Episode 232 Featuring Alex Bond

Creating and Maintaining Partnerships with Caitlin Teed

Creating and Maintaining Partnerships with Caitlin Teed

Caitlin Teed is a Partnerships Manager at Ryder E-commerce by Whiplash, where she works with enterprise brands and their integration technologies to deliver exceptional fulfillment experiences across the country. Caitlin has worked in tech and ecommerce for most of her career — growing up at companies like Shopify and Apple, she knows the transformative power technology can have on our lives and is a huge advocate for ways it can bring us closer together. 

On this episode, we discuss the underrated value of networking, how to create worthwhile partnerships, her time working at Shopify, and much more.


What is Ryder E-commerce by Whiplash

Caitlin Teed: Yeah, I know. It's a full sentence, a full mouthful. And we do a lot of amazing things there. So jamming it all into one full word makes a lot of sense. So we are a 3PL, which is a third party logistics provider. So a lot of companies when they're starting out, maybe they're, you know, a direct to consumer customer. company selling things from their home or maybe a small warehouse they need to scale that eventually.

And so we work with some really large enterprise customers that need a lot of custom fulfillment and you know, they're fast fashion brands or apparel brands or like a bit of CPG. So anything we can handle and do in our warehouses. Yeah, I've been here for almost a year. 

Alex Bond: That's great. And so y'all aren't specific to any one sort of industry.

Caitlin Teed: No, we definitely like, I always call it our bread and butter is like the fast fashion. Definitely apparel. We have a lot of amazing customers that can, we can do pretty much anything custom in our in our warehouses as well. Anything from actual production though.

But you know, let's say we're chatting with power bikes is one of our customers and like we can do some of the bike testing for them. A little bit of assembly as well. We do also what we call value added services. So if you're looking for custom embroidery or maybe like custom packaging, we can handle all of that as well. Very high touch.

Alex Bond: So, yeah, that's great. So you've been there for a year now as a partnerships manager, right? What are your primary responsibilities in that role for the company? 

Caitlin Teed: Yeah, that's such a good question. So I work a very, we have a partnerships team that's been around for about two years now. And I think the partnerships didn't really necessarily exist at the company before. And I've done e commerce partnerships before understanding the ecosystem is thriving with anyone who can offer, you know, services to apps, to themes, to it's overwhelming almost how many apps Shopify app store.

And so we at our 3PL, we focus on partnerships that add value to our customers. So we kind of provide that consultative arm and making sure that we're, you know, if our customer success team says, Hey, all of our customers are having issues with returns.

Like we understand our platform is really great and can handle like the basic level of things, but you know, people have custom needs. That's why you come every. e commerce company runs differently and everyone wants different things and resonate towards different brands. So how can we find the technologies that match that for our customers?

So on partnership side, I manage the relationships with the technology companies and services that offer that. And so I build strong relationships with them. We figure out the kind of mutual success story we're telling and why it's a value to our customers to kind of get their eyes in front of potential solutions for them. So like returns ERPs, enterprise resource planning, order management systems, inventory planning. I handle a lot of like the backend guts of things to help the kitchen work. 

Alex Bond: That's cool though, because you're also like client facing at the same time. Is that accurate to where you're actually hands on talking with people while also solving problems behind the scenes? Because you are extroverted and charismatic. So I would imagine that that's a skill set that would be best utilized talking with other people, you know. 

Caitlin Teed: A hundred percent. I started my career in e commerce at Shopify on the support side. And I like my job was just to inbound customer calls and like chatting with folks, you know, it could be as something as like aggravating as like, hey, the CSV won't upload to like, hey, I'm thinking of like, you know, expanding shipping internationally.

How would you recommend doing that? So like I, that was an early muscle. I started flexing. And that's why I love the partnership side because it is very internal in a lot of ways. It's more strategic being like, hey, what are the common gaps we're seeing for our customers and how can we help that? But we do get on consultation calls with our customers as well to be like, hey, you know, what are your business goals for the year?

