Kelly Port - Leading Product From Revenue Decline to Successful Exit
When I took to social media a few months ago looking for more product leaders for the series, Kelly Port, VP of Product at Elsmere Education was recommended by a mutual contact. We talked about her time as the EVP of Product Development and Commercialization at GutCheck leading the product from revenue decline to successful exit. We talked about the importance of curiosity for product leaders, how to realign the organization around a new product direction, and her advice for other product leaders who need to reinvigorate a stale product.
I love what Kelly says about inviting people to critique your idea to make it better. Rather than allow ego to fool us into thinking we alone have the answers. When done well, strategy is a collaborative activity undertaken across the org rather than concentrated in a select few. It was fascinating hearing Kelly’s approach – it’s a powerful way to set strategy and bring the team along.
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Can you introduce yourself?
My name is Kelly Port. I live in the Denver area with my family: my husband, two kids, and two dogs. We've been here for about 12 years and are originally from the Midwest. I've been in product management for 20 years, which feels crazy to say out loud.
I kind of stumbled into product management when I was in a role where they needed someone to help translate between the engineers and a team of nurses and they couldn't talk to each other effectively. It turns out that was a really useful skill to have. That grew into this love for the intersection of technology, people, and business and creating value amongst those three things. I kept going from there, growing into product management. I've worked at mostly healthcare technology companies, including Optum and Davita. Three years ago, I left to try a new industry. My most recent role was at Gut Check, which is a market research boutique. I'm about to start a new job at a company called Elsmere Education. They help universities with their online programming, helping them to be successful. I’m excited to start that role and explore another new industry.
How did your role as EVP of product development and commercialization at Got Check come about? What attracted you to that opportunity?
I was at Optum in a corporate strategy role, really far removed from product development. A recruiter I’d talked to a couple of years prior reached out. It turned out they had turned over most of the leadership team at GutCheck and were looking to reinvigorate growth. They had been unique and differentiated but had lost that edge and started to decline in revenue. The product had become somewhat stagnant. They needed a new group of leaders. I was excited by the challenge of a new industry. If you've worked in healthcare at all, or know people who have, it's a tough space to be in for a prolonged amount of time. I needed a bit of a break from those challenges, so decided to try something new.
This was an opportunity to build a product development function that was cross-functional, driving rapid innovation. It was exciting for me. I had a really good feeling about my leadership peers. I thought it would be a really nice change of pace and an exciting opportunity to build something different and challenging.
People are really smart and they ask really hard questions, which can be frustrating as a leader, but it's really important to allow that to happen. It helps you refine and make sure you haven't overlooked critical things.
Had you been in senior leadership roles before?
I'd been in VP roles for a couple of companies but was not the head of product or general manager of product in those roles. It was the first time I was fully responsible for and in charge of product management. There was an appeal to be the “boss” of product in a company of that size. I love growth-stage companies that are building out product discipline, homing in on strategy, and getting ready to scale. It was a great growth opportunity.
How big was the company when you came in?
We were 80 - 90. Not so big but not a startup. The product team was about four people, so pretty small from a product development perspective.
You mentioned that revenue was in decline. Can you tell us more about the state of the product?
When I came in, they had been without a product leader for about 18 months. The CEO was running double duty as product and CEO. It’s tough to split time like that when you’re trying to innovate. They had a good portfolio but it was stale. They had 18 or so products which felt a bit big for a company that size. We needed to figure out how to freshen that up without losing the goodness that was in there. We had to build on that foundation, cut away the things that weren’t adding value, and then figure out how to augment the portfolio so we could be more competitive.
The challenge with the aged portfolio – which is a challenge anywhere, but particularly in market research – is that space is so crowded. It’s a sea of sameness. Everyone is saying the same things. Everyone is using the same buzzwords. We had to find something innovative. We had to get back on the map, in front of our customers and in front of new prospects. We needed to give the sales team something interesting to talk about with clients. They were really hungry to have new things in the market.
People are really smart and they ask really hard questions, which can be frustrating as a leader, but it's really important to allow that to happen. It helps you refine and make sure you haven't overlooked critical things.
