Learning on the Job

Margaret: I'm Margaret Jastrebski. My title at ShopRunner is VP of Enterprise Products.

Suzanne: Now, I don't know if you know this about yourself but you are a bit of a legend here in the Chicago product community. Am I bringing this to your attention of the first time?

Margaret: Completely. I am flabbergasted at the idea that I might be a legend.

Suzanne: You know, what's been so interesting for me being here in the city and getting immersed in a new product management community, especially having spent so much time doing that in Southern California's, you learn what are the different companies, what is the tech that people are focused on. I've learned, for example, that Chicago has an emerging data science platform, race to the top, a lot of players in it. And then there are these cults, or hubs. Orbitz being one, Groupon being another, I think GrubHub being the vet. It seems like everybody who's working in product at some point worked at one of those places. And then if they did, they worked with you and then they went on to do other things. But then they say, "If you're talking to product managers you have to talk to Margaret because she's the best." So no pressure.

Margaret: No pressure.

Suzanne: Yeah.

Margaret: I'll do my best.

Suzanne: Alright. So have you been in this game a long time?

Margaret: I’ve been in Chicago, I moved to Chicago in 2000 for a start-up and ever since I've been in Chicago I've been in tech. So yeah, 17 years going strong so far.

Suzanne: Now a start-up in 2000, I would imagine, was a very different kind of beast than start up as many of our listeners even come to know what they are. Can you take us back in time? And what does that look like?

Margaret: It was glorious; it was amazing. A start-up in 2000 versus a start-up today was so different. Of course back then we had no idea what it was gonna become or what the community would become.

I started as a QA person and then I taught myself how to be part of the company. I had my box under my computer. We had our server farm in the closet. I taught myself how to develop with a VB book that was 1,000 pages long with a disc in the back. I had to install that on my box underneath my desk. I had to go through all the exercises. So there were no frameworks. There was the internet but that was mostly Napster at that point back in the day. Again, the frameworks, the community, none of that was really there. It really was us figuring out how to do it ourselves. We built our software. We would install it. Back then even it was a CD not even a DVD. And we had to send that to our clients, they had to install it. Just the effort you had to go through just to get code out the door was just insane.

Suzanne: Just to see ... You started in quality assurance and I mean no disparagement here but I don't know anybody that set out in their career with that as their desire. So I sense there was a path you were exploring before you ended up doing QA at a start-up. Was there?

Margaret: Completely.

Suzanne: What was that path?

Margaret: Completely.

I graduated from Emory in '99; I graduated with math and econ, double major. I love math. I love patterns. I had that more analytical and structured and systems type thinking and mindset. I started interviewing at banks. I interviewed at Susquehanna Trading Company. It was a little trading firm, right. I just hated it. I hated these companies; they hated me. I had bleached hair, I had a nose ring, I thought I was cool. There wasn't emotional fit; there wasn't personality fit.

So I was completely confused. I had no idea what to do. Back in '99 it was like, “Sweet, there’s this internet thing, there's this bubble. All these companies are getting funding, I don't even know what funding means but it seems interesting. So many people do it.” And so I started looking around, talking to my friends. I was in Atlanta and I was like, "I wanna move to a bigger city. I'm gonna go work in this tech thing."

So I happened to find a company, got hooked up with a company here in Chicago. They took a little bit of a chance on me and I took a little bit of chance on them. I said, "Sweet. I'll come learn it, you just teach me what to do. I know I'm smart. I can do math. You can help me understand this." I moved up here and haven't looked back. It was an amazing opportunity to get started there and I've had just amazing opportunities all along the way. I'm very lucky.

Suzanne: So you were doing QA and you took it upon yourself to learn programming just because you wanted to understand more of what was going on? And then were you able to transition into a developer role?

Margaret: Mm-hmm (affirmative) Actually, this is a really great call out for that company, even back in the day. It was a company named Telusion, not around anymore. We were a 30 person company. They officially put in a training program for people that wanted to be developers. The company couldn't find enough developers so they thought if they can get people in and train them ... But the fact that I was a woman and the fact that my boss was a woman, they were really excited about that. They wanted to help facilitate that.

On nights and weekends I taught myself how to do it, but then they were willing to transition me into a developer role. I look back and it was so forward thinking, back in the day for them to take that ... It was kind of an apprenticeship program.

Suzanne: I don't wanna dive too deeply off the bat into diversity, which is of course a big topic, but given that you were programming as a woman with one other female colleague, and we're talking about almost 20 years ago, what was that like then? Was it worse than what we experience today and read about today or was it strangely better and different 'cause everybody was still at the beginning?

Margaret: I don't know any different. I had that experience and that was the environment in which I worked. So because that's what I was comfortable with, because of that experience I didn't know that there was a different way. I as lucky that the men that I worked around, the people that I worked around were great guys.

I think back in the day there wasn't really this sense of brogrammer. There wasn't a culture community around it. It really was a lot more the geeky people and more the outcasts. So I think just by nature of that you’re already a little bit of a misfit. I never felt like I was different because I was a woman. I'm lucky because it occurs to me second. I don't often think of myself as "I'm a woman first and then thus I'm gonna be this way or that way in this environment". It's more like, "This is the environment. How do I approach this environment" and then, "Oh, shit. Wait. It's a room full of dudes," etc., etc., etc.