Where do you want to see yourself in the next six months? Like, let's check back in again. And Hey, if you want to open up international selling, like what tools do we recommend and partnerships we have that we would like highly. Like that we've highly vetted that we would easily recommend that it's going to help them make more sales and help us mutually be more successful. 

Alex Bond: Is your background, or at least, is it very important to have a sales acumen working in partnership? Or are they kind of a little more complex than that?

Caitlin Teed: It's complex. I feel like it's almost like a Venn diagram, kind of I always think, like, partnerships as a discipline, you know, you can't really, like, necessarily go to school for it. It's something that a lot of people stumble into like when I was in support, I kept getting these calls from like theme developers and app developers calling it to Shopify support being like, hey, can you help me with this or that?

And I would get so anxious about it. Cause I was like, I don't know about APIs. Like, I don't know HTML aside from basic, you know, ABCs, but it sparked curiosity in me. And I was like, oh, I want to like learn more about this. And that's how I stumbled into partnerships and ended up managing a bunch of agency partners and a couple of theme partners as well moving within the company.

But I agree with you. Like, I think it's like this hybrid of like sales meets customer success. Like I think direct sales folks, I think they have a very particular way of looking at partnerships. It's almost like more affiliate, like referral generated partnerships, which is important. 

And it's a piece of the partnership network, but It's not everything like there's definitely like an endorsement from someone and building a strong relationship. And like that customer success side of it is still just as important a muscle to flex in the role. 

Balancing partner appeal and company interests

Alex Bond: And that kind of leads into my next question, which is how do you tow that line of appealing to partners, clients, customers, while still ultimately ensuring that you have your company's best interests simultaneously. 

Caitlin Teed: That's such a good question. And it's actually something that we were looking at as a team into like our KPIs. So we're thinking about like you were saying, like, at the end of the day, like our core is like, we need to be successful so that we can continue this generation of like, you know, our customers being successful, our partners being successful.

And at the core of it is like, we want to make sure we're recommending technologies that, that are solving that customer problem. But at the end of the day are going to also help us, like make more sales, like through like our warehouses, right? Like it's actually kind of a beautiful, it's interesting.

Cause like I'm in partnerships and obviously my identity of a partnership is a technology partner or a service partner. We're working together, but internally sometimes our folk, our customer success team refers to our customers as partners because we're in business together where. If they're successful and like, you know, meeting their service level agreements and like they're making more sales and they're expanding, which we've seen a lot of our customers be able to do that.

And we've been able to scale with them because we're recommending the right technologies for them and we're unblocking them and we're giving them more. More channels to sell on. So, you know, we are able to, you know, yes, maybe they're doing a majority direct to consumer, but maybe they want to start selling in Nordstrom's like we have the partnerships with technologies that we can say, hey, go connect here so we can help you fulfill those orders.

More orders at the door for you, more sales for the customer. It's a beautiful like, always talk about partnerships being like that ecosystem. And I think the eCommerce ecosystem is one of the most fluid and just like able to like feed off of each other in the best way. Like not in a cannibalistic way, but like generating like this energy from being able to see the value of that, you know, and like the more customers were able to provide to those connectors, the more.

You know, they're going to say, hey like eCommerce, like they get it. Like they're working with really cool people. We should be recommending it when we hear that a customer needs a 3PL. There's someone that we would recommend because we know they have the customer's best interest at heart.

Alex Bond: Yeah. And I think that's extremely valuable is that little level of altruism to it, where you are trying to do a job and increase revenue. The simple matter of the fact. But there's also that matchmaker aspect to it.

Tell me I'm wrong, but from what I'm hearing, Caitlin, is it sounded like that was a learned thing is not trying to put a square peg in a round hole, but to actually try to find the two accurate pieces that work together. Not just I have a partner who needs client and a client who needs partner type of type of thing, you know, what were the growing pains for that like? 

Caitlin Teed: I mean, I think you have to fail a lot, right? Like you can look at it from that high level and say, oh, you know, what are the technologies that our customers are using the most?

