Reaching a Constant State of Improvement: How to Build Confidence Within Yourself & Your Team

Aydin Mirzaee (Fellow.app)  00:29

Carly, welcome to the show.

Carly Brantz (DigitalOcean) 00:33

Thanks so much for having me. I’m excited to be here. 

Aydin Mirzaee (Fellow.app)  00:35

Yeah, I’m very excited to speak with you. I was just I actually have your LinkedIn profile open. And we’re going to talk about a bunch of these different places that you’ve worked at. But awesome companies return paths and grid. Twilio today you are the CMO at DigitalOcean. But before we get to all the different experiences and the really interesting career that you’ve had, do you remember when you first started managing and leading teams? And in those early days, what were some of the mistakes that you tended to make?

Carly Brantz (DigitalOcean)

Yeah, I definitely had a small team when I was at return path, just a couple of people that I was managing, and then sort of grew over time through my years at SendGrid. But the main mistake that I have made, and I think getting older, maybe is making it better or just wiser, is just around avoiding conflict. So I am normally the Peacekeeper, I want everyone to be happy. One of my strengths and Strength Finders is harmony, I want everyone to be at peace. But a lot of times there are bigger issues or shift in attitude or behavior that needs to be addressed. And I would just sort of let it fester inside of me and let things go on too long. And I think, you know, once I recognize that it is better just to have the conversations even though some of them are really difficult to have. I’ve almost always seen a turnaround and behavior attitude, and just sort of clearing the air and that energy is been really beneficial. But yes, I think that was one of the big mistakes that I made just letting things sit when they needed to be resolved. And do you remember like, what series of of events kind of led you to get there? Or how did you get good at that? Is there? I mean, I know this is maybe a basic question. But do you have like triggers that oh, if I feel like this, I’m going to write it down or, you know, just like some sort of prompting system because like behavior change. Like that is not usually an overnight thing. I’m just wondering how you got there? Yes. One of the things that I was realizing as part of management is, you know, when I was losing sleep at night, it was never because you know, a marketing campaign didn’t go as expected. It was always something that was team and management related. So I think that’s probably my first trigger is if I am losing sleep if I’m just uneasy about something and then taking note of it. You know, you don’t have to address every small thing that ever happens on that.

Carly Brantz (DigitalOcean)  05:00

Team. But if you start to see this persistent behavior coming up, then I knew that it was time to address it. And I would say, How I got good at it is just more of having those experiences. And sort of seeing on the other side, the positive outcome by addressing things instead of just letting it sit. Most of the time, you know, if somebody’s attitude was infringing on the whole team, or just sort of a shift, and once I brought it up, then they could maybe share certain things that were happening in their outside lives that were impacting their work, which could help me to be a more empathetic leader. But without addressing it, you never can get to the heart of you know why these things are happening.

Aydin Mirzaee (Fellow.app)  05:43

It’s not always like, I mean, it’s probably shouldn’t ever be in an accusatory, it’s more like, I’m curious, I’ve noticed and, and that just curiosity may help reveal some more interesting things and allow you to diagnose what’s actually going on?

Carly Brantz (DigitalOcean)  05:58

Yes, absolutely. I think the curiosity on all elements of the business, including management is really important and has been really important to my career and success is, that’s what keeps my job fun is being curious about why prospects are behaving this way, why a customer signs up? What sort of the psychology behind different actions? And the same is definitely true for management as well.

Aydin Mirzaee (Fellow.app)  06:25

Yeah, I think that makes a lot of sense. So if we were to get started and start chatting about some of your management career, one of the things I’ve noticed is that you have had lengthy stays at all of the companies that you’ve worked at, I think, you know, six and a half years return path SendGrid and Twilio together close to a decade. You know, that’s not super usual. So one of the questions I actually had was in, like, when I, you know, when we did our research, you joined SendGrid, when you were less than 30 employees. And you know, I don’t know how many were there when SendGrid sold to Twilio? But I’m assuming at least hundreds, if not over 1000.

