Caroline Carter is an account executive at The Duckbill Group, having joined the team in July 2019. Prior to this position, she was an enterprise account executive at CB Insights, a senior account executive at Square, a client operations associate at BlackRock, and an account manager at Savoir Faire Paris, among other positions. She also worked as an English-speaking teaching assistant in Paris for a year.
Join Corey and Caroline as they talk about what it was like for Caroline to learn Ruby on Rails in France, how Corey and Caroline met and how their relationship has evolved over the years, how there’s a whole society of people who hate their jobs yet stick with them for years and why Caroline never wanted to be part of it, why Caroline believes you should take job interviews regularly—even if you love your current job, why Corey thinks a successful mentorship depends more on the protege than the mentor, how everyone is doing sales even if they don’t realize it, the difference between working in enterprise sales and working for a startup, and more.
About Caroline Carter
Caroline is our sponsorships manager at The Duckbill Group for our three media publications: Screaming in the Cloud, AWS Morning Brief, and Last Week in AWS. She also helped us create our first-ever re:Quinnvent
digital conference in December of 2020. Before joining the Duckbill Group, Caroline sold market insights software to Fortune 500 companies at CB Insights and payment software to businesses at Square. Prior to her sales career, she worked in client operations at FutureAdvisor helping clients invest their money digitally. She lived in Paris for 3 years, which is where she caught the tech bug and did a coding boot camp.
Join Corey and Caroline as they discuss their mutual love of fintech, how learning to code in a foreign language can be tough, why people are reluctant to make changes in their careers, how to find better mentors, and more.
Announcer: Hello, and welcome to Screaming in the Cloud with your host, Cloud Economist Corey Quinn. This weekly show features conversations with people doing interesting work in the world of Cloud, thoughtful commentary on the state of the technical world, and ridiculous titles for which Corey refuses to apologize. This is Screaming in the Cloud.
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Corey: Welcome to Screaming in the Cloud. I'm Corey Quinn. I'm joined this week by my colleague, Caroline Carter. Now, we've worked together now, but we've also worked together in the past and we've known each other and been friends for years. Caroline, welcome to the show.
Caroline: Hi, Corey, thanks. Great to be on with you today. This is different than my usual working with you.
Corey: Right. Normally, you're an account executive here at The Duckbill Group with an emphasis on media sales. So, whenever there are ads in this podcast, for example, which I'm sure we've already played at least one of by now, that's a company has chosen to sponsor my glorious love affair with the sound of my own voice, and they always go through you to do it. So first, thanks. You're helping put my kids through college someday. It's appreciated.
Caroline: You're welcome. It's always a fun experience to work with you.
Corey: I want to get into that in a little bit, but first I want to talk a little bit about career progression. Because your background is fascinating. You got a liberal arts degree, you went and lived abroad in France for a while, you went to a boot camp, if I'm not mistaken, in France which means that you learn to code in French.
Caroline: That is correct, yes. So, I was learning Ruby on Rails for a summer in French, which was definitely a challenge learning it in another language because obviously, Ruby is its own language in and of itself. But I did learn how to code.
Corey: That's on some level, it seems insane to me of, “Okay, I'm going to take a coding lesson in a language that is not my primary language.” But that's an incredibly, I guess, ethnocentric view of the entire world where, surprise, there are more people in this world who have to learn how to code in English or some form, and that is not their native language, then folks who didn’t if we look at this in terms of aggregate populations. So, on some level, if English is your first language, and that's the language you're learning to code with it, you're sort of playing on easy mode.
Caroline: Yeah, in some ways that you are, so I envy the people who are able to learn to code in English. But I think that's probably one of my strong suits, languages in general; I learned French, and Spanish, my mom speaks Polish, so I learned a little bit of that at home. So, in some ways, coding is just another language.
Corey: So, after you did the boot camp thing and decided that living in France, was for one reason or another, not what you were going to continue doing, you somehow decided to go to California and found yourself working at a fintech startup, which is where we met.
Caroline: That's correct, yes. So, I was in France for about two and a half years after college. I was teaching English and working at a couple of American companies part-time and decided that tech would be this new, amazing field I could join, but I didn't have any technical skills. So that's why I wound up doing the boot camp, and then decided all these companies were out in San Francisco, and so that's really where I should go to start my journey in tech.
