Ep. 123

Breaking Barriers in Tech: An Interview with Annie Tsai, Interact COO with Annie Tsai

Welcome to a special episode of Interact’s Grow Podcast,  where we share insights and strategies to help you scale your business. Today, we’re celebrating International Women’s Day by interviewing one of the most influential women in our company, Annie Tsai, our COO! 

Annie has been a driving force in the tech industry for over two decades. From her early days in tech to her current role at Interact, she has consistently pushed boundaries and championed for change. In this episode, she shares her journey, her passions, and her approach to balancing a high-powered career with all other #life things.

Hi guys, and welcome back to Interact’s Grow podcast. So great to be with you as always. We have a very special guest today with all of us, Annie. Annie Tsai, welcome our COO of Interact. Hello. And Annie, not only a COO, but you have like, I mean, you’re kind of everything at Interact. But you also have a ton of stuff that you do outside of Interact.

Do you want to give a quick intro to the Daenerys Targaryen, Annie side? We’re just talking about how you’re pretty much the mother of dragons here. Sure. Well, I you know, I’ve, I’ve been in tech for, I don’t know, 20, 23, 24 years, something like that. And you know, have had. A lot of fun doing a lot of different kinds of jobs and helping to start companies and grow companies and sell them.

And these days you know, interact is my primary focus, the day job, right. And we, we all wake up every day to build for creators and entrepreneurs. And my night and weekend. Activities you know, it ranges a lot. Like, you know, I like to invest in companies and advise other founders. But I also love sustainability and gardening and making sure that, you know, we’re leaving a better planet for our kids and all of those things we do I’m really involved in our public education system through a couple of nonprofits and And I, and I write for our local newspaper on on the peninsula.

I live like right between San Francisco and San Jose. And so it’s it’s, it’s sort of like the heart, I call it the heart of Silicon Valley because now Silicon Valley has expanded well beyond, you know, South Bay only. So yeah, those are some of the things that I do. For most of it’s for fun though, just because I get bored very easily.

And so I want to keep doing things. I want to call out for our listeners that you don’t watch TV. I remember you telling us this, don’t watch TV because your day is full. Well, you know, so like I, I’m in this mom group and it’s, it’s called moms in tech and we’ve been, we’ve been growing it for like five or six years or something.

And the you know, there’s always this question and people always ask like, how do you do so much? And I’m like, well, I’m never, I’m never offering what the latest show to watch is because I have no idea. And I just, you know, I save two to four hours a day by not watching tv. My son and husband like to watch tv, so they do all of that

Yeah. But although I did watch Ready Player One last night, it was pretty, pretty cool. That is a good movie. Good one. Yeah. Who knew? And, and then the other thing is, I think that lends to productivity is I also, I think need less sleep than the average person. Like my whole life, I’ve probably slept five or six hours at night.

And which terrifies me because I think my daughter’s the same. She doesn’t sleep. sO so I think there are going to be a couple of us in that family, in our family. I love that. It’s going to be a mini you. And you’re also a mom and a wife to, at the top of all of those other titles. Yeah. My husband’s in product management.

He’s been in product management for a couple of decades and has, has worked on some really cool products over the years. And I also have a 10 year old son in the fifth grade. Who’s amazing. I love it. He does almost as much as Annie when you talk about Brendan. Oh, yeah. I mean, this summer, he’s like always dreaming up little businesses.

And so I have to end up doing a lot of research about how to be an entrepreneur because he is naturally an entrepreneur. So you know, we grow a lot of food in our garden. Like we live on a little. A regular suburban plot of land. It’s very small. Right. And but I ripped out all of my lawn so we could grow grow some food.

And so he like, made enough money selling my vegetables and fruit last summer. So he opened a Roth IRA, which is amazing. Yeah, I know what I knew about when I was 10 ahead of the game. That’s great. Yeah. Yeah. It’s great. I’m really proud of him. But it’s all him. I love that. Yeah. I just think back to when we had like our.

I think at the beginning of our year, Empower, whatever our 401k is through, and we have this meeting, and they’re like, Groth IRA, this and that, and we’re all in Slack. Does everyone know what this means? Or are we all just lost of where we’re supposed to be putting things or what we’re supposed to be doing?

And I love that he was just like, selling dragon fruits. And a Roth IRA, we should have got him on the call. Yeah. Explain it to us. That’s right. That’s right. It’s the next reader stories. It’s going to be featuring him. Founders episode with our CEO. Yup. Yup. ANnie. So you mentioned you’ve been doing tech for like 20, did you say 25 years?

20. 20. 20. Three. I mean, I, it’s a, there’s a little overwrought because I was, I was at Berkeley doing my undergrad and building websites and and working on intranets and stuff like that for Lawrence Berkeley labs while I was in college. And so, you know, professionally since 2001, but before that I’ve been working on the intranet in the intranet world since 97.

