How I Got Hired in Product with Amy O’Callaghan

Tim Winkler: 00:00:00

Hey, listeners, Tim Winkler here, your host of The Pair Program. We've got exciting news introducing our latest partner series Beyond the Program. In these special episodes, we're passing the mic to some of our savvy former guests who are returning as guest hosts, get ready for unfiltered conversations, exclusive insights, and unexpected twist as our alumni pair up with their chosen guest. Each guest host is a trailblazing expert in a unique technical field. Think data, product management, and engineering, all with a keen focus on startups and career growth. Look out for these bonus episodes dropping every other week, bridging the gaps between our traditional pair program episodes. So buckle up and get ready to venture beyond the program. Enjoy.

Becca Moran: 00:00:53

I'm Becca, and this is How I Got Hired. How I Got Hired is a series of interviews where product managers share how they landed great product roles from PMs who made a career pivot into tech to those with more formal training. How I Got Hired captures the various ways to open doors into the world of product. We'll be talking about each guest's recipe for success, what motivated them to get into product, how they prepared for the interview, and what they

Amy O'Callaghan: 00:01:20

did to set themselves apart.

Becca Moran: 00:01:25

Today, my guest is Amy Hoek Callaghan. Amy is a product veteran with over 10 years of experience. Amy started in product at Snagajob, who we'll talk about today, then worked for Launch Media, CarMax, and was most recently VP of product

Amy O'Callaghan: 00:01:42

at Vanks.

Becca Moran: 00:01:44

A talent marketplace for the regulated cannabis industry. Amy, welcome to the

Amy O'Callaghan: 00:01:49

show. Thank you so much for having me, Becca. I'm really excited to get to talk with you today.

Becca Moran: 00:01:55

I'm excited too. Um, so for listeners, um, Amy and I have not had the opportunity to work together yet. Hopefully maybe one day in the future. Um, but we were introduced by my boss a few years ago, and I've always really admired, uh, the work that you've done, Amy. Um, thought that others would enjoy hearing about your unique product journey and, and learning from you. So excited to get into it. Um, okay. So I thought of a fun way to get started just to give a little bit of a color to, to who you are, uh, and continue to share fun or embarrassing facts about myself. would be to do a little bit of two truths and a lie. So, um, I can, I can kick us off, uh, with my

Amy O'Callaghan: 00:02:48

list this time. I'm exceptionally bad at telling when people are lying, so this is always great for the person playing with me.

Becca Moran: 00:02:55

I, um, I'm, I'm not sure I'm a good liar, but I really, I probably put way too much thought into what these should be. You're a great

Amy O'Callaghan: 00:03:06

strategist. Yes. I, exactly.

Becca Moran: 00:03:09

Um, and, uh, yeah, so I, there's a theme to these. Um, okay. So number one, I have won multiple first place ribbons for showing dairy goats.

Amy O'Callaghan: 00:03:23

Number

Becca Moran: 00:03:23

two, I have ridden a horse around the grounds of Versailles. And number three, I grew up on

Amy O'Callaghan: 00:03:32

a 200 acre farm. Hmm. I'm gonna say, uh, you have not ridden a horse around the grounds of Versailles. You would be wrong.

Becca Moran: 00:03:47

So cool! Um, that was an incredible experience, uh, totally random, just like found this thing online and,

Amy O'Callaghan: 00:03:57

um, The reason I picked that one because I was like, that's a historic property. There's no way they're letting tourists clip clop around. But I found

Becca Moran: 00:04:04

somebody on TripAdvisor that, um, does these tours and, um, it was an incredible experience. But, uh, the, the lie is maybe the most. You would think as someone who rides horses and shown dairy goats that I would have grown up on a farm and in fact, I grew up all over the place, but mostly in like suburban New Jersey. So,

Amy O'Callaghan: 00:04:28

oh, my goodness. I have a great fondness for goats. I have never shown them, uh, won any ribbons on their account. Uh, but one of the developers in my last company had a farm that he was working from and he had a live goat cam going in our slack channel. So anytime you just needed like a pick me up, you could hit the goat cam. It's amazing. They're so

Becca Moran: 00:04:49

sweet and so fun and what's not

Amy O'Callaghan: 00:04:52

to love. So, all right. All right. I, I think mine, there is significantly less detail though. Um, So, all of these are things I am claiming that I have done one time. Skydiving, mountain climbing, motorcycling. Ooh,

Becca Moran: 00:05:18

I'm gonna say motorcycling?

