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DigiCom Interview with Alanna Gregory, Head of Growth at Cash App & Afterpay US

Alanna Gregory is the Head of Growth at Cash App and Afterpay US and we’ve invited her to join us in our latest podcast episode. Alanna shared her incredible journey from Wall Street to leading growth teams at some of the most innovative companies in the fintech and beauty industries. 

Here’s a closer look at our conversation:

Alanna's career started on Wall Street as a research analyst. There, she developed her skills in analyzing quantitative and qualitative data, problem-solving, and clearly presenting complex ideas. These skills became significant when she transitioned into the world of growth marketing.

"Looking back on it now, having transitioned into marketing and growth, to me, it makes a lot of sense," Alanna reflected. Her ability to understand data and convince stakeholders with her recommendations provided a strong foundation for her future roles.

The Leap into Entrepreneurship

After five years in finance, Alanna ventured into the startup world by founding a company called Veev, which operated similarly to ClassPass but for the beauty industry.

Veev offered last-minute appointments via a network of salons in several cities. Despite the challenges and eventual "soft landing" with another company in 2017, this experience was invaluable for Alanna.

The transition from Wall Street to entrepreneurship wasn’t easy, but it allowed her to explore various aspects of business, from sales to product development. Her journey highlighted the importance of versatility and resilience in the startup ecosystem.

Scaling Brands: From Hair Story to Afterpay

Alanna joined Hair Story, a direct-to-consumer hair care brand, as one of the early employees. She played a role in scaling the company’s digital marketing efforts for both B2C and B2B channels. This experience was a significant stepping stone before she joined Afterpay, where she led the global growth team across multiple regions, including Australia, New Zealand, the UK, Europe, the US, and Canada.

With Afterpay's acquisition by Cash App, Alanna took on a broader role, overseeing media and performance marketing, CRM, customer engagement, MarTech, and growth marketing operations for both entities in the US.

Key Advice for Founders: Zero to One, One to Three

Alanna offered some advice for founders working through different growth stages:

Zero to One:

Great Product: Start with a product that has a compelling value proposition. It’s important to know exactly why your product matters to your customers and what makes it unique in the current market.

Know Your Customer: Deeply understand your target audience. Identify where they spend their time, what they care about, and how they interact with similar products.

Build Repeatability: Once you’ve nailed your messaging and identified the right channel, focus on creating a repeatable and scalable process to drive consistent growth.

One to Three:

Unit Economics: Understand your unit economics to scale. Know your customer acquisition costs and refine your strategy to enhance profitability and efficiency.

Scalability: Instead of spreading your efforts too thin, concentrate on a few highly scalable marketing channels. This will help in maintaining focus and driving sustainable growth.

Supplier Relationships: As your business grows, use your increased purchasing power to negotiate better deals with suppliers to lower your costs and improve your overall margins.

The Future of Digital Marketing

Alanna sees AI playing a transformative role in digital marketing over the next few years. She predicts an increase in high-volume, low-quality content, making high-quality content stand out even more. She also anticipates significant changes in SEO, with video content becoming increasingly important.

"The format in which people want video is going to increase," Alanna noted, emphasizing the rising importance of platforms like TikTok and YouTube in search behaviors.

Embracing Failures and Non-Linear Careers

Towards the end of our conversation, Alanna highlighted the importance of embracing failures and understanding that careers are not linear. Her journey from Wall Street to leading growth at Cash App and Afterpay illustrates the value of diverse experiences and continuous learning.

"Careers are not linear," Alanna reminded us. "It's taking those moments or those failures alongside the things that have worked and thinking about how to add value."

Connect with Alanna Gregory

You can find Alanna on LinkedIn and through her website.

To hear the full conversation with Alanna Gregory, check out our latest podcast episode here!

Connect with Digicom:

We at DigiCom are obsessive data-driven marketers pulling from multi-disciplinary strategies to unlock scale. We buy media across all platforms and placements and provide creative solutions alongside content creation, and conversion rate optimizations. We pride ourselves on your successes and will stop at nothing to help you grow.


Hemant Varshney (00:00.433)

Alana, thank you for jumping on our podcast this week. Very, you know, very, very excited to have you. You've had a tremendous career. Thanks for jumping on.

Alanna Gregory (00:12.782)

Thank you so much for having me. I'm really excited to be here.

Hemant Varshney (00:15.985)

Of course. Could you tell our listeners a little bit about your story and journey?

Alanna Gregory (00:22.926)

Sure. So currently I am the head of growth at Cash App and Afterpay US. And so I lead our media and performance marketing, all of our CRM and customer engagement, MarTech and growth marketing operations.