Wow. I know some of you weren’t born yet. I was okay. I was here. I was little. Can we stop talking about ages and numbers? Life. Life experience. Yeah. So it’s, it’s. It’s crazy how much the industry has changed so much, you know, I mean a lot for the better, but also a lot, a lot of things, um, you know, happened that we’re still learning from and trying to improve, like, you know, the impact of social media and children and stuff like that.

And so. I’m glad that, you know, as people are learning about the impact of technology on humanity you know, we’re, we’re trying to make those adjustments but there’s still a lot more to learn. And, and I think we’re still in the early days of, of tech. Yeah. And we were talking earlier about how for us, I feel like this question came on.

Did we just hire Evan at the time when we were like, who are you, who are you most worried about interviewing with? And it might have been Evan, but it or was it Damaris? Was it you that we were talking about? Like, who are we ask somebody like most worried about interviewing with? Yeah, I think we were all having a conversation and I think you were there to Annie.

And then I was like, oh, I was like, really, really scared when Annie got when I had to interview with Annie and I don’t mean that in a bad way. Yeah, no, no, no. I was just going to clarify that. I was like, I think it’s because. It is incredibly rare to see, like, you know, somebody in your position, right, in your journey and things like that.

And sometimes it can be a little intimidating to try to say the right thing. So, um, I guess, like, maybe you were going to do this, Jasmine, but I’m very curious to, like, sort of hear, like, your story of, like, how. You became who you are now, right? Like, well, you’re now the CEO of Interact. And so it’s like, how did that, how did that spark start and then continued?

Yeah. Well, I first want to put out there that I too am intimidated by a lot of people in the industry. And I consider myself to be like extremely socially awkward going into public settings and yeah, it’s, it’s kind of. Sometimes it’s kind of comical, but, you know, it, we all have, you know, people in communities that we feel really comfortable with.

And for better or worse you know, the, when, when I was in tech in the early days, I w it was not uncommon to be the only woman in the room, nor was it uncommon to be the only Women, you know, on a leadership team or the only person in the boardroom or the only female sales engineer. At the time, I think there was only one other female sales engineer of 20.

And that was my first job in tech, like for a software company. Working with almost entirely, you know, 35 to 45 year old salespeople on site, you know, in Europe and in Asia and that, and throughout the U S and so. Those situations and being put in those situations was, was really intimidating. You kind of just got to fake it in the beginning.

And even sometimes today I still do. But you know, so my first job in tech was being as a. As a full time employee was being a sales engineer and that was, I think to date, probably my favorite job still, because it was really this cool intersection of being very technical you know, cause I was coding already and it was I, I could design stuff in and, and use all of the software that.

My technical peers were using and product manager peers were using. But there were the, the aspect that was really important for sales engineering was to be able to pitch and sell and you know, demos. Demo environments and really listen to prospects and your customers and figure out how to translate those problems that people are experiencing into technology that can be implemented by what we were selling and, and I think back then that was still kind of a new concept, and that was the beginning, I think, of understanding a real gap that that had existed in tech, and I think was part of the reason why SAS took off in the way that it did, because we were able to really accelerate the rate at which software could be implemented, because there were There were business minded technical people that could go out there and say, Oh, you said this, you actually mean this.

And then the engineers could say, Oh, okay. Right. And so and that was really fun. And that, I think that was a real confidence booster. So like, once you find a job in tech that I think really speaks to. Your, your secret sauce and everyone here has their own secret sauce. Right. And sometimes you’re, you’re working on a project and you really feel it.

And other times you’re like, eh, not so much. Yeah, that was, that was like probably the first time in my life where I really felt it. And the next step I think, you know, was, was really taking on. Anything that would come my way that was potentially interesting, even if I’d never done it before, even if I had no skills to do it you know, we could just figure it out.

It’ll be fine. Right? And back then we didn’t have the level of resources that people have today. You can learn anything online. You can, you have access to so many people, so many courses, so many potential communities. Anything can be learned online if you have the mindset and the, the grit and the determination to do it.

And so that was. It, you know, I graduated with a degree in communications and I don’t, I probably could have gotten better grades in, in college, but, you know, it’s, it was really just about learning how to learn. And so that was what I took away from Berkeley. They were great at that. But I got opportunities to launch marketing programs, launch new products in different global markets.

I got opportunities to build a cool voice of customer program. That was a global program, got to work on, you know, increasing revenues and decreasing costs ended up. moving into marketing strategy at the same company and, you know, was 25 or 26 at that time and ended up being like a director level marketing person at a publicly traded company.

