[Top SaaS & Agency Series] Revolutionizing Small Business Digital Marketing With Cory York

Cory York is the CEO and Co-founder of Webware AI, a digital marketing SaaS platform that helps small businesses grow online. With over two decades of entrepreneurial experience, he has successfully launched and scaled two businesses to over $14 million in annual revenue and grown teams to over 350. Cory’s prior ventures include founding Gift Cards India and spearheading Shopify’s expansion into the Indian market. Returning to Canada, Cory leveraged his business acumen to transition Webware from a white-labeled Shopify to a leading digital marketing SaaS platform.

Here’s a glimpse of what you’ll learn:

• [04:38] Cory York discusses how Webware AI empowers small businesses with AI-driven marketing
• [05:26] The origins of Webware as a white-labeled Shopify
• [10:09] The power of relationships in landing big deals
• [14:24] The art of door-to-door sales and its lifelong lessons
• [19:43] Cory talks about the evolution of Webware and initial challenges
• [29:20] How a near-failure led to a million-dollar pivot
• [34:56] Webware’s customer success stories
• [36:31] Webware’s white-label opportunities for aspiring entrepreneurs
• [42:23] Webware’s team evolution
• [52:07] The critical path of choosing and evolving with mentors

In this episode…

Mastering the art of digital marketing is no longer just an option — it is necessary for businesses eager to carve out their niche and capture the attention of their target audience. Yet, navigating this complex terrain poses a unique challenge, demanding a keen understanding of the latest trends and technologies and an agile approach to engagement. So, how do entrepreneurs harness the power of digital marketing to propel their startups toward sustainable growth and success?

Cory York, a serial entrepreneur and digital marketing mogul, shares his incredible entrepreneurial journey that started with door-to-door sales and evolved into founding a game-changing digital marketing business. He recounts the challenges he faced and successes he achieved while building companies, including his partnership with Shopify during its early days and his venture into India’s digital space. Cory recalls the evolution of Webware AI — from its original concept to a platform now helping thousands of small business owners automate their marketing efforts.

In this episode of the Inspired Insider Podcast, Dr. Jeremy Weisz interviews Cory York, Co-founder and CEO of Webware AI, about the challenges and triumphs of building a digital marketing SaaS company. Cory discusses how Webware empowers small businesses with AI-driven marketing, its origin as a white-labeled Shopify, its evolution, and its white-label opportunities for aspiring entrepreneurs.

Resources mentioned in this episode:

• Cory York’s Website | LinkedIn
• Webware AI

Special Mention(s):

• Dan Martell
• Buy Back Your Time: Get Unstuck, Reclaim Your Freedom, and Build Your Empire by Dan Martell

Related episode(s):

• “Automation Solutions with Wade Foster Founder of Zapier” on the Inspired Insider Podcast
• “Pipedrive: Brain Surgery, Married, & Moved Company from Estonia to U.S. All at Once – with Urmas Purde [Inspiration]” on the Inspired Insider Podcast
• “[Top Agency Series] Navigating a Merger and Becoming an End-to-End Digital Partner With Kevin Hourigan of Spinutech” on the Inspired Insider Podcast

Quotable Moments: :

• “Every day is constantly a list in my head that I go through to say, ‘what could I push over the line today’?”
• “If you meet 50 people a day for six months, you’ll learn to make an impact immediately on someone.”
• “Building a relationship is what will get you through the doors of big companies.”
• “If you do the same number consistently, you’ll see predictable results, and that’s been key in both sales and business.”
• “When technology falls short, a person can step in to bridge the gap until automation takes over.”

Action Steps:

1. Leverage data-driven tools for efficiency: This addresses the challenge of time management for small business owners, allowing them to focus on relationship-building and sales.
2. Prioritize continuous learning and adaptability: Staying informed about the latest trends and updates in your industry ensures that your strategies remain relevant and effective.
3. Cultivate strong relationships: This can lead to unexpected opportunities and partnerships.
4. Utilize CRM systems for enhanced customer engagement: This helps address the challenge of identifying and engaging with your hottest leads more effectively.
5. Explore white label opportunities for business expansion: This presents an opportunity for growth, especially for consultants or agencies with strong client relationships.

Episode Transcript

Intro 0:01

You are listening to Inspired Insider with your host, Dr Jeremy Weisz.