Corey: So, what was that like? When I talked to most folks who do the boot camp thing and then go work at a company in San Francisco, the role is generally focused around writing code full-time. Your role wasn’t, so I have to put myself in a different position, in some respects, and try and imagine the insanity of startup culture through the lens of someone whose role does not involve writing code as a part of that culture. Was that as bizarre as it sounds like it was?
Caroline: It was definitely different. But after the coding boot camp, I figured out I really liked working on the client-side, talking to customers every day, so I actually started out in an operations role initially, but I was able to bring in some of the coding background by just spinning up email templates so that our team could automate certain things faster. So, it was definitely interesting joining tech, but I'd say because I was on the client-facing side, I actually wasn't as exposed to engineering teams, as most folks are.
Corey: And what did your role involve?
Caroline: So, I think our first interaction was at that startup I was working at. It was a robo-advisor helping people manage their assets digitally. And this was before people knew about services, kind of—now, I think they're more mainstream, like a Wealthfront, Betterment, Robinhood, so this was one of those earlier iterations of a robo-advisor.
Corey: It was a lot of fun. There were a lot of good stories that came out of that place, and it was a blast to meet some of the people I got to work with there. And you were one of them. It was very interesting because we started talking, and that turned into, “Let's go get a cup of coffee.” And that turned into, “Let's get coffee,” a few times a week.
And over time, we just started having longer, deeper conversations about careers, about job satisfaction, and the rest. And over time, you became, I guess, annoyed with the lack of advancement opportunity at the company. And what I found remarkable was, you complained about it, like we all do. But you didn't stop there; you did something about it.
Caroline: Yes, well, I think it's very easy for people to get complacent. And I see people who complain about their jobs, go in from nine to six every day, stay in the same role, maybe in the same company for three or four years, and you just have to hear this person complain. So, I never wanted to be one of those people. I wanted to always find a way to move on to an opportunity with more responsibility, something that was going to be more challenging for me. So, I know that that's always been a driver when I think about making career moves.
Corey: There's an entire society of people who don't like their jobs. It’s called everyone, and they meet at the bar to quote some comedian here or there. The difference that I found was that there's a certain, I guess, subset of people who will, at some point, decide enough's enough and start looking for something else to do. And as I recall—please correct me if I'm wrong on this—my thought at the time was, figure out what growth looks like here and what success is, set metrics around it, make it clear that you're looking for those opportunities, and time-bound it. So don't let companies lead you on for extended periods of time.
And at some point, like, all right, things have been promised or assured me that are coming, but they have not happened in the timeline I gave them. Let's see what else is out there. Which, frankly, I advise anyone to do, regardless. And again, I know I run a company, I still maintain that everyone—including people who work here, including you—should always keep your eyes open for other options. Just because, you should be where you are because you like it not because you believe it's the best you can do, or there's not some other place where you might fit in better. Validate that assumption, continue to talk to places.
Caroline: Definitely. And I think career stuff is not unlike relationships or other areas of life where you have to look at the words versus actions. So, a company maybe tells you, “Oh, we'll consider you the next go-around for a promotion.” And then it gets delayed, or, “Oh, we’ll think about giving you that raise.” And then it doesn't happen, or the title bump.
So, I think at a certain point, companies do the same thing where they promise these things. And then, like you said, there's a time limit, and you have to decide, okay, am I willing to wait that out for a year or two years? What does that horizon look like for me personally? And something you encouraged me to do that I find to be very helpful, and I tell everyone I know this as far as career advice goes, just take interviews. Take some calls once in a while because honestly, the best time to make a career move can be when you're doing well somewhere because then you can really evaluate opportunities more objectively than if you're in a bad place or not performing well at work. And I think that's always been helpful to me, too, just to get a better sense of what opportunities truly exist out there.