And was one of the few women. You know, there, it was, it was really it was really intimidating, but was, I was lucky enough to have a couple of champions in the company who were willing to continue to just give me a shot and that’s the most important thing. So that was the thing that I think people misconstrue about being young and wanting to advance your career and design your life.

It’s, it is a little bit about what you want to do, but there’s a lot that. If you only focus on that side, there’s a lot that you’re missing out on. It’s, it’s really also not about, you know, going out and finding mentors that can give you advice here and there. You really have to find champions within your company that are thinking about you as someone who could potentially take on something new, interesting, or challenging when you’re not in the room and continually proving yourself to have a lot of upside potential, have that grit, have the desire.

To just want to win no matter what that, that is, what’s going to get you champions, no matter where you are. And then they’ll always say, Oh, you know, Jackie took on this project and she didn’t know how to do it, but she figured it out. She. She didn’t know the right questions to ask, but she found out what questions to ask and then found the way to get the answers and then brought in people to implement it.

And it was great. And, and, you know, those skills of figuring out what the right problem is that you should focus on and then finding the help to help you solve that problem in the right way. Those skills can be applied to anything. I definitely feel like that has trickled down to us through you like you’ve been such a champion for all of us And I feel like interact for me This is the first position where I’m encouraged to you know Do things wrong and then go from there like you guys don’t expect me to get it right the first time you guys know What I’m capable of or what I may know or may not and I feel like that’s true for all of us but you guys are just kind of like try it see what happens and You know, we come back with what we’ve learned.

It might not be like right on the dot, but you guys help us get to that end goal of, okay, we’re getting closer to it. But just that, like you guys encourage us to do it wrong, but you know, do it anyway until we figure it out. I feel like that’s so different about interacting. I think that’s definitely a culture that you bring to the table here.

That’s awesome. I’m so glad you feel that way. I think, you know, there’s a little bit of sort of that, like. Startup velocity that comes with that. But I think that, you know, Josh and Matt and I really, the, like one of the values that we spent a lot, actually a lot of time talking about was like that good ideas come from anywhere and everywhere.

And and it’s really, really important, not just to have the good idea, but also to have the ability to execute on it, right. And so there’s all this learning that comes from that. And and I think that’s really cool. So I’m excited to hear that. Yeah, you once gave us an analogy. I think it was also from an interview, but you were like, we’re looking for somebody who doesn’t need to follow a recipe.

Like we can be like, this is what you have to make and figure it out. And it was so funny. I was cooking something yesterday. My boyfriend, actually, I don’t know how he knew this, but I obviously must’ve told him. I did the recipe exactly as I was supposed to. And he was like, Annie would be so disappointed in you, you have to add your own.

Flare and seasonings. And I’m like, Oh my God, I thought I would just try it correctly the first time and improvise the next time. But he was like, no, Annie would have preferred that you just season it how you wanted to. So funny. Well, so speaking of cooking, so my husband, Tom, he’s the baker. So he makes like desserts and ice cream and stuff like that.

And and I am like the stew and the stir fry and, and, and that kind of person. And some. Some things are very specific. You have to be very specific about because if you put the wrong amount of baking soda, it doesn’t rise. Right, right. If you put the wrong amount of salt and does something happens, if you don’t whip it with the egg white for long enough, then your, your cake won’t rise.

And so, like, there’s this chemistry component, right? And then, like. There’s an art component. And I think cooking is really interesting because sometimes you’re like, sort of like on the spectrum of like art over here and chemistry over here, and sometimes you’re over here, sometimes you’re in the middle, sometimes you’re over here.

Startup life is, or working at a, for a tech company is no different from that. There will be times when you have to get really, really, hyper specific about how you do something like, you know, financials, right? You have to do it a certain way. Compliance. You have to do it a certain way. But all the stuff that we work on, how we go to market, how we get creative about telling our story, how we engage with our community.

Like there is. There’s no limit to how creative you guys can be, or you, you can be. And, and I, I think that this is a perfect place to just like go all art on that with science and data on the back. I’m curious to, to ask you obviously you’ve been on this tech Journey for quite some time and you’ve seen different things and being a woman in your position when you came to interact, it was probably different than what you see now, like, how, how, what’s your thought process when you come into a startup company and you’re like, okay, there’s 5 people.

Now my job is to like, I have to grow this company and try to get everybody together and somehow build. Community and a team from there. Like, how do you how do you even start that? Right? Like, yeah. Yeah, that’s a great question. I think a lot of a lot of entrepreneurs struggle with this because especially during the time that we’ve been doing it, you know, through a pandemic through lockdown.

Interact, I think, was very lucky because in 2019 the company went remote. And so Jessmyn, you were around when the team was in Oakland commute and everyone was commuting in every day. So it was Jared and and the shift to sort of fully online and. The process of acclimating to a remote culture the team had an entire year ahead of everybody else in the world that, that was working in the office.