Amy O'Callaghan: 00:05:24

That is the lie. Cause I used to motorcycle way more than once. I don't know if

Becca Moran: 00:05:30

that was what I was thinking, but

Amy O'Callaghan: 00:05:34

yeah, the original I was going to do is I have an intense fear of heights. I have climbed a mountain and I've been skydiving. And I'm like, no, those are all true. I can't do that. I've got a lion. What's a cool way to lie and make myself sound cooler. But yeah, no, actually I went through a motorcycling phase up for kids. And now the gear is actually directly above my head in the attic because I spent months finding women's riding gear that was neither pink nor glittery, nor in blinds with, you know, hearts or butterflies. So that's the one thing I sold the bike. Do you still have a bike? Okay. I don't know for right now, I'm like, all right. The plan, because I too am strateging, uh, strategering, is that, uh, when my kids get to the age where they think everything I do is lame, I'll bring a bike back in, and then either they'll think motorcycles are lame, which is a great win for me as their parents, or they'll think I'm cool. Like, one of those two things has to become true. And either one of them is great for me. Yes,

Becca Moran: 00:06:30

um, my mom actually used to ride motorcycles, um, broke both of her legs, thankfully not at the same time. Um, although I don't know how much does that matter. Um, yeah,

Amy O'Callaghan: 00:06:44

yeah, it was a, you know what? It was a risk assessment. It was a basic risk assessment. I was like, all right, uh, you know, if I'm out of commission, these kids are going to be in a pickle, so I can at least wait, you know, 20, 25 years to get back on, I

Becca Moran: 00:06:58

think my mother made the same kind of calculation. So, uh, thank you on behalf

Amy O'Callaghan: 00:07:03

of your children. Absolutely.

Becca Moran: 00:07:06

Well, awesome. Um, so let's get into it. I think, um, a great place to start is at the beginning. So, um, And I think the story we want to talk about today really is how you got into your first product role, which I think is super cool. And there's so many different ways, um, to get into product. And I love hearing people's different stories. So. Maybe we can just kind of start there and start with, um, you know, what did, what did your early, very early career look like? What were you doing right before you ended up transitioning into a

Amy O'Callaghan: 00:07:48

product role? Yeah. Um, that's a great question, especially, I think it's been fascinating to watch how The types of beginnings people have in a product career have shifted over the years, right? Because when I got into product, there was no product level training at college or university. Those things didn't exist, right? Like the only way in was really to kind of get adopted by an organization that was doing it. Um, I, uh, speaking of college and university, I went to school for, uh, a very practical bachelor of fine arts in animation because I was convinced I was going to go be a video game animator. Um, but it's

Becca Moran: 00:08:26

interesting because I was looking at your LinkedIn and I literally had to Google what is it called? Kinetic kinetic

Amy O'Callaghan: 00:08:32

imaging. Yeah. Well, that's because I went to an art school and they wanted the fanciest way possible to say animation. Um, yeah, I rarely actually put my major on. I'm like, I just have a BFA. Don't worry about it. Um, yeah, so I had an internship though while I was in school and that was in web design. Um, so when I graduated, I actually stayed in a small web design firm for a little while. It wasn't a lot of mobility though. It was a great opportunity to kind of learn everything, touch everything, do some basic front end coding, get some account management under my arms. Um, eventually I wanted to move on to a bigger place. So after six years there, um, I transitioned to snag a job, which was my first real like corporate experience. Um, they were a good midsize startup at that point. Um, I think I was higher number 256. So, you know, good midsize company, um, lots of good practice in place. And they were one of the first organizations in Richmond, especially to be doing product management. Um, I joined as, um, somebody who was working in their marketing department. And as I got kind of my hands into the business, like understood from my little vantage point where the problems were, I eventually worked my way into being, um, social media manager there. And social media management is great. Because it is basically one long user interview all day long, uh, often with the extremes of your user base, right? You're getting the people who are really happy and you're getting the people who are really mad. And they're all talking about it real time on Twitter or Facebook or, you know, today Instagram, but it was, it was wild, but it was great. It was the perfect kind of immersion. And just hearing the problems and the successes over and over and over again. Um, and so I. I would not have had the language to phrase it this way, but what happened was I just started hearing the problems that I was kind of fixing one off one at a time, doing my best to solve the problem for each individual user, and I sort of followed those problems upstream into the product experience where they were happening and tried to figure out. Well, what change could we make that would solve this problem and prevent it from ever hitting social media? Right? And I would put together absolutely gorgeous mock ups in a program called MS Paint that hopefully no one actually knows about anymore. And, um, send them along with my idea and proposal by email over to our team of product managers who I had met on my first, like, building tour. And I was like, Oh my God, the cool people are over there. Um, and I would just email them all my ideas. Um, and eventually I sent exactly enough emails and I don't know what the number is. Otherwise I would share that. I wouldn't gate keep that kind of knowledge. Um, but they were like, Hey, we should just train her to be an associate PM. Um, and so like, there wasn't even really a rec open. Um, it was really just kind of putting myself in a place where I was consistently demonstrating the, um, the affinity and the skills of an associate PM and making that knowledge. Open to the product team, right? Like I know a lot of incredible people who I think could make great product managers who are kind of doing that in their own space, but it never reaches the product team. And so we don't know to reach out like the claw and drag them into product and make them one of us like weird tech zombies. Um, but I think that was the thing that helped was that I was doing that work, but then I was sharing it with them. And so they had visibility into what I was doing and thought that it was a good opportunity for me. Um, so there was some conversations between the head of product and the head of marketing and they kind of did a little work around like how we were going to make that transition. Um, but ultimately that was a really, really seamless one for me. That's super interesting.

