Product Hero: Rose Grabowski

by C. Todd Lombardo

Rose Grabowski

Creating insights from analytics weren’t enough to fuel Rose Grabowski’s curiosity of the world around her. She took her passion of understanding drivers of human behavior to the world of product management, now as a Director of Product Management at Invaluable, a product for high-end auctions. Being a product manager isn’t just a trade or skill for Rose, it’s a state of being. She’s tapped into her users and stakeholders at Invaluable, making sure that each group is being heard and aligned to the product vision. She’s always questioning how she can get closer to each of the audiences she is working with daily. Rose’s innate love of working with groups of creative folks, and her ability to lead various groups in complicated coordination are just a few of the reasons why we think Rose Grabowski is a Product Hero.

I had the opportunity to ask Rose about her career and the product management industry. Below is a revised and condensed transcript of our conversation.


C. Todd: I am here today with Rose Grabowski, who is a Director of Product Management at Invaluable. Rose, welcome.

Rose: Thank you very much.

C. Todd: Why don’t you tell us a little bit about you and your background? About how you arrived at being a Director of Product Management. I know you’re formerly from Boston, and you’re now in Chicago.

Rose: Yes. Absolutely, I am Boston born-and-raised. I started my career there, and just recently moved to Chicago a few months ago. My husband is an academic and is now a professor at a university here, so that brought us out to Chicago. I started off in Boston, went to college in Cambridge, and started working in marketing analytics right after college. I learned a lot about Excel formulas and models, which was very useful in a lot of ways, and very interesting. I moved from marketing analytics and strategy into product management about eight years ago. That makes me feel really old. I worked with a variety of internet companies, I was at BuyerZone, which is in Waltham, a B2B lead generation company for a few years, and then moved into a more scrappy start-up situation at Gemvara, then moved over to Invaluable, which is a marketplace for fine art and collectibles, primarily.

C. Todd: Tell me a little bit more detail about how you made that transition from a strategy analyst role into a product manager role.

Rose: I was doing marketing analytics and strategy for two or three years, and there were definitely parts of it that I enjoyed. I enjoyed the analytical piece of it. I enjoyed working with really creative people: designers, copywriters, and marketing managers. That was fine, but I started to feel like I was trying to find the best way to sell something, and analyzing it: “How well did we market something?” “How well did we communicate an offering?” and “How much can we convince people to buy something?” but I really felt like, “I want to effect the thing that they are trying to buy. I want to make it so that the thing that we’re trying to get someone to purchase or use sells itself. That we’re solving the problem in such a great way, that we don’t need to do promotions or have snazzy campaigns. There’s got to be a place for that in the world.”

I started thinking about that, and trying to figure out, “How do you do that? What’s that even mean? Is there even a job where that’s done?” I was poking around job descriptions trying to find out what my next move was. I actually left my company thinking, “I have to rethink what I want to do. I’m going to take time and make pottery, and travel, and figure out my next move.”

I just happened upon a product manager description online and thought, “This is cool. You get to be creative. Right-brain, left-brain. You get to work with all sorts of people. You have to solve problems. Yeah, that’s it!” I found my new career accidentally on LinkedIn or Indeed.

C. Todd: You’ve come so far from your first product manager role, to now being a Director of Product. You have a whole team. What’s your structure at Invaluable right now?

Rose: We have a product and design team that’s kind of combined, so our VP of Product, Josh Hale, is whom I report to. We have two Directors of Product actually, and three Senior Product Managers and Product Managers who report in to the Directors of Product. Then the four people on the User Experience Design Team also report in to our VP of Product.

C. Todd: Got it. What are the things that you typically focus on in your day-to-day activities?

Rose: What I try to focus on is some of the medium to long-term initiatives that we’re trying to figure out. For example, on our marketplace, payments are a pain point. Every auction house and seller handles collecting payment differently. Sometimes it’s through credit card. Sometimes it’s through a check. Sometimes it’s through PayPal. We are working on improving that process. We’ve done something to have payment processing domestically, but now we need to figure out the international market. Right now, I’m focused on looking at, “Okay, what’s that landscape? Who can we work with? What are the options? What are the pros and cons?” Trying to figure out, “Who should we be partnering with for this major initiative?” That’s a multi-month evaluation. “Who would even make sense? How is it going to affect our organization? Do we need to hire people to look at the fraud issues related to this, or can we get that outsourced?” That kind of thing.