And I think that was to great benefit to the company. I don’t know, Jessmyn, if you have any thoughts on that. 100 percent agreed because everyone was freaking out. How do I do this? And I was like, Oh, making my coffee, just reading these posts online. I’m like. Yeah, you’re just like watching the, the fire, right?

Yeah. All around us. And we’re like, everything’s fine. I think that’s funny. I was going to say when Jared joined, he, it wasn’t remote yet. The day he went in to like meet everyone, he got to the office and the office was getting emptied out. And I think his old manager then was like, Oh, by the way, like, we’re going to be remote.

And Jared was like, I like this job even more now. Like, I’m excited. And me on the other end, I was, yeah, yeah. And I was going into the office and I was like, wow, what a lucky little ducky. He didn’t even know it was going to be remote. He gets there the first day and they send him home for good. Like he was stoked.

I remember like it was, yeah, like fully remote was kind of unheard of. Like he was used to commuting into the, like into the city, taking BART every day. And I was just curious. I was like, let’s see, like, how this goes, you know, like, what is it like working fully remote? But I mean, he’s loved it since and I agree that I think Interact was definitely ahead of the curve.

Like when my company went remote or the old company I worked for, we were lost, you know, how do we do things like understanding how to use Slack or like Microsoft Teams, it was completely different. As to how Interact operated. Yeah, and I take no credit for this decision. You know, Josh and I had been talking for several months before I joined the company just as friends.

I was winding down my startup and taking on consulting work to sort of prolong the decision of winding it down. And you know, He was thinking about op ex, so like managing expenses and things like that. And we, we, we sort of talked about going remote. I had done half my career remote or traveling anyway.

And, and so it was it was a motion that I was really comfortable with, but at the same time, I think, in Silicon Valley in the Bay Area, having a high velocity remote startup was absolutely unheard of, like not a lot of people could do it successfully because there was so much pressure, especially for venture capital.

There was so much pressure to be in the room together. And like, you know, for days at a time, not showering and like eating the snacks that were provided by your WeWork or whatever. And that was. That was just how everyone existed. And so I, I’m, I thought it was a great decision that he had, he and Matt had chosen to make but but, but we all benefited from it.

So anyway, you know, we, we had a year up on everybody else. And when, when when things shut down in March of 2020, it was just business as usual for us. And we were starting to see some high velocity because a lot of these brick and mortars were trying to go online and figure out how to, how to really translate that relationship to online.

The the company, like I was brought in to really help Josh. Operationalize a lot of parts of the business that, you know, what the company had reached sort of this product market fit with their target persona. Like we know, we knew who we were selling to. We knew that what the product was solving for, we needed to go to market more effectively.

And bigger, we needed to make sure all of the Lego pieces, like in the foundation of our building for the company, that those were in the right place. And we wanted to work on churn because, you know, targeting small businesses, churn is going to be high anyway. And so always focusing on activation and churn forever is, is something that anybody that sells to small businesses needs to focus on.

So those are kind of the three, three directives. And as you can see, not much of that has changed. And, and we continue to do that. Yeah. But I think I speak to at least us or maybe most of the team. I really do feel like you’re like the glue that keeps everything together. Because I know if, if I have any questions, I’m like, you’re the first person that pops up.

I’m like, Oh, I’m just going to ask Annie. Yeah, there’s a lot, there’s a lot that happens behind the scenes. I think, you know, because someone asked, you know, I was talking to someone about. International women’s day. And they asked about like invisible labor. And first of all, everybody here has invisible labor.

Everybody, right? Like nobody is out there telling some like their coworker a hundred percent of all of the stuff that they do every day. Cause that’s ridiculous that we all have it. Right. But, but yes, I have it too. And, and there is, there is a lot that goes on behind the scenes that just is required to keep the company.

Running and then there’s a lot required to keep a company growing. There’s this balance of like upside and risk management that is constantly happening. And then there’s, you know, this. The on sitting right on top of that is like the story, right? Like, what is our story today? What is our story a year from now?

What is our story five years from now? How are we connecting the dots? How do we take that story and turn it into a plan? And then how do we turn that plan into something that people are? Doing things with so all of that stuff happens in the background. Every day. Yeah, I have all these endless questions.

So if anybody else wants to ask, feel welcome to ask.

I was just kind of curious, Annie, have you always worked for smaller companies or? Have you done like the big corporation style where, you know, 50, 000 employees? Well, I mean, I, I worked, my first job in tech was for a publicly traded company. It was 600 million, so it wasn’t massive. And then I went to a startup.

I was employee 75. We took it to acquisition by Intuit, which was at the time was a 4 billion company. And I was running customer experience and marketing at the time. And that was the biggest company that I’ve worked for. I’ve had a lot of really big enterprises as clients over the years, but but working at a very large company, I think what was, what was really hard.