Jeremy Weisz 0:22

Dr Jeremy Weisz here, founder of inspiredinsider.com where I talk with inspirational entrepreneurs and leaders today, is no different. I have Cory York of Webware. You can check them out at webware.ai. And Cory, before I formally introduce you, I always like to point out other episodes that people should check out of the podcast. This is kind of, I don’t know, kind of mix agency and SaaS. It’s kind of the SaaS series. Some of the SaaS interviews that were good, the co-founder of Zapier, Wade Foster, talked about building up Zapier that was good. One Pipedrive, one of the co-founders of Pipedrive, that was a crazy story of how he talked about his moving to the US, from Estonia, getting married. He also was going through some treatments for brain cancer at the time, so it was kind of a lot of topics covered there. And then on the agency side, Kevin Hourrigan of Spinutech, he had an agency since 1995 Cory. So it was really interesting to hear the landscape of business the internet and agencies throughout the couple decades. So that was an interesting one as well. Check out more inspiredinsider.com. This episode is brought to you by Rise25.

At Rise25 we help businesses give to and connect to their dream relationships and partnerships. How do we do that? We do that by helping you run your podcast. We’re an easy button for a company to launch and run a podcast. We do the strategy, the accountability and execution. Cory kind of like the magic elves that run in the background to make it look easy for the host so they can develop amazing relationships and create great content. We were talking about before hitting record even, people realize the strategy and the accountability are more important than even the production part. But for me, the number one thing in my life is relationships. I’m always looking at ways to give to my best relationships, and I found no better way, over the past decade, to profile the people in companies I most admire and share with the world what they’re working on. So you’ve thought about podcasting, you should, if you have questions, go to rise25.com or email us at [email protected].

I’m excited to introduce Cory York. He’s CEO of Webware, which is a digital marketing and AI firm. Cory has over 20 years of experience building companies. He’s actually started and grown two companies from zero to $14 million plus in annual revenue. He’s grown teams to 350 plus during international expansion. He’s secured financing for multiple companies, and has raised venture capital and has had a successful exit as well. He’s built partnerships with large brands like American Express and Shopify, helping launch into international markets and actually Cory, it’s really interesting before starting Webware, I know you founded Gift Cards India, right? And it was India’s largest gift card distribution network. He worked with over 500 retailers to power their gift cards across over 70,000 distribution network points, both online and offline, and that includes being the launch partner for Amex prepaid gift card. And he’s also helped Shopify in the Indian market when he was the exclusive rights holder to the Indian market, back when they were unknown. And we’ll have to talk about some of your days living in India.

I know you moved there in 19 and after a few years, you sold the business eventually, and returned back to Canada and had the idea for Webware. I actually watched one of your pitches on YouTube. He pitched it to extreme Venture Partners, and with their funding, he brought Webware to life. So Cory, I’m excited to have you, and thanks for joining me.

Cory York 4:16

That was a great intro. That is the best intro I’ve ever been given. So thank you. It’s all factual. Yeah, no, that was very well done and well researched. Thank you.

Jeremy Weisz 4:27

Well, we’ll go back to India for a second, but I want to start present day and just start off talking about webware.ai and what you do.

Cory York 4:38

Yeah? So, Webware right now we’re a digital marketing SaaS technology platform, where we are autonomizing and making, doing your digital marketing now for small businesses, leveraging AI so that they can do the things that they should be doing, which is building a relationship with their customers and spending time on sales efforts or being with their family, and we kind of take all the heavy lifting off the small business owner so they don’t have to worry about the web and their digital marketing.

Jeremy Weisz 5:11

I want to talk about the evolution, right? What was the original idea? Because I know Webware has evolved over the years, the original idea and what it was then and compared to now. What was the original idea?

Cory York 5:25

Oh, the original idea was a white labeled Shopify. Okay, so I’ll tell you the story I helped when I was living in Mumbai, India, and my partner, Pharaohs Khan, who also works with me now Webware we wanted to build up the gift card business, and we needed an online website, and we started looking for technology, and that’s when I found Shopify, and I called them up.

Jeremy Weisz 5:59

What year is this? Because this is early on. At that point, probably most people would never have heard of Shopify.

