Episode #39 – The Performance Marketing Spotlight with Harry Dixon

Marshall Nyman [00:00:02]:
Hello and welcome to the Performance Marketing Spotlight. I’m your host, Marshall nyman, founder and CEO of Nymo & Company. Each episode I will be bringing you someone with deep experience in the performance marketing space where they highlight their experiences within the industry. Today I have Harry Dixon, co founder and CEO at Checkmate. Welcome to the podcast, Harry.

Harry Dixon [00:00:22]:
Hey Marshall, thanks for having me. Stoked to be here.

Marshall Nyman [00:00:25]:
Of course. Excited to have you on today and let’s jump right into it. Can you briefly introduce yourself to the audience?

Harry Dixon [00:00:31]:
Yeah. Thanks again for having me. Excited to talk about Checkmate. We’re a shopping platform that helps connect brands with shoppers. We’re known mainly for our app extension where we’ve onboarded millions of shoppers, but we also partner with publishers in the space to help reach new audiences with our unique content. And so we deliver value to both brands and consumers through our shopping assistant.

Marshall Nyman [00:00:54]:
How did you get your start in marketing?

Harry Dixon [00:00:56]:
Yeah, I’d say marketing. This is really my start in marketing. Checkmate is it. But my background and my e commerce experience goes back a few years where I was at a business called easypost Multi Carrier Shipping API and I was the director of partnerships there. So that is where I cut my teeth in E commerce. Easypost is not a super well known name but they power shipping for a lot of brands like Walmart and Casper and Lulu’s and things like that. So I was fortunate to work with a lot of brands and a lot of platforms and so that’s where the origin story of Checkmate really started off at my time there.

Marshall Nyman [00:01:35]:
What led you to start Checkmate?

Harry Dixon [00:01:37]:
Yeah, so we started Checkmate probably what, two, three years ago? So it’s pretty new. I started with two friends in the Bay Area and now live in la. But we approached it both from a consumer pain point. We started during COVID where everything went online and the original thesis behind Checkmate was that we wanted to aggregate shopping. We found that we were really failing to get all our orders in one place. We weren’t able to see what sales and deals were happening. And so our original product was an app and extension that integrated into your email inbox and pulled out those offers. How we started that was I’m a Converse wearer and they would always send me single use codes.

Harry Dixon [00:02:23]:
I would without a doubt miss those codes and they would be sitting there. So the brand was always trying to deliver the value to me and I just wasn’t receiving it as a consumer. So that was really the spark for the business which is really servicing all that missed information. Whether that is offers sales, package tracking. We really wanted to pull that into a single place. And since then, as startups go, you know, expanded into a lot more than that. But that was really, you know, the consumer pain point that we’re trying to solve in the get go.

Marshall Nyman [00:02:53]:
What is Checkmate and what makes it unique?

Harry Dixon [00:02:56]:
Yeah, so as mentioned, we like to call ourselves more of a shopping platform today. And I think that lends itself into our wider vision, which is we call ourselves a first party data company in the business of shopping. And that’s because we really partner with brands and consumers to create personalized content. So I like to think about right content, right time, right surface. What that means for our app and extension is we partner with users to essentially grant a small bit of information. So we ask for your email and date of birth and things like that. We also get a read only access and then we partner with brands to be able to communicate in a more meaningful way. So we use data to essentially convert shoppers for brands, but also create a really positive consumer experience that helps them along the shopping journey.

Marshall Nyman [00:03:52]:
What types of brands are seeing success with Checkmate?

Harry Dixon [00:03:54]:
Right now we work across the whole of the US and Australia. The brands and categories that we’re seeing a lot of success with is beauty and fashion. Anything D2C I think has been really successful for us because we are online only. We have some great partners like colourpop, Milk, Makeup, Suasu, l’ange that are all in the beauty category that are seeing really high conversions for us. I think for makeup and beauty in general. A lot of people shop on a regular cadence and we leverage first party gated offers. And so what that means is we tailor deals to specific people that expire. And so people are always looking for an offer in that category.

Harry Dixon [00:04:44]:
So that’s where we’re seeing a lot of success. One of our brands, we were able to drive over $600,000 in new sales in the first month they onboarded. So that’s a pretty big case study that we’re proud of. And we’re looking to work with more brands across general fashion and beauty.