And like, just defaulting into that without actually maybe doing some proactive research and being like, is there something better? Like, it's like asking yourself those questions. Are we just, you know, using this platform or using this technology because it is the best or, or just because we've always used it.

And because we've always thought it was the best, I think it's a learned skill as well. It's interesting in the partnerships ecosystem, you build such a strong connection to a company, not just because of the brand or what they're offering, but the people behind it. And that's what I think also kept me at Shopify so long is like just amazing people that are doing really cool work.

So when people like, and it kind of, to answer your question, like mood, like how do you like really like figure this out? You kind of follow good talent as well. Like when you, when you get to know someone and you say, hey, they just moved from like this place to that place, oh what was that about? What's going on over there? Like asking those questions and trying to figure out, hey, is this something I should be exploring more? 

Alex Bond: And that's why people start their own business is because they build these relationships so easily and fruitfully that they, I have these relationships with people who will say, I'll follow you wherever. So they're like, okay, I'll just do it myself then. 

Caitlin Teed: Right. It's this beautiful loyalty to like, and you build it beyond the brand. I was very fortunate when I was at Shopify to be behind such a strong brand. And yet people got excited and their eyes lit up. Oh, you work at Shopify. Like what's that like, but really at the end of the day, it was amazing people behind it.

And I think that it was a marriage of amazing product and people like something that was really able to help solve customers problems and build profitability on both sides. But yeah, I think people make a world of difference wherever you go.

And like you said, it's like, you know, people can start their own thing. They can be their own entrepreneur and not necessarily have issue with finding their customers if they have a good, good, solid following and really believe in what they're doing. 

Her 7-year journey at Shopify: insights, experiences, and growth

Alex Bond: You mentioned that you initially started in customer support at Shopify and you were there for about seven years, you know, from 2015 to early last year.  What was that trajectory like? I mean, was that a jarring experience? Was that the goal? Because you started in customer support and ended up as a program manager. Is that correct? 

Caitlin Teed: Yeah. That was a journey. I mean, kind of what I had mentioned earlier when I was in support, I was getting all these calls from partners and I was like, who is this? Like it literally show up as like, partner calling. 

And I'm like, what is a partner? Like I was so confused by it, did a bit of research into like, you know, oh, there's like a team internally that's focused on not just working directly with our customers, but with this ecosystem of entrepreneurs who are building themes, building apps, like doing custom work for these Shopify stores that are popping up because they need a level of service. 

And I was like, that's so cool. So I jumped into that. And then I was able to manage at one point, I had like 2000 partners in my portfolio. Cause everyone wanted to partner with Shopify and anyone who signed up for our partner program in a specific like geographic region was assigned to me.

Those were busy days. We slowly learned to like pull back a bit, but it also gave me a lot of exposure to all these cool entrepreneurs that were doing things beyond just, you know, building a product and selling it. They were beyond like building like a physical product or like a direct to consumer store.

So I fell in love with that. And then I moved over to like community side of it. And I started doing community programming and how partners could learn from each other in the same way that this podcast exists to help entrepreneurs help other entrepreneurs understand what a growth path could look like for them.

So we did that on like just the partnerships, agency, app developers, and tech side of things. And this really beautiful ecosystem blossomed. And I was able to do projects like meetups and awards. I got my hands on our product conference for a while. And then I realized that the pandemic hit and we kind of stopped doing events as much.

And then I stumbled into using those same skills into program management. And by that point, we had had an upper echelon of partnerships because I think we all can appreciate and understand the, once you hit a certain level, like you kind of think what's next for your company or for anything. 

And so Shopify built out the partner program so that you could just not just sign up to be a partner, but you could become Shopify expert, or you could become a Shopify Shopify plus partner or Shopify plus certified app partner and what that looks like. So I helped with the app side of things. 

And I've helped manage that program and help on board and maintain Shopify. Folks that were in that space. And it was really cool. I got to like connect with the partners directly, but also work again, like internally to figure out what the gaps were and how, like, were we prioritizing the right folks based on our customers.