Carly Brantz (DigitalOcean)  07:10

Yes, I think it was about 400 When we were acquired, and then of course, Twilio had 1000s of employees as well. But yes, my tenure is lengthy. And I’ve worked with the same set of people in many cases at both SendGrid Twilio, and now it DigitalOcean as well. But yes, I started at SendGrid, when I think I was employee 30, right around there. And it definitely seemed like probably five different companies, we had different leadership come and go, just different approaches in general. And as my career growth happened, the company growth happened sort of simultaneously. And it was definitely an interesting ride along the way.

Aydin Mirzaee (Fellow.app)  07:54

That’s super interesting. So when you got to SendGrid, I’m just looking again, at your LinkedIn director is senior director, VP. So I’m assuming that during those times, like I assume, like there were other VPS that were there, and they came and they left and but you continue to rise up through the ranks, despite like, I guess, like changes that continuously happen at the top? Yes,

Carly Brantz (DigitalOcean)  08:19

I think a lot of that is just being adaptable. And you know, figuring out where I could serve a bigger purpose within the organization. And I well, it sort of goes back to that curiosity piece, I was learning so much at different phases of the company, it was really interesting to sort of be a part of the whole adventure. And, you know, finally, funny enough, a lot of the VPS that I was with, were actually there for a long time, you know, some definitely came and went, and the executive team was totally turned over at different times. But a lot of us were sort of a core group of VPS. We’re all still very close today. But we sort of rode the whole wave together, which was pretty interesting.

Aydin Mirzaee (Fellow.app)  09:04

Yeah, that’s awesome. And so I guess one of the questions is for all kind of rapidly scaling companies, you inevitably you start in a role, and maybe when there’s only 30 people, you know, you kind of run a function, or you run a department, and then as your scale, you know, sometimes more experienced people are brought in. And so I’m just wondering how you navigated that, I mean, SendGrid was obviously very, very fast growing. I’m just wondering how you took those opportunities, when I guess like, bosses were hired that you reported to, and that how you actually leveraged that. And over the course of time you like, ended up running the function yourself?

Carly Brantz (DigitalOcean)  09:44

Yeah. That’s a really interesting question. I think a couple of things played a part in that. So one of them was I made it a point early on in my career, and I think it was our first CEO at SendGrid was Jim Franklin and he was As a big proponent of making connections, so let’s talk to every other, you know, person in your role in this community. And so I started to do that. And then I started to sort of expand that. So I would do these trips to San Francisco, I would include members of my team at SendGrid, we would go and meet with people in our same role at companies like Salesforce or Marketo, or Atlassian, I would just try to make the connections and just do sort of a listening tour with other leaders within the marketing space and just hear how other teams were doing it and expanding. So I think that it sort of lends itself to that same curiosity, I was also trying to do any kind of public speaking, training, any management training, any kind of learning and development piece that I could get my hands on to continue to evolve and grow in my career. And so I think that was it. I also, you know, I think experimentation has been really important to me. So just sort of experimenting with our marketing programs, and then running tests, and then going back and doing them again, and just that continuous state of experimentation, not only in our marketing programs, but also in the team dynamic and how we could function together. So there’s just more self motivation, and learning along the way.

Aydin Mirzaee (Fellow.app)  11:27

That makes a lot of sense. I think the just concept of peer groups, you know, continue to be very important. And I think maybe today, it’s slightly easier, because you may not need to fly anywhere. Exactly, yeah. And zoom can facilitate some of this stuff. So that’s awesome. So you saw that as a core, you know, way to kind of learn from others and like, continue to grow in your career. What is this constant state of improvement? So you talked about it a little bit right now. So you’re always running tasks, always trying to figure out, you know, how to make things better? How did you think about feedback from your team, and the ways that you would organize your team or divide things up like Were there a lot of people experimentation, things going on, just from like a team perspective, too.