Becca Moran: 00:12:21

And I, I love the way that you described that as kind of like going upstream. I think that's really at the heart of like kind of what makes someone a product person, right? That you're like, okay, I'm, I'm not satisfied just kind of treating the symptom of this problem. Like I want to go to. The heart of it and, and stop it at the source, uh, prevent it. And I think that kind of just taking that initiative and being proactive and, and yeah, like I was, uh, saying with another guest about how the product doesn't have a swim lane, right? You just kind of have the whole pool. And I think that's kind of it, right? Is like, you didn't look at that role and say, Oh, I'm just the social media manager. I just, you know, You're these things and try to, you know, make people happy. Like you said, Hey, I don't have a swim lane. I'm going to go that step further and figure out like, how do we prevent more people from running into these

Amy O'Callaghan: 00:13:25

same issues in the future? So I do think I was, I was cautious of not stepping on too many toes though, which I'm grateful to my time in marketing, because I think it actually did a good job of teaching me like. How to talk about a success in such a way that you look great, but more it's about talking about the team, right? You're not talking about how great you are. You're talking about how great the work was. Like it was a very good, like small public relations bootcamp of like, and I've used that for every product team and every product org I've been a part of since then. Cause I've definitely had people that were like so hungry for the role that they were like constantly just like founding a product team. Like, Hey, look what I did. Look what I want. Like, here's what I am. And I think there's a fine line, right? And I probably stepped over or towed the line a couple times in ignorance. But, but yeah, it was ultimately just coming from a place of, I wanted to fix stuff. Like when people ask why I got into product, it's like, cause it's just solving problems at scale. And that's so delightful to do. Yeah.

Becca Moran: 00:14:27

And what was that role like this? So you were hired into was it an associate product manager role initially? Yeah. I'd love to hear more about like, what that role actually involved and how you actually kind of. Started to dip your toes into actual product

Amy O'Callaghan: 00:14:48

responsibilities for sure. Yeah. And Snagajob actually did a really nice job. It's one of several orgs I've been fortunate to be in where they created a really intentional pathway into product, um, both for external and for internal talent. Um, and so what happened when I moved into product and that associate role was, you know, got invited to all the product meetings. It wasn't a huge product team. I think it was about like eight to 10 people at the time. Um, we, they pretty quickly, uh, put us all on a plane and send us out to Marty Kagan's weekend workshop, which I was like, this is the best thing ever. Um, I don't know that there's any better way to start your product career than like sitting in a room, listening to Marty Kagan talk about eBay. Um, and, uh, so really they, they, they carefully positioned me so that I could form relationships with other product managers and like build mentors within the group. They also put me in a space. Where the harm I could do was very limited and the ability to learn was extremely high and granted, I still managed to do some dumb stuff, but, um, I think that's really important, right? The first job that they positioned me for was helping our customer and member support agents. Um, understand like where they could gain efficiencies and taking the bugs and issues that they were hearing. It was a larger role of what I was already doing as a social media person, right? I was like just opening the floodgates from social media to and everyone who talks to an angry customer or user all day long, right? And synthesizing that information across escalating the important stuff that I couldn't handle up to the rest of the product group managing what I could on site and finding ways to close gaps. So one of the very first things I did was identify that, um, all of our support agents kind of had to roll their own support scripts every time a question came in. So we put in place a single unified like four set of support scripts and made them accessible to everybody so that everyone wasn't trying to constantly a You know, reinvent the wheel, which was great because from a branding perspective, it gave snag a job a lot more control from a customer service perspective. It gave people more time and energy back to actually answer calls rather than kind of doing copywriting on the fly. And at the end of the day, it results in a more reliable customer experience, because now you don't have like. 15 to 20 different people making 15 to 20 different ways to respond to a single incident. Um, so it, I think it was great because oftentimes I see organizations start associate PMs in places that they can really get themselves in trouble. You know, the business has a ton of urgency there, you know, there was an opening because they needed somebody. I think customer support is an amazing place to start somebody out. There's several of those like little safe havens around an org where you can almost always use the help. And the amount of damage somebody can do is kind of a little bit insulated from the rest of the org, like they're not going to bring down the OKRs for this quarter from the member support side.

Becca Moran: 00:17:49

Yeah, that actually, um, kind of gets a little bit to a question that came to mind. Like, did you ever find in that role that you, like, was that frustrating at all? Did you find that you were like in conflict potentially from maybe more or with like the bigger top down organizational priorities? Cause it's, I'm thinking about like my experience, um, working and like trying to prioritize those types of ideas, things that come from your customers that, you know, there can be a lot of noise, right? Like you don't want to jump at every single issue that a customer brings up. But at the same time, like, If you can cut through that noise and you can see things kind of thematically, you can actually identify some changes that can be equally as consequential, I think, as some of these more top down driven initiatives. So I'm just curious, like. Is that something you ran into? And like, how did, if so, how did you handle it?