And so prior to this, I joined Cash Up actually via the acquisition of Afterpay, where I was leading our global growth team across Australia, New Zealand, the UK, Europe, the US, and Canada. And so before that, before Afterpay, I was working at a company called Hair Story. It was a direct consumer hair care brand. Started, you know, I think I was maybe the 10th employee. The company was still...

pretty early, had a product but no real marketing, so had the opportunity to join and lead all of our digital and kind of grow the company while I was there across the marketing function, the digital function, and serve marketing not just for the DTC channel but also for our B2B channel because we sold into salons and into hairdressers.

Before hair story, this is where I guess things get real interesting. I originally started my career on Wall Street and I know a lot of people are probably like, what? You know, what is, like, I don't think it's as common now, or maybe it is. But so I started as a research analyst where I spent about five years.

publishing research and I always say I think it was like a great like looking back on it now like having transitioned into marketing and growth I think like to me it makes a lot of sense but as a research analyst you have to

Alanna Gregory (02:16.91)

really understand quantitative data, qualitative data. You have to learn how to analyze, synthesize, problem solve, present your ideas in a very cogent and clear way, both in written form and to clients and salespeople and in verbal form. And you have to eventually learn how to convince people with through your data and your reasoning and your logic and your research and your presentation skills that this is actually a good idea.

for them to take on. So all of those things, I think, like looking back, were really great to learn. And then, you know, ultimately decided, well, as much as I enjoyed finance, it wasn't for me. So I left, started a company. We went through YC, raised a few rounds of funding, ended up like having a soft landing with another company back in early 2017.

And after my company, it was a fantastic experience. It was called Veev. It was essentially like class pass for the beauty industry. Last minute appointments via a network of salons in a handful of cities. We kind of had that founder dilemma of like, I'm a jack of all trades, but master of none. What do I do?

I'm not like I can't go and be a salesperson or I can't go be a product person like I've never done that one job before so in my crisis of confidence I had a few friends from YC reach out to me and and wanted my help and my expertise in marketing their companies and so started doing like fractional marketing work for a few of my

my few YC companies, some of whom were friends, some of which I had the opportunity to meet. One of them was Flutterwave, which is essentially like Stripe for Africa. I got to join them shortly after their series A and I'm still tight with the founders, but it was really fun to basically build their growth team and build their growth motion.

Alanna Gregory (04:27.47)

for both their B2B and their consumer app product as well. And then had the opportunity to work in a few other companies along the way at various stages as that fractional head of marketing, fractional head of growth. And then over time, got to realize, wow, I'm actually good at this thing. And now I want to go in -house, which is how I ended up at Hair Story. And yeah, that's me.

Hemant Varshney (04:55.491)

That's, yeah, that's an incredible journey. You've helped so many brands along the way, you know, really, really grow. And it's kind of cool because, you know, how you'd mentioned you worked on Wall Street and you were a research analyst and there's a quant and a qualitative end presentation, like all of that and how it ties together, especially in growth and in the startup space where, you know, you're raising capital.

You're pulling a lot of insights and then it's like, okay, here's our growth trajectory, right? Here's what we have to do to go hit X and Y. And I just think it's really cool that you started your career being a research analyst. And now, for me, especially working with you, it's like anything Alana touches, crushes.

Alanna Gregory (05:54.094)

that's really sweet. Yeah, thank you.

Hemant Varshney (05:54.481)

It's really cool. Yeah. With all of the brands you've worked with, everybody's in different stages, right? You're going from like zero to 1 million, one to 3 million, three to five, and then you're trying to get to 10. And in each stage of growth, founders need different resourcing or...

Maybe it's inventory, maybe it's digital. What's a piece of advice you can give founders going from zero to one and then one to three?

Alanna Gregory (06:33.71)

Yeah, I think when you're going from zero to one, the most important thing is first of all, you have to have a great product. So and let's assume you have that great product. You have to know why your consumer values it and thinks it's great, which is like essentially like a very crisp value proposition that resonates with the customer. So you have to understand. And it sounds so simple.

But ultimately, it's pretty difficult because there are so many products. And pretty much any vertical, there's always noise and competition. So you have to figure out that value proposition that really lands with your customer. And then on the customer side, you really have to know that customer. So where do they spend their time? What do they value? What are the kind of everything that you would need in terms of?

building the product in the first place. But so I'd say the combination of like really nailing your messaging, your value props, your positioning such that when you start to market and let's assume you pick the right channel to start with, you can very quickly get signal around how to.

like whether or not something is going to work and if you need to make a shift. So let's say you've done that, you've found your first channel and then it's really about like building some repeatability in that motion.