Alex Bond: And it's interesting to me too, because the more I learned about the more you tell me about it, partnership and that kind of ecosystem, as you described it is a little bit more macro. It's kind of intangible. It's kind of esoteric, you know, it's a little bit, I don't want to say like Bigfoot, but it requires kind of like doing a little bit to understand it from, from what I'm kind of hearing.

You say is that it's not as easy to draw up as like web design. I say that, and everyone knows what that means, you know, and someone says partnership and I think that I'm working at a law firm or something like that. And so the way you describe it is really elegant and it kind of helps clarify the complexity of it without making it convoluted at the same time. So I do appreciate that. 

Caitlin Teed: The one thing I loved about it especially from the Shopify side is that they always took so true to the values of like, you know, we're here to make commerce better for everyone. But it was always like entrepreneurship focused and merchant obsessed. And it was cool being an internal advocate for our partners because they while they weren't the end user, like they weren't the shop like.

The Shopify store owner, they were so important and pivotal and entrepreneurial in their own ways. It was really beautiful to help explain internally the value of them. And I would go to bat for them so many times. If I felt we were making decisions that maybe we're too lenient on like the customer versus not thinking about how this impacted the partner and how this could impact the entire ecosystem. 

You know, when we make a change that like, yes, maybe benefits the customer, or if the dial is towards Shopify, it's like, this is only going to benefit Shopify. It's like, well, you're cannibalizing your ecosystem. If you're taking things away from them as opportunities to grow, I just wanted to toss that in there. Cause I think internal advocacy as a partner manager is an extremely important skillset to have. 

Alex Bond: Extremely valuable. So how did your experience at Shopify end up influencing your current outlook on the eCommerce community. So I know that that was probably like a year ago, but a little over a year ago that you left, but over that time, what kind of influence did that have? Cause it's pretty foundational on the e commerce space now. I mean, Shopify is pretty much synonymous with the word e commerce in mind, you know. 

Caitlin Teed: Yeah, I think it was just so, I mean, it was was cool to see this I always called it like the army of ambassadors that partnerships became like, I think, I don't think Shopify can claim its success at all without understanding how valuable this brand ambassador ecosystem was that they inadvertently built in a lot of ways.

And like, you know, would always say, yeah, it's important that we have these folks to offer services beyond what we can offer in house, but I do think that partner like, and it's interesting because you look at other industries and it feels like it's way more competition over collaboration. 

And I've also never met an industry as the same as e commerce, at least, and maybe they exist out there, but I haven't had exposure to them where you get the opportunity for people to not feel like they're like holding onto a secret sauce.

Like I've seen agency owners who like, you know, definitely have competed on bids together, cheers at a bar together and, and be able to like, talk, still talk best practices. And, you know, I've heard folks say like, hey, when we lose that bid maybe we didn't get that customer that we wanted, we lost it to someone else.

It didn't, they didn't harbor and hate on like losing the business. They're like, I'm going to try better next time. And I think that's just such a beautiful entrepreneurial spirit that you can't teach someone. It just has to come with the territory. And I think what makes folks that are successful, the most successful in the space is they don't let the little things get to them.

They can really take that as a learning opportunity and say, hey, like I want to be better. I want to do better. I'm going to come back stronger. I don't know if that answered your question, but you've been on a little tangent. 

Strategies for entrepreneurs to forge successful partnerships

Caitlin Teed: Oh, that's such a beautiful question. There's always that concept of like, never burn a bridge, but sometimes like it's, it is so important. And I hold this true cause like the people I met at my time at Shopify, I built genuine friendships with outside of work, outside of like what we could like get from each other.

And I do feel like you kind of said, it's like this Rolodex of like, Oh, if I need something, where can I get it? And I think you have to remember that. Yes. Like that's maybe that's like the salesy perspective of looking at it, but where's the customer success side of it? Like, where's the, like, is there a trade I can offer this person?