Marshall Nyman [00:05:06]:
How can a brand get started with Checkmate? Do you work on the affiliate networks?

Harry Dixon [00:05:10]:
We do, yeah. So right now we are working deeper with brands. So we have recently launched a direct integration by Shopify. So with Shopify we are able to partner to essentially originate those expiring codes. So we think about uplifting incrementality. We don’t like leakage and things like that. So that is why we have that integration. But we do leverage affiliate networks, cj, awin, RECT and things like that to help aggregate Web brands are trying to do their performance marketing initiatives.

Harry Dixon [00:05:46]:
So we’re very seamless in that sense. We want to be helpful to the brand. So if they leverage affiliate networks, great, we’ll be there too.

Marshall Nyman [00:05:54]:
What exciting things are ahead on the roadmap for Checkmate?

Harry Dixon [00:05:57]:
Yeah, where to start? There’s a lot in 2025. I think being an early stage startup we have the ability to be nimble and flexible and what we’re really seeing is strong traction in personalized content. So we’re thinking about delivering that content in more places. So we recently signed a pretty large morning show that we’re not allowed to say the name of, but it’s an example of a publisher that we can essentially use our content to help their users or help their audience. So we’re thinking about taking our unique content with brands and making it accessible to more places. So the benefit for brand is you can partner with Checkmate and we can essentially find you more high quality eyeballs in different places. So you know, think of it more like, I think like DSPs and SSP. So demand side platforms and spice side platforms.

Harry Dixon [00:06:55]:
We’re thinking more about Checkmate holistically helping brands find customers. We really want to help marry that demand and supply.

Marshall Nyman [00:07:03]:
And what has been your favorite part of Checkmate so far?

Harry Dixon [00:07:06]:
There’s so much, I mean I think the day to day, you know, when you’re in a startup grind, you have to enjoy working with the people and unfortunate. We’re a lean and mean team, but started the company with two really good friends and everyone is really fun to work with. I think we’re creating pretty innovative solutions in a space that I think is right disruption and so it’s really exciting to work in the industry and really see these kind of data changes because the whole landscape is shifting. So I get really get really like nerdy and jazzed by working with smart people on these pretty chunky problems. So I’ll call my day to day with smart people my highlight.

Marshall Nyman [00:07:48]:
And now for a quick message from our sponsor Affiliate Summit West 2025. We’re here to let you know that tickets are on sale for ASW 25 which is taking place at Caesars Forum in Las Vegas February 3rd through 5th. Don’t miss out on the biggest and best affiliate conference of the year and you can save 20% off with code NYMO20. The three day event brings together all the key players in the affiliate marketing space with plenty of Opportunities to network head to affiliatesummit.com west to get your ticket and join us at the world’s largest affiliate marketing event. Use code NINEMO20 to save 20% off. We look forward to seeing you there. Will we see Checkmate at asw?

Harry Dixon [00:08:31]:
Certainly will. We’ll be there. A few people from our team will also be there. So yeah, reach out. I’d love to meet in person if anyone’s attending.

Marshall Nyman [00:08:41]:
And that’s how we first met two years ago. So always a great way to start those relationships. Any other upcoming conferences or events that you’re planning on attending this year?

Harry Dixon [00:08:52]:
That’s. That’s it. Yeah. We met in the line to collect our batch so I love that that it’s turned into a podcast, but other events be participating in. If you’re in LA or New York, There is a D2C conference called League of Originals that we’re a part of. We’re also going to. I think Rakuten Dealmaker still call it Dealmaker might get trouble for that one and then CJU will likely be there. So we’ll be across a few different conferences.

Marshall Nyman [00:09:27]:
Yeah, we’ll be at those. And I think it’s optimism now for Rakuten. They change it this past year.

Harry Dixon [00:09:33]:
I knew it changed. I knew it changed. Yes, I’ll be there.

Marshall Nyman [00:09:38]:
Awesome. Any predictions on the future performance marketing?