Amy O'Callaghan: 00:18:52

Yeah, I, I think everyone in product probably runs into that all the time. Um, or I'm just a very, uh, contrary person who's constantly just asking. People to prove to me why the things we've prioritized are the way they are. But, um, I think you actually described it really perfectly, which is the, the layer that was missing, because obviously there was a ticketing plate, like in place, there was, uh, you know, uh, SLAs in place, response times, all of that jazz, all those things already existed. What I really was able to do in that role was to synthesize the things that were these individual floating bugs and say. Here's why all those things are happening, right? Like and make it easier for a product team upstream to take the work and say, like, Oh, we see what the benefit of solving this would be, and they've already done the investigative work, so it's much easier for us to pick up and do our Q. A. Isn't going to spend like two days this week, you know, looking into this and trying to figure out how all these bugs are connected. Um, and the other thing is, I think that this was part of where I started to leverage the work. Discovery to help make sure that the things that I truly felt were important were given consideration, even if they weren't ultimately prioritized because I never want something. To get prioritized that shouldn't be right, like, no matter how passionate I am about it, if they're literally working on something more important than I should be waiting my turn, so I love to make sure I put it forward and I make sure there's shared understanding between me and that other team about here's the actual customer impact, right? Like, let me let you listen to the customer call from one of the 60 people that talk to customer support about this today. And here's the percentage of customer support time currently going to this issue. Thank you. And here's like, you know, just kind of putting the whole opportunity assessment, um, together for the team and just making it more consumable. Because I think so often, I don't know about you, but in the times when I've been on the incoming side of a stream of bug tickets, just the sheer work of sitting down and Sherlocking which ones go together and solving the jigsaw. Can sometimes prevent you from picking up those tickets and moving them across the board. So I was kind of solving like half the puzzle before I asked anybody to take a look. I love that.

Becca Moran: 00:21:09

I'm thinking a little bit more about kind of this associate product manager role. Um, would you say that, you know, for anyone who might be interested in getting into product and looking for those types of roles? Um, like, you know, aside just from kind of like searching for that title, like what types of companies do you think should have associate product manager roles? Like, I, I think that and, and if you have any thoughts on maybe what prevents more companies from having that kind of position, but it strikes me that maybe Snagajob was at a certain

Amy O'Callaghan: 00:21:51

scale that could

Becca Moran: 00:21:52

support that. Like thinking about my experience working very small, early stage startups, like. I know like we're not in a position today to have that kind of role, although hopefully at some point we can kind of support that. And I think it's incredible in terms of like giving people career paths and everything. Um, but yeah, what's, what's

Amy O'Callaghan: 00:22:17

your take on kind of that role?

Becca Moran: 00:22:19

Who, who is doing it right? Who should be doing having that position that doesn't? Um, yeah. Yeah.

Amy O'Callaghan: 00:22:27

I mean, I think to your point about why more companies don't have this role. I think it's because people hire product managers when they have a problem to solve, right? And the only companies that I see proactively putting product learning agendas in place and associate product management, um, tracks in place are those that are concerned about home growing their talent. And having a bench of people to fill roles and solve problems when they come to them. And that does take a certain amount of capacity. It takes time away from your more senior people. Like there's a whole slew of things that have to happen for an associate product manager to actually get good experience. Um, speaking a little bit to the size, I think it depends, right? Like my last product organization was pretty compact. You're about 25, including engineering. And. I looked around the org and very early saw somebody and was like, I think they might be a great product manager. Like I think they've got the stuff. I came into the org and discovered they were like personally holding up like six manual processes that were keeping things running and like never taking vacation and just like solving all the problems as they came up. And I was like, yeah. Um, That's it. And so, I mean, what we fundamentally did there, you know, I talked to them about it and just sort of, you know, talk to them a little bit about what product was, what it is as a career and kind of the opportunities that having that experience unlocks. And talked about the rest of their career aspirations. Like what were they thinking about? What were they interested in? And at the end of the day, I was like, look, I don't know that your day to day will change a ton because you're still going to be accountable for some of these things. But I think we could work together and get some of these processes to be more efficient. You know, get them into a place where you don't need a human in the loop all the time. That's a business resilience thing that I could talk about for ages. But, um, and at the end of the day, what we ended up doing was moving them into an associate product manager role, and they were still triaging bugs and doing customer support and all those things. Um, but on the other hand, they were coming to the product team meetings and we were taking the bug tickets and we were making sure that we were following a rigorous prioritization process and like they owned that process and they were making the tickets for the bug. So it was a very early primer and like. You know, baby steps into product management. Um, I definitely wasn't able to send them to Marty Kagan and, you know, there was a, a limited pool of product people to hang out and become, uh, in a mentorship relationship with, but to your point about just making opportunities for people, I am constantly blown away that I get to do this job that somehow like. I got I got lucky enough to be in it. And so I'm always looking for ways to pull people in because I don't know about you, but I just I see product people everywhere. Like, I see someone solving a problem and I'm like,

Becca Moran: 00:25:31

yeah, that's that's

Amy O'Callaghan: 00:25:34

the DNA. Um,

Becca Moran: 00:25:37

for those that might be listening to this and are maybe not in a, like, product

Amy O'Callaghan: 00:25:44

adjacent

Becca Moran: 00:25:44

role. So, like. Thinking about what you were describing, this kind of exposure that you had in the social media role, I

Amy O'Callaghan: 00:25:52

think, to your point, customer support is a

Becca Moran: 00:25:55

great one where, like, there is a very natural kind of

Amy O'Callaghan: 00:25:59

overlap, but, like,

Becca Moran: 00:26:01

what if you're working for a part of the company that there's less of that or less maybe opportunity to interact with someone from the product team where you just may not have that exposure. Any thoughts on how someone in a role like that might be able to, what, what they could do to maybe, um, like start to get more of that exposure and build certain skills that could help them be a