So it was a great environment. I think we were able to thrive and do a great job. On the bigger scale in which we're working now ... The bigger scale and for community perspective ... You get to see a lot more instances of where we have an opportunity in front of us to do better from a diversity and culture perspective.

Suzanne: Right.

How did you finally end up into a product role?

Margaret: I did QA, I did development, realized I was never gonna be a great developer, so I moved into consulting. Did IT consulting for a little bit. Learned how to do project planning and learned how to think on my feet and be in front of people and set expectations and stuff like that. But I wanted to get off the road. I was traveling every week, five days a week and I didn't own anything. I wanted to get off the road and I didn't own anything that I was doing. So I started looking around to work for a brand or a company that I could actually just own and be responsible for my own work. If I was successful, great. If I failed, great. There's opportunities to learn in both of those things but I wanted to be able to own. In consulting you tell people what to do and they might implement it, they might not. You never actually really get to reap the rewards or face the music.

Suzanne: Yeah. I can definitely relate to that. Some projects you're happy to see go. Like "Whew. Bye". But more and more, especially as you get clearer about the types of plans that you like to work with, you can fall in love with the product and then you're sort of clinging and they're like, "No we're good. Thanks for helping us insource a team. Thanks for helping us set a process. We're good now. Go". So I get that.

What was the first product then? Where did you go from ...

Margaret: I went to Orbitz.

Suzanne: Orbitz cult?

Margaret: The Orbitz cult. This is where I first joined the Orbitz cult and started drinking the Kool-Aid. I am not gonna lie; it was amazing. It was such an amazing experience. I was there six years. I mean absolutely Orbitz University and I would wear that t-shirt proud. The people I got to meet and the things I got to do were amazing.

When I started I was a product manager for an API and or our API side. It's really a private label groups. So what we did was package up our Orbitz technology and basically resell it to companies that needed travel solutions but didn't want to build it all themselves.

Suzanne: Right.

Margaret: So it's back-end technology and I had to learn on the job. My boss at the time was like, "I want you to be responsible also for our RSS feeds.” I was like,"Sweet. I'll do that". And then of course I turn around to Google, "What's an RSS feed".

Suzanne: (laughs)

Margaret: I had no idea.

Suzanne: After you accepted the position.

Margaret: After I accepted the position, of course. "I'll figure it out".

I was at Orbitz for six years. Started as a product manager and when I left I was Director of Product Strategy for the whole group for a private label. In that time, the scale at which we operated ... I think we were doing zero amounts of bookings through our APIs when I first started 'cause they hadn't built them. By the time I left we were doing over $1,000,000,000 of travel transactions.

Suzanne: Wow.

Margaret: That handful of years later, that I’ve been away from Orbitz, they're doing multiple billions of dollars with those products. So, the scale at which I got to operate, the things I got to see was ... I learned. I learned really quickly and I learned on the job.

Suzanne: Let's talk about back-end products for a moment because part of what we seek to do on this show is bring a broader definition to what is product management and what are all of the ways in which it can manifest and how can it look differently. And I think our instinct when we think about what is product is to think about consumer products in particular. If we're experienced in working in organizations that are using SAS products of some kind or another, maybe Basecamp is another big Chicago organization so we're familiar with those types of B to B services. When you say my product is our API that ... again, it's not what we would readily think of.

Margaret: Mm-hmm (affirmative)

Suzanne: And I'm curious how does the role ... You would have to answer this retrospectively of course, but knowing now what you know, looking back on what you were doing, how is the experience of being a back-end product manager different?

Margaret: I think it's a great question. I think there's a spectrum of companies, right. So my expertise and most of my experience has really been in the B to B side to where I'm selling products or sharing products with other companies rather than consumers. That being said, at Orbitz 6 years there's a huge component of the B to C side. I as luck because I was selling products to companies that were selling solutions to end consumers. So that was B to B to C.

Anytime I had a question or anytime I needed to understand like "How do you do AB testing?" Or "How do you do marketing and broad market scale?" Some of these things that as an API person I didn't have to deal with. I had somebody I could turn around at Orbitz and say, "Help me understand." There's this world where I think these big B to C companies also have this large B to B side. There's always partnerships, there's always solutions.

Groupon is another great example. They're a marketplace in Chicago but they're a marketplace so they have a whole world of merchants and then they have a whole world of consumers. So the products that you and I see as consumers that's what you see on groupon.com but there's a whole experience around the merchants that Groupon has to think about and Groupon has to solve for. Same with Airbnb. Think about the entire homeowner experience and how do they sign up and how do they understand if this solution ... If Airbnb is good for them or not. So for me there's this B to B component. If you're in a B to C company there's also a strong B to B component.

Since Orbitz ... I left in the beginning of 2013. I've worked at a couple first stage companies in Chicago that were entirely B to B. A company named Signal; they used to be BrightTag. And a company named Narrative Science. We were selling our solutions, specifically to other companies. The scale at which you operate is different. You're hoping to win a handful of companies a year, right. You're not, you're not hitting millions. You're hitting tens or twenties or hundreds maybe. The level of investment in terms of educating companies about your solutions may be different. There's a lot more documentation. There's a lot more marketing position and then there's a lot more partnership throughout the process. I really like that side of it. Like I said, it's been most of my experience but depending on the type of person you are, depending on what type of company you're in, you can go straight B to B or this B to B to C opportunity is really interesting.