Cory York 6:03

No one ever heard of them. They had less than 10,000 customers. They have a million now. They had 18 employees. And to show you how small they were, when I called the number on the website, I said, hey, who handles partnerships, international partnerships. And the guy said me, and that’s how easy it was to get in touch with Shopify that time, because they were so small. And I was in India, and I’ll tell you what India wanted, because I was there selling a solution from a company called Novatore that sold a basically a Shopify, similar company, but it would cost you 100,000 to set up, and it took a year and a football team of developers and a large room of servers, and it would be 30k a month to just keep it running without any help. It was very, very expensive, and we sold the big brands. And when I tried to sell that in India, it was almost a full stop no, I did help the biggest department store in India go online, which was pretty much India’s first online store period. But that was a one and done, and then no one else really wanted to pay that.

So when I had my own first business in India, I needed an online store and Shopify fit like a glove, because it was cheap, it was fast to get online and cheap to maintain it. And that’s what the market of India wanted. Okay, so I called them up, and I said, I need a website for my business, but I also see potential for you guys in India. And I pitched them on being their partner for India, and I landed the rights for a partnership, exclusivity in the country, in the whole region, and I helped them get their first online store in India, which was for Tata Group. And if anyone knows India, Tata Group is India’s largest company, top five, for sure, but most well-known company in India, and the best reputation out of all Indian companies is Tata they own Range Rover, Jaguar, Tetley Tea, to name three of the 150 companies they own.

Jeremy Weisz 7:45

Talk about selling them, because obviously they’re a big company.

Cory York 8:09

You walk in there, like you said earlier, it’s relationships, okay. My first before I talk about the call coming out, Chroma is the Tata Group that I took online. If we want to just talk a second about how I land big deals, it’s because what you said, it’s all about relationships. When I was selling, so my first job in India was door to door sales when I was 18 years old. That’s what I did in India for my first year. And when I was doing door to door sales, I was selling children’s books, and I met this lady named Shilpa Sharma, and she was the VP of the largest department store in India, VP of marketing, and I sold her a book for her kid, and I kept her card, and I stayed in touch. And a year and a half later, I found myself in a position to be helping a large e-commerce company that wanted to build brands’ websites.

I felt I got in a position where I was able to leverage relationship up there, and I connected them together, and it got me a great job, because I got the lead Novatore India, and I leveraged that relationship that I met from a previous sales role right to then get my foot in the door with a large retailer and help India launch its first online store by a brick and mortar proper retailer, and it was all about relationships. So when it came to Tata Group, I had already by that time through my gift card company. I had met them, and they had been part of my gift card catalog. Was several Tata Group companies. How did I know the Tata Group first off? I got to actually think a little. I think, Jeez, I don’t even remember how exactly, but the point is, it was definitely through my network.

Jeremy Weisz 10:06

You probably have thousands of retailers, so it’s hard to remember one of them.

Cory York 10:09

Well, they’re the biggest, and I did their gift cards, and I also did their online store. So if I spend another two minutes, I dig it up, and I’m sure it’s a good story, because it all is and I’m in a CEO global networking group, where we get together once a month, like 10 CEOs, and we, we talk about this stuff and the question was, hey, how do you land big deals? How do you land all these big deals? I’ve done American Express’s website. I’ve done Tatas Chromas website. I’ve done shopper stop I worked with Shopify, and there’s other brands.

I’ve landed a PepsiCo website and built a Gatorades website in Canada for a short period. We have colonels popcorn in Canada. I can’t remember if you’re Canadian or not, but that’s 150 location retailer in Canada. It was all from relationships, right? Just networking, keeping relationships, building relationships. And that’s how you get into these bigger companies. Just work and relationships.

Jeremy Weisz 11:13

Talk about staying in touch. I found that people dropped the ball with that. And you talked about Shilpa, and you say staying in touch, and maybe it comes natural to you. I’m wondering what that process looks like for you, even maybe it’s an unconscious process or conscious.

Cory York 11:33

Well, at first it was unconscious. It was like obsession to succeed every day is constantly a list in my head that I go through to say, what could I push over the line today that’s going to get me closer to the goal? But now it’s systemized, right? In fact, Webwares, it’s funny we found our way here, but Webwares just launched an automations feature where, basically, AI will design a drip campaign for you, and then you can have it set up in the automations, where it’s like, day one, you meet someone, and you meet someone at a conference, you add them to this list in Webware, and now this drip starts. And that’s not a new concept, but AI is now in the middle. So it’s like, what do I drip? Right? How long does it take to set up this drip and then someone touches the email? Can I do something about this quickly that I can close the deal? And that is essentially what I did manually over the years with my relationships. Webware now automated that.