Harry Dixon [00:09:42]:
I think we discussed this a little bit offline just before this and I think it’s really topical. There is a trend sweeping the affiliate world in terms of honey and what they call cookie stuffing and how it’s hindered a lot of influencer creators. And so I think incrementality and attribution has been really, really big in affiliate marketing. I’m newer to the space, but it had really been a key topic when I went to my first ASW where we met two years ago. And so I think multi touch attribution is going to become into the spotlight because a lot of the issues that are getting brought up in these youtubes that are going viral and Reddit posts is that multi touch attribution is really needed and I think a lot of the networks ultimately need to create the infrastructure to support it. I think brands obviously are looking for solutions to adopt it. And so I think for how Checkmate sees the space, we’re an early stage company. We’re kind of in phase one in our journey, but with data, I think it is possible to do this fractional attribution for a multi touch approach.

Harry Dixon [00:10:59]:
So as a prediction, I think that will come into the spotlight that there will be players that would either try and innovate or networks getting the pressure turned up to try and solve a lot of this because it is pretty topical. I hope that’s, that’s one also on your bingo card. Do you have any other predictions?

Marshall Nyman [00:11:19]:
Oh, I have quite a few. I definitely think it’s going to be an interesting year and you know, it’s just like we’re one weekend and it’s already all these things that are starting to change. I think just with TikTok there’s a lot of interesting things of what could potentially happen. The change with traffic, with Google, that’s going to be a big topic. You know, I think couponing in the space has changed a lot. So obviously that’s a hot topic to start the year right away. So a lot of interesting things I think that we’ll probably see this year and in the years to come. What is a major challenge that you face and that you’re trying to overcome as a publisher?

Harry Dixon [00:11:55]:
Yeah, I think piggybacking off the honey conversation. We started out Checkmate really with a thesis to help both consumers and brands and we wanted to create a win win scenario that I don’t think was existing in the existing ecosystem which was generic codes clipping the end of a shopping journey. We have built a first party gated discounting engine. So what that means is we figure out who users are and if they are approved by a brand, for instance, if they’re a student or if they’re a military personnel or you can create subcategories like they like concerts or they’re into golf or they’re going away this summer. All those different subsets or personalized groups we can create gated offers for. And so the challenge is that I think sales is really one of the highest intent drivers of conversion. And so really normalizing that targeted sales approach is a really good way to target different groups and incrementally convert different users based on who they are. And so treating say coupons or offers in this kind of catch 22 that they’re all bad.

Harry Dixon [00:13:15]:
I think when used effectively the data we’re seeing is that they actually can be really, really additive to your strategy to try and convert shoppers because a lot of the time brands have done the hard work to get them either to the store or not using them as a top of funnel approach. So that’s a challenge that we’re trying to educate which is we’re not blanketing, you know, Welcome 10 is our biggest enemy and we want to use, you know, Marshall 18754 type code that is single use and expiring. So we can really measure that performance. So that is something that we’re constantly overcoming and it’s of a challenge. But I think we’re turning the tide.

Marshall Nyman [00:13:59]:
And what has been your favorite part of working in the performance marketing industry?

Harry Dixon [00:14:03]:
Yeah, it’s, it’s been cool. It’s been cool to come in from I was in technically logistics and you know, at EasyPost and Touching E comm from a different lens. Coming into performance marketing, the industry is small but mighty and so it’s been amazing to go to a lot of conferences and see familiar faces. I think it’s really awesome that there’s a lot of smart people attacking the space. So I’ve been really pleasantly surprised on learning about technology and then being able to actually talk to that person who’s created it. I think that’s a benefit. That Affiliate Summit west, for instance, you can actually have a meeting with Adam from AWIN or things like that. So been really pleasantly surprised by the industry in general.

Harry Dixon [00:15:00]:
And as things start shaking up in 2025, I want to see how the whole industry adapts.

Marshall Nyman [00:15:06]:
Well. A big thank you to Harry for joining the podcast this week. Some great insights into his background and how you can leverage Checkmate in your affiliate program. What is the best way for listeners to connect with you?

Harry Dixon [00:15:17]:
Yeah, either hit me up on LinkedIn, Harry Dixon, or my email is harryoincheckmate.com so either either all work.

Marshall Nyman [00:15:28]:
Again, thank you to our sponsor, Affiliate Summit West 2025. Our guest today, Harry Dixon, and to our producer, Leon Sonkin. If you’ve enjoyed this content, please give us a like and a follow. Thank you for listening in. I am Marshall Nyman, host of the Performance Marketing Spotlight and founder and CEO of NYMO and co. Signing off. Thank you and have a great day.