Suzanne: You brought up a couple obviously well known marketplace type products. I say this a lot to people who come to me. They have an idea for a marketplace product or an ecosystem and I say, "I want you to know that you've immediately duplicated or triplicated all of the work that exists." Because it's enough to bring one product into market that might have two or three distinct user personas. It's another thing to have to think about because, you're right, the hosting side of Airbnb is it's its own business with it's own user goals and objectives. And yes, as a solution it matches a very specific need of a homeowner with a very complimentary need of a traveler. But that's the beginning and the end of where it's simple. The rest is just mountains of work.

Margaret: The thing that I come across a lot is too, is there is the buyer persona versus user persona a lot in B to B. Who you sell to is not always actually the person who's gonna use your product at the end of the day. Often times you're selling to a C level or a VP level because they're the ones that can sign off on procurement, they can sign the contract. But once you install your software there's the day-to-day person that has to maintain it, and implement it, etc.

In the world that I'm in today with ShopRunner, we have javascript that our merchants install on their pages, and so we have a developer persona. Our developers on our merchant side, our retailer side, have to be able to understand our code easily, implement it easily, and be able to move quickly through that. That's part of what I focus on my job today is how to make that experience as seamless as possible and as easy as possible.

Suzanne: Yeah, and I think the levers of value and use are important to understand, as you framed it. If you're selling B to C, then talking to a person about what would be valuable to them, that's when you're talking to the customer. Would you pay for this? Would you use it? Would you tell your friends? Then you might have to within the same conversation shift toward, "Well tell me about some of the other products you currently use? Why do you like that product? What are some features that you respond to?" So you're covering a spectrum with a single person and in some ways that's easier. The minute that you carve all those out and realize, "Well we gotta talk to the CFO about how this is gonna impact the bottom line." But then we also gotta talk to the creative directors about what kind of tools the designers like to use and they're particular. And then we gotta check in with accounting. It's a lot of very different types of people.

I would think that that could quickly lead to losing the product vision when there’s so many different users in the ecosystem and they're so different in their needs. Can you speak to that at all from your own experience, either challenges you faced or how you have stayed away from that potential pitfall?

Margaret: I think staying away. I think I've been able to find myself into plenty of pitfalls and, fortunately I think that's how we all learn, right? But, when I think about .... The vision side especially with B to B, the vision side is really, really important in the sales cycle. Getting people to buy in initially the implementation and usage of it, that's where you've gotta really nail it. Because often times you sell to a C level and the VP level but you have the day-to-day managers and directors that are using this tool, if that experience sucks for them, if they hate it, that VP is gonna know about it. If it's not delivering real value, if you're not actually helping their lives, if you're making it harder, then it's gonna come back around just as much as if you were a B to C side and you're not delivering real value you're gonna see you consumers drop off. Uber.

Suzanne: (laughs)

Margaret: Sorry. I had to say it.

So I think there is this world of referencability and quality that you really still have to think about. And you have to make sure you nail it on the little things because then you're gonna get that repeat. People will re-sign the contract; They'll re-up. But then there is a life cycle to it because when they’re-up, are you still delivering value? Has their business changed? And that's where the vision comes back into play. Where you still have to come back and be like, "Hey, okay. Let me come back and paint this next long term vision. You've been with us for a year or two or three, you need to still know where we’re going and what we’re doing.

Suzanne: How big was Orbitz when you joined and when you left, just to give our listeners a sense of that?

Margaret: It was about 1,500 people the whole time I was there.

Suzanne: Okay.

Margaret: So it didn't really expand or contract too much while I was there. The change really happened within my group. When I started I was the very first official product manager. My boss was the product director and he was painting more of the vision. But I was the first official product manager owning this stuff, and owning our APIs. By the time I left, we had probably three or four product managers, director. We had probably like 60 to 80 developers. And when I started again I think we might've had six or seven. So the scale at which we operated, we really became a business within the Orbitz arm and the entire strategy within the Orbitz arm. We kind again went from pretty small, I almost think of it as like a start-up within this big company environment to becoming a significant part of a new generation with the company.

Suzanne: Right. 'Cause what I really gonna ask you is, was that jarring to go from that environment to ... You said that since then you've mostly been working in early stage growth organizations and a scale that's probably 30, 40 people at most. Given that it was more start-up inside, was it actually more seamless than it sounds from the outside?

Margaret: I mean it was amazing; so seamless. I made no mistakes, it was great.

Suzanne: Alright. I sense sarcasm. Tell us about your experience of going ... You know, you rise, you ascended through the Orbitz ranks, you exited as a director-level person, and then you were back to small time shops.

Margaret: Yeah.

Suzanne: Director level but then you're director of one?

Margaret: Yeah, basically. Basically. You've got it. Orbitz was great. 1,500 people ... I actually think ... You and I have talked about advice or how to think about young people coming up into the product world or people early in their product careers ... I do think working for big companies is such a great education. Big companies are big for a reason. It's because they've faced adversity and they figured out the operationalizing of themselves and they worked through the kinks and they've got a lot of great processes in place. Sometimes they might be over processed but that's okay. They've got a lot of the great foundation. They had get that in place to get to the scale that they are.