Like well, what it that they're looking for that I can help provide? We often talk about it in partnerships too, about deposits. Like sometimes we don't get a lot of leads from our partners necessarily. Cause we have a very high minimum echelon of customer we work with. We really try to punch up to the enterprise.

So in a lot of ways, we're giving a lot of leads to our partners more and we call it deposits, right? So it's like, we're constantly giving back as much as we can. And I think as an entrepreneur, that's like, you know, being a thought leader in the space, like offering advice, offering free consultation, putting those deposits in to the folks that you.

Either admire or that you have really like high trust in, or you pride and then understanding that, you know, you'll be able to take a withdraw eventually. And if you're just living in a relationship where like you're just withdrawing from them, or they're just withdrawing from you, then it's not going to work.

And you have to be very cautious of that because people will burn out and they'll say, they'll see you just as someone who's take, take, taking and not actually genuinely interested in, in their objectives as well. Right. And I mean, we all have to acknowledge we're all selfish humans, so pay for their selfish interests.

And I think it's not uncommon too, for someone to reach out to me that I haven't heard in years and say, hey, I'm looking for a job here. hey, what'd you offer? A referral here and like, that's fine, you know, cause I know I've made deposits in the past and same to them. So I think in the networking stuff, I can tell right away who's just there to do their elevator pitch and who's just like pushing business cards in your face.

And that can be, it can be overwhelming sometimes. I think there's authentic ways of approaching it. And I think just coming to those places and actively listening is something that I don't see a lot at networking anymore. I just hear people feeling anxious and nervous. And maybe it's because we spent two years behind a screen, not really sure how to engage or interact with each other.

But I do think that it's important for you to present your true authentic self and also come curious to networking events and you're gonna get those deposits, take those intakes and see where it goes from there. And yeah, don't be afraid to to reach out to folks. No matter what, you know, see what you can also offer them in return or down the line.

Alex Bond: I think that's extremely valuable advice in terms of active listening. I took a class on that one time. And one of the bigger things that I took away was one, reflective listening, which I thought was really important. And two, that most people conversate via waiting to respond instead of actually responding where people sit and wait for you to finish your thought so that I could say what I want to say instead of actually like taking what you're saying and responding to what you're saying.

Caitlin Teed: Yeah. And I'm going to need to look up reflective listening because I feel like I probably do that in practice, but yeah, because most people, when you're seeing like a circle, people are just waiting to like talk about themselves and I guess that selfish interest, but the way you got to come into any of those spaces is come curious.

Like come with questions, come acknowledging that you're probably not the smartest person in the room. And it's not that you need to go find them and become best friends with them, like be in a space with them and, you know, ask the questions and actively listen. Cause I think people sometimes say, oh, this could be a stupid question.

And then they take something that you would just said and like help continue the conversation. And I think it is like that deposit, right? It's like, hey, you just like, you know, gave me something. I'm going to give something back. I'm curious to see how like dive deeper into something. 

How Caitlin's journalism background shaped her skills

Alex Bond: Since you bring that up, I did notice you do have a journalism background from when you were in college, right, where you were like an editor of the newspaper. You currently still blog too. So is that how you kind of keep your skills sharp? How did you get out of that? And how do you still use that skill set?

Caitlin Teed: Oh, it's such a good question. Well, I mean, my last year of university in journalism, I started realizing that this is like the emergence of Twitter. Like it was very interesting studying journalism at the time I did, because like over those four years, like it just went from being something I had like glorified and like, and like idolized of, you know, being this intrepid television producer out in the field.

Like I never wanted to work behind a desk. I was like, I don't want to be stuck in a cubicle. Like my dad has been like, I want to go be out in the field. And so for me, journalism just felt like that. And the skills I learned and the like media production and everything, I loved it, but in my last year. It was like this theory of journalism and everyone was basically just talking about how there's no money in journalism.