Amy O'Callaghan: 00:26:30

good candidate for sure. And I think this applies not only to people who are in an organization that has product, but they're removed from it. Um, but also to people who are not in product at all. I was speaking recently, um, to a class. Of people that were, um. In product, uh, master's work over at VCU and there were people from, you know, Richmond public schools in the room and I'm like, you guys are solving problems all day scrappily with no resources. Like you can turn that into a case study and I think it's a combination of having again that raw ingredient. If I want to solve the problem, I'm not going to like, let resource constraints. Keep me from doing it. I'm not going to fall in love with the first thing I think of. I'm going to look for the right solutions or the best solutions instead of getting laser focused on, on whatever's the most interesting solution. And then you pair it with the language and the understanding and how you talk about it, right? Because I think you and I probably have met a lot of people that solved a lot of cool problems in a lot of ways, but they would not describe it in a way that speaks to the product management lexicon. And I think for the people that are really interested in pursuing this as a career, identifying where you're solving those problems and how you're doing it in a product way and being able to speak the language is really important. And like the master's programs that are popping up, like. Our local university does a master's in product innovation now. And I'm like, dang, I went to this school and you guys wouldn't have known what I was talking about if I asked for this as a major. Um, and like there's a whole class of people coming out of schools now that are classically trained in this and that's awesome. But I also still have a major soft spot for the rogues that are like sneaking in like we did around the edges. Um, and I think it's that combination of like problem solving. And being able to speak to it that way. And I mean, one of the strongest product people I know, she was actually at Snagajob when I was in, um, the marketing department and she was an events planner. She planned all of our major corporate events. She like did all of our, you know, conventions and managed when we went to the national restaurant association to sell software. And she was amazing at that. She had a ton of energy, was outgoing, um, excellent organizational skills, was able to rally everybody, sometimes literally get them on the bus and get them where they were going. And you see all of that in her product, right? And that was, that was, I think, part of what got her in, you know, I, I don't actually know the specifics of how she transverse going from events to product, but she did it inside snag a job. And I would. I would argue that you can see a direct line between the amazing events manager and the incredible product person she is today. Yeah,

Becca Moran: 00:29:25

yeah, I, I think it's such a great point about kind of the lexicon of product. And I recall a few years back having a conversation with someone who similarly wasn't in a product role was looking to kind of make that shift. And I had worked with them and I knew that they would be good at it. And my advice to them was like, you just need to learn how to talk like a product person talks. And, um, Like, to be able to do that super fluently takes time. But I think to be able to do it well enough to go into an interview and just, like, frame your experience in a certain way, ask questions in a certain way, um, like, think through a problem in a certain way, I don't think that's actually that hard to, like, build some of those fundamentals. Um, and I think it that can be, um, a huge way, I think, to, like, level up going into an initial product interview where I think a lot of hiring managers, you know, if you haven't had the opportunity to be exposed to that person, you know, they're not like an internal candidate that maybe you've seen

Amy O'Callaghan: 00:30:42

some of these. In a traits, um,

Becca Moran: 00:30:46

if you're just kind of interviewing an external candidate, that's trying to make that pivot. A lot of hiring managers are going to kind of screen out people that can't really talk through some of those fundamental product. Concepts or or ways of thinking and so. I think it's a really great point that, like, if you're the kind of person that feels like you have some of those innate abilities and characteristics that we're describing, and you're not sure kind of how to break through, I think building that lexicon of, like. How do I talk like a product person is a really great way to

Amy O'Callaghan: 00:31:24

think about it. Yeah. I usually advise people. I'm like, look at a problem that you're trying to solve today. Does not have to be a tech problem, right? That's the great thing about product. We're everywhere solving everything doesn't matter. And, you know, put together your personas, do a journey map, you know, put together, uh, uh, opportunity solutions tree and pick, you know, some things to run tests on and do an opportunity analysis and a risk analysis and like, just practice these things. Um, to your point, it's like gaining fluency, right? And you're going to be so awkward at it the first time. And the fifth time that you do it, you know, you're going to, you're going to be a lot better. Um, but for sure. And the other thing, and I think this makes product hard too, is every organization does product a little different, right? And so the lexicon that, you know, Microsoft wants and the lexicon that the Amazon hiring manager are looking for probably a little different. So I always try to advise people to at least do enough networking to have one conversation with somebody from product or engineering or design in the org that you're interested in. One, just like make sure you actually want to go over there. Right. Right. And two, what do they care about? Like what's the framework? Like what are the things they do? Are they running jobs to be done? Like what? What kind of words do you need to be able to be fluent in? Um, we can say it's the regional accent of your company, right? Like you walk in there and you don't, you don't, you don't talk the same way they do and they're going to kind of look at you and be like, I don't know, but you can get in there and talk, you know, the lingo that they're comfortable with. I think it, it gives you an advantage. Yeah, I,