When there's change, there's always fear. People are worried that something's going to be different. That’s really scary. You have to understand their concerns. One of the best things you can do is be authentically curious.
How did you figure out what to do?
Most of the leadership team was new including a new head of sales, a head of ops, a new CEO, a CFO, and a head of marketing; everybody except the head of research. We did deep strategy sessions into things like what our customers currently liked about us, what attributes we broughtg to the table, what customers were looking for that they weren’t getting, and where were the unmet needs? We looked at the whole space and one of the things that stood out was that our customers liked our people. They valued our expertise, they trusted our findings. That said, we were relatively expensive and standard, and not particularly speedy. Based on this, we decided our best play was to develop offerings that provided greater depth than our competition, getting closer to the person than traditional research could do efficiently.. We started to do some experimentation with technologies that used natural language processing and extracted emotion from product reviews, blogs, and other sources to understand where critical emotions were emerging in a given space.
This allowed us to build our flagship new product, which was highly differentiated and innovative and aligned tightly to our new strategy. This product helped our clients figure out where and how to innovate to be most competitive, but much more quickly and cost effectively than common alternative methods. This product was fundamentally rooted in getting to what matters most for the person and understanding what's behind their decision-making. Then we started to look at ways to build that into the portfolio more broadly.
How did you sell the new strategy across the company? The leadership team was new but others had been at the company a long time.
Oh yeah, and even within the leadership team, there were different points of view. We had a lot of great discussions as a leadership team. Once we were all aligned, we were big on transparent and repeated communication. We were also transparent about where we were making bets, and what we had yet to learn.
It was a lot of repetition, a lot of time spent with individual teams, in 1:1s to get more feedback and get people excited and answer the questions.
When there's change, there's always fear. People are worried that something's going to be different. That’s really scary. You have to understand their concerns. One of the best things you can do is be authentically curious.
This applies to so many areas of product leadership. If product adoption is not where it needs to be, if people are resisting something, go find out why. They're probably not doing it to be difficult. There’s something they're legitimately concerned about or struggling with. At the end of the day, you are all on the same team solving problems together.
If you're curious and you're genuinely trying to understand and have empathy for what that person is anticipating or experiencing, sometimes it’s as simple as clearing up a misunderstanding. You can adjust your approach. You can help people see why the current path is not working anymore and why. You share market data and feedback from clients. You help them understand why the new path is a better bet. You ask a lot of questions along the way, then at some point, you have to decide and go.
You never have perfect information. You have to be bold and make a hard decision with imperfect information. That’s the thing that’s gotten me farther in my career than anything else. There are times when I’m terrified but at some point, you have to decide to go otherwise you’re going to be stuck in analysis paralysis and then it’s going to be too late. You’ve got to move.
Decide and go — that's so good. I love what you said about curiosity. It’s so important for leaders to understand and to get people aligned. It’s so powerful.
100%. I came up as a business analyst so it was all about asking questions. It’s actually very powerful to offer up vulnerability and be secure enough in yourself to know it’s ok to not always have all the information and that you don’t have to be right all the time. It takes a lot of pressure off!
It’s incredibly important to be empathetic and curious and demonstrate that you’re a team player and want to collaborate as you’re figuring out all the product things. But at the end of the day, it is your decision. You have to help people understand why the decision was made. When you’re transparent about the reasoning behind it, people are usually ok even if they don’t love it.
What happened to the existing suite of products?
It was a combination of things. We deprecated a few things that were hard or costly to execute or very low revenue. We up-leveled other items in the portfolio, evolving them to more closely fit the refreshed strategy. Some of those products were performing quite well, but they weren't necessarily distinct. We wanted to leverage what was good there and then zhuzh it up a bit. The portfolio was all over the place. We had to create a more curated portfolio that told a cohesive story about our strategy. That allowed us to have a more strategic portfolio by the time we got acquired.
I understand that in the first 18 months, you launched seven new solutions after only one was launched in the two years before. How did you go about that organizationally?