Journalists are unfortunately like under attack, more so now than they were even like the 10 years ago when I graduated. And it's just scary to see the world it is and like, they're like, Oh yeah, basically, if you want to succeed, you need to do an unpaid internship, which was a whole other conversation about economic disparity and how like rich families could have helped people like students afford the ability to be an unpaid intern, nothing about that appealed to me. 

So I just continued the writing skills and I met a local entrepreneur and he took me under his wing and we built a writing for the web course together, which was my first introduction into that kind of simplistic writing style and how the importance of content has always continued throughout my life.

And then when I was at Shopify, I met an amazing person who introduced the a hundred day project to me, which was committing to a hundred days to something and I committed to 100 days of blogging and I don't blog as much as I did those 100 days straight. It was really cool being able to push myself to continue that skill because it's something I love doing. I loved storytelling. 

When I was an editor, I was the editor of the perspective section and that section only existed because there was nothing. There was like a piece they wanted to write that was somewhere between features and like a newsworthy article and their like perspectives was this like profile piece almost of like either a local business or a local person or a local question or concept. 

And I found that a really beautiful way of approaching journalism because it can sometimes we can only be one extreme or the other your hard news or your storytelling. And I liked that middle ground there. We found we did a lot of cool things at the paper. 

And I do like to, I think storytelling is something that is continued throughout my career, no matter what, and it's such an important skill, especially when you work in partnerships, because you're trying to explain what you do. And you're like, it's like this, but like that.

Her goal of engaging in diverse networking communities

Caitlin Teed: Oh, that's such a good question. I think each of them started for different reasons and each of them continues or stopped existing for different reasons for me, creative mornings is such a beautiful outlet for to connect with the creative community beyond people you might work with women and Shopify was something that was fostered based on like the pandemic really.

Being a place where we felt like we couldn't connect anymore. So it was a virtual meetings. We were doing partner meetup. It's an event series. We've been running now for a couple of years locally in Ottawa and in Toronto. And I think for each of them, there's never like, it's not, it's hard to describe, right?

It's like, it's this feeling I walk away from where my cup feels full again, where I feel like I've had again, those, those deposits, like we're talking about networking, like, hey, I made a couple deposits. I was able to like, have an opportunity to see people that, you know, have been in my network and maybe I never got to see in a long time, but I got a quick checkup with them and actively listen and been like, where are you at now?

Like, are you enjoying it? What are like, what are your plans for the future? Like being able to get those little deposits. For so many amazing people in this community. And by say that this community, I think it expands a people, a place or a reason that people gather while it could be all different reasons, like gets people out of their house and gets them excited to talk to other people is prospect and opportunity. 

And I think there's always something that comes out of that. And I will say that sometimes like I said earlier, you can tell when someone's just there for the elevator pitch. And those people I find don't succeed well in communities in the long term, because if they don't, get that direct sale or they don't feel like they satisfied that then they just end up finding a way of like, it's like a weed in a garden.

Or like it's someone who doesn't necessarily belong in that space, but that's not to say that the space isn't for everybody, but it's just something that doesn't feel right. So for me, what I get out of it to like answer your original question is again, like a sense of belonging and purpose.

And I think it's something that I never, I got the office a lot. And it's funny. Cause I say like, I wanted to be in journalism so that I didn't have to be in an office, but there was something special about the Shopify office. And it was designed and manufactured to be a place of meeting and a place of like serendipitous interaction.

The joke of like the water cooler conversation. I could like walk down the hall and run into someone I hadn't seen in weeks on a different team, like ask them how things are going, grab a coffee or a lunch with them. The serendipitousness, I think I now have to create it in other areas of my life because I don't get it at that meeting place that we did once have a couple of years ago. That's what it brings to me. 

Alex Bond: No, that's wonderful. And I really think that if what I'm hearing is correct, Caitlin, that going into certain scenarios like that, like those communities like networking and having kind of an ultimate goal or plan of I want to meet this many amount of people or make this much amount of money or, you know, create this many types of relationships with these types of people.