Becca Moran: 00:33:09

I totally agree. And I think the idea of like doing informational interviews, um, is huge. I, um, it makes me think a little bit about when I took this role at Procurated, um, I hadn't been actively looking and, um, I, I was really excited about the opportunity, but I had this like kind of feeling that I was like, oh, like I would have wanted to be much more intentional about where I go next. And I felt like, Oh, I, I should have stopped and thought about, like, what my next role would look like and, and whatever. And so I kind of, like, forced myself to go and do some informational interviews with people at other types of companies really quickly to be like, okay, I just want to kind of have a point of comparison to make sure that this is what I want to jump into. Um, and I, I was entertaining the idea. I thought for a minute I wanted to work for, like, a digital agency. Um, because I've worked with some, um, shout out to the team at Vigit, who I've worked with at a couple organizations, and they're super talented, and they do great work, and I've just always thought, like, that would be such a cool environment to work in, and, um, you know, I would probably learn so much from the people there. Um, and I, I did an informational interview with somebody just to kind of explore that path a little bit and ultimately concluded that I didn't think that that environment would necessarily be the right fit for me. Um, and it can certainly be a very intense type of product role. Um, but

Amy O'Callaghan: 00:34:52

yeah, I. massive advocate of informational interviews in like every aspect of life. Um, yeah. If it weren't for an informational interview series, I wouldn't have known. I didn't want to be an animator, right? Like I was like, Oh, I want to work at Pixar. I want to work for blizzard. And then I talked to a couple of the other, like, no, you work incredibly long hours. And unless you're in a major gaming studio, you get laid off at the end of the project because they don't have funding lined up for the next one. And then you have to move wherever the next job is. And I'm like, Oh,

Becca Moran: 00:35:21

okay. Uh, this, this sounds,

Amy O'Callaghan: 00:35:25

and you know, like. Even I was in a, um, a coaching group, uh, a little while ago, shout out to my swell people and um, and we had a, a member who was talking about like, just not being sure about whether she wanted to move to pursue an opportunity or whether she wanted to stay where she was and like pursue a promotion or whether she wanted to do what or what. And we were like, what do you want your life to look like in like 10, 15, 20 years? Right? Mm-hmm. like, what do you imagine for yourself? And she actually had a very clear end state she was going for, and I'm like, Well, one, I think that clarifies some of the things you're currently stressed about. Like, I wouldn't worry about scenario A, because it has nothing to do with the future state you think you want. I would put yourself on the path, and then I would go find some people that are living that life that you want for yourself in 20 years, and make sure that the things that they have are the things you actually want, right? Because you would hate to do all that work for 20 years. It's a very product mindset. Like, when you were talking about Doing an informational interviews because you were like, Oh, it's just so great. But I don't want to just jump on the first thing. It's very much don't get shiny object syndrome, right? Exactly. I love that your instinct when presented with this amazing thing was also like, I'm going to look around. I'm going to make sure because you didn't want to make like a binary decision. And that's amazing. Yeah.

Becca Moran: 00:36:36

Well, and it's funny because I think, you know, we're talking about this product lexicon and a way of thinking like a product person. And I think Once you start doing it, you kind of can't stop or if you, you always have kind of thought that way, but it's something we talk a lot about, um, within procurated, like, how can we approach. Every problem, problem the same way we've approached product problems, right. And like apply product thinking to lots of different things, like how, like company culture or whatever, right. Things that maybe are not immediately where you would think to apply that. I once took

Amy O'Callaghan: 00:37:16

a team's, uh, retrofeedback for a year and we were struggling. We'd been pulled in a lot of different directions. Um, it was a great team, but they'd been given too many different types of work. And so we'd had to split people up into like little miniature teams inside the team. And so like the culture in the team was really fragmented and like no fault of anybody's. It was just how we were surviving the workload. And I took the retro feedback from the year. I sent, I put it into optimal sort and I sent it out to the team and I was like, if you have time, if you're interested, I want you to do a card sort. And I had them like affinity map the cards together into themed groups and then name them if they wanted like do a classic digital card sort. And then used that to create the bones of an opportunity solution tree and held like a retro roundup where, sorry, this is my very small, great Dane. Um, basically said, okay, here's the things that are going well. Here's the things that aren't going well. Here's the themes, like, what do we actually want to pursue? And we got down to like branches of the tree where we wanted to change outcomes. And we started identifying. Things we'd even tried throughout the year. We were like, okay, this was an experiment. We didn't talk about it this way, but this was the thing we tried to fix a thing. Do we like how it went or not? Like, do we consider this a pass or fail? And like, yeah, it's great to use like product tools all over the place. I can tell how much my, my friends and loved ones like me at any given moment is when I'm in a good place with them, they think it's amazing. And not otherwise they're like. Why is business Amy at Thanksgiving, you know, business

Becca Moran: 00:38:48

Amy wasn't invited to this conversation, but that's hilarious. Um, I want to just touch kind of quickly as we move to wrap up the episode. Um, you know, I think we've talked a lot about how you got into product and I think that's an incredible experience. You've also moved up and had incredible success, um, in more senior roles. Um, is there anything you want to share about kind of that process? If, if there's anyone listening, that's maybe at a more advanced stage in their career and is not looking at how to get into product, but maybe instead how to, to continue to move up into more senior roles, um, just any thoughts from your experience that you think would be helpful for someone in that kind of position. Absolutely.