It’s a mix of that longer-term evaluation, and working with the team to get feedback on initiatives that are in current sprints. Also, looking at bugs that come in and trying to make connections between issues that are happening. There’s definitely a variety of high-level and very granular type things day-to-day. That’s the life of a product person, right?

C. Todd: Of course! Tell me a little bit about some of those more granular things, in terms of the feedback and the sprints. Tell me a little bit more about your sprint cadence and how that works.

Rose: We adopted Scrum about a year and a half ago. We currently have three sprint teams. One of the Product Managers is a product owner for each of those. We operate on two-week sprints. Each of the sprint teams is responsible for a domain of items. We switched that three or four months ago from a user-based domain setup: One team was looking at the buyer side, one team was looking at the seller side, one team was looking at our business partnerships.  Now we have a different structure based on our initiatives for this year.

We looked at the teams and said, “How can we divide this in a way that will have every team be productive?” One of our challenges is figuring out how we have all those teams work together, and yet not be dependent on each other as we restructure this. People are working on the same codebases for different kinds of initiatives. That’s probably going to take a little while to figure out. We’ve made a lot of progress, but it’s not a simple thing to do, as far as I can tell.

C. Todd: Are there specific metrics that you track from a product perspective or even from a customer perspective?

Rose: Yeah. On the buyer side, we look at the total number of buyers, visitor-to-buyer conversion rate, the number of transactions per buyer over a given time, and the value of those transactions. Those are the big ones on the revenue side.

On the seller side, we look at number of auctions posted by auctioneers, number of items posted by sellers, the sell-through rate, and our own share of gavel: What portion of the dollar value sold at an auction is sold through us? Then we look from a requisitioning position at how many of the top houses in the world are clients of ours. How many of the top galleries, and dealers, of the world are clients of ours?

C. Todd: I’m curious, since you mentioned buyers, and sellers, and partners. How does your product team interact with those different stakeholders, external stakeholders, that is.

Rose: In the past, when we divided our product team and our sprint teams across those three stakeholders, each group was responsible for having regular interaction with those audiences. I was, at that time, managing the bidder side of things. We would have research projects where we would sometimes have specific features we want to get feedback on and we would reach out to buyers and users and ask them for survey information or interviews, or do usability tests with them. Sometimes I would develop a relationship with specific bidders based on an interview here or there. They would reach out to me and say, “Hey, I noticed this thing. Have you guys thought about adding this feature?” Or, “I got really frustrated with this auction house. Here are all the problems. Please help me.”

Developing longer-term relationships with some people helps get more consistent feedback over time, and more raw feedback on things that I may not have realized I needed feedback on, that I didn’t even realize were hot topics for them. Sometimes we would just do open-ended interviews. We would email them and say, “Hey, can we just chat for half an hour?” We’d ask them some questions to start things off, but then just have open-ended discussions to see what was on their mind, how their experiences were.

Definitely having that first-person interaction is important. Often, we’d find that every time we’d talk to a person, we’d go, “Gosh, that topic, shipping, is something that we keep putting down on our list but every time we talk to somebody, shipping is something they want to talk about.” It’s just a reminder of the stuff that our users actually care about that we might discount because it’s hard, or internally, people wouldn’t be talking about it. It really brings you back home to what’s important.

C. Todd: Tell me about how your team manages priority roadmaps. Unpack that a bit further.

Rose: Sure. This is the thing that, to be honest, our team is evolving as we mix things up. Right now, the way it’s working is that each product owner and product manager is looking at what’s been put into the bucket for their sprint team, the large initiatives, and working with the tech team to figure out what is a general right order of things. They’re working with their manager to sniff that out a bit, and we’re rolling things up into one larger roadmap that we get feedback on, first within the product team, and then across stakeholders. It’s something that we’re trying to revise every few weeks, and re-present to stakeholders regularly.

We’re trying to do a little roadmap roadshow in the next couple of weeks actually, to make sure that we at least get people looking at the rest of the year, and understanding where we’re going.

We’re going to be talking through that with each of the major groups in the company. Customer care will get a presentation. The sales team, the marketing team, and the larger tech team. Each sprint team has seen the roadmap that their team is working on, but they may not have full contact with what the other teams are working on. They all work together and give advice to each other, working on the same codebases so it’s important to make sure that they all understand the full roadmap too.

At our leadership team level, they’re looking at this roadmap too, thinking about reorganizing the general company priorities throughout the year, which will affect the roadmaps.