And then everything after that has been startups because I had an epiphany. And, and that was that you know, I’m probably more of a small company person for a few reasons. One is The larger the company and the more product lines or business units that are in place the more, the more, as a leader, you spend time negotiating priorities and resources you know, and, and you’re just playing hockey all day long.

And a lot of it is in meetings and a lot of it is in. Like slide decks, frankly and that’s not very enjoyable to me, but, you know, I know I’ve, I’ve had to do it and you know, it’s not something that I think it’s not something that I think I couldn’t do for, for the rest of my career, but I, when, when you spend 70 or 80 percent of your time in meetings with, with your peers, negotiating for resources and prioritizing things all the time, That is time that you’re not spending like out there with your team and working with people or talking to customers.

And I think like, that’s really where my love is. And so if I had to make a choice, I will always make the smaller company choice because I do less of this and I get the chance to do more of that. I’m curious to, to know, and just a little bit of background story coming from a corporate background, having to work with Different management styles with different age groups.

There was 21 of us as managers. That was one of the youngest, maybe there was like three of us that were in the younger generational group and the rest were older. It’s definitely a political game, right? When you’re in, in a situation in that sense, because you’re, you’re, you’re You have initiatives that you want to do and present, but then there’s challenges that come with that.

And so, and, and you’re, you’ve had roles like this that you’ve excelled in, in the past, right. Of like, Oh, you know, you really have to advocate for what you think is a great initiative for the company. Like, how do you go over the hump? Like, and you can talk about it in terms of like. You know, just like, interact, like, presenting new ideas, or maybe in your previous jobs, just like, how do you then present it to where they actually buy in right?

You’re a woman in leadership, the challenging position to be in, like, how do you, um, is it literally just competence? Or is it just like. I think it’s about knowing who you’re, who you’re trying to get to buy in and what’s important to them. Like every single negotiation for the rest of our lives is always going to be, it’s not about what I want.

It’s about what you want and how I can make you feel like you get, you’re getting what you want or some part of it. Right. And and the, the more I, and I think that lesson came with. Time so in the beginning, you know, I was presenting data and presenting an argument presenting an opportunity and it’s like, oh, that’s nice.

But, you know, as time went on, and as my champions gave me some feedback about, what, what was it that we were actually trying to achieve? And I wasn’t actually trying to achieve what I wanted. I wanted to achieve better outcomes for our customers via this idea, but it’s not the idea that matters.

It’s the outcome that matters. That’s for our customers and how we get there might have some part of my idea in there, but it probably will be a part of it and not everything. And by sort of melding together all of these different. Areas of expertise, all of these great insights from people who have different experience than me we can probably get to a better outcome for our customers.

And so as I, as I learned to kind of shift how I was thinking about what winning felt like, or, or looked like, I think I got a lot more successful in, in those types of conversations. I like that. Okay. I have a question for you. Okay. If you. You know, if you were thinking about one thing that you always wanted to do for like work or like to, to sort of buy 10 years from now, 20 years from now, right.

One thing that you want to say that you did and you were proud of, what do you think, what would that be? 20 years is a long time.

Well, I’m going to take a stab at this one. I truly feel like I’m living it right now. It’s not necessarily something that I’ve done at work, because if you’ve ever asked me before I knew of interactive course, if I would want to make online quizzes for people, I would be like, what in the world is that job?

Is that real? That’s what my parents tell me all the time. Do you have enough money? Are you getting paid for this? And seriously, they like, have no idea what we do, but I never thought like this is, I want to be a partnerships manager for an online tech company. That’s not really like what I. I thought of, but the day to day of what we get to do, the time and the freedom and the creativity that we get to implement into the tasks and the jobs that we do, the ability to travel the world while I’m able to do that is been everything I’ve been working for, for the last, probably five years.

Very, very seriously. And five years before Interact, I’ve already been at Interact for three years coming up on. So I think for me, that’s, that’s what it, that’s what it’s always been. It’s not necessarily. The job it’s, what does my life look like in tandem with that job? And my days are so awesome. I love my life.

So I’m living it. That’s great. Yeah, I agree with that. I was going to say like, probably mine would be like, I guess alignment, just making sure that every choice I made was aligned with who I am as a person, my values, and I guess like what I enjoy, you know, I, I listened to a lot of people who are like, You know, I hate my job, but the job market is so bad right now.

I can’t leave, you know, like, I don’t want to be here, but like, I also don’t want to not have a job. Like I need to be able to pay the bills. And I think for me, like, I I’m very lucky to have this opportunity at interact because I do love my job every day, but like. Because I get a choice and autonomy, like I want to make sure that what I’m doing is in alignment with who I am as a person.