My experience at Orbitz was phenomenal. I learned what product was. I had a strong community. I'm still really close to all the product people there because I respected them so much. They were so smart and I learned so much from them. So when I had question about how to do something there were plenty of people for me to turn around and either emulate or ask advice from. Through practice, I was able to get better and learn all the foundational stuff.

When I left Orbitz, I went to a company, BrightTag, now Signal. Amazing company; amazing technology. But it was a 30, 40 person company. So I came in and I was like "OK. Well what is our strategy? How does our strategy feed into our goals? And how do our goals feed into our product affects ..." and then etc, etc. It was like, "And we're gonna meet on quarterly basis for this and we're gonna meet on a weekly basis for this and ..." It was very, "Okay, this is the structure." Seriously, I almost got laughed out of the company. It wasn't the right fit. My kind of heaviness of how product operated at a company that was that small and needed to be a lot more nimble didn't fit. So I had to learn really quickly what was important and what wasn't. And what do I take from my past experience and put forward and then what do I slough off and learn new?

Suzanne: So what is important then? Given that you have those two extreme experiences, if you were giving advice to somebody who was just launching a company that was 10 or 20 people ... Maybe gets hired in to be the product manager in that position, what would you tell them to focus on and what would you tell them to ignore?

Granted, if anyone's listening and then you take Margaret's advice, this is a recommendation only.

Margaret: Recommendation-

Suzanne: Don’t send a nasty letter later.

Margaret: Yeah, no binding legalities in this.

Suzanne: Okay. Now go ahead and tell us.

Margaret: In getting to some of the specifics, I think more broadly in a small company you can't be scared to try; you can't be scared to start something. Again, at Orbitz if I wanted to start something I would turn around and be like "How did somebody else do it?" At a small company chances are nobody else has done it. You have to be willing to start and you have to be okay starting badly. You just need to have that starting point to get the conversation going and to get the dialogue going, and to be like, "Okay, this is what I think is best. Can I put it out there and then see how people react or respond?" From an advice perspective, I would say don't be scared to try because the more you try the more refined you're gonna get. The first time you try it you're gonna suck at it. That's just fine ... Be okay with that.

Suzanne: Right. And I think the other thing that goes along with that a lot of the time is just as you say, no one else is gonna know what to do. No one else is really gonna tell you what to do either. Which is why startups can be awesome to work at. If you're like me, I don't like being told what to do so that's perfect. But some people prefer that structure. “Give me a constraint and then I know where be to inside of.”

Margaret: Yeah. Yeah. It's funny, I think I toe the line on both. I do have that kernel inside me that's like "Screw you, authority. You're not telling me what to do"-

Suzanne: Well that nose ring so ...

Margaret: Oh, I know. Yeah. I think-

Suzanne: She doesn't have the nose ring anymore.

Margaret: I means seriously, I thought I was so cool.

But there's definitely that sense of "You're not gonna tell me what to do" but then there's also like "I have no flipping clue what to do. I am so clueless. I'm scared; there's a lot of things riding on this. We're a small company, we're resource constrained. We've never done this before and we need to get it right." And so I think that there can be a little bit of analysis paralysis. So for me, work through that. Just try to rely on your allies. I've listened to some of your other interviews. They're amazing, some of the common themes are.

A large part of product is influencing and diplomacy, kinda pulling people together. That's where you have be the one starting the conversation.

Suzanne: There's a great Dilbert strip about agile, something to the effect of "We're going agile".

"What does that mean?"

"It means no more process".

I use that as a segway to ask, are there, in your opinion, some fundamental processes that can really help you from Day 1, even if you're small, even if you're not yet at 1,000 people and even if you have to iterate on them and what would some of those be in your opinion?

Margaret: I think one of the things that I've just seen over and over is just get really crisp and clear on what the priorities are. And then make sure you get crisp on the immediate priorities but don’t get confused with that for the long term vision. Every company I've worked for there's the big vision and grand things, etc, but you still have to deliver today and you still have [inaudible 00:27:37] to time, resources, etc. Getting really, really clear and getting everybody's buy-in in terms of like, "These are the top three things we're working on" on five things or whatever your capacity is, you have to drive that. You have to own that and you have to be always referring back to that.

In terms of a process around that, that to me is just prioritization. Just getting really clear on prioritization. But then having that prioritization transparent to the organization, transparent to your stakeholders, transparent to your peers, your team, etc. So you always are referring back to the same list of things. Everybody is working at the same list because it's really important. Any company I don't care if you're big or small. It's really easy to generate a lot of ideas and get distracted by the flashy thing. I think it takes a lot of discipline to always refer back to "Hey, this is what's important. How are we gonna always operate to that or how are we gonna all get agreement and buy in when we're ready to change it?"

You will use that through your entire product career.

Suzanne: I think it's a good answer and why I’m maybe pressing around about this in particular is because I think there is a pressure for all of us product managers to "do it right"; Whatever that means. And in so many ways it's an old profession but it's a new profession. It's a known profession but it's a mysterious profession. Part of what we're doing on 100PM trying to demystify it and make it more accessible and invitational. But I think that part of that fear that you described when you say "Don't be afraid, just kinda go and start something or try it" Comes from "Well I don't know how to do a road map." Or "I don't know if this is the right format" or " I don't know ..." So you're always sort of looking for a clue of how does somebody else do it. But I think, certainly in my experience how somebody else does it doesn't always provide the right clue, either. Have you ever felt that sense of "Am I doing it right? Are they doing it right? Are any of us doing it right?" You've done it a long time now.