Hemant Varshney (08:10.257)

Yeah, and I think also oftentimes working with brands in their nascent stages going from zero to one, when we're working with those brands, also founders have this idea of, hey, this is my messaging that works, only to go in market to figure out, hey, this works sometimes versus this other specific product benefit is what drives sales, right?

Alanna Gregory (08:40.046)


Hemant Varshney (08:40.625)

I think very much in that form, it's like you had mentioned, it's testing and learning and understanding the messaging. And as you're launching more and more products and also as your company is evolving and growing, once you're getting to that one to three, that messaging can change over time.

Alanna Gregory (09:03.118)


Yeah, I mean, because your initial target customer is probably going to grow and expand. And so as the pool gets wider, the value proposition that will land with your initial beachhead customers could be very different than who your expansion customer would be. So yeah, I actually think the connection between growth marketing and product marketing is almost synonymous in the early stages. And that's kind of a misconception.

Hemant Varshney (09:24.369)


Alanna Gregory (09:35.04)

like to be a really great growth marketer from zero to one or one to three even like you really need to understand.

Hemant Varshney (09:43.569)

Yeah, I couldn't agree with you more on that. What's a piece of advice that you could give founders and our listeners from going from one to three?

Alanna Gregory (09:58.99)

So one to three, I think the most important thing is to really understand your unit economics. And so, let's assume you've validated that messaging, you know the channel or maybe a couple of channels that are working to drive your customer acquisition. The next part is kind of upping the ante on that repeatability.

for some more scale, which is being quite vigilant about those unit economics and finding channels and ways to scale. So I think that's like, and zero to one, I wouldn't even care that much about like,

Let's say how much our cost of customer acquisition. I mean, I'm not going to, I mean, it has to make sense, but it doesn't have to be like the destination, right? Like the next one to three is really about like, how do you refine that?

Hemant Varshney (10:51.793)


Alanna Gregory (10:57.39)

to a place where you can confidently scale and find new channels and test into new channels or scale channels even, I think is often overlooked. Early companies usually want to jump from channel to channel to channel and sometimes fewer more scalable channels can be better, especially to drive focus.

Hemant Varshney (11:16.945)

Yeah, I think very much like there's also like the other portion of unit economics, right? Because like we're sitting and doing the math and we're looking at your P &L and it's understanding your breakeven point and then what is profitability. And then I think once you are scaling past the $1 million in revenue mark and say you have a couple of products that are selling, you also have buying power.

with your suppliers, right? And so like a portion of unit economics can also go back to at least like this is how I'm thinking about it. It's like you're going back to your suppliers and maybe your POs are going to be bigger for specific product types. And so you can start talking about better pricing. And I think there's, with a lot of the brands we're working with from the one to three mark, we don't see that happen enough.

Because as soon as you bring down the cost of goods, right, if it's 10, 15, 20%, it's just made your life so much easier in terms of a CPA, CAC goal, you know, to become profitable.

Alanna Gregory (12:20.27)


Alanna Gregory (12:26.19)

Yeah, it's also funny. I mean, I don't know if you do this at one time.

I guess you could start, but like, there's also like a shortening of your supply chain timelines and how you manage inventory at each stage of a company, right? It's like, and if you know that this, the more and more you scale, like the faster you can turn things around, like the more leverage that also gives your, your marketing machine. So I, yeah, I know, I agree. Like you have to think about holistically, like all of the levers. And sometimes, you know, even later, like that's customer service or.

retention and increasing the average order value or the lifetime value of the customer.

Hemant Varshney (13:07.665)

Where do you see digital going in the next two to five years?

Alanna Gregory (13:12.43)

I think it's a really interesting time, like with the advent of AI. I think...

Like many others have said, I can foresee a lot of really high volumes of bad content and quality content really standing out. So I think there will be probably more of an emphasis on, if I, you know, I would emphasize more on quality rather than quantity.

I think it'll be quite interesting to see what happens with SEO. That probably is a channel that is gonna change. I think there's also probably gonna be more of a swing towards brand marketing and providing more, kind of with that quality, how do you think about every single touch point as a representation of your brand?

And I think it'll elevate the importance of brand marketing, mainly because a lot of the digital touch points can become much more.

one to one instead of one to many. So with AI, like a lot like, for instance, like your emails already been increasingly personalized or like SMS, CRM, although everything is increasingly personalized, like, I think we'll just continue to see that move even further. Such that, like, you know, your marketing channels can almost feel a little bit like sales channels. And then you have really,

Alanna Gregory (14:51.278)

like your big, broad brand channels that give you that more of like awareness and brand halo.

