Leader Spotlight: The ability to weather change, with John Karwoski

John Karwoski is Chief Product Officer at Andr3w AI and former VP of Product, Strategy & Innovation Lab at LPL Financial. He began his career as an engineer and spent nearly 20 years at Boeing, where he transitioned to product management. Following Boeing, John worked at Prowess Consulting and Octout, a cloud-based solution to simplify IT tasks. Before his most recent roles at Andr3w AI and LPL Financial, he served as CPO at Projul, a construction project management tool.

John sat down with us to discuss the importance of everyone in the organization owning the voice of the customer, which, in turn, promotes hardiness and empathy to change. He talks about the importance of listening and being authentic and transparent, and how that earns trust with customers. John also shares insight into his latest endeavor with Andr3w AI, which is designed to provide scalability, predictability, and cost efficiency to organizations.

Connecting with the product and its customers

You’ve worked at a variety of companies in different stages and industries. Could you walk through your background and what you did in each of these roles?

I spent almost 20 years leading products at Boeing. After that, I worked at three early-stage SaaS startups, primarily in the B2B space. Alongside those startups, I led engineering at a martech consulting firm for companies such as Microsoft, Intel, and SAP. The number of concurrent projects and the rate at which I had to work on them definitely kept me young. To be successful that late in my career was a pretty cool challenge for me.

After that, I joined LPL Financial, which was my first and only foray into finance. I’ve been in a lot of different verticals, but that one was very unique because people in finance often stay in that vertical for the entirety of their careers.

Then, when I was at Ventures and Innovation Lab, I worked with the board and senior executives to expand the backlog and plan the roadmap. I helped determine viability in that backlog, and, if they were viable, I would strategize how to bring them to market. We’d set them up for scale and then send them off. It was a great holistic experience that taught me a lot.

You started your product career at a time when product management wasn’t necessarily a formal title. How did you transition into product?

Well, it was not intentional. When I started my career in tech many years ago, I had very little exposure to product management. The product function wasn’t in the limelight nearly as much as it is now, especially at Boeing. As a developer, system engineer, and architect, I had to leverage project managers to track tasks and determine outcomes.

The problem with that scenario was that in companies like Boeing, projects and products were led separately. That was the catalyst — my struggle to have any control. That’s why I stopped and ultimately moved away from the project management role. That transition got me closer to connecting with the product and its customers. My goal was to better control the outcomes, make things happen faster, and make customers happier.

The importance of listening

How did the two decades you spent at Boeing shape your learnings and approach to product management?

In the early 2000s, Boeing and many other large enterprises were looking at different product development methodologies, so I was trained on ITIL (Information Technology Infrastructure Library), Waterfall, and several other large frameworks. The goal was that they would outline the best practices for providing IT services, but that didn’t really correlate with us. I was building and leading teams of high-performing software developers, even though Boeing wasn’t a software development company.

The biggest problem with ITIL was that it really stifled creativity. For the leaders who were in charge and micromanaging it, the passion for the framework was exponentially stronger than the passion for the product, and that was not successful. Our goal in moving to agile was to develop and meet customer needs more quickly, and let the customers help steer our product.

That was the catalyst of how things changed for me early in my career and influenced my pivot into product management.

You described needing to recover from having an engineering mindset before moving into product management. How did you go about that?

Listening. Specifically, listening to potential customers and learning to empathize with their jobs and understand their tