From Retail to Tech: Annie’s Journey of Growth and Resilience

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Annie Dean | BJT30 - Main
[00:00:00] Episode Teaser: Career Transitions in Tech
[00:00:00] Annie: it's hard to be the new guy. and so we do mentor matching.
[00:00:03] Annie: We do community supports. We've got like monthly alumni meetups and things because, I almost always get a phone call somewhere between month three and month four. Oh my God, I think I've made a terrible mistake. the training wheels have just come off. They're usually managing their first few accounts.
[00:00:19] Annie: Maybe their first call on their own didn't go well, and they're like, I don't know if I can do this. Maybe I should go back to my other industry, and if we can get them past that hurdle, 30 days later without fail, I'll always get a call like, oh, I was just overreacting. I don't know what I was thinking.
[00:00:33] Annie: I really love my new job. I think it's totally natural. And having a community where there's other people going through something similar is incredibly helpful. So they know they're not alone and they can also see people that are a little farther down the path to envision what it's going to be like for them and inspire them to stick it out through the hard part at the beginning
[00:00:52] Introduction to the Podcast and Guest
[00:00:52] Cesar: [00:01:00] Hey friends, this is our host Cesar Romero, and you are listening to beyond the job title podcast. Where we share the journeys of successful. Underrepresented founders, executives and professionals in tech. Whether you're seeking inspiration, mentorship, or actionable strategies to advance your career. Our podcasts is your go to resource. In this episode, we dive into career transitions and the challenges that can come with breaking into the tech industry. Our guest Annie Dean shares her wealth of experience and the support systems that recast success provides to. Help career transition, nurse break into tech. Especially into customer success. Throughout the episode, we discuss her career journey from retail into tech. The struggles that she faced from overcoming imposter syndrome to recognizing the value of your own unique perspectives as a career transitioner, the power of building community and surrounding yourself with believers. The [00:02:00] importance of mentorship. And so much more. Annie's story. It's a Testament to the power of resiliency and adaptability. And our intention is that. By the end of the episode, you can walk away with some valuable, both lessons on seeking out opportunities that allow you to shine. And push beyond your comfort zone. I hope you enjoy this episode as much as we enjoyed recording it. And if you find it valuable, please. I consider sharing it with your network. Together we can inspire and empower underrepresented professionals in the tech industry. Thank you so much for your continuous support, and please make sure to subscribe so that you don't miss out on any future episodes. And now let's go beyond the job title with Annie Dean.
[00:02:44] Diversity in Tech and Customer Success
[00:02:44] Cesar: why is it important to you to bring in more diverse voices into tech and why customer success?
[00:02:52] Annie: when I was in leadership for quite a long time in customer success, having come from [00:03:00] being a career transitioner myself, I really wanted to bring in more folks that I walked a mile in my customer's shoes, who are reflective of the people they were representing as the voice of the customer.
[00:03:11] Annie: And the industry is not that old, but it has become progressively more and more homogenous. looking at the statistics a few years ago, it was 85, 80 percent white, 85 percent held a college degree or higher. 90 percent lived in a major metro urban area, one of 15, and that's globally.
[00:03:31] Annie: that doesn't represent the customers. and so customer success plays a really critical role in companies of being that voice of the customer, bringing their feedback back, helping to direct the direction of software development and having that all filtered through this really homogenous lens, I think does a big disservice to the
[00:03:52] Cesar: It does. It does. And that statistic is, it's astonishing. and you're right. When your customer base is, diverse, it doesn't make [00:04:00] sense to have a, a non diverse workforce, right? Cause, then they can relate to the customer base. and that's especially in customer success.
[00:04:07] Cesar: And that's critical, right? That's one of the most important things is being able to relate to the customer. Take us back to the
[00:04:12] Annie's Journey into Tech
[00:04:12] Cesar: beginning of your journey into tech, when did this interest started, why pivot into tech and. coming from a non traditional background, why, what prompted that decision to, to make that pivot?
[00:04:27] Annie: Yeah, it's a funny question given my background. I, I remember the moment when I really started thinking about tech differently. I, was probably 21, 22, managing a cost plus store. and. It was a couple weeks before Christmas. It was incredibly busy. You had lines around the corner, lights out the door.
[00:04:49] Annie: and I had been working with this woman had come into my shop in San Francisco from the Gap headquarters, and she designed all of their window displays [00:05:00] and she came in and decided she wanted to order some bamboo blinds for every single store in the United States.
[00:05:06] Annie: and we had been working on this order and I went to put it into the register system so that we could record. It was a 1. 1 million sale, which is, by far the biggest sale any of us had ever seen. and we typed this order into the register system two weeks before Christmas and the register system crashed.
[00:05:28] Annie: not only did it crash for us, it crashed for every single store in the chain, and The registers apparently could only take sales up to 999, 999. 99,none of the information uploaded from the sales up to that point, we had to go back through on paper rolls, And rekey in from our really old register systems, rekey in every single
[00:05:54] Annie: of the busiest days of the year across the entire chain.
[00:05:59] Annie: and so from [00:06:00] that moment on, I really wanted to be more closely involved in what technology was being used, wherever I was in leadership. I didn't immediately leave retail at that point, but I did get much more involved in operations and understanding how to. provide better business requirements as we were choosing software moving forward to make sure that, something like that would never
[00:06:22] Cesar: right. Yeah. technology, It's, it can help you scale and get rid of those headaches. especially, with operations and made the experience better and seamless, And how did you. Get involved in, in, in retail, right? Before, before even thinking about tech, what was your path to retail?
[00:06:43] Cesar: what were some of the, decisions or events that,push you towards that path?
[00:06:49] Annie: Yeah, I, resale wasn't a, wasn't really a career destination for me. I had been attending UC Berkeley,I came from a pretty poor [00:07:00] family and my mother was in an accident and I needed to help take care of her and, didn't have the money to keep going to school full time and working a couple jobs full time and taking care of her.
[00:07:12] Annie: And so I had to drop out of school. luckily I was working at Nordstrom and, as like a cashier at that time, and they immediately drafted me into their leadership development program. and I got a really good crash course on kind of the basics of business and leadership. I was a lady's shoe buyer for a, multi million dollar department by the time I was like 19.
[00:07:35] Annie: And it put me on this path where I had the opportunity to, really understand what made business work from marketing and product selection to HR and operations. and that would serve me really well moving forward and serving customers in tech later. I
[00:07:50] Cesar: And what was it about the way you carry yourself that they notice and they decided, you know what, I think any, it would be a great fit for the leadership development [00:08:00] program.
[00:08:00] Annie: I think it's just because I'm a pain. I don't know. I was seeing things that were, Not operationally efficient and pointing out things that we can improve, or just taking it upon myself. I think a lot of people in those kinds of roles in those stores are looking to get into commission roles and they really just care about sales.
[00:08:17] Annie: I've always had an operators, mindset to things. So I would look at things and go, huh, if we, move this inventory closer to where we needed to get it, we can save everybody, five minutes every time they. They had to run into the stock room. so just thinking about things from that perspective, caught the eye of
[00:08:32] Cesar: Absolutely. And I think he will, he would get the attention of anybody, especially in this job market that is very saturated with. automated applications. I think candidates that, that can, at least point something, hey, I think you can do this better, or I think, I have a better way of, doing X process.
[00:08:54] Cesar: I think that immediately helps you stand out, right? Whether it's as a candidate or even in, in your current [00:09:00] job, right? In your current role, if you're, if you're someone that is constantly looking to improve things, make them better, I think that definitely sets you apart, Do you have,on a, I guess on a tactical level,a way that you approach, how do you identify things that need improvement?
[00:09:18] Cesar: Is it by mere observation or, do you talk to people or a combination of both and what's your process?
[00:09:26] Annie: Yeah. these days running a company and working with a lot of early stage startups and that kind of thing, it's a lot of kind of digging into people's business. one of the first things I usually do when we're working with the early stage founders map out the customer journey and,what team is handing off to, to which team, what systems are they using and how are all those pieces working together to create something really seamless or oftentimes not really seamless and trying to understand where those systems break down.
[00:09:54] Annie: but I think, career transitioners especially are really good at. Approaching things with a [00:10:00] fresh set of eyes, understanding having walked a mile in their customers shoes, really understanding where those pain points might be, and then being able to ask the right questions to understand, how things might be better in the future, and then bringing, hopefully bringing that back to their product teams so that.
[00:10:18] Annie: You can not just better meet your customer's needs today, but you can the Wayne Gretzky saying is, like skate to where the puck is going, understand what might be changing, what pain points could help you get ahead of problems. They may not
[00:10:31] Cesar: yeah, absolutely. it's important to put yourself in a customer's shoes. I think that's the whole game, right? For a customer success, or any role in, in general, I would say when you finally, made a pivot into tech, what was the most unexpected challenge for you,in that first role or, that first fully, tech company.
[00:10:51] Annie: it took me a while to break in. Once I made the decision, I wanted to come over into tech and, I'd run, a hundred million dollar retail business with like [00:11:00] hundreds of employees. And I thought I had really good transferable skills, but I just didn't have a great way to translate those.
[00:11:07] Annie: And so I lost a lot of confidence in the interview process, going through and being told like, no, you're not qualified, that experience doesn't count, I didn't have a college degree, and I was going up against people that, might have an MBA, even for entry level jobs. And so it shook my confidence quite a bit.
[00:11:25] Annie: and so when I first landed my first individual contributor job, like very entry level, working for learning at Cisco, I came into that thinking my opinion was maybe not as important as others. And, thinking I would just keep my head down and try and learn as quickly as possible, which I did try and learn as much as possible.
[00:11:44] Annie: But what I really had to relearn, was that my voice mattered, that I had things I could contribute and that. having a fresh perspective was actually an advantage, not a disadvantage. and so once I got over that initial challenge of doubting [00:12:00] myself so much, it actually was quite lovely to be able to contribute some new things.
[00:12:05] Annie: Cause most of the folks had been there for an average of 15 years. and so being able to approach it, with a fresh set of eyes was, I think, in a collaborative way, it was really helpful for
[00:12:16] Cesar: Yeah, I think that's probably one of the biggest challenges and probably something that you see often right with the recast success alumni, how to talk about your past experiences and your transferable skills in a way that comes across as a strength and as a advantage as opposed to a weakness. And for a lot of people and myself included,It's almost like you, you think that you have to start from scratch, right?
[00:12:46] Cesar: Because you don't have the exact experience in the industry. even you might have been in the workforce for 10, 15 years, but there's something that, sets in, what you said, rejection after [00:13:00] rejection takes a hit on your confidence and then imposter syndrome, Krip skin, and.
[00:13:05] Cesar: I'm curious, right? Do you have a support system in place? Do you have mentors? do you have a network that you can rely on?
[00:13:12] The Importance of Mentorship and Community Support
[00:13:12] Cesar: or was it more of individual effort?
[00:13:16] Annie: Yeah, a lot of what we've built is what I wish I would have had in those early days. So at our company, it is very common, I think, to have to face some level of imposter syndrome. most of the folks coming through our program are coming from being in another industry for. an average of 10 years. and a lot of times they were, they were the one with all the answers.
[00:13:38] Annie: They were the one people came to when they had questions. And going from that to, walking into an industry where you aren't the expert anymore. You've got way more questions than answers, even though we provide them training before they go in. it's hard to be the new guy. and so we do mentor matching.
[00:13:56] Annie: We do community supports. We've got like monthly alumni meetups and [00:14:00] things because, I almost always get a phone call somewhere between month three and month four. Oh my God, I think I've made a terrible mistake. the training wheels have just come off. They're usually managing their first few accounts.
[00:14:12] Annie: Maybe their first call on their own didn't go well, and they're like, I don't know if I can do this. Maybe I should go back to my other industry, and if we can get them past that hurdle, 30 days later without fail, I'll always get a call like, oh, I was just overreacting. I don't know what I was thinking.
[00:14:25] Annie: I really love my new job. I think it's totally natural. And having a community where there's other people going through something similar is incredibly helpful. So they know they're not alone and they can also see people that are a little farther down the path to envision what it's going to be like for them and inspire them to stick it out through the hard part at the beginning
[00:14:45] Cesar: Yeah, absolutely. having that support system and network. it's critical, right? Especially when. Before it gets better, it's going to get worse. And at that point of Oh, I think I made a mistake. That's exactly when you need to double down on your efforts, [00:15:00] because once you get past that hurdle, you come out on the other side, even better.
[00:15:04] Cesar: But typically it's at that point that most people give up, right? a lot of people give up in, in whatever pivot they want to make. Whether it's tech or, maybe another industry,it'll be tough and it'll get tougher before it gets easier. but that's when you rely on your support system, which is why I'm not a big fan of what you're building with, Raycast success.
[00:15:25] Cesar: and speaking of challenges,could you share like, maybe one of the lowest points, And in your career where you felt like to the point of giving up, overwhelmed. By the challenges and questioning yourself. if you made the right decision to pivot into tech,
[00:15:42] Annie: Yeah, I've got like a very crisp image. there was this moment in time where I was sitting in this hotel room in Bangalore, India. I just finished a full shift with my team there. I was about to hop on a call with my team, in the U. S. and Europe. I had probably 10 hours worth of work left to do. [00:16:00] I was still totally jet lagged.
[00:16:02] Annie: I was at LinkedIn, and managing the operational merger of lynda. com and LinkedIn. it's a billion and a half dollar. acquisition. So there's a ton of pressure. we needed some results to talk about our next earnings call. I was leading this very large global team working kind of 24 7.
[00:16:21] Annie: and I realized I had missed calling my son before he left for the day for school. And that was the moment where I was like, one of the reasons I left the retail wholesale world was that You're working every holiday, lots of evenings, lots of weekends. You're on call 24 seven.
[00:16:39] Annie: And it just wasn't the quality of life that I wanted. and as much as I loved, leading large international projects and, all this exciting stuff, what I really enjoyed the most was that building phase, and starting and scaling something quickly, but what I didn't love was that kind of long term.
[00:16:58] Annie: enormous [00:17:00] organization that's like working for the government in a small country or something like Cisco had been where it was like 100, 000 employees. This is not really where I thrive. And so I had to have kind of a moment of realization that just because you can do something doesn't mean you should do it.
[00:17:16] Annie: and take a step back and be a little more reflective with myself about where I'm really the most successful, which for me is much earlier startups. And so that's the moment I made the decision, I'd finished that project out, we immediately got acquired by Microsoft, which seems like a great time to go back to the smaller roots.
[00:17:36] Annie: and just a few months later, I made the hop over to Coursera, which was like a
[00:17:40] Cesar: I love that you mentioned that because a lot of times the advice that, career pivoters get is,for example, If they want to pivot into customer success. Yeah, you should pivot into customer success. But what's lacking is that you also need to have the self awareness of where do [00:18:00] you work your best, right?
[00:18:02] Cesar: It's a big company. It's a small company. It says enterprise customers. It's a small business. And it takes a lot of trial and error and self awareness to, to realize, where's your sweet spot, within tech and within customer success. cause it can be very broad, right. And I think it can be overwhelming also trying to figure that out, On your own. But the tricky part is that nobody can do it for you, except you, right? because. That's just how it works, right? So you gotta do a lot of trial and error and what you said, right? Have the courage to recognize, and have the self awareness that, Hey, this isn't working for me and I think I need to make a pivot within my pivot, if that makes sense.
[00:18:44] Annie: Yeah, no, 100%. And a lot of times career transitioners don't know the questions to ask, right? They just know it's tech. But tech is, 100 billion plus industry, like it encompasses a lot of different flavors. Customer success has, [00:19:00] hundreds of different iterations. And so they may not understand what's the difference between a publicly traded company and a seed Transcribed stage VC.
[00:19:09] Annie: So asking those right questions to find the right spot. Cause sometimes even if they know the answer, like I do really well on a team of this size under this kind of a leader with this kind of a culture, they don't know how to determine how to identify the companies that fit that bill. and so that one of the things that.
[00:19:28] Annie: I think it's really important to find mentorship or find experts in the industry who can help you navigate that and say, if you, a lot of times people come to us and they go, Oh, we want to work for the really big companies because we want to have a career path forward and we want career stability, and somebody in the industry may be able to say okay, 90 percent of the tech layoffs came from the top 10 largest companies.
[00:19:50] Annie: and. if you look at career progression actually happens way faster in a small earlier stage company where kind of the tide raises all ships than in these [00:20:00] large companies that have a lot more competition for every single role. and. Like really well defined HR bands and things like that, where it's a slow progression into the upper ranks of leadership there that can take a decade where you might be able to go to an earlier startup and be in one of those roles in two or three years.
[00:20:21] Annie: and so having that insider insight can be really helpful
[00:20:24] Cesar: Absolutely. And there's two things that you mentioned here. one is questions to ask yourself and the second one around mentors and mentorship. And, I'm curious, what were some of those questions that you asked yourself, when you were at Linda that eventually led you to Coursera, what were some of the questions you asked, some of the, criteria that you came up with?
[00:20:46] Cesar: Maybe if you have any, strategies or frameworks that you can share,for someone that might be in a similar position, Trying to figure it out. what type of company and role they might be, best suited for [00:21:00] and. what, mentors or role models, can they look up to, as they're trying to navigate this path,
[00:21:07] Annie: Yeah, I took a weird approach to this. I don't know if this is the right approach. I'm sure there's like career counselor kind of people that have like whole programs on this, but,I'd worked at that point in a number of different roles, even though they mostly were in the retail wholesale world.
[00:21:23] Annie: but I just went back through every role I'd had and. What were the key skills that I got to use what I liked about the role and what I didn't like about the role Which helped me create a vision for myself of what were the trends like where did I where was I really? unhappy And where was I most likely to be happy and what skills did I have that?
[00:21:43] Annie: I really felt like I needed to be putting to use And so that had really helped me figure out like LinkedIn was one of the first was probably the first company I ever worked for that was really mission driven, where I felt like I was having a greater impact on the world than just [00:22:00] creating money for shareholders.
[00:22:02] Annie: Like in the retail world, you're just, you're selling a lot of stuff for the sake of selling a lot of stuff. I was working with talent acquisition. So helping people find jobs, and connecting the right talent with the right opportunity, being able to contribute to a bigger mission was really.
[00:22:16] Annie: Something that I didn't want to give back up. and so every job since then, I've made sure that, I really felt strongly that it was a mission I could get behind, keep myself motivated. I also really, there are certain kinds of leaders that I really thrive under, and had the opportunity to work with some pretty amazing role models and some mentors over the years.
[00:22:36] Annie: Alessandra Marionetti is what I'll call out. She's a dear friend who is my counterpart at LinkedIn. She used to be,run education programs for the United Nations before she went into customer education. she met, she's now leading, customer education for Asana. but she, really helped me see how to collaborate and how to put the right information in front of the right.
[00:22:59] Annie: [00:23:00] People in a way they're really going to retain and understand. and I've also had the chance to work with some pretty amazing customers. Pretty inspirational. one that really stands out is,Bernard, Tyson, who was a former CEO at Kaiser, just his commitment to putting his patients first at putting your end users, your customers first as a leader, and as a business, having that at the heart.
[00:23:25] Annie: I really wanted to work places where I'd have the opportunity to work with pretty amazing
[00:23:29] Cesar: I love that. And I love that you give shout out to, to, specific people, Alessandra and Bernard, And it's important, Because, I'm a big believer that there's no such thing as self made, I think all of us, Need help at different points throughout our career, right? And being humble enough to know that and to receive, the coaching or the advice, when it, when is well intentioned, right?
[00:23:54] Cesar: when you can see that the other person really cares about your growth. I think that's, that's,underrated, Success [00:24:00] hack, having people in your corner that are really rooting for you. And I really care about your next step, the next step in your career.
[00:24:09] Annie: Yeah, a hundred percent. I'm so grateful we have this mentor network. They're all volunteers, probably a couple hundred people. Most of them are CS leaders and a lot of them just want to give back, they feel passionately that customer success should be more diverse. But, early days, we were all career transitioners because the industry didn't exist before.
[00:24:29] Annie: and so a lot of us old timers, have been around for 10 to 15 years. we've seen this progression in the industry where, people who come from the field are less and less prevalent. And We want to give back and open doors to folks that better represent customers in general and having someone like that who isn't associated with your company, they have, their only interest is in helping you thrive as a person, is incredibly powerful.
[00:24:55] Annie: And I'm so grateful to all of the folks who volunteer and, take on. [00:25:00] A career transition or to help them find their place in the customer success world and feel that sense of belonging, even if they may be the minority in
[00:25:10] Cesar: Yes,people that want to give back, those, they deserve a special place in heaven.
[00:25:16] Annie: Yes,
[00:25:16] Cesar: your experience is so rich and diverse, right? living on a farm, you also are a native sign language speaker, you're a world traveler, former chef's apprentice, and I'm curious how, all of these experiences,
[00:25:30] Cesar: influenced your perspective and approach, right? in your career, in your personal life,and especially in customer success.
[00:25:39] Annie: yeah, let me break those apart. Maybe a little bit of the living on a farm part. So the way that really impacted my career was, I wanted to found a company for a very long time, but,I guess some of that imposter syndrome as well, looking at it as a woman as a middle aged person, whatever, from a [00:26:00] venture capital perspective, women only get about 4 percent of VC deals, and 2 percent of VC capital, which means that you're very unlikely to get the funding that you need to start a company.
[00:26:14] Annie: and, I maybe didn't have enough perspective back then to really understand that VC is not the only path and it's not always the right path for everyone. and so I waited for a really long time before founding a company. And part of what allowed me to do that was, living in the Bay Area, you definitely need a couple salaries or more just to survive.
[00:26:35] Annie: and so starting a company without having to take VC meant that I needed a long enough runway to really get my company up and running. and moving out to the country allowed me to do that.
[00:26:47] Moving and Adapting: A Founder's Journey
[00:26:47] Annie: selling my home in the Bay Area. Moving out towards Yosemite, it's also beautiful, and it's a much more serene way if you're going to be a founder under a lot of stress,
[00:26:56] Annie: that's how that impacted my career.
[00:26:59] Sign Language and Customer Success: An Unexpected Connection
[00:26:59] Annie: I'll [00:27:00] say, sign language, I think, started setting me up for customer success from the time I was a really little child. I had,I was born into a family that had adopted three deaf boys, who were 16 years older than me, and so from the time I was old enough, sign language was our primary language in my household growing up.
[00:27:24] Annie: and from the time I was old enough to start learning English as well, I would often be tasked with going out and being their interpreters. So taking them to doctor's appointments or accompanying them to doctor's appointments or, school meetings or,whatever, grocery stores, whatever they needed.
[00:27:42] Annie: and so I started building those skills of how to interpret from one culture and one language to another. from the time I was, maybe three or four. And I think in customer success, that's a really important skill that we use as well. Just like, [00:28:00] how do you talk to a customer, hear their pain points and interpret those in a way that really is going to resonate.
[00:28:07] Annie: Back with your software engineering teams, engineers speak a totally different language to, and so that ability to get at the root cause. It's not translation. It's interpreting, right? It's, what's the underlying concepts? and then how do you communicate that? in a way to each audience that they're going to understand.
[00:28:23] Annie: and so I think that kind of got in my blood early and it's been something that
[00:28:27] Cesar: that.
[00:28:27] The Sacrifices of Founding a Startup
[00:28:27] Cesar: And talk about making sacrifices to bring forth the kind of change you want to see in the world, right? Like selling your home and moving to a farm in a country, to give yourself runway to, to build a business. And to fulfill your vision and your mission. I think a lot of people sometimes feel trapped in, in their routine, in their, lifestyle.
[00:28:51] Cesar: but they don't realize that,you can always make a change, right? Even if it's like a short term sacrifice. maybe I have to sacrifice living in a city for the [00:29:00] next. Three years, right? But that means that I'll have the runway and the bandwidth to, build my business or, maybe my next move.
[00:29:09] Cesar: so I think that's so important. And I think, we need to talk more about that. cause,on social media, all you'll see is the highlight reels of people having their best time. Sometimes it's Oh my God, what's going on.
[00:29:21] The Reality of Founding Companies and Venture Capital
[00:29:21] Annie: the story we tell about founding companies is not really a representative story, right? It's here is the way that, the privileged few start companies. That's not the only way, right? I think venture capital has its place, it's giving up big, a big piece of the leadership in your company and giving up, equity so that what you're building, you're working really hard.
[00:29:50] Annie: A lot of times founders are, significantly underpaid, for years and years. In return, they're getting equity in their own company, but they're having to keep giving that [00:30:00] equity away just to keep raising the next round. and when we celebrate, Hey, they raised a round.
[00:30:05] Annie: Good job. You're like, you know, me that opens some doors, but it's not necessarily, like the pinnacle of what everyone should be trying to achieve. If, underrepresented founders have a great idea, a mission they really care about, they're willing to make some sacrifices. the sacrifices don't have to go to venture capital.
[00:30:26] Annie: Those sacrifices really could be reinvested in building their vision and supporting their end users without the oversight of a venture capital company. Cause it's been really lovely. it's just me and my co founder,she's also been in this space for a really long time.
[00:30:41] Annie: There's no one telling us, Hey, you have to, you can't offer this service. That's not that profitable, but it's really tightly aligned with your mission. because we're, we want you to make more money. We don't have to push back on our decisions. We can just make the decisions we feel like are in the best interest of our customers.
[00:30:57] Annie: and it's been really liberating
[00:30:59] Cesar: having [00:31:00] complete ownership of the direction of the company and the impact they want to make and not having to raise money. I think it's a, total freedom right there. And, but, I think the message out there is that, VC racing VC money is. Like sexy and that it's,the only way to grow and scale, that's not true in my opinion.
[00:31:23] Cesar: one of the best ways to grow is customer success, right? you get to retain the customers and expand those accounts.
[00:31:29] Annie: A hundred percent. Yes.
[00:31:31] Cesar: since we weren't on the
[00:31:32] Navigating Gender Bias and Discrimination in Tech
[00:31:32] Cesar: topic, before we transition into, the last segment here, I want to ask you about, gender bias and discrimination, especially in tech and with. With women, right? That's unfortunately, that's very in tech. and I want to ask you if you ever experienced, any of, gender biases or discrimination, or any advice that you would have to, women professionals or, women in leadership positions as how to navigate, that,I guess a [00:32:00] delicate balance between, being assertive, but also, knowing how to navigate, the politics that can happen within an enterprise.
[00:32:09] Annie: Yeah, it can be especially complicated in customer success. I've definitely been the only female on the leadership team at several startups now, which, I think respect is something that's earned and not given. And that's especially true if you're from an underrepresented population.
[00:32:29] Annie: and so sometimes Have to learn very quickly. I think knowledge is power. So the more you can talk in the language of the people that you're trying to get your message across to. if I'm talking to a CTO,I've taken the time to understand enough of the technical underlying concepts that I can hold my own in a conversation where they're going to respect what my opinion is, it's harder with customers.
[00:32:54] Annie: so for example, I was an executive for a company that did safety [00:33:00] software, primarily with, transportation, logistics and manufacturing companies. And there was at one point I took a step back and I was like, I have done executive business reviews across 15 states, with all these enterprise companies.
[00:33:14] Annie: I've been the only woman in the room for the last four weeks straight,hundreds of executives. I. I remember launching our program, with the Merchant Marines, and being at the docks in New Jersey, where I was definitely the only female on the dock, maybe the only female to ever be on the dock there, I'm not sure, and I had someone with me who was a brand new hire who was just shadowing along with me.
[00:33:39] Annie: who'd been on the job for about two weeks and the head of the union would not talk to me. He would ask the question to this gentleman, new hire of mine And this guy josh would turn to me and be like annie
[00:33:53] Cesar: That's crazy.
[00:33:54] Annie: the expert you tell us, and we walked around everyone else in the group, you know By the end of that i'd [00:34:00] won him over and Over the next months and years, we actually became friends, but, sometimes it really takes having a lot of patience trying.
[00:34:08] Annie: Not to take things too personally, and making sure that you've really got your ducks in a row. So you're earning that respect, even if you have to work twice as hard to earn it, which is unfortunate that we have to do that. And I think over time, that hopefully will shift seeing positive.
[00:34:24] Annie: Positive movements in the right direction. Unfortunately, a lot of the tech layoffs, the statistics show that, women and especially women in leadership, and minorities in general, have been hardest hit by the tech layoffs. So I'm hoping we don't lose too much ground there. But I'm, confident that over time, if you look at where we are now, compared to where we were like 15 years ago, I think we're
[00:34:44] Cesar: We're definitely making progress. And this is why, companies that recast success, podcasts like this one, where we help elevate, the stories of underrepresented professionals and help people, make a pivot into tech. I think it's more important than ever, [00:35:00] to be the advocates, of diversity and inclusion.
[00:35:04] The Birth and Evolution of Recast Success
[00:35:04] Cesar: And Man, I wanted to ask you something, but I think it's, I think it's related to, with recast success, right? So it's been going on for two and a half years, right? give and take. And I was curious about the moment where you decided to commit, fully commit to recast, recast success. what was the moment like, what was going through your mind?
[00:35:31] Cesar: and. And what were some of the, what was the vision initially? Has that vision changed, over the past two and a half years,
[00:35:41] Annie: I was incredibly lucky to have an amazing co founder, who was somebody had already known for several years. And I remember very vividly this conversation we had, it was the middle of the COVID pandemic. Everyone had been in lockdown. I hadn't seen her in well over a year.
[00:35:59] Annie: she'd [00:36:00] had a baby since then. and she called me up and was like, Hey, I am leaving my company. I just don't want to do this anymore. And I said, What are you going to do next? And she said, I really don't know. And I said, she's if you can do anything, what would you do? And I was like, I would love to found my own company.
[00:36:20] Annie: And she's okay, let's do it. I'm like, I have a full time executive. I live in the Bay area. Cost of living is high. Like I can't just quit my job. it's going to be hard to fundraise all those things. And she's okay, I'll tell you what I'll. Let's come up with this company together and we'll beta test it.
[00:36:35] Annie: I'll work on this full time for six months. And if our beta goes well, you'll come join me in January. and so I helped her kind of evenings and weekends, to build out a beta. We put a posting on LinkedIn, Hey, any career transitioners do want help breaking into tech? But one post on LinkedIn, we had 30 people apply to the program that day.
[00:36:56] Annie: and so we ran our beta test. Almost everyone had a job [00:37:00] within a couple weeks of graduation. and so I said, you know what, I think you're right. So put my house up for sale, moved out to the country and really haven't looked back. It has changed a bit over time. It originally was just the boot camp. as we had grads who were, we, we trained them in a 10 week program as we had grads joining companies, we had companies reaching out to us and saying, these people are incredibly well trained, could you put together a training program for the rest of our employees?
[00:37:29] Annie: And so we branched off into that. And then over the last, year or so. We also started a fractional head of success program because we had a lot of early stage founders, especially underrepresented founders who we tend to work with a lot, who, we're starting customer success from scratch. And they were looking to hire someone who just graduated from the program who'd come in with no oversight, no managers, no, no, the infrastructure in place to really make them successful, or they were looking to hire one of our [00:38:00] volunteer mentors who is really experienced to just come work in the trenches.
[00:38:03] Annie: And we're like, that's not the best, that's not the best for an IC or a super senior person. Why don't we do something that's best of both worlds? And so we spun off a fractional head of success program, where they get a leader one day a week and a full time individual contributor who's.
[00:38:19] Annie: Ben's got like the oversight and stuff they need to be successful. not where I thought this would go at all. but it's been really fortuitous as the job market's gotten more challenging, and it takes more time to get people new roles, especially as career transitioners. this has given us the runway to be able to continue supporting those folks, cause we typically, we set it up where we don't get paid until they get a job, and so this has given us enough, operating capital and we're still able to make the impact that we want to make, not have to sacrifice our mission, but can still, also help, additional
[00:38:50] Cesar: Absolutely. And it's all at the core of customer success, right? Listening to, to the customers, to the market, what are some of the needs or the gaps that you [00:39:00] can seize in and capitalize on,like a fractional. The customer success or doing trainings for companies. and always paying attention to what the customer needs and where the market's going.
[00:39:13] Cesar: I think it's,fundamental, for the success of any company.
[00:39:17] The Future of Tech and Underrepresented Professionals
[00:39:17] Cesar: So what's next for you professionally and, how do you envision, what's your vision for the future of tech, for underrepresented professionals,
[00:39:28] Annie: Yeah. Our vision is, as we're working with early stage founders, creating a culture from the very beginning that embraces, diversity at its core. getting to work with early stage founders who then go on to be really successful, we're hoping we build more community that is invested in our vision, Being able to bring diverse voices into the tech industry, not just in engineering, which a lot of companies, their DEI initiatives are only focused on engineering, which engineers just build what they're told to build, right?
[00:39:57] Annie: the people who are calling the shots are the ones who [00:40:00] really need to be,representative of the customers that they serve. we're really excited to work with early stage founders in this way, and to continue to help career transitioners,potentially across More levels of roles and customer success right now.
[00:40:14] Annie: We're really focused on that mid career But the more we can help support, entry stage we launched an apprenticeship program fairly recently for recent college grads who are first in their family to graduate from university training them and putting them in six month and apprenticeships for digital customer success.
[00:40:31] Annie: and so we'd love to see that expand to help with diversity across the industry as well as upscaling into digital success, which is a
[00:40:38] Cesar: Yeah. It's a big need, especially as, technology changes, AI is more prevalent. I think, giving people and professionals, the. The tools to, to pivot and to make changes and to continue growing in their careers. I think it's just going to become, even more, more critical, right?
[00:40:58] Cesar: so companies like Rick has [00:41:00] success. I think, you're definitely on the, on that path of helping people, not get, left behind, by. By the constant waves of change and disruption, especially with technology.
[00:41:12] Annie: Yeah, I'm so excited about some of the AI things that are coming to the industry. I think it's a really game changing. I think most of them aren't quite there yet, but it's not going to be. It's not far off. It's,
[00:41:23] Cesar: Yeah. It's scary, but exciting.
[00:41:26] Annie: And yeah, no, I am super excited by it. We're spending so much time right now, just demoing and talking to early stage founders and understanding what's coming and what's next.
[00:41:36] Annie: and I personally spend a lot of time A lot of the technology that is most useful for customer success isn't being built for us. which I think for a long time, the industry, even now, like less than half of customer success managers have access to a CSP, a customer success platform. so they're repurposing technology that's built for other teams and then just trying to hack it into [00:42:00] doing what they're to meet their needs.
[00:42:02] Annie: and so I'm spending a lot of time pushing in the industry. to get folks thinking about customer success earlier and not just building for sales, building for marketing, but building for the use cases that the majority of revenue in the SAS industry is recurring revenue, renewal revenue.
[00:42:18] Annie: and so if we can get past this growth at all costs mentality and start investing in where, most of the business actually lies, we could be.
[00:42:28] Annie: Building to suit tools that are really going to be transformative
[00:42:32] Cesar: So this day I still don't understand, right? Cause I learned that, my, my parents taught me that, Hey, if keeping a customer is 10 X more profitable,and I just made the number up, it's more profitable than. Getting a new customer. and I don't know.
[00:42:46] Cesar: I feel like that's a fundamental business But I don't know what happened in tech. It's I don't know I guess what you said right growth at all costs which is not a recipe for sustainable long [00:43:00] term success
[00:43:01] Annie: Yeah. Which is why we're having such a big market calibration, right? Like people were building
[00:43:06] Cesar: Yes,
[00:43:07] Annie: was best for VCs, VCs want you to grow to a certain rate so you can get a certain valuation so they can get their money back as quickly as possible. that's not necessarily, and in most cases it's not just period the right.
[00:43:20] Annie: Long term recipe for unit economics and profitability and, a sustainable business. and so they build like crazy all rapid growth, and then they go IPO. And then all they have to completely reset because everything they've learned up to that point is actually not sustainable and will quickly crush a publicly traded company that doesn't have this constant influx of more capital.
[00:43:43] Annie: And so this market reset of it being much more challenging to raise VC in general, is forcing earlier stage companies to really think about how to be profitable, how to extend runway, not just to raise more, but be a responsible and sustainable company. and so it's really [00:44:00] shifting a lot of the responsibilities of customer success teams, and forcing them to learn new skills that they
[00:44:05] Cesar: Absolutely. yeah, I think it's,I'm excited for the next stage. after this, correction is done, cause you're going to see some companies really start with the right foot on the ground, keeping sustainability in mind, over. Cause, awesome. And it, I want to switch to the, second of the episode where I like to call it rapid fire closing.
[00:44:27] Cesar: And I basically ask you a question and you give me your top of mind, 30 to 60 second answer. And let's do it. And the first question I wanted to ask you is, do you have a book that has greatly impacted your life?
[00:44:43] Annie: One of our mentors recommended thank you for the feedback. Which I absolutely love. I don't remember off the top of my head who wrote it. but it's really about in all areas of your life, it can be really useful. It's asking the right questions and how to frame feedback, [00:45:00] constructive feedback, in a really positive light.
[00:45:02] Annie: I think it's super helpful
[00:45:03] Annie: Yes, feedback is, I feel like it's underrated, giving it and receiving it. I think it's important to, to learn that skill. So I'll definitely add that to my ever growing book list. thanks for sharing. Second question here. one of the most impactful travel experiences. travel. I think it's funny. I think it was, I was staying at Airbnb in Sweden and talking to the host. I had been there for work. Before Ed was coming back for a personal and was like, man, I really wish I had more time to spend getting to know the city. And he's why do you have such a limited amount of time?
[00:45:35] Annie: I'm like,we only take off a week or two a year and he was just like why? it just helped me reframe the whole work life balance from a PTO perspective, especially it was just like This is an American thing, and it's not healthy. I'm like, huh, now that you mention it, yeah.
[00:45:53] Annie: try to actually unplug now when I go on vacation, which I absolutely didn't used to do. and try and make sure [00:46:00] that I'm taking a healthy amount, and really being intentional about getting a
[00:46:03] Cesar: being open
[00:46:04] Annie: and then.
[00:46:05] Cesar: shift in perspective, especially when you travel. I think it's super powerful and very underrated. Awesome. Next question. Quote that you think of often or a mantra that you live your life by.
[00:46:21] Annie: I find myself saying this every now and then. If you find yourself in a hole, stop digging. which I think was said by Wilt Rogers. I just, I think a lot of people, that sunk cost fallacy, right? you've put a lot of effort into something, it's not working.
[00:46:37] Annie: And they'll just keep going after it just because they've already put a lot of effort into it. And I think, especially being an early stage founder, it's really important to be able to admit when you're wrong. have an open growth mindset where you're like, what can we learn from this? What can we do differently next time?
[00:46:53] Annie: Instead of just trying to pound a square peg into a round hole.
[00:46:57] Cesar: yes, that's so important. I make that mistake [00:47:00] often. I relate to it so much. over, over the last year, is there a habit that you have implemented that you have seen the, I guess the impact or the ROI of, Implementing this new habit into your work, life, or I guess professional life.
[00:47:18] Annie: Yeah, I think this is a good example of this. I was talking to you today. I hate public speaking, but I, and I would always defer to people on my team, who were better at it, who enjoyed it more. but I think, one of the habits that I've changed this year is trying to say yes to be a better representative of the causes that I really care about and let people hear it directly from my mouth, even if I'm not the most eloquent one to probably be representing it.
[00:47:48] Annie: I think it's. It's good to hear from some other voices in the industry occasionally. So even if I'm not like a, an official influencer, using [00:48:00] encouraging myself to, to be open to saying yes, to actually sharing my voice with people who want to
[00:48:04] Cesar: That's amazing. And kudos to you for stepping outside the comfort zone, right? It takes a lot of growth and, yeah, especially for reaching out. And one thing I've found out. One, one thing I'm finding out is that I'm becoming this, a resource for, for people that want to have a platform where they can come in and practice their story, and practice their, public speaking, cause someone told me the other day that, Hey, thanks so much, this is like my, I think it was, it's the second or third podcast that she did.
[00:48:38] Cesar: And she was like, yeah. the more I do of this, the more comfortable I'm getting in my own voice and it just felt good to know that, I'm Part of that journey and I hadn't even considered that, some guests, might not be,might not be their prefer way of sharing their story, and helping them step outside that, that comfort zone.[00:49:00]
[00:49:00] Cesar: I think it's also part of the reward here, when, whenever I guess comes along, helping them feel comfortable and that they can share their story right with, with the audience.
[00:49:09] Annie: you're really, you're very natural and easy to talk to. So you make this easy. and I know a whole lot of people that have pretty amazing career transition stories. but part of what inspired me was, thinking back to when I was questioning whether to start a company or not, I would have loved to hear from somebody with a story like this that showed.
[00:49:29] Annie: It could actually be done and, taking some of that fear away. So I figure if I can pay it forward a little bit, I'm happy to do it. And I'm really glad that you have a platform like this that helps
[00:49:38] Cesar: yeah, absolutely. stories are powerful, right? And if we can find someone that we can relate to, right? Because then the person listening to your story can say, man, my story is so similar. And then if any can do it, then maybe I have a shot, right? So that's the goal here. thanks so much for coming on the show.
[00:49:58] Cesar: And, one last question I have for [00:50:00] you here, looking back at your incredible journey. what's one of the most valuable lessons you've That you would like to share with listeners, especially, from underrepresented backgrounds and are looking to break, to overcome challenges, just like you did
[00:50:15] Annie: I'd say, look for the situations that really help you to shine and help you to thrive and push yourself even when it's uncomfortable. That's where real growth comes from. If you're not feeling imposter syndrome at some point, then you're probably not taking big enough risks,get outside your comfort zone and, be open to learning and,
[00:50:38] Cesar: awesome. thanks Annie for coming on the show, sharing your story and helping other underrepresented professionals, get inspired and motivated, to go after their goals and dreams, especially, if they're making. Considering making a pivot into tech or growing within their tech career.
[00:50:56] Cesar: thanks so much. And, yeah, it's been fun.
[00:50:59] Annie: Thank you for having [00:51:00] me.
[00:51:00] Cesar: all right. I hope you enjoyed this episode and thank you so much for listening all the way through. I appreciate you. And I hope that you get some valuable information that you can apply to our personal and professional life. If this story resonated with you and you would like to support the podcast.
[00:51:23] Cesar: Please make sure to subscribe. So you don't miss out on any future episodes. Thank you so much for the opportunity. I appreciate you. And I look forward to serving you in the next episode.

Creators and Guests

Cesar Romero
Cesar Romero
Helping startups and SMBs build strong customer relationships that drive product adoption, reduce churn, and increase revenue | Community-Driven | Podcast Host
Annie Dean
Annie Dean
B2B SaaS Sr. Exec - Customer Success Expert - Entrepreneur - Ex-LinkedIn
From Retail to Tech: Annie’s Journey of Growth and Resilience
Broadcast by