Corey: Let's also not lose sight of the fact that when we're having the job interview conversation and evaluating people to hire, we're fundamentally judging people on the basis of how well they perform in a job interview, which is its own separate set of skills in a lot of respects. And a lot of those skills are only ever relevant in the context of a job interview. So, one of the more hilarious series of interviews you'll find is when you find someone who's been working somewhere at the same place for 15 years and hasn't been interviewing, and now they're starting again, their reflexes are all wrong; the muscle memory for how to feel the question just isn't there. And it takes time to wind up getting back into the swing of things. So, why not do that when you're happy and enjoying what you do, just to see what else is out there and keep those skills sharp?
Caroline: I agree. And I think a lot of people when they realize maybe this opportunity at their current company isn't working out, or they want to go somewhere else, they do it from a place of desperation, or, “Oh, I got to hurry and find something new.” So, when you're under that pressure, you can't make a good logical decision for your next move. Whereas if you're happy in your role, or you're feeling so-so about it, but you look at some other companies, talk to folks maybe in other roles that you're interested in moving towards, I think that can inform you better. And then you're making the decision from a place of confidence and certainty, after doing some research.
Corey: I will also point out, just as a footnote for history, that I was told one of the most abhorrent things I've ever heard in corporate America back when we were having those almost daily coffee chats. Specifically, that the two of us going out and getting coffee once a day had questionable optics, and as a manager at this company, I should definitely make it a point to not spend a lot of time one-on-one with a woman. I really regret in hindsight, not telling that person to go to hell just on the spot. I mean, I'm sorry, I'm not Mike Pence. Stories like this are how folks who don't look like me wind up getting shut out of an awful lot of opportunities that otherwise come about through building those relationships in the workplace.
And yeah, spoiler, that doesn't always happen on company property. And it doesn't always look like people sitting down in the formal confines of a one-on-one in the conference room. I just found that to be one of the most disturbing things I was ever told. And every year that goes by, I find it even more questionable.
Caroline: Yes, I mean, I definitely think a lot of times we talk about mentoring people in a professional setting and how certain groups—women, in particular—that they don't always have role models, or people to look up to, or mentors, and from my perspective, in a way, many of the best mentors, I've had yourself included, it's come about, sort of organically, like you mentioned. We just went to coffee, talked a little bit about tech, traveling, things like that. So, I think it should be more encouraged, and there's so many things I learned from some of the mentors that I might not otherwise have that have allowed me to get to the place I am in my career, and I hope to have those people for years in the future.
Corey: Well, first, thank you, it's very kind of you to say that. Something I've learned is that mentorship is dependent much more upon the protegé than it is the mentor. It has to be driven by the person who is basically trying to improve their own situation. Otherwise, I'm just sitting out here shouting advice, and no one wants to hear it. That's not particularly compelling. That's called being a white dude on tech and Twitter.
Caroline: Definitely. And I remember at that time, I was pretty junior in my career. It was the early days. And so you're right, I think we talk about mentors, but they can really only do so much. It's up to the mentee to go out of their way to ask questions, ask if the mentor will be willing to look over their resume, their work, how they can improve.
And I think the other thing is usually a mentor is someone who, maybe not always age-wise but experience-wise, has a bit more experience under their belt, and so if you can talk about where you're looking to go, or you have some examples of people you look up to, the onus really is on you to ask questions and see how they can help or strategize a plan for what your future will look like. And I think a lot of people think about the next role, but not the longer-term where, “Hey, where do I want to be in 10 or 20 years career-wise?”
Corey: Yeah, forget the next job. Tell me about the job after that and how we help you get there. And I did get some feedback on our spending as much time talking as we did that was less horrifying, and more to do with the form, “Look, Corey, you're in the DevOps group, and she's basically in the customer service org”—which is an understatement of what you did, but okay, fine, it's directionally correct so we'll roll with it—“Why are you spending all this time working with someone who's not going to be in a position to help your team?” Well, turns out, I occasionally take the longer view on things. So let's move on. You left that company, what happened next?
Caroline: After that company, I actually decided—so I was working in a client-facing role; I was onboarding new customers, and I decided, to your point because I really was driven by metrics and always going above and beyond just getting through a to-do list, I decided sales might be a good path forward. So, I actually went on to work at Square. I worked in their New York office’, they were just building out a sales team there. This was back in 2016. And so then I was there for about three years working on their SMB and mid-market sales, selling software. Which I realize sounds crazy because most people when they think of Square, they think of the point-of-sale system, which it is, but they have a lot of software that businesses can use, too.