Margaret: Can just I say every day? Quick aside, I think that's the thing that I just love about products so much is that I always feel like I have something to learn. I always feel like I've never mastered it because the problems are so complex and so deep. In terms of "Am I doing it right", I truly believe there's no right way. There's no right way, there's no wrong way. So much of what a company is and what a company becomes and what a product is and what a product becomes has to do with the people that are owning it and guiding it. It's great to have KPIs and great to have OKRs and it’s great to have specific metrics you're trying to work towards, but there is lots and lots of different ways to skin your cat. What you're trying to do for yourself is just get a little bit more information with each decision you make. You're just trying to get a little bit more validation to know am I headed in the right direction or am I not.

So when it comes to internal structure or processes etc, etc- prioritization, roadmap, etc put something out there, hear people's feedback and then figure out is that feedback helpful or not. Does it actually drive to the outcome that I'm trying to achieve or is it something that's just noise and people are "I don't like green, I want blue". That type of thing I'm like, "Sweet. Thanks for telling me". It doesn't help. When you're trying to get something out the door for consumers, or B to C, B to B, I don't care, it's how you get a test scenario out just to get a little bit more information to make sure that you're validating the next step. Make sure that you're headed the right direction. So using sound terminology that I use here is ... We do paper prototypes. So when we have an idea, before we actually quote it, can I write it up? Can I describe what it is? Can I show it to somebody and get their feedback on that to know if I'm even on the right track or not. Because I don't want to waste any of my developer's time. I don't even want to waste product time to do any of this stuff if it's not gonna be beneficial.

And then moving through, you have paper prototype, your alpha, your beta, your GA. Those tools and that feedback process is so valuable. You're creating actionality for yourself. The more information you have, the more indication you'll have to know what direction you go. So how do you give yourself that luxury? How do you give yourself and get that information in your hip pocket so you can know where to go?

Suzanne: In that prototype lineage that you just described, what's the earliest or crudest stage that you would take an idea out into the street, so to speak, and show it to a customer for feedback?

Margaret: So again my expertise is more on the B to B side, so I can speak from that angle. It's honestly, who are your friendlies, who are the companies that you have really good relationships with. You have to have some, right? Hopefully.

Suzanne: Yeah.

Margaret: Hopefully a lot.

Suzanne: I was gonna say hopefully a lot but yeah-

Margaret: Definitely some. So who are your friendlies? Have an idea, turn around, be like "Hey we're thinking about this. What's your gut reaction? Give me a blank reaction. Good, bad. Yes or no. Does it pass the sniff test?" That's about as low fidelity as I think I can get. But like I said, to get the idea in front of them, I like to do kind of, "Here's a write up". And I know that Amazon does the press release before they build a product. So it's a little bit about the press release, it's a little bit about "Hey this is the value you're gonna get. This is the way in which we think the product's gonna work. This is the work it's gonna take for you. This is what we think the lifts might be. Can we just talk through this. Give us your reaction to it". That's something that they're gonna actually ... Like a dashboard or a feature or something that they're gonna interact with. Can you do a … mock wireframes? There's no secret to this, right? It's literally just getting examples in front of people and having them react. And then you move from mock wireframes to the bigger, the more interactive prototypes and things like that.

Suzanne: Right. Well no, there's no secret to it; well, maybe there is a secret to it. Maybe folks are listening going, "No these are the secrets we've been waiting for".

Margaret: There are no secrets. I truly believe it's just hard work.

Suzanne: Why I like that example, is it's a great example of how minimum viable products or experiments or facades can continue to be part of your toolkit even when you go beyond the initial idea, the sort of initial “should we stop or should we go.” And finding clever ways to say "Well let's just do a mock up, send a note" and if our clients all write back and say "Please don't; we won't do this" that's a good experiment.

Margaret: Yeah.

Suzanne: It can be that kind of small and crude sometimes but I think, especially ... Why I asked you the question is I think when it is B to B sometimes the stakes can feel a little higher. I don't know why that is. Maybe just because B to C is a certain kind of horizontal scale. It's like "I need 100,000 people to be mad about this before I let it rock me too much" or whatever. Whereas in B to B, it's like if one big account doesn't like it, that could be significant. Statistically significant. So, I think that's good.

Margaret: It's all about how to break it down into the smaller parts so you're not making the big bets first, right? But I think the feedback process isn't so unique in a B to B world. You can use a lot of the same frameworks in both.

Suzanne: Tell us about ShopRunner for folks listening who haven't heard about it.

Margaret: ShopRunner, we're a free two- day shipping offering. We work with retailers like Neiman Marcus, Saks, Tory Burch, Kate Spade, etc. And if you remember the ShopRunner network, as a customer you can go to those websites and you can get free two-day shipping. It costs $79 to sign up. We like to think of ourselves in the luxury apparel space as a strong competitor against Amazon Prime.

Suzanne: Right.

Margaret: It's been tons of fun. We talked about marketplaces a little bit. We're absolutely that two-sided marketplace. I’m on the merchant side so my relationships are all of our merchants. And then we have a consumer side where we're building up really great products and tools and capabilities and services.