Amy O'Callaghan: 00:39:46

Um, I think a big one and this is kind of just life advice is self awareness, right? Like, understand your strengths, understand where you have opportunities and sort of assess, right? Like, is that an area where you need to build competency where you need to build strength? Or is that an area? Where you can actually succeed by over indexing in another spot, right? Like I personally, not the strongest analytics person, right? If you give me a math problem and you need me to answer it right now on the call, it will be an absolute disaster. You'll really see that BFA shine. Um, but in a lot of organizations, I'm either afforded like an Excel spreadsheet with which to do my calculations or partnered with an analyst. And so I've really leaned in to like the discovery side, the storytelling side, the empathy side as like my area. But there are some incredible people on like the business analytics side of products that like, you know. If we were both passionate about something, we could talk each other under a table on completely different terms. And like, you know, the tide, the leader who was tie breaking, um, you know, and there's that same deal on the tech PM side, right? Like technical product management is a whole nother thing. So like really understanding what gives you energy and like where you're going to bring your special, like verb to the, to the role and investing there and growing yourself. And the other thing, and this is something I think I carry from my time in marketing. I had an incredible leader in the marketing organization at Snagajob. It was Mike Ward, was a great guy, led the team with empathy, but the other thing he was really good at was always making sure the rest of the organization knew what the Marcom team was doing. That was so great and why it mattered to the rest of the org. And so there is a, a piece of our work that is making sure that our team's value is understood. You need to also be able to do that for yourself, right? Like, and oftentimes if you're making sure the organization understands the value of your team, they will see that as a reflection upon you, but doing great work in a vacuum in an organization that's happy to just like, say, cool. Thanks for doing the great work. Keep doing great work. It helps to have a little bit of hype man, right? Helps have a little bit of theater kid in you and be able to write like a really good internal press release or be able to do a really great shout out at the team meeting. Um, because sometimes I see people doing amazing work, but they don't elevate it to the rest of the org in a way that gets them the next opportunity. And I think those things are really important. And then finally, like, Finding your advocates, finding your mentors, turn all of your great discovery abilities on the leaders in your org and the product people that are above you in an organization or other orgs and understand what they think it would take for you to leave that gap, right? Like, what are the competencies you need to build? Um, CarMax does a really good job of actually putting people through a structured program for their associate product managers. And also for their leadership product roles. Like when you move from, from competency to competency and from level to level, they do a really good job, um, giving you the opportunity to invest there. So there's companies that do that, but they are, I would say, less than, than the norm. I'd say most of the time you're going to be, you're going to be doing it on your own. And so making sure, again, you use those product skills on your own career and think about what you need to do to make the next steps, because it's going to be different for everybody, but the tools you use to figure out your pathway are kind of the same.

Becca Moran: 00:43:20

Yeah. I totally agree. And I think in some ways it kind of comes back a little bit to where we started, like this. I liked what you said about really getting smart about how you communicate and, um, share the great work that you, your team are doing. Um, and I do think that's a really important part of Most product roles and and using that same lens to think about how you apply that in your career it but also balancing, you know, it's not like shameless self promotion, right? In the same way that you were talking about, um, there's a nuance to you weren't just. Bombarding the product team, you know, when you were the social media manager with like all of these, you know, you weren't annoying the crap out of them. I

Amy O'Callaghan: 00:44:13

don't think so, but I actually know one of the people that was on that email distro and I'll ask him just to see like, Hey, how bad was it? Um, yeah, no, for sure. And I think, I think you can always put this in customer parlance, right? Like if you wouldn't send an update to a customer about it, because it's not valuable enough, like, and it might cause them to unsubscribe from your email list, why would you tell anyone in the company about it? Right? Like always put yourself in that person's shoes and ask, do they care about this news? And if they don't care about the news, is it because it genuinely doesn't matter because they don't understand why they should, in which case, like figure out how to make that connection spark for them. And if it doesn't matter to them and you just wanted them to know, then like leave them alone and they'll listen harder next time. Yeah. And you know, I think at

Becca Moran: 00:44:56

the core of that is. Empathy, which in my mind is like the number one trait that you must have if you're going to work in product, right? The ability to think about like, what does this person want? What do they care about? Not just what do

Amy O'Callaghan: 00:45:13

I want to tell them? I definitely think I can see people that do not have the empathy chops making their way to a certain level in product. But most of the time, at least in an organization where you really want to spend time, they hit a ceiling at some point. Where, you know, whether that's before they're managing people or something and they just sort of hit that empathy wall and they either have to, like, learn the empathy skill or kind of just stay where they're at. I think you're right.

Becca Moran: 00:45:44

Um, all right. So to wrap up our conversation, I have a short list of my rapid fire questions. So I'm just going to, uh, fire these at you and and we'll turn through it quickly. But okay. So, um. Do you think that a close friend or family member could accurately describe what

Amy O'Callaghan: 00:46:06

you do? Um, it varies, and I know this specifically because every Thanksgiving I ask everyone at the table to describe what they think my job is, and the person who gets it closest gets the first slice of pie. Nice. Yes. Last year my partner did a pretty good job. They got real close. They got first piece of the pies. Yeah, my parents have no idea. They think I make the internet. My dad tried to give me a bug report for Google once and I was like, let me talk to you about what happens when you submit this bug. I can't control it, but let me tell you what, what's about to

Becca Moran: 00:46:40

happen. Yeah, no, my, my parents have no idea. And, and honestly, I think last time the conversation came up, uh, one of them thought that I still worked at Xometry and I was like, I haven't worked there in like almost five years guys. Um, all right, what is one product or tech like word or phrase, maybe something from our aforementioned lexicon, uh, that you wish you never had to hear again?