Corey: I was about to say that. [laugh]. They've really moved up-market in a large degree. They're now directly competitive with Stripe in some respects, for example. And, yeah, they were there for three years, which is obviously not a short term role for basically anyone. I've never stayed at a company other than this one for that long. And so you went there; it was a better situation. You were doing sales, for the first time in your career. Was that a hard transition?
Caroline: It was in the sense of, okay, I have to call a lot of people, run the full sales cycle, prospect to people, but it's really not that different than if you do work in some client-facing role, it's just that there's some more metrics around it. And I have a lot of friends and people, I know who, when they hear sales, they're like, “Oh, I'm just too risk-averse for that. I could never do that. That's terrifying.” But I think if you're friendly, and you like talking to people, it's actually a really great career path for a lot of folks.
Corey: I would also take it a step further and argue that absolutely everyone is doing sales; not everyone knows it. Whether you're selling a product, or a service, or an idea to your colleagues and suddenly the light goes on for some people, you're trying to persuade people in one direction or another. And I think that there's a strong negative reaction to the idea of sales that is almost entirely based upon people's experience with terrible salespeople and terrible sales processes.
Caroline: For sure, and I have actually the same feeling when I see someone that says sales, I immediately cringe because I have had those interactions with bad salespeople in the past, too. But I think now we're moving away from this era of the really pushy car salesman, and with a lot of these technology salespeople, they have to be more customer-oriented, finding custom solutions for folks. And so I think we're hopefully coming into an era of more, I guess, humanizing salespeople.
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Corey: The idea that you're immune to sales pressure is a common misconception. We see it with advertising in the same boat. And I feel like one of the painful parts about that is no one wants to be persuaded to do something. They want to believe the rational creatures who would absolutely do the right thing. And I get it.
Counterpoint: for anything that is more complex than punch in a form and give a credit card. Very often you need to have conversations with folks, especially at enterprise scale. It turns out that you don't get to go to any website in the world for the big management consultancies and purchase, “One consulting, please,” and put in your credit card number, and then they'll send a team out. These are complex processes; there's a nuanced discussion.
And I think that anyone who winds up saying that, “Oh, sales is useless,” or, “Sales is full of bottom feeders,” or the rest doesn't truly understand what sales is. I think that when you run a company, as I've learned, you've got to be in sales mode to some extent, all the time. But that doesn't mean what most people think it is when you say that.
Caroline: I agree. And I think a lot of sales really is—it boils down to relationship-building. And I was in an enterprise sales role after Square, and in that role, it was very much talking to a lot of teams at Fortune 500 companies, and sometimes even if you were speaking to a team who wasn't going to be the ultimate buyer if you had an in with them, they liked you, they would be a great person to introduce you to the person who was actually going to buy the software. So, I think you are always doing sales in some regard, and if you can build those relationships, it makes the whole sales process a lot easier.
Corey: So, what happened next? You were at Square for three years. And then you left and went somewhere else that was not here. What happened? Where do you go? And why did you leave?
Caroline: [laugh]. You know, three years is a decent amount of time to be at a company, and I decided Square at the time, it was really focused on small to medium businesses, or kind of, the mid-market segment. They have since moved up-market, and they do have a small enterprise team, but I really wanted to get into enterprise sales. I always enjoyed fintech, so I wanted to stay within that area, and had an opportunity to go work for a company called CB Insights where they do market intelligence. So they're looking at all these different data points that allow these huge companies, like a Microsoft or Amazon, to make corporate strategy or corporate innovation decisions based on some of that data.
Corey: That's a much more complicated sale. At that point, no one is going to sign up on a website for something like that, I would imagine. It becomes a much more nuanced story of what value it provides to a company, who when the company is going to care about those things, and it becomes an enterprise sales conversation.