Carly Brantz (DigitalOcean)  12:15

Yeah. So when I was at return path, each year, we would hire a CMO. And that cmo would restructure the team. And so let’s say one year, I would get moved to do event marketing. And then a year would go by that cmo would be let go, we’d bring in a new cmo who would restructure the team. And it happened, you know, I was there for nearly seven years, I bet. I had six different CMOS during that time. And so for better or worse, I think for better, I was exposed to different areas of marketing and different work structures. So when I started at SendGrid, I was, you know, one of the first marketing hires, and I was doing a little bit of all of those pieces. And thankfully, I had had exposure to all of those little pieces, because of all the changes that I experienced at return path. Anyway, we’d restructure the team each year. But when I started at SendGrid, I sort of got to start from scratch. And so I was doing all of these little pieces of marketing that I had been exposed to, while I was at return path. But as the company started to grow, then there were one, you know, area that I needed extra assistance. So I would hire those people in. And then it was sort of their own specialty areas. And so it just kind of happened naturally on what area needed the most focus. And so it definitely grew over time. And those subgroups became larger in and of itself. But those same sort of buckets of work continued to be pretty much the same throughout my time at SendGrid. And it actually scaled very well. I’ve been surprised at some organizations, pages grow really quickly. And they didn’t have the foundational pieces and the structure to their team and the systems in place. At SendGrid, we had a really solid foundation that just sort of expanded in each of those sub buckets over time. And then at DigitalOcean, I’d say it was more of the not maybe such a sturdy foundation that I had to come in and make a lot of operational changes and structure changes, but at SendGrid sort of scaled, how I wanted it to overtime.

Aydin Mirzaee (Fellow.app)  14:32

That makes a lot of sense. And I’d love to dig into how you did that. Because I suppose there’s like a few ways to scale a team. And it seems like the way that you’re saying is that when you felt that something was a you know, like it was a good chunk of work or it could now become a full time function, then you would hire an expert in that area to take it on. How did you think about you know, hiring for functions. so that, you know, maybe hadn’t gotten there or like something was brand new, you hadn’t done it before. But you thought that maybe it’s a good thing to do like for things like that, do you often think that, hey, maybe we should try this or ourselves or like, dip our toe in the water? Or do you think like, it just makes sense to go hire an expert or team and get them to work on

Carly Brantz (DigitalOcean)  15:21

it? Yeah, I think in the early days at SendGrid, I was outsourcing certain pieces of it. So we outsource some of our demand gen pieces and SEM, we outsourced and I outsource some of the content creation. But once we started to get more technical, we brought it in house. And I’ve always found that to be the better route is to bring most things in house that you can just because as you’re changing sem ads, it’s important to know who your competitors are and what they’re doing. And it’s just a lot more difficult to do that with an outsourced company. Not to say it isn’t possible. And I think early on, it’s best to try some of that. But I think for the most part, you know, it was when I started at SendGrid, I modeled it very closely to this HubSpot inbound marketing model, where I was pretty much responsible for anything that came to the website, once it came to the website, I was doing all the email, nurture the content, marketing, the events, marketing, all of that to get them to close. And pretty early at SendGrid. as well. I was sort of funneling tons of leads to the sales team. And we were seeing a dip in people just coming to the website signing up for an account and starting to pay. And so the CEO at the time, had tasked me of like, can you focus less on the leads, and more on just this whole end to end self serve motion. And so that is sort of what the bread and butter had been for SendGrid up until the time that we were acquired is really driving revenue from marketing through this self serve channel, which was the majority of the revenue,

Aydin Mirzaee (Fellow.app)  17:05

was it the majority of the revenue before you started working on it, you are no, you turned it into that into that something that I guess was like a very brand new endeavor for you, when you first took it on,

Carly Brantz (DigitalOcean)  17:16

you know, when you have a sales team that are hungry for leads, I was getting all of my content and sending everybody that I could collect information to you directly to sales, it was impossible for them to follow up on 1000s of leads. But if I held them for longer and tried to get them to sign up for an account, and then even grew them through nurture campaigns, we saw especially our audience at SendGrid, and actually at DigitalOcean, as well as developer focused. So developers especially are resistant to talking to sales folks, and they like to figure things out on their own. So helping them to feel like they are doing it all on their own with sort of gentle assistance throughout the process just was very worthwhile. And so yes, we then eliminated many of the sales reps, those sales reps that we did keep were focused on the much bigger deals. And the rest, we just, I mean, it’s an incredible customer acquisition tool, and very low cost cost effective. Because you’re not paying, you know, commission on a $10 a month deal. It’s all just coming through that self serve funnel.