It's not so clear cut, you know, you're definitely looking for something that is more intangible and a little metaphysical in terms of, you know, purpose. Going to a community to find a community seems like a simple answer, but it makes sense to me, you know, and, and that's, I think how to make the most out of something like that is kind of what I'm hearing you say. And I think that's really beautiful.

Caitlin Teed: Part of the journalistic research, you know, I like going all these different things and seeing like, what are people talking about? Is there a common thread? Is there a common theme? What's the story of, you know, that ties these things together? And it's never always the same, but you get to like, maybe you see the same people at all.

You know, I'm going to all four different events. So maybe there are folks that are there doing the same thing, but if not, then, hey, you get to get to meet folks that are doing something unique and special and you get to ask them why it's important to them. 

Shopify Commerce Awards

Caitlin Teed: Yeah, that was very fun. So when I had moved from support to partner management, and then I moved from partner management to community partnership community, which is a new team. 

And it was this concept of like understanding how this ecosystem of partners, apps, agencies, theme designers, like everyone, what they could learn from each other. But also how we could reward like certain behaviors so that folks can see like, Hey, Oh, this is like the epitome of like a Shopify build. This is what I should be striving towards. 

So we wanted to build a program that could help elevate that. And in the past, it had been just. I think it was the Shopify e commerce design awards was the full name, kind of like Ryder E-commerce by Whiplash, like big names. So I was put in charge of rebranding it and building out a new experience. And of course I picked a long name as well, the Shopify commerce awards. 

But I wanted it to be all encompassing and realizing that it's not just about the design of a store, but the functionality of it can be a game differentiator for a customer, for a brand, for everyone. So we did that and we built out like, I think the first one had like 18 categories or something crazy between like apps and themes and custom store builds and custom product pages. 

Like we really, I wanted it to go all out. It was a very complex project. I learned a lot about international competition law. Apparently you can't just run competitions and anywhere in the world, but you learn by, by osmosis. And we had a lot of fun doing it.

It was a complicated project with lots of judges and criteria and interviews. And I got to run that for two years, not two years in a row. We took a little break and then the pandemic happened and we were like, Hey, let's bring this back up.

And I do find kind of like you were saying earlier about community and you're going in and like, you have this like list of goals. And I think some people just think so binary, like it's a yes, no. Or it's like, am I getting this value out of it? And if they don't see that result right away, then they. Push away.

But I found that interesting every once in a while, the resurgence of something at Shopify would come back and they would be like, Oh, why did we stop doing that? It's like, oh, well, like you didn't see the results you wanted to quote unquote, but oh, well, we need to do more things like that. And sometimes you have to do things that don't have a tangible outcome or don't, you don't see the results. 

Maybe you think you would have, and you know, this competition and this award program we ran, it was so fun and it was so cool. We got to announce them at the product conference in person for the first year we did it. We had like a nice dinner with all the judges and lifelong mentorship was built from it.

And then the next year we did it, it was very similar as well. But in the same way, like. I think people get very opinionated when they see these things too. And they say, oh, like, well, what's the result you're driving there. It's like, it's a community initiative. Why can't you just understand that?

Don't you understand? It's the same like the Oscars, how do you like run aside from saying, yes, we awarded like X amount of Oscar winners. And like, you know, there's some statistics around who was the first or second time they won one of these or whatnot, but it's hard to like equate that into a perspective, where's the money. And I think the money flows when you know, when you're doing the right things, but you won't know until you try and fail, but it was a cool program. 

Her insights about freelancing and short-term work

Alex Bond: I noticed on your LinkedIn. That a lot of your experience now, definitely not all of it, but a lot of it is a year or two at various companies. Now we mentioned that you worked at Shopify for seven years, but I think aside from that, and maybe one other job, you generally been kind of like a hired gun. 

Trust me, this isn't obviously like a job interview where it's like, so why have you jumped around jobs or anything like that to be totally honest, it's a career arc that I've been inclined to do myself, you know, is a lot of freelance work. I don't know mercenary is what I like to call it. 