Suzanne: Does it ever feel, you know because you are sort of ... Amazon is Goliath. And it's like you turn around, press release, Amazon just spent x billion buying a whole industry while we were sleeping and ... I guess what I want to feel into is what it takes to keep focusing on differentiation keep focusing on value creation, even when it can feel like you're looking at a giant tidal wave that wants to come crashing down on you.

Margaret: Oh my gosh. It's hard. It's hard. Amazon spends 13 to 14 billion dollars a year just on R&D. It's insane because Apple's entire e-commerce is 13 billion. Walmart's entire e-commerce business, 13 billion. And then Amazon's like, "Oh that's cute. That's just our R&D budget".

Suzanne: It's a drop in bucket for playing with stuff.

Margaret: That's exactly it. And I'm like "Oh my gosh. How are we even gonna compete?" But we have great relationships with the merchants. We have great technology. And we're delivering real value. You know really real value to both, and so my feeling is as long as we can figure out continually kinda inspect and evaluate it like, "Where are we? We do we sit in this ecosystem? Are we actually delivering value? Are we helping the merchants in our network be better at what they ultimately came to do which is selling more products. Always keep that kinda customer’s interests be up front and know exactly, “hey, we can help.”

Suzanne: So thinking about B to B and remembering to some of my early experiences with it, part of it is remembering that it's still a bunch of people; It's still a bunch of customers even under the umbrella of what is a company. But your clients, the customers that you take care of here at ShopRunner are the enterprise side, they're the companies, they're the Neiman Marcus's, etc, and meanwhile Shoprunner itself is yet another growth stage company. You're not enterprise, but you're servicing enterprise. Is that a challenge in finding a right rhythm? Because when you were at Orbitz you were much more, I would imagine, in league with many of the clients that you worked with from a scale perspective. Even just to use your reference from earlier, you all know the weight of process, you all have strategy decks. You have that shared vernacular. Now you've been playing in this early stage growth space, you're much more nimble, you love that. That's why you're here, but you have these clients that aren't that.

Margaret: Yeah.

Suzanne: Does that trip you up ever?

Margaret: That's exactly what the opportunity is.

Suzanne: Okay.

Margaret: And I think it's actually really, really funny. I have two examples to share with you. One is just kind of the broad market space. We're working with retailers that, like I said, are experts at fashion, or retail selling, like a lot of the brick and mortar, they’re not experts at technology. We're experts at technology. We have great technologists and product people here so we can fill that. We can be an extension of their R&D. We can be really great partners in terms of checking out what's on the horizon and so we find that actually the dialogue is a lot better because of our size and our nimbleness and because of our focus.

The second example that I was gonna share kinda much more specific. We were talking to a very large company that all of us know that might rhyme with Schmoogle. There's always conversations with lots of companies, but we were talking about potentially can we partner and a handful of different ways. We asked,"Well why would you work with us. We're too tiny Shoprunner. We’re the David and Goliath, we're trying to fight the big guy. This company was like, "We're a big company now. We've got a lot of innovation but we don't move as fast as we used to and you're able to move really, really fast." I like to think of it as an asset. And I like to think of it as, "We don't have to be big". Look at what Snapchat was. Wasn't Snapchat tiny when they first started, or Instagram?"

Suzanne: Now they're swallowing up all of Venice and people are mad.

Margaret: Exactly. I don't think, again, the enablement that software and technology and the internet, and devices and etcetera, the enablement that all of that brings to us. It means that you don't have to be a huge company to actually really carve off a really interesting business and to deliver real value. I do like to think of where we are as actually a really strong asset. I don't think we need thousands of people to actually be really effective at what we're gonna do.

Suzanne: Could you ever go back into that type of environment now having been in these smaller, more agile places?

Margaret: I think it'd be hard.

Suzanne: Yeah.

Margaret: I think it would be hard. I could imagine it would be nice to go to a bigger company at some point, again, to have a little bit more, you know, that people and that network around you a little bit more to where you're not living on the edge as much as you do. But it's so great to build a team, to be a part of a team, and to go through this. That's something that I think is so important. There's no shortcuts. There's no shortcuts in life, there's no shortcuts in what we do. Being a company of this size, you’ve gotta do the hard work. You gotta roll up your sleeves. You gotta be a part of it but what comes out on the other side is what's just so rewarding and on it. And you can make a difference. You can make a real difference.

Every individual, right now we're about 60 people, every individual that we hire right now is such a big deal. I don't care what your title is or who you are. Every individual that comes along, that joins our company makes such big difference. That, I think, attracts certain type of people. If you're that type of person, come aboard and let's do awesome things together.

Suzanne: Right.

You said something to me in one of our earlier conversations. The quote was, "Bringing the human into what you do". Would you speak to what is the meaning behind that for you?

Margaret: Yeah, sure. Absolutely. I know early in my career, even me interviewing for all these banks, I was following what I was told would be good. What I was told would be like, "That seems like a good career move for you. You should go do that. You'll make lots of money". And what I've realized in my career is when I start to listen to myself, my own intuition a little bit more, I found success and I found the right opportunity. So as soon as I have ... And I'll make this more concrete in a second ... But as soon as I kinda start to listen to that part inside of me, that voice inside of me saying "Maybe you wanna think about this". And as soon as I am able to articulate it, maybe talk to my friends or talk to my network about it, it's amazing where external starts to meet the internal and I start to find the opportunities that are right for me.