Amy O'Callaghan: 00:47:10

If I hear us talk about touching customers again, I'm going to just climb under my desk and hide there until the next ice age, because it's creepy and it's weird. And I don't know who started it, but we need to all get together and stop it. Yes. Nobody should be touching anybody if they're not expecting it. I don't care what part of the journey they're in. This is a virtual world, you

Becca Moran: 00:47:31

know, so. It should be easier now than ever. Um. Yeah, plus one to that. Um, how often, uh, maybe think of in recent history, most recent role, uh, how often do you actually talk to your customers or

Amy O'Callaghan: 00:47:52

users? Um, most recently, um, I would go unfortunate long desert like spans of time not talking to anyone and then I would kind of go on a discovery binge, right? I would clear my calendar for two weeks and I would just look back to back to back to back to back to back to back. Um, I typically like to shoot for like five customers a week, right? That's gonna give you a nice diversity of opinions. Um, you've got more than... One persona, you might need to think about how you split that up. But like, I think that's a great way to keep yourself from getting too pinned into a single customer story. Like our empathy is a superpower, but it is also dangerous because we can get hyper focused on fixing it for a single person. And then we build something that is really great for that guy over there, but doesn't work for like the rest of the users. So, um, Yeah, it really depends. I'm all over the place. My best weeks, I talk to a lot of customers. Yeah,

Becca Moran: 00:48:48

I, I find the same. I think it's very common to kind of have these like ebbs and flows with these customer conversations. But like, I think the ideal everyone strives for is like, how do we make that a more consistent part of our process? So, um, all right. What book or person has been most influential in your career?

Amy O'Callaghan: 00:49:12

I'm going to say, um, one of the leaders that I had in my product time at Snagajob, um, her name is Megan Overton. She is a fantastic, she actually just changed. She was at Capital One for a long time and she is now, um, moved into a startup role, but the thing that she did was she was always incredibly transparent with her team. Like I always felt like I could trust her. Um, Like, even when the news wasn't what I wanted it to be or the feedback was challenging. I always knew that like it was coming from a place of genuinely wanting me to do well and me to do better. Um, and then finally, like she really advocated for my team to have the breathing room in the space to solve problems rather than to chase specific outcomes that leadership was pushing. And it resulted in some of the most absolutely magical practice. Perfect years of my product career so far. Um, and I have also seen not just for me, but for other people, she has created this incredible nest of product managers. Um, and you just know if you're talking to somebody that's worked under her that you're about to have a great conversation. That's amazing.

Becca Moran: 00:50:26

Very cool to hear about people that are doing so much good for the product community in that way. All right, last question. When you were a kid, what was your dream job? Obviously you didn't think you were going to be

Amy O'Callaghan: 00:50:40

working in product. Nobody knew what product management was. So what did you think you'd be doing? I was very specific. I was very specific and I had three jobs. I was going to be Batman. It's going to be Indiana Jones, and it's going to be Peter Pan.

Becca Moran: 00:50:57

Just like rotating in different days of the week.

Amy O'Callaghan: 00:50:59

I really hadn't thought it through. I mean, particularly Batman and Peter Pan, they're going to have some hours overlap there, right? Like they're both nocturnal. Like Indiana Jones can get some stuff done during the day, but I don't know. I don't know. Younger, it was very aspirational. Clearly it likes a costume. It sounds like

Becca Moran: 00:51:17

you wanted to help people, which, you know, that ties in, I think. So I'm here for it. And I think you could probably still wear a costume to work

Amy O'Callaghan: 00:51:27

if you want. Oh, for sure. Oh, I've dressed up as Indiana Jones for multiple holidays, uh, for Halloween. Like kind of my classic, like if I don't, if I'm not part of a group, I'm going to show up as a disturbingly accurate Indiana Jones and that's just my call sign.

Becca Moran: 00:51:42

Love that for you. Amazing. All right, well, we'll wrap up there. Thank you so much. I mean, this has been a really fun conversation. I know I learned a lot. Um, a lot of really good kind of reminders and great perspective. So. Thank you. Thank you. Always great chatting with you. And, uh, yeah, thanks for being on the

Amy O'Callaghan: 00:52:02

show. Fantastic. Thank you so much for the invite. It was a great conversation and, uh, grateful for the opportunity.

Tim Winkler: 00:52:29

Calling all startup technologists. Have you ever dreamed of hosting your own podcast, but don't know where to start? Well, here's your chance to shine. We're thrilled to introduce Beyond the Program, our exclusive miniseries, and we want you to be a part of it. As tech leaders and mentors, you'll get the exclusive opportunity to become a guest host right here on the Pear Program podcast. Share your expertise, insights, and stories with our audience of startup focused technologists. Excited? We knew you would be. To be considered, head over to myhatchpad. com backslash contribute. Fill out a brief form and submit it our way. Let's co create something amazing together. Don't miss this chance to elevate your voice and expand your personal brand. Visit myhatchpad. com backslash contribute.