So you can just shove someone on a list in our CRM and it’ll start dripping the customer. And if I were to do it, I drip someone for years, I would set up like, a five year drip, if I were to get going, right, if I was in biz dev right now, starting from day one, I would set up a five year drip anytime I met someone valuable. And the drip would be in a way where it’s not, it doesn’t matter where they are, what they’re doing. It’s just stay in touch. What are you doing these days? How’s it going? AI can personalize it now, right? So it feels real, and you could essentially automate what I did to get successful. But those are drip emails. You still have to go to a conference and meet people. You still have to make an impact at the moment of contact, and that’s something that’s hard to train and explain. That’s something you learn by meeting lots of people, and you just got to put yourself in a position where you talk to like 200 people a day, like a waitress or working door to door.

You put yourself in any position where you talk to 50 more people in one day. You do that for like six months. You’ll learn what, you’ll actually hone it where you can make an impact immediately on someone. And I don’t care if you’re an extrovert or an introvert, if you put yourself in the position, you meet 50 people. Hi, how are you? How’s it going? Here, Yo, you got to go here. You got to choose that, that interaction muscle, whether you’re introvert, extrovert, you’re gonna get used to it. You’re gonna start liking it. You’re gonna get good at it.

Jeremy Weisz 14:13

So Cory, when you were going and doing door to door sales, were you actually going door to door? Were you selling children’s books. You were just going from door knocking on each door.

Cory York 14:24

So, the way I got to India is, I have a bit of a hard start in my life. I was born to a single mother who died from a drug overdose when I was 13, and my father was a musician. I never met him, so I’ve been on my own for a while. So, I was a bit of a troubled kid, and I did get in the hockey which probably saved me from going to jail. I probably would have ended up in a gutter somewhere without hockey. And I was lucky that that happened. But that kind of led me to do some things differently. So hard start, you get a lot of resilience. Also not a lot of people saying, don’t move to India. So I met this long lost relative who had been working in India. He’s like a third cousin of mine, and he’d been in Mumbai for about 12 years, and he had just retired and left. And he had a business there, a direct marketing company, and that sounded really cool to me. I was a hockey player, and of education, my hockey career, is kind of winding down.

I didn’t look like I was going to go the NHL. I’m five six, and you know, I was, infatuated with his story. And I’m like, I want to come to Mumbai and see your business. And I got on a plane with him the next time he was going to visit. And we got there, I’m like, let me go in the field. I want to try it. So he’s like, go. So I went with this guy yogi, and I sold books all day, like door to door, this guy yogi, and they explained to me the business model. And it was like, you do this to learn how to interact. You do this to learn how to grind. You do this to learn how to talk. You do this to learn sales and human psychology, because when you put yourself in front of 100 people a day, you have no choice, and one sit position to me like that, I was kind of like, let’s do this door to door thing. So I did it for like, a year, and every day I train people, and I try and build my team. And we’re selling personalized children’s books where we go, and I’d say, hey, how are you today? Do you have kids? You’d say, yeah, it’s okay. Does your kid like Lion King and stuff like that? Oh, yeah.

Well, here I got this, this series of books that, and they were all kind of Disney themed, where I could print it with your kid’s name and three friends, and I’ll ship them out to you within three weeks. And what’s your kid’s name, I go straight to the form, and I learned to assume the sale. And you’d be surprised, like people just started like, oh, it wasn’t Johnny, but I’m gonna say it’s Johnny, you know. But it was a much different name. I’d actually hand the clipboard over and, like, once you write the kid’s name in here, because it’d be like, say that again, especially as a little white kid from Toronto, where I didn’t know I’d be like, so Akash, like, Sonia. But, you know, it’s different now, but back then, it would have threw me off.

Jeremy Weisz 17:23

That’s pretty wild. First of all, sorry to hear about your mom. And I was wondering how you made it to India, so that was kind of a crazy, windy road. What was like a close rate, like, if you knock down 100 doors?

Cory York 17:42

I would do 100 doors and sell 12 books. And what was really cool is the person who brought me, his name was Coleman, he would teach me that as long as you do the same the number like, the average is 100 if you do 100 a day, you’ll sell 12, and you set the pace on your product, and then you would say, okay, now, anytime you do 100 doors and you don’t sell and you don’t hit the number of 12, how to analyze what happened? And it was very simple. It was, did you not do the 100 doors, or did you lose your attitude doing it? It was either or. It wasn’t complicated. And I would say 90% of the time, when he asked me that question, if I didn’t hit 12, he was right. I lost my attitude, and I went and sat in a donut shop.

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