Being a little bit more specific, I took a job once because it was a product role and it was title and opportunity, etc. But it wasn't the right fit for me. So I looked a little bit more at the form factor of it as opposed to the nature of it and people and the opportunity of it. And that experience was really hard. It was really hard. It was with a great company but really hard for me to have lived through. So when I turn around and I think about it, I'm like title isn't worth it. The wrong fit isn't worth it. Sometimes you have to live through it to learn that. I did it but it's not worth it to try to follow what somebody else says is a good opportunity for you.

You have to figure it out kind of internally what you really wanna do and what you're really good at. But you also have to be willing to roll up your sleeves, do the hard work. My feeling is you can be in a high performance environment and still be yourself. You can be in a hard hitting environment that's absolutely succeeding and if you need to, if you have to you work long hours that are demanded of you but you can also be quirky and funky and make horrible jokes, have piercings or tattoos. You can find a balance in those two things and you can find environments where those things fit. I think it's really, really important to make sure you stay true to yourself in your job search process and in the product development process. Because ultimately what you're gonna do is you're gonna find success and you're gonna do a great job and people are gonna value you for who you are. Those things will work together to create a great career path for you.

Suzanne: Yeah. I think that's beautifully put and great advice and a nice segway to a piece that I like to do called 'Get the Job, Learn the Job, Love the Job'. But I want to ask you this question. What advice would you give to somebody for finding what's right for you because what you're describing is kinda like the reverse intelligence. I went to a place that sucked for me and it was painful and now I know I never wanna be in that. Is there anything that somebody listening in could do now, especially if they're early in their career or starting to think about a change, that could help them get connected with possibly what is the right environment for them?

Margaret: I think, especially with product, you have to be fascinated by the nature of the product or the space, the domain. I work for ShopRunner right now. I love it. I love fashion, I love apparel, I love e-commerce. Orbitz I loved e-commerce, loved travel. These were industries and problem spaces I loved; I could really get behind. So the work that I did and do now in these spaces is all helping me learn more about these areas that I really, really like. I think you really do have to be true to yourself and where you're trying to grow you product career. I will never be successful in healthcare. Healthcare is just not a challenge that's interesting to me, but I'm very thankful that there are a lot of people out there that it is. Same thing with education technology. I was talking to a friend last night about legal technology. Those are spaces that just aren't a fascination for me so I'm not gonna read about it. I'm not gonna learn, I'm not gonna educate myself on the industry, I'm not gonna know the key players. But in these areas like I said, travel, fashion, those things for me are very, very interesting. I can get behind it. I enjoy talking about it.

I do believe you have your 40 hours weekly on the job. You make friends with people you work with. You think about your job at night. You think about it on the weekend. And so think about how much your job is going to be apart of who you are and make sure that it aligns.

Suzanne: I think that's good advice and I have spoken to people who have had similar paths where they just say "Well I love football so I was like how can I be in football somehow". Do you think that if you're not a user of the product that it fundamentally prevents you from being great at being the product manager for that product?

Margaret: No.

Suzanne: No.

Margaret: I don't think so. I think that's where empathy comes in. I think you have to educate yourself. I think you have to do the hard work if it isn't something natural or like "Hey I can log in to Orbitz I can see what the path is I travel". Then you have to do the hard work to go learn the context in which your users are. So you have to go out. You have to find them, you have to follow them, you have to observe them, see them in their natural environment because if you don't then you're not gonna understand. You're not gonna be able to understand the context of the user and you're not gonna be able to represent that effectively from a product perspective. But I don't think you ultimately have to be a user of the product to be successful. I think you can be successful, I think you can find success other ways.

Suzanne: You say you make mistakes. Tell us about one or two that you've made that give our listeners a pass so that they can say "Oh thanks for giving me a heads up. Now I won't make that mistake. Margaret made it for me".

Margaret: Oh my gosh I wish. That's a good question. One of the first things that comes to my mind ... And I know better. I'm still kicking myself. A few weeks ago my CEO who is amazing and awesome and brilliant, he has an idea that we're trying to share with some of our merchants to help build business. To help convert users. And he's talked to me several times about it. He was like, "You know what, we’re gonna do this and you do this and yada, yada, yada". And he finally was like "Are we really gonna do this? Can we prioritize it 'cause I'm selling it?"

And I'm like "Yeah. Done".

Did I talk to my product people? Did I talk to my developers? Did I talk to the lead engineers? Kinda ... Broad brush strokes but I turned around and committed to my CEO that we’re gonna do this and he's out selling it and I did not walk the walk there and go back and really validate like "Do we have the bandwidth? Is this a priority? What else is on our roadmap? What else is on our backlog?" I just said yes. And it was because he really wanted to do it and it's hard to say no.

Suzanne: Also you talked earlier, it seems like you have a history of say yes and figure it out later. That's an old habit. So were you able to do it? Did you go back to the team and they were like "Uh Margaret, no. We can't do this".

Margaret: We haven't tackled it yet-

Suzanne: Oh they don't even know. They're gonna hear this episode and they're gonna be like-

Margaret: "She's a shithead".