Caroline: Exactly. So, that was within the enterprise sales framework. And it was very interesting because I got to work in a lot of different segments, whether it was digital health, autonomous vehicles, fintech, there was a lot happening there. And so, what a lot of people don't realize is, a corporate innovation team at say, LGs, they are trying to think five or ten years down the road. And so they're trying to analyze technology, but because they themselves are not technical they don't always know what's possible, or where they should be investing their resources, whether they should build technology in-house or outsource it, or potentially considering acquiring a company. So, it was a very interesting sales product as well as sales role.
Corey: Something I've learned is that as you start talking to bigger and bigger organizations, the organizational distance between the person who is paying for the thing you're selling them, and the person who's benefiting from the thing that you're selling them, and the person who procures the thing that you're selling them, and the strategic drive behind the benefit from the thing that you're selling them is all separated out; the organizational distance between those functions dramatically increases, and that makes a much longer drawn-out sales process that requires an awful lot of, I guess, project management style approaches to those sales conversations. And no one is on the other side of that issue in those conversations; it's just hard as you negotiate through a large company process.
Caroline: Exactly. That's a really good way of describing the enterprise sales cycle. And what I found is, yes, the deals take a lot longer, just because you are trying to coordinate between the decision-maker themselves, then you're doing demos with people who are actually going to be using the product, but they obviously aren't the ones with, necessarily, the budget to purchase the software. And then there's the procurement or legal teams you're going to have to go through, so it is an involved process. And they often say that enterprise salespeople are quarterbacks where they're managing all these different relationships, keeping everybody on a timeline, making sure the right stakeholders are involved.
And I think that's part of what makes it so interesting, but I also think if you want to do that, you have to have an internal drive because no one is going to check in on you and say, “Hey, are you getting the deal done?” It’s sort of on you to go to all those different teams and make sure people are staying on track and heading in the direction you want them to, which is usually a signed contract or a closed deal.
Corey: So, how long were you at CB Insights?
Caroline: I was at CB Insights for about a year and a half.
Corey: And then as all things do, it came to an end, and what happened next?
Caroline: So, I decided to actually make a move because I think, you think about that if there's a better opportunity presented. And so I was chatting with you and Mike over at the Duckbill Group about building out a new segment of your business, and I wanted to go somewhere where I could really take ownership of a sales cycle and potentially build out a sales team. So, that was the motivation for coming over to The Duckbill Group and joining you guys.
Corey: And may I just say, that that solves so many problems at once. First, there are never enough hours in the day on my side of things to focus on everything. And the weird thing about going from doing it all yourself to hiring a team is that every person you hire, without exception, is better at the thing you're hiring them to do than you are. It's an incredibly humbling experience.
Caroline: Yes. And the interesting thing is because I've worked at companies that are different sizes, everything from the small startup, to a company that was acquired, to a larger public company, and then now back to a smaller company, I think it depends on what skill sets you have, or which ones you want to cultivate. And I think anytime you're working in a smaller company, you're obviously going to be wearing multiple hats, and a lot of the responsibility falls upon you because you don't have maybe a sales engineer who can do the demos for you or a sales development representative who can do the prospecting, so you have to be comfortable taking on a lot of different roles at once.
Corey: It goes beyond that, too, at least for me, one of the problems I had is that when people started asking if they could sponsor my nonsense, my response was, “Of course you can give me money to mention your name. How much money?” And in time as these just became a larger and larger, I guess, phenomenon, I started to feel really weird about it because, “Ah, my voice talking about you is so valuable that you should pay me an insulting pile of money for it.”
It's weird. I still don't understand why anyone cares what I have to say, but they do. When you find you and the market disagree, assume you're wrong. But it was, seriously, a difficult thing for me. The fact that I don't have to deal with that at all, when people say, “Oh, what does it cost to sponsor your stuff?” I can give the honest answer, “I don't know, talk to Caroline,” and the problem goes away. It is incredible just as a stress relief from that perspective. Which is not a common problem, but it's definitely one that resonated and kept me up at night.
Caroline: Yes, and I think a big advantage you have with that is it allows you to stay independent in the content that you produce. So, you can go about your normal Corey ways, talk about companies in a snarky format, say your honest feelings about them without even knowing who a sponsor will be that week, so there's that nice delineation between the content side of things and the creativity that you bring to the table, versus businesses who want to basically be a part of your audience and get in front of those folks.