Aydin Mirzaee (Fellow.app)  18:28

Hey there, just a quick pause on today’s episode to let you know that we’d really appreciate you helping us spread the word about the Supermanagers podcast, if you’re enjoying what you’re hearing so far, dial into your podcast app of choice, whether that’s on Apple or Android or Spotify. And just leave us a quick review. Now back to the interview. You know, when the question that like maybe comes to mind for me is, you know, as you’ve kind of risen up the ranks, you know, the companies that you’ve been at, how have you seen that, you know, your role has changed, the more senior you’ve become, the sense I get is, maybe the more senior, it’s about people like it becomes more of the people job.

Carly Brantz (DigitalOcean)  19:12

I think I’ve gotten as I’ve progressed, I needed to really learn how to delegate things that I would have done myself and really encourage my managers to delegate as well as a form of trust in the people that they have on their teams. So that’s been a big piece is delegation of some of those tasks. And I think unfortunately, as I’ve been at a bigger organization and risen in the ranks, people seem more scared of me. So I do a lot of activities to trying to connect with people, setting one on ones doing skip levels, just so that people see me more as a person. I think I’m sure that COVID has contributed to that as well. It’s just I’m just this person on the other side of the screen. For many people, but really trying to make that connection with the each individual on the team, when a new hire starts, no matter their role, I want them to set up time with me. And they many times just seem totally terrified, like, what does she want from me? And then I just tried to make it clear that I’m approachable. And if they have ideas, or a good book recommendation, or they’ve been just a great TV show, I’m just a regular person. And I want to connect. Yeah,

Aydin Mirzaee (Fellow.app)  20:30

that makes a lot of sense. I mean, what I really liked about it is I mean, as you said, it started from not being the largest revenue driver, it was something new, and then you were able to take that and then turn it into the biggest revenue driver for the business. So that’s awesome. And I guess one of the things that you have also talked about is, as it relates to women in tech, and then leadership roles you’ve talked about sometimes there can be a lack of confidence to try things that may not work, am curious about maybe you can elaborate on maybe kind of like, how things have been, and what are some of the things that you have been focused on to kind of change the way of being today for women in tech.

Carly Brantz (DigitalOcean)  21:18

Many years ago, I was at an NC WIC conference. So National Center of women and technology, I went with SendGrid, a group of folks from SendGrid. And I listened to this speaker who was talking about this book called The Confidence Code. I mean, it’s an incredible book I’ve had, it’s pretty good. Yeah, it’s really good. And there’s actually one for young girls that I’ve had my daughter’s read as well, like Confidence Code for girls or something like that. But I was just really struck by one of the examples that this speaker was referencing at that conference about young girls in high school that these girls that are excelling in math, but then they don’t go on to pursue math or science related majors when they go to college, because they don’t feel like they’re good enough, while they’re better than their peers that are male. And then the males are going on and pursuing those careers. And I was just really struck by that, that we just never feel like we’re good enough. And I really started to encourage myself first, and then members of my team to really focus on the things that they are really good at, and sort of expose that in new ways. So if you are really good at creating slide decks, then let’s figure out different ways of you helping us do that. Or if you’re really great at creating content for a new ad campaign, then let’s try to expose that in some way. I did sort of these buddy projects, at SendGrid, where, if you’re, you know, specialty areas in email marketing, and this other person is in SEM, let’s partner them together on a project. So they can learn a little bit of the other area, but they can also be a coach and mentor for their specialty area. And that helped, you know, not only myself, but other members of the team sort of see their strengths and shine in new ways that they wouldn’t have otherwise done. I’m a big believer in Strength Finders, too. We did it as a team at SendGrid. And I do it as a team at DigitalOcean of not only taking the test and finding your strengths and figuring out how you can maximize those, but also mapping it out as a team. So if there are areas that you’re less confident or less strong in, you know who to lean on within the team who does have that strength. So we do that as a team, we update it on a regular basis. And then I would also say, just having this growth mindset, it’s another book that I love and have the teams that I work with read and think about is always trying to rethink things as an opportunity. So you might not know how to do it, you might not be great at it. But you can learn and you can try and being open to learning new skills is really important.