Yeah, it was tough, especially for people who had been there a long time, and we had a lot of amazing people who had been there for several years. That's a very big disruptor to their world, having to absorb a new product every couple of months,and some of them were significantly different from what we’d had previously. For example, the machine learning product was an entirely new execution model. It was an entirely new philosophy. We had to educate our clients as well as our internal teams on that one.
It was a big change management effort. The first step was making sure folks are comfortable selling and executing on this new product. We joined sales calls. We devoted a lot of time to supporting the big launches. The other way we managed to change was pacing. We tried to stagger the complex releases with ones that were more familiar to our staff. We’d do a big new thing and then add something to an existing product.
We wanted to make sure that we weren't scaring our internal folks with all of these new products.
It was a lot of communication, a lot of conversations with the leaders in those areas to make sure we understood what else was going on. We maybe could have even done more, but I don't think that the business could have absorbed it. And I think it helped us get to better quality on what we did put out there because we made ourselves wait a little bit and continued to do some betas and refine things so that when it launched, we were more on target with the solution.
There was a lot of change management support and a lot of that included reminding folks of the strategy and then revisiting previous proof points. Hey, when we launched this product, we brought in X thousands of dollars in the first X months; this is awesome and exciting. And we tried to reinforce that the things we were launching were thoughtful; we weren't just kind of throwing spaghetti at the wall. We were being purposeful.
People leave during times of high change and that’s ok. I don’t hold the position that it’s a bad thing. It happens. Departures are normal. I want to normalize that. Organizations are living, breathing, dynamic entities. They're never static. And during times of change, you just have to expect these things.
Did you expand the team much?
We didn't grow much. My team grew a little bit because we were doing more innovation. My product managers also did a lot of product marketing activities so we needed more capacity there. We had fantastic retention in the research and innovation groups. So the engineers, the product folks, and the research science team, like that were really solid. We had quite a bit of turnover on the operations and sales side. Some of that was just kind of natural attrition. Some of it was that coming out of COVID a lot of people were exploring and looking for the next thing.
We did a lot to try to actively manage that as a business. We kept a close eye on the engineering team because we knew that was a risk. Fortunately, we had a tight group and built trust early. My team worked really closely with the engineering leadership to make sure we were all on the same page and give them the opportunity to ask anything they wanted. As a leadership team, we were cognizant of the attrition problem in general at that time. There are lots of single points of failure in a company that size so you need to be close to those folks and make sure that they were feeling supported and clear on why they were valuable. But it was a tough time.
You never have perfect information. You have to be bold and make a hard decision with imperfect information. That’s the thing that’s gotten me farther in my career than anything else. There are times when I’m terrified but at some point, you have to decide to go otherwise you’re going to be stuck in analysis paralysis and then it’s going to be too late. You’ve got to move.
Yeah, it strikes me as lots of change and moving parts.
Oh yeah, the whole leadership team changing over was a big change. Some of the folks stepped away because they didn’t really mesh with the change in strategy or the new leadership approach. And that’s ok. It doesn’t have to work for everyone. Or we needed new or different skills. It doesn’t mean they weren’t amazing and talented people. Sometimes it’s just time to transition. I had someone resign on my team who was super talented, but that person wasn't quite the right fit for what we were trying to do going forward. So it's, you know, shake hands and it's all good.
People leave during times of high change and that’s ok. I don’t hold the position that it’s a bad thing. It happens. Departures are normal. I want to normalize that. Organizations are living, breathing, dynamic entities. They're never static. And during times of change, you just have to expect these things.
Totally. We lost a couple of people that were certainly disappointing to say goodbye to, but that's part of a shift like that. You kind of transform the business into something different. It's not going to be for all people.
You have to have an open conversation with your folks about how they’re feeling about the change, their role, and if they’re feeling frustrated. Especially if it's one of your high performers who could easily find something elsewhere, get close to them, talk to them. And if they want to leave, then that's fine because that's their choice and I want what’s best for them. Change is also an opportunity to manage people into something better, whether that's internally or externally. I had an employee once who was struggling and I said, ”I can coach you to be successful here, but this does not feel like the job you want. It feels like you want that job over there and unfortunately this isn't that job. Would it make sense to try to find you that job somewhere else?” That's what we ended up doing. And she was so much happier. And it was a tough conversation at the time, but it was the right thing for everyone.