So I think that’s also why I’m very much like, like, Oh, I don’t know if that like makes, like, if that looks good, like from an outside perspective, if someone’s like, Hey, what if we post this? And I’m like, Oh, no, like sometimes I’ll say no to things because I’m like, if I were looking in at this, would I be like, would I, as a person of who I am be like, Oh, I love that.

That’s great. Like that is like makes you makes me feel good or makes people feel good. Yeah. And, you know, that, I think that really aligns well with who, what we value as a company too, because we’ve said no to a lot of partnerships and a lot of collaborations because they don’t necessarily align with our target customer or they don’t align with our business values or, you know, our personal values.

We, we have, right. I think for me, if I like looked at it, I love solving problems. Like I, I like math problems. I like doing things like that. And I think I interact every day. I mean, we’re a small company, but we have a little, lot of little problems, you know, and getting down to figuring out what problems to work at, what things to solve and how we can help each other and help other people.

Like that is huge to me. I love being able to work with. Every single person on this team on a new problem week to week, you know, it’s not just the same problem. It’s something different every time. And whether I’m directly helping a customer solve a problem, like maybe that’s more what, what like Damaris does, you know, and support, I like working with each other every day to work on little things like that, that like sparks joy for me, I guess.

So I’m glad that we get to do that. That’s awesome. I think I always complicate the question. I’m always like, oh, you know, because I want to like answer. So are you saying 20 years from now or like what I’m living now? Like, where do I see? What’s the answer the question that you want to answer? Okay. There you go.

I think that it’s been a unique journey for me because coming from a a management role to an individual contributor role, and then sort of becoming then a little bit of a management role. I can, I think it’s made me realize that, My, my true, my true passion. It has always been leading and teaching, but I also really enjoy the individual contributory side.

I think. And I think it’s me trying to figure out how can I use my skills with interact and then kind of grow from that. Right. And then also contribute. I, I come, I probably, I mean, I have. Had these conversations also learning, like, not to be an insane workaholic and trying to have a better work life balance with my, my daughter and my family, but working here has really helped me understand that.

There’s certain things that I’m good at and there’s things that I’m not very good at, and it’s okay to not be very good at that. And then ask questions and then try to figure it out and then try to do something else and then try to grow from that. And so I think that’s just going to be a role that just continues to expand.

And I’m, I love the change. I love learning things. I love the adaptability of it. So I’m not really sure that answered the question, but. No, I don’t know. I was listening to an interview. I don’t know, 3 weeks ago or something and something. The guy said something that I thought was really interesting. He said parents are doing it wrong right now.

You know, Parents today are saying, my kid is great at tennis and he’s terrible at math. We got to find him a math tutor. And they’re like, you should be finding him a tennis coach. And, and I think that was really counterintuitive for me because because my whole life I, there were, there’s like a minimum, a minimum standard for like the required things that we have to know and be able to do well.

Right. And I think in today’s. economy, today’s world. It’s really necessary to like flip that formula, right? Really like double down on the things you’re really good at and then find help to help you help augment the things that you’re less good at. Of course, don’t ignore it. Like you still got to be pretty good at math, right?

I mean, we have calculators in Excel or whatever, but like you have to be able to do like fast math at restaurants, right? Yeah. But, but the tennis coach thing, like really has really stuck with me. I do a hundred percent. I’ve been meaning to post this on LinkedIn. Cause I found this meme like a few weeks ago, where it was like all the kids who used to get in trouble for talking too much in class, like, what are your jobs now?

And I was like, Oh my God, that was me. And I literally talk all day. Like that is my whole job. And so like, that really spoke to me of, of, you know, one, like always feeling like. Like bad, I guess, for getting in trouble for talking. And not great at, I was really bad at math. I wasn’t terrible, but I was pretty bad at math.

And you know, me, I’m like, don’t ask me about numbers. I, I don’t know, but you know, in that same example, it’s like, how can you, how can you like as a society really cultivate people’s natural talents and like build that up so that way they’re always in the right job and they’re always doing the right thing at the company that they’re at.

Yeah. Yeah. There have been so many people throughout my career where, you know, they’ve come in in one role and you just spend a little bit of time with them. And it’s like very, very obvious that they should not be doing that job. And then, you know, we slowly like get them to a different place. And you look at the, the state of like tech layoffs in 2023 and like guarantee, I guarantee you at least 30 percent of those people were not in the right job anyway.

Yeah. That’s so true. Yeah. That’s so true. And then I want to, I’m going to sound philosophical, but then I think of like. You know, we have, I have my daughter that I’m always, I’m her role model. Right. And so she sees what I do. And there’s been a couple of, of situations where I’ve done things that she mimics and I’m like, Holy moly, if I would have done that the wrong way, that would have gotten a whole left side, you know, she’s only seven guys, so I’m like, Lord have mercy, please help me.

So it’s, and it’s, and it goes back to like the, the second generation of like women, right. Are we, are we, are we providing them with. The right vision of being able to excel and how you can do things. So yeah, just made it sound philosophical. Sorry. No, I agree. Yeah, there’s a lot resting on our shoulders.

And I think part of it. Part of the challenge is that, like, our society has not, has done us no favors you know, maternity parent, new parent leave is still the worst in all of first world countries. I mean, I can’t harp on it enough anywhere. It’s, it’s pretty pathetic. I, I don’t think there’s any other way to say it.

Right. And the, the government system and our healthcare system is, is designed to sort of be like a net to catch people as they fall as opposed to, you know, but like, nobody should be falling. Yeah, yeah. And that’s really sad for me. So, so I, I really hope that this next generation of entrepreneurs and, you know, sons and daughters and whatever gender people are you know, they are able to have, have positive relationships in their lives.

That give them what they need so they can become who they were intended to be. I know that, you know, I, I I technically like a gen X person. Right. And like during that time, like we had nothing, we had no parents. Our parents were working. We were home until alone until six o’clock. And you know, there was money in a yogurt cup in the freezer if we needed anything.

And there was no internet and all of that stuff. Right. And so like, we were just like feral, feral animals. It’s like you get hit by a car. And, and, and we don’t want that for our kids, but you know, we also don’t want helicopter parents mandating who they should be. And so I hope this next generation is has the opportunity to, to be able to explore like all of us get to explore, interact every day.

Yeah, this is giving me vibes from the episode that we did with Evan, where it was like, what’s the one thing that you have to implement on your team? And basically the answer was team vibes and making sure everybody was like the smartest person in the room, but also okay with not being the smartest person in the room so that we can all use each other to get to where we need to be.

So it’s really cool to hear you talk about this in terms of kids and school systems and governments because it’s so much bigger than just what happens at work, honestly. Yeah. Yeah. Yeah. Yeah. And that, by the way, is also why we spend so much time, thank you for doing all of the interviews, by the way, team, because it’s why we interview 800 people to hire one person, right?

Because, because it matters. Yeah. Company culture matters every time. I was going to ask you earlier, Annie, when we were talking about moving when Interact moved to become a remote company we kind of, I mean, we’ve done other episodes where we talk about the benefits internally to each of us when we do that, but like the talent pool that opens up when you expand the reach of who can apply to that job, because they don’t have to be just in this area and the diversity that comes with that and the creativity and new mindsets and all of that that comes with it.

I mean, I guess I maybe I just answered my own question, but that was what I was wanting to ask you is what does that look like? Because it’s other than a lot more interviews. Yeah, no, I, I love that. You’re bringing that up because I think it’s so important to to highlight that. There, the primary benefit, I mean, there are a lot of benefits of going remote, but the primary benefit is that you expand your talent pool.

One day when we expand our abilities to hire and employ people worldwide that’s even, even more right. Opportunity for us. I mean, we have global customers and they’re all over the world anyway. And so that’s only to our customers benefit to be able to do that one day. Right. But today let’s say us only.

We’re going from a talent pool of, you know, maybe a couple hundred thousand in the Bay Area to mi a few million from all different walks of life. And, you know, one of our values is that, you know, we strive for our team to have the same similar life stories and experiences as the people who use our products.

And there’s no way that we could do that if we only hired in San Francisco there. It just wouldn’t happen. It’s not true. That’s true. We have to hire people like Evan who experienced winter and Jackie because here in California, I don’t know what snow is. Okay. That’s right. I don’t know what time it is over here.

You know, that are multi generational mid from the Midwest. That that understand what the mom building a business out of her house with three kids between 10 and three, because that’s the only time she can work what she’s going through, you know, because those are her, those people are his friends.

And I think that that really, especially like our customer base that really matters. Oh, yeah. 100%. Do you have advice for people who are like either entering the job market or thinking about starting their own business of like, cause earlier you mentioned saying yes to opportunities. Like, how do you know which opportunities to say yes to and which to hold off?

Even if, you know, maybe you’re like, wow, am I making a bad choice by saying no to this? Yeah, that’s hard. I don’t, I don’t know if I know the answer to that either. I think you, there’s going to be a lot of gut involved talking to people that you trust. Although I will say that talking to people that you trust has a tendency for you to make a less riskier choice.

Et cetera. But if you can find a way to build a decision making framework, like I’m a framework person, if you can find a way to ask the same questions for every opportunity the, there’s a methodology called decision analysis, which applies numerical probability to like, Very emotional decisions.