Aydin Mirzaee (Fellow.app)  24:20

There’s a lot to unpack there. And I agree on a lot of the books that you mentioned, certainly mindset and competence code, digging into the the string finder that you mentioned, you mentioned that you update this a few times a year, and the biggest value that you get out of it is on a team basis, or do you think it’s something to help people work on?

Carly Brantz (DigitalOcean)  24:43

Yeah, so we don’t update the test. We’re not taking the test twice a year, but as new members of the team join, they’ll take the test will map it out. It’s really interesting to me to at least at DigitalOcean where certain groups have certain strengths. I mean It doesn’t. So if you’re a content team and you’re writing, you might not be as analytical, which makes sense. But it’s interesting to see it all mapped out and see some of the similarities and strengths for some of the different subgroups. So that’s the main thing that we’re revisiting a couple times a year is, you know, here are the teams are the individuals who might complement some of the areas that you are less strong in and how you can partner and work together with them.

Aydin Mirzaee (Fellow.app)  25:28

Yeah, that makes a lot of sense. Instead, the idea is not necessarily to solve people’s weaknesses, but allow them to actually spend more time on their strengths. That’s awesome. And so one thing that I did want to dig in on and we kind of touched at it in the beginning, around, you know, staying at the companies that you have for a longer period of time. You mentioned one thing as we were getting ready to record was just a concept of relationship building. I’m curious, like what you’ve learned in building relationships throughout your career, and what advice would you give to people who want to invest in more relationships and seeing like, how they can basically just strengthen the relationships that they have with people around them? Yeah, I

Carly Brantz (DigitalOcean)  26:16

would say so. Our CEO at DigitalOcean, Yancey, Spruill, he was our CFO at SendGrid. And we formed a very tight connection, because marketing was so influential on revenue, I needed to build those relationships with finance. So I would say, to think, in terms of building new relationships, to think outside what you might normally think of who you need to build relationships with. So traditionally, in marketing, you know, you need to build relationships with sales and customer success, you might not think as much, you know, building relationships with finance. But because the financial metrics were impacted by what activities we were doing, on the marketing side, I needed to see that correlation. So I built those relationships with finance. And I would say, I think now, you know, finance and marketing is just as an important relationship, as sales and marketing, not to say one is more important than the other. But all of those are really important. So I would, you know, reach out and just learn about different areas and how you can work together. A lot of people, even within the marketing team, say, oh, you know, I’d really love to learn more about project management, not because I necessarily want to do that, just because I would want to learn more about it, and see how, you know, we could work together, and I’m always encouraging them to reach out in pre COVID days, you know, have a coffee date, where you’re talking to them, and just learning more about what their businesses are their area of the businesses, and then I think just building those relationships over time. So at SendGrid, you know, I worked with the same team of revenue marketers, really, for most of the decade that I was there, and many of them have come now and work with me, again, at DigitalOcean. And so once you form those relationships, you know, their strengths, and how they can help how they can plug in and get going. I just think it’s so powerful to have those relationships over time. So people can see, yeah, how you can work together and benefit a different type of business as well.

Aydin Mirzaee (Fellow.app)  28:34

I really buy into this, there’s this, I’m sure you’ve heard of like similar anecdotes, but basically, you know, if you take the the star player in a team, and you put them in another sports team, they’re not necessarily going to be as good as they were. Or even, you know, basically, I think, like there’s a study done a financial analyst, you take a star analyst from one company and put them in another one. Like it takes almost five years for them to get to the same status of stardom that they had, except in the case where they go with their team, because that is really interesting. I love that. Yeah. Which makes a lot of sense, like you’ve spent all this time gelling and learning how to work with each other, and who’s good at what, and so on and so forth. It’s kind of sad that in a lot of places, you know, teams disband so often, and they’re not often there for a very long time. But it’s amazing that you’ve, you’ve done that with the people that you’ve worked with, and you’ve all followed each other from team to team and company to company.