Hemant Varshney (15:00.177)

So AI is getting more and more, like you had mentioned, it'll become more and more prevalent. And I think your take on SEO, like I've just spoken to a number of folks that do AI SEO over typically having a person go in, pull your metadata, fix your title tags. A lot of that can now be done via AI. Also, I think with

the advent of like Shopify or Wix, or depending on the type of business you have in the tech stack you're using, it's a lot easier to input your information field, which is more consumer facing for something like SEO versus in the past when all these sites were custom built, you had to go in and add all of these tags and ensure the taxonomy of the site is set up in the optimal way versus now you just...

add in a few input fields and, you know, there you go.

Alanna Gregory (15:57.134)

Yeah. Yeah. I mean, it's also interesting too. Like I think the definition of a search engine is going to change. Like video will play a much larger role, I think, in SEO in the future. I mean, the number of times I have heard or read something that says TikTok is like Google's biggest competitor, you know, because people are just searching on TikTok. Like I think that's going to prevail. Like the format in which people want video is going to be...

Hemant Varshney (16:18.065)


Hemant Varshney (16:24.337)


Alanna Gregory (16:25.198)

much more is going to increase. And so like, again, AI content creation and like, we'll probably facilitate more video.

Hemant Varshney (16:34.257)

Yeah. Yeah. And you know, this like, I agree with you very much. I do so much research on YouTube, right? And like, even when you're Google searching, right? One of the graphs below the sponsored ad is like almost always a video carousel depending on specific topics, right? Or questions you're asking. If there's a video about it and the...

that video has indexed on YouTube, it will also likely index on search. And then it's like, wow, this could also become a sales channel for the brands that aren't leveraging as a sales channel. And then now, like you had mentioned, right? Like TikTok videos, they have YouTube shorts, which is another area to serve both organically and through paid.

Alanna Gregory (17:25.966)

Yeah, totally. I think, yeah, it's a very exciting time from a video perspective.

Hemant Varshney (17:31.921)

Yeah. What's one question you wish I asked you and how would you answer it?

Alanna Gregory (17:39.118)


Alanna Gregory (17:47.47)


Alanna Gregory (17:52.11)

I don't know the question exactly, but like, something to the effect of.

like talking about failures and specifically like the perception of growth, you know, at least from like sometimes I think we hear a lot about the success stories, but we don't hear about like the failures.

Hemant Varshney (18:22.353)


Alanna Gregory (18:23.726)

And so something along those lines, I think, especially people in growth, they always want to hear about the thing that grew 10X, 20X, and like, those are sexy and cool. But I think, yeah, the other examples, which aren't as sexy or cool, can shine a light on learnings too.

Hemant Varshney (18:47.089)

Yeah, and I think on a smaller scale, it's like, hey, I have this cool test, and you did this product build, and only to test and learn that maybe it isn't working as well as other products. Or sometimes, I have a client example. A client of ours launched this SaaS platform. And it's similar story to an Instagram, where it's this cool SaaS platform does

all of these different workflows for you, only to find out that people only wanted to use this one SMS list signup. So essentially what they pivoted their business into is now when you have an organic post, client's called high tide, you have an organic post, there is an auto DM flow that occurs, which people have been leveraging, but in that DM flow,

What they do is they serve you a link to capture your information, and then they're able to track the sales all the way through from an organic perspective where, you know, originally they had built their entire company and model, not for this SMS organic, like lead capture business, but it has totally evolved into this SMS lead capture business. And now they're working with some...

you know, household like brands that were startups and, you know, and are starting to work much more and more with startups.

Alanna Gregory (20:22.126)

That's cool. Yeah. No, you always love a good pivot or like product evolution. But yeah, I mean, back to kind of the question I would have asked or answered. Like, I think sometimes it like I would I would probably remind myself that like careers are not linear. And like someone would look at my career and think, you know,

Hemant Varshney (20:28.241)


Alanna Gregory (20:47.182)

you know, how did she go from A to B to C? And so I think it's taking those moments or those failures or both alongside the things that have worked and like coming to a situation and thinking about, you know, like at least when I decide to work on a product or like have the opportunity to and like say yes, it's always like, what is the...

you know, do I have conviction in the product and in the category and do I have conviction that I can add value? And so it's sort of like the happy marriage of the two. So.

Hemant Varshney (21:25.937)

Amazing. Where can our listeners find you?

Alanna Gregory (21:31.054)

so I'm on LinkedIn. So on LinkedIn, and then I do have a website as well. So I think it's alanagregory .co.

Hemant Varshney (21:42.001)

Cool. Well, thank you for jumping on today. Of course.

Alanna Gregory (21:45.07)

Thanks so much for having me.



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