They know enough now. We're going through the prioritization process to where we're getting everything in the mix and Sam's gonna come back and be like "Oh wait. This that I thought was so important, why is it now to twentieth on the list?" So we're gonna have that conversation. We haven't had it yet. Again, product at least 10 years, 17 years of my career and I still make those types of mistakes. You're human. I say so often you have to be a masochist to be in product. To wanna be a product manager you are a masochist because you please all of the people none of the time. Everybody wants something. There's always pain points and you job is to sell for pain points. So it's hard to be the person that says no; that tightens the belt that says we only limited time, bandwidth, resources, etcetera, but when you get it right and as you get it right it's so rewarding. I think it's a little it like gambling. Like we're like "Ah man, I hit the big one. I nailed it. People are gonna be using my product and they like it". That joy you feel really makes it all worth it.

Suzanne: That's the variable reward in the hooked model that keeps us putting the quarter back in. It's like nine out ten start-ups fail, which I still think is a generous statistic. Nine out of ten fail but here we are plunking quarters saying, “Maybe I'm the next Instagram. Maybe I'm the next Snapchat.”

Margaret: Exactly.

Suzanne: So if product management is masochism why keep torturing yourself for 19 years? There must be a reason you love the job.

Margaret: I think it's that build side of it. I'm such a builder. I love creating something and having that reward. I love the context switching. Context switching sucks, don't get me wrong. You need time to think about stuff. But as a product person, you have to think about so many things. You have to be good at business. You have to be good at tech. You have to be good at user. You have to be good at empathy. You have to be good at relationships. You also have to have, I mean you have to put your ego in check. You have to put that aside. You have to be like, "I don't know what's best. I have to listen. I have to hear. And I'm probably gonna get it wrong. I'm probably gonna get it wrong a lot before I get it right". So it's like you're the glue amongst this entire organization across this entire ecosystem of consumers to users. Yet you're always kinda on that edge of like, "I'm probably getting it wrong and I don't know what I'm doing" and all of that. I think that that drive around all of it to make it right and to make great experiences for others it's amazing. Again, constant learning. Constant learning. I'm still always a work in progress.

Suzanne: Any recommended resources for folks listening to our show? Books, blogs podcasts, just general good suggestions for learning.

Margaret: You probably have covered a lot of the big ones. Absolutely Silicon Valley Product Group and kind of listening to Mind the Product stuff and paying attention to that. Some of the books that I've read ... I'm an avid reader ... Some of the books I read kinda have focused on more of ... Who are you and how do you create your life and your own best life, but I think it's really kind of leaked into my product experience. So talking about ego, there's a great book called 'Ego Is the Enemy' by Ryan Holiday. It's all about, "Hey, you know what? You can't follow somebody else's path because you're gonna get it wrong. That's somebody else's path. You gotta figure out how to listen to yourself to get to your own.

There's a great book called 'But What If I We’re Wrong' by Chuck Klosterman. That one's fascinating because he basically takes a future look at today and says "Hey what are people in 50 years or 100 years gonna look back at our culture today and say what was important just as much as we look back and say "Hey, Moby Dick is the book to read" from the best literary novels of the 20th century. Like how did that decision happen? And how are you gonna get it wrong because if you try to evaluate today's things with today's viewpoint you're gonna get it wrong but if you try to play it out into future a little bit and realize that the mindset in 50 years or 100 years can be very different. How they're going to evaluate today is kinda mind blowing the way he positions that point of view.

Suzanne: I think people in the future are gonna be looking back at a lot of what's happening in tech right now and saying "I can't believe those folks that were doing tech in the mid, early 2000s were doing. Look what they destroyed. Look how they"-

Margaret: Well just like I look back 17 years and I'm like I had my box with my DVD and my CD and I taught myself how to code with a book. I mean like Oh my gosh. How much has it changed in 17 years. What it's gonna be in 50 or 100 is amazing.

This is also the thing I think is so fascinating about product is that I still feel like we're still early in this as a discipline, as a practice. I mean people like yourself doing 100 podcasts. This is helping advance us as a community and it's helping us be better at our craft. I think it's gonna be crazy how much better we're gonna be in 20 years. I would say technology product has really come about only in the past 10 or 20 years. These resources are so very, very new, very early in the life cycle.

Suzanne: Great recommends. We'll put them up on our website. 100productmanagers.com/resources for anyone listening in. Last question for you, have you picked up along the way a soundbite or mantra that helps us to understand who you are in the world?

Margaret: I think I don’t really share it with a lot of people but I often say to myself "the only way out is through". Like I mentioned a little bit earlier, you can't avoid the hard things. You're not gonna avoid messing up. You're not gonna avoid failing. You're not gonna avoid pain. You're not gonna avoid trauma and misery and all of those things. Those are all kinda part of life. So there's no free ride here; there’s no easy success. Being a product manager is hard. And you're not gonna have the vision handed to you. You're not gonna have clarity handed to you. So you have to fight for it. You have to put yourself out there and get that clarity yourself. Again, there's no shortcuts in that so you gotta kinda be present and you gotta live in it and you gotta be part of it and you gotta realize the journey is the thing you gotta live through.

Suzanne: Margaret Jastrebski, Goddess of the Chicago PM Community.

Thank you for your leadership, specifically I know there are so many people who are grateful for the leadership that you've brought through the years being such a part of this community. Thank you for being a part of our show and sharing your insights. Really grateful.

Margaret: Oh my gosh, I'm so happy to be here, Thank you for what you've done.