But I essentially do it because I like building different skill sets and because I can get bored of a job easily. And instead of just trying to like, I'm definitely more of a jack of all trades, master of none.

And I think that's so much more fun to me, but essentially prior to gen X and millennials, the general career trajectory was to get a job, you know, climb the ladder, put in your 45, then retire. Do you think it's more commonly acceptable to freelance and work for shorter extended periods nowadays? 

Caitlin Teed: I will start this with a story that when I decided to leave Shopify, I told my parents and my mom looked at me and said, they've been so good to you though.

And my dad, I had to take for a beer and just like sit him down because he's been at like the bank for 40 years or so. And I think it's one of those things where, you know, the bank was good to him. He was good to the bank. Like it was, it was a symbiotic situation. And I think similar to your point, like it's just something that you did, you know, that was the status quo. 

And I think that we're living in a time now where, you know, people don't necessarily want to settle. I think we also live in a time where it's unfortunate, but true, but you get higher salaries sometimes when you push around, it can be a competitive space and it can bridge a lot of opportunity.

I think it's becoming more acceptable. I think we've had to, I think there'll always be someone that feels like you should, you know, have that stable career and have that stable income. And I've even taught my I've caught myself. I always said if I left Shopify, it would be to start my own thing.

And even I'm too scared to do that because I think sometimes it I get in my head about it. And that's why I have such admiration for entrepreneurs. And why I have so many of them in my life. And do these events in these meetups so I can learn through osmosis about like, I overthink it when I get stuck in that one of a million cases of like, hey, maybe I'm not going to make a paycheck this week.

Or hey, maybe I need to go get a full time gig or a secure job somewhere. I think there's still this fear of failure. And I think that might also be why people just, you know, stuck and hankered in on that, like one career and felt that loyalty and that tie and got the white picket fence in the home and did all the things they had to do. And I think we're living in a time where. Alternative lifestyles are more accepted.

And I think that's a beautiful time to live in. And I think it can go bridge to your career. And I think people will always have their own skepticism and their own narratives they want to impose on you, but you have to write your own story and you have to feel empowered and have your connections and have the balance in your life that you need, because otherwise you're going to be miserable.

And I'm not saying that anyone who does stay one place and hankers down is miserable. I think there are some people who crave, like you said, like I've always just, I've been a curious person. I made my first move at Shopify because I was curious as what a partner was. And then I was curious about how the connect community was interconnected. 

I was curious about how we ran our events. I was curious about how we built programs and all of those skills are definitely, I would definitely say it's not like master of none. It's like you're building those skills in different areas. And then you can take that wherever you want.

And it's okay for it not to be a forever thing. And I think that people should also, like I am terrible at this and I'm learning this every day is like not being afraid of failure, not being afraid of trying something and it not working out because I'm living proof. You can, you can try something and you can say, hey, all right, maybe that wasn't for me and you can move on.

But I'm so, and doing a flip to warehousing and fulfillment, I would have never seen this for myself. I keep telling people, like I've been in e commerce. I've been like the hostess at the restaurant. Like I was like serving and waiting on tables and now I'm in the kitchen. And I'm learning that the kitchen system has its own way of doing things.

But oh my God, is it like you have to deliver on that front of house promise, right? You have to deliver on that time. And like, and I'm learning a whole new side of e commerce behind the curtain that I would have never experienced, even though I'm doing something that I've done before from like partner management.

But I think it's very creativity and like curiosity is something you can't teach someone. And if you can find it in someone, that's an amazing employee to have. Even if you won't necessarily have them for their entire time that you would hope to. So gotta let them free. 

Alex Bond
Alex Bond

Meet Alex Bond—a seasoned multimedia producer with experience in television, music, podcasts, music videos, and advertising. Alex is a creative problem solver with a track record of overseeing high-quality media productions. He's a co-founder of the music production company Too Indecent, and he also hosted the podcast "Get in the Herd," which was voted "Best Local Podcast of 2020" by the Richmond Times-Dispatch in Virginia, USA.

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