C. Todd: In your experience, have you seen any mistakes, or faux pas, that maybe you’ve done yourself, or other teams have done when they’re making and sharing roadmaps?

Rose: Yes, a lot of times myself, I’ll definitely take that on. I think one thing that I’ve seen in the past, for myself and for others in past companies that I’ve worked at, has been having a tough time showing the roadmap knowing it’s going to change. It’s always going to change “tomorrow.” Even when you get to tomorrow, it’s going to change the next day too. Maybe not literally “tomorrow,” but you know you’re always learning and thinking about course correction. It’s tough sometimes to bite the bullet and say, “We’re going to show something and we’re going to couch it with all sorts of notes on this being a living document. Things always change. These aren’t committed dates.” That kind of thing.

People hear that and are still going to hope that those are commitments, and hope that nothing changes, or the thing that they don’t want to change doesn’t change. It’s important to still have the conversation, and just accept that nothing is perfect. Under-communicating the roadmap is a big mistake that can easily be made.

C. Todd: Speaking of relationships in different departments, what’s the relationship between the product team, design team, engineering team. You mentioned it briefly before about how you’re structured. How does that relationship work?

Rose: I’d say pretty well. We have a really collaborative team, amongst product, design and engineering that I really have enjoyed. It’s funny. Our company has grown so much that we moved from being on one floor of our building, to two floors. On the bottom floor is product, design and engineering, and on the top floor is sales, customer care, marketing, and finance. It’s sort of funny because in some ways, that’s a natural thing, to group product and engineering together. We wanted it that way. We work with them the most of anybody on average. But inevitably, that physical distance impacts how people work together, so we have to be very active to make sure that we are talking with the other groups in the company as much as we need to be. That’s interesting to learn. It’s kind of like, “duh” once you think about it. Of course, that physical distance is going to matter. That’s why we wanted to be next to engineering when we had to make a choice. So, we have to be very active on that.

Because we’re doing Scrum, we work everyday with our engineers. It’s great. They’re a really great group of people. Very collaborative, like I was saying. We have engineering leadership, who we have frequent discussions with, talk about long-term items, hear their concerns, and talk about technical issues that we need to deal with. We have stand-ups every day with each of the Scrum teams. It’s pretty effective. I’d say one area that I’m thinking about is: How do we bring the design team more into the Scrum environment in a way that makes sense?

C. Todd: What are some big mistakes that you’ve made, that you’re willing to own up to?

Rose: I think, the first part of my career I was really focused on putting myself in my customers’ shoes. Now, I’m trying to be much more conscious about the other stakeholders’ shoes. Not just thinking about what drives them, but really, deeply thinking about, “If I were them, what would I want?” In this case, I’m thinking about the sales team, the engineers, the marketing people. Internal stakeholders. Where I’m trying to be better is, really thinking deeply about what their concerns are, and how I can make sure that I take those concerns truly into account at a deep level. I put myself in their shoes.

C. Todd: What advice could you offer to someone who wants to become a Product Manager?

Rose: What I first tell people is that they should read the book, The Design of Everyday Things. It’s one of my favorites. It’s one of those books that, for me at least, shifted my brain as to how I think about problems, how I think about user experience, and understanding what user experience really could and should be. I never will look at a door the same way.

C. Todd: If you could learn how to do one thing – because learning is obviously part of any product manager position, always learning something new – What’s the one thing you’d want to learn, like you’d want to be an expert at in an instant?

Rose: I would say to speak and understand Spanish. I say that because it’s something I’ve tried in the past, and I’m really bad at it. It would be so useful, so if I could just get a shortcut to knowing that, that would be really great.

C. Todd: Rose, thank you so much for being part of our Product Hero series. Thank you for spending some time with us today, and sharing your knowledge and expertise with the world.

Interview notes:

  • Rose’s tips for product roadmapping: Get everyone on the same page. A product roadmap is a living document that changes daily. Make sure the team knows that dates and features can change. Communication amongst all stakeholders is key
  • Rose has developed long-term relationships with users. They give more consistent feedback and will freely offer up comments because of that relationship.
  • Rose’s favorite resource: The Design of Everyday Things, by Donald A. Norman
  • Connect with Rose on LinkedIn and Twitter

Know a Product Hero? Email us with who we should interview and their contact information.

About C. Todd Lombardo

C. Todd is a leader who wears many hats, all at once: Author, designer, scientist, professor, and visualizer.  After originally beginning his career...