And, and I think it’s a really interesting way to sort of apply a framework to an emotional decision like that. And, and so that’s 1 of the frameworks that I could apply the something else that you could do is, you know, you could. You could just take the risk aside and only look at what the potential upside is.

Now, I will say that there are some, like, if you’re doing it right, if you’re doing work, right, regardless of what your job is, there will be something that you can learn and take away and use for your next job. Like, I’ve worked at Starbucks and, I was terrible at working at Starbucks, but I can make a really, I can make every drink on the menu delicious.

And so it’s really great at dinner parties, right? I’m really great at dinner parties because I can make an excellent cappuccino. And like, that’s a skill, you know? So there’s always. There’s always something that you can take away from your job. Yeah, I would, I would, I would add to that and say if you’re scared of change, just think of, if you’re scared of change, obviously what Annie said, the pros and cons, and then always think like you have enough experience to go back to what you were doing before.

So sometimes you have to have a leap of faith and just, just go with your gut, right? Like, is this gonna, does this feel right? And if it does, You gotta, you have to do it. Otherwise nobody else will do it for you. Totally. I think, I think that’s a really important point. Like I’ve been having this come to Jesus moment the last year and a half about this, the concept of failing up.

And I think that’s wrong. I think failed the, I, the concept of failing up is wrong because what do we tell our kids every time? What do you, what do you do when you fall down? You get up and try again. Right. And so we should all be failing up. All the time, you always get up and try again. And so yeah, I, I really had this like deep crisis with the concept of failing up.

Yeah. And I agree with you. I agree. Yeah. It’s funny though. Cause then like you’re in your thirties and you’re like, dang, like I’m still failing all the time. Like I thought this would be done by now, but like, here we are, like, I’m still failing all the time. It’s okay. It’s the question is, you know, what do you do with that information?

Right? That’s true. I kind of have one silly little question, but Annie working in tech, you’ve worked remote a lot. What are your thoughts? Can you work from home successfully in pajamas? Or do you feel like you should dress up every day? Because I’m curious where you are on that subject. Yeah, I mean, I I think you can’t, I mean, it depends on what your pajamas look like

yoga pants every day and just like a sweater, you know, and I wear yoga pants to sleep. So I, yeah, I think tech is, is definitely a lot more casual than than other industries. When my first job we worked in the, our office was in the financial district at and during that time in the early two thousands everybody, all the bankers were suits full suit and tie and I wore a full suit and tie with heels downtown every day on bar and, and all of that.

And it was, it probably wasn’t until 2000. So it was several years of tech recovery before, uh, jeans went beyond Friday and yeah, it downtown San Francisco. Yeah. It like that, that sort of shifted to MoMA south of market and then it shifted to a little bit like Jackson square and shifted a little bit to The mission district, those parts of town are more casual.

But like, if you were downtown San Francisco, like I still wore a blazer most days for a long time. And and and traveling to see clients, like, especially if you went to see European clients, you, you were in a full suit or the East coast. I was always in a full suit for years until 2010. And, yeah, it’s pretty funny to think I’d still have those suits, but they haven’t been worn in in a decade, you know, yeah Yeah, that’s crazy. Maybe it’s time to hang up the suits for good and just let them go That’s what I’m hoping for. I don’t know if you ever I have worn a suit like for fun, but I do really enjoy wearing suits because you feel different.

Your posture is different. And you know, when we talk about like faking it till you make it or like manufactured confidence, like I, I think what you wear does have an impact. If you’re standing versus sitting in an interview, if you’re walking slowly versus, you know, with your shoulders back all of those things, those little posture things they play a big role in in how your voice comes out and then also what your like internalized confidence levels are.

So, I, I’m, I’m still very pro suit. I haven’t worn 1 in a long time, but I still love them. Yeah. Yeah. And I actually kind of miss it sometimes, to be honest. Yeah. Yeah. I mean, you work for a bank. Yeah. Yeah. I still have a whole section of suits and I just refuse to get rid of them. And I sometimes miss wearing it.

You’re right. It does make you feel more, I guess, important in some way because you’ll feel different. So your shoulders look great. I just knew that was going to be awesome. The features are great. Everything’s great. Everything’s like sharp. Yeah. Yeah. I will die in my fuzzy socks. Fuzzy socks on me. You be you.

I support that. Love it. Well, Annie, thank you so much for hopping on and telling us all about you. Thanks for having me. Yes. And happy International Women’s Day to all of us. And all of our listeners out there and we’ll see you next time. Thank you all. Happy International Women’s Day.

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Jessmyn Solana

Jessmyn Solana is the Partner Program Manager of Interact, a place for creating beautiful and engaging quizzes that generate email leads. Outside of Interact Jessmyn loves binge watching thriller and sci-fi shows, cuddling with her fluffy dog, and traveling to places she's never been before.