You all had a successful exit. Was that something you thought about when you came to the company? Was that the plan?
I think it was always sort of on the plan. It was one of the, hey, we've got investors. We've kind of been in their portfolio for a while. We need to do something. We want to have some sort of event and acquisition was an attractive one. It wasn't the primary motivator for the strategy we built out, but it was in the mix.
It was in the back of our minds in terms of what would generate great value and help make us stand out in the market. We know that would inherently make us attractive as an acquisition target. So the main goal was growth and the next level down was potential exit. We were able to do that quicker than we anticipated. I thought it would be a three-year path and ended up closing 25 months after I started.
Product management requires a balance of conviction and humility. You have to be able to make those decisions and move forward, but you also have to be humble enough to know that you don't have all the information. You need to be open to new information. It could mean your roadmap needs to shift or you need to pivot. Finding that balance is critical to the success of a product manager.
That's really great to go from, you know, a stale, product suite that’s in decline to then, you know, acquisition is really, that's an incredible story.
It was. We had a hypothesis that played out.
What was most rewarding about leading through this transition?
The hypothesis panning out was fun because sometimes you make all the right decisions, have all the best data and it still doesn’t work out. So when it does, it’s satisfying and special.
The other one is the team. We had an amazing team. They were maybe the best team I've ever had, which I don't know if I should say, cause I've loved all my teams. This one was really special. I inherited some amazing folks that stayed throughout and I got to hire some really special folks and we were able to build a sub-team culture that was very close, solution-oriented and had a “how can I help?” mindset. That was super, super satisfying. And then the cross-functional teams. It was fairly siloed when I got there. Everyone was kind of doing their own thing. Working with the engineering and research science leaders to bring together a close collaborative group was really satisfying too.
I think the rewarding part about the exit was being able to do it with integrity. I don't like politics or shadiness. We were able to do it in the right way in my opinion, and do it with collaboration and positivity as opposed to being cutthroat and you know, those icky things. So it can be done, which is really nice. I think folks get this impression that you have to be willing to play all those games to win in business, but you don't have to. You can do it the right way too.
Acquisitions are tricky. I led through one as a COO. They can be tough.
It was very hard. It was super stressful.
They can also be beautiful. I love that you talked about doing it in a way that felt like integrity.
Right. It wasn't easy for everyone. We had some challenges with it, but by and large, I liked how it was handled and how it all turned out. So that's good.
Product management requires a balance of conviction and humility. You have to be able to make those decisions and move forward, but you also have to be humble enough to know that you don't have all the information. You need to be open to new information. It could mean your roadmap needs to shift or you need to pivot. Finding that balance is critical to the success of a product manager.
What advice would you give other leaders facing a product challenge like this?
If you're stuck somewhere, be curious, you're never going to have all the information, but if something's blocked and it feels frustrating, go dig into it, talk to the customers, talk to your peers, talk to your internal customers and stakeholders and partners. See if you can get to the bottom of it. If you come from curiosity rather than trying to force things or making negative assumptions, you’re going to have more success. It does a better job of building relationships, collaboration, and respect. Always be curious.
The other one is to be gutsy. If you're in product, you're going to have to make hard decisions. One of my first really big decisions was within my first few months, a couple of jobs ago. We were trying to get to a client launch but it wasn’t going well; every meeting it was like one step forward, two steps back. And I asked my boss, the CPTO, what should we do? He told me it was my call.. That was the first time it was fully my decision. That was really uncomfortable, but you have to use the information you have and make the decision. You're not always going to be right, but honestly, I've found there are a lot of good enough decisions. And making the decision is almost always the more important part. Sometimes you'll be dead wrong. Set yourself up so you can pivot away from that, but make the decision so you can move forward and find out.
Finally, try to stay out of politics as a product person. You need to be as impartial as you can and not play favorites. Have humility and try not to get sucked into politics.