Carly Brantz (DigitalOcean)  29:31

Yes, I would say two, I really prioritize team building. And everyone would always joke about it at SendGrid that I was sort of the leader of all team building activities. But I really prioritized one in person team building activity each quarter. And so we did it in terms of tenure. So the person who had been with the company for the longest would choose the first team building activity and it could be something of their choosing. So we did, you know, bike riding and Newport Beach or we did cooking classes or baseball game all. But each quarter, we would get together and do something outside of work that was fun and connected us. And I do think there’s an element that, you know, also building relationships you understand who’s the star performers are and how they can execute in different areas. But you also know them personally, you know, I know their kids, I know their husbands and wives or relationships that they’re in. And that also builds this sort of connective tissue, that also helps, you know, some of that loyalty, I think, over the years, I’m not just a manager that doesn’t know or care about employees, I take the time to invest in their personal well being, as well as what’s going on in the workplace.

Aydin Mirzaee (Fellow.app)  30:54

You know, I think this is so important, especially now that a lot of companies are working fully remotely. I mean, you mentioned team building, and you mentioned in person, what are some things like for super successful team building event? You know, for those who want to do more of that? Like, what are the things that need to happen? You know, for it to be very successful one, are there things you could do that are better than others?

Carly Brantz (DigitalOcean)  31:18

Yeah, I mean, I definitely enjoy the having fun doing something fun outside of the office. And it is, has been very challenging over the past two years, you know, I joined DigitalOcean in January of 2020. So not the most ideal time for that connective tissue and really getting to know people. We have been using a tool. It was called icebreaker. Now, it’s called gather round. But it’s an icebreaker app, you log in, we log in at the beginning of every marketing, all hands meeting, before we log into zoom, we log into this tool, and it sort of round robins you to a different person, and you answer personal questions like what was your favorite song in high school? something silly, but something personal. I think that’s the key to team building is separating from work for just a little bit and making a connection on a personal level. And that’s harder, online, virtual, we’ve done painting classes online, we’ve done some cooking classes, we did a really great pie baking activity all virtually. So it’s definitely possible, just trying to get creative on things. And especially now, I would say the best type of team building is getting away from your screen, especially after the years that we’ve had. But if you’re unable to do that, there’s still ways to connect and have fun. But I do think it’s more on the fun. On a personal level, I think, yeah, that just builds trust within the team. And yeah, I do think it inspires more of that loyalty and connection. If you know some things about people personally, it also helps people to be more forgiving in a workplace when you feel like, oh, I don’t know why that person snapped at me and you get less angry, more forgiving. If you know and know what’s going on outside of work.

Aydin Mirzaee (Fellow.app)  33:17

That’s really good advice. And I agree it can be done. I think you just need to be more purposeful and more thoughtful about like making sure it happens. So Carly, we’re just coming up against time, we’ve talked about so many different things, you know everything from longevity to relationship building, your constant state of experimentation and all the teams that you’ve been at, and also just the importance of team building. One final question that we ask all the managers on the show is for all the managers, leaders constantly looking to get better at their craft? Are there any final tips, tricks, resources, or parting words of wisdom that you would leave them with?

Carly Brantz (DigitalOcean)  33:59

Yeah, I’ve really been tapping into all the podcasts I like to, especially these days, have some time away from my computer. So I pop in my air pods and go for a walk with the dog. And I think that’s been really beneficial to me. So one that I have really, really enjoyed. And it goes back to the connection and more of the art and science around happiness is called the happiness lab podcast. It’s by Laurie Santos. She teaches at Yale, this happiness. It was a big thing a few years ago, but she has so many incredible insights. And she has different speakers on about maybe some of the things that we think will make us happy that but don’t. And some things that we wouldn’t think would make us happy but do sort of tapping into that. And then this season is a lot around some of the negative emotions and things that have come up during the pandemic and how to do go with that. So I think it’s helped me tremendously in my personal life but also in, you know, forming connections and creating a happy team at DigitalOcean.

Aydin Mirzaee (Fellow.app)  35:10

That’s awesome. I hadn’t heard of that one. But that sounds exciting, and we’ll definitely include it in the show notes as well. Carly, thanks so much for doing this.

Carly Brantz (DigitalOcean)  35:19

Thank you for having me. It was great.