Corey: Oh, for those who aren't aware, I know there are ads in this episode, as there are in all of them, but I record the ads in a batch, and I don't ever know who is sponsoring a given episode, which means I don't have to shape what I'm talking about to not inadvertently offend a sponsor. And it's never been a problem, but it's an editorial firewall that I find incredibly stress-relieving as well. There's also—and this is something I want to get into as well with you—there have been times where someone has reached out wanting to sponsor, and we as a company will sit there, think about it and the answer becomes no, for a variety of reasons. Either it's something that we don't generally believe is the right answer for a customer to use, possibly there are ethics violations. There was one security product a while back that I looked at and found absolutely horrifying and didn't want to be associated with. That's got to be challenging as a salesperson to be told, “Yeah, you went to all the trouble of finding and getting someone ready to buy, and now we're not going to be able to proceed with them.” But you haven't rage-quit yet, so apparently, it's manageable. But we'll talk about that. What's that like?
Caroline: You know, every company—and I think we're seeing this, obviously, in the news, when you're a private company, you have the ability to make decisions as to who you want to work with or who you don't want to work with, and something I've always admired about The Duckbill Group specifically is that you guys stay true to your word with that. So that's what makes going to work really rewarding is being able to work with customers that we like and we think are a good fit, and then if they're not, telling that honestly and keeping that credibility.
Corey: My argument has always been that if I wind up turning down money in favor of authenticity and building relationships, either with people individually or with the audience, in time, that relationship can turn into money, but I can't sell that out and then wind up biasing for money, and then turn that money into relationships. I think it's short-sighted to go down that path. I'm just disappointed by how, I guess, infrequently it seems that this mindset takes root in companies.
Caroline: I agree. And maybe because we're a smaller company, it's easier to do that. I think when you have a huge market share and a lot more shareholders, it becomes harder, maybe, to turn down certain business opportunities. But for now, I think The Duckbill Group, we do everything with a sense of integrity, and yeah, it's what makes it worthwhile for sure because I think I would maybe rage-quit if I had to work with companies I didn't believe in or stand for.
Corey: At some point, you have to wind up being true to your own values. Or alternately, if you're just chasing money above all else—which again, that is a choice people make—why are you working in tech as opposed to investment banking? Or going down and making land mines, or whatever it is that is the number one amoral dollar you could possibly make for your time? Good for folks who are into that. I don't ever find that philosophy to be compelling. But again, I'm not trying to judge unduly. Everyone has their own situations and I'm not going to blame people for chasing money.
Caroline: And you talk to a lot of people who maybe aren't happy in their careers or their jobs that they're in right now, and a lot of times it's because they don't always think about, hey, what gives me a sense of purpose when I wake up every day? What is the specific industry I like? And within tech, I think what's so exciting is you can work in digital health; you can work in financial tech stuff; you can work in so many of these different areas, so for me, I always wanted to sell something I was actually interested in because I knew that I’d then be able to do a lot of research, stay up to date, like, that would motivate me and excite me, as opposed to just taking any random job for sales. And I think a lot of people would be better served if they've thought about, “Hey, what do I get excited about?” As opposed to the money because I think they always come together when you can find an area of interest, and then a practical application of it.
Corey: Caroline, thank you so much for taking time away from actually chasing deals down to come on the show and have a conversation with me. If people want to reach out to you to either talk about career trajectory, or buy sponsorships on various properties of The Duckbill Group, or attempt to hire you away and thus lead me into a very expensive bidding war to retain you, where can they find you?
Caroline: Well, Corey, thank you so much for having me on the podcast. It's been a ton of fun. I'm not used to actually being on shows, so thanks for again, having me and hosting. If you'd like to get in touch, feel free to reach out to me. My email is [email protected]
and we'd love to chat with you.
Corey: Caroline Carter, account executive at The Duckbill Group. I'm Cloud Economist Corey Quinn, and this is Screaming in the Cloud. If you've enjoyed this podcast, please leave a five-star review on your podcast platform of choice, whereas if you've hated this podcast, please leave a five-star review on your podcast platform of choice, along with an incoherent comment explaining why I'm completely wrong to wind up spending time one-on-one with a colleague who happens to be a woman.
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