tuning into another episode of Retain Grow Thrive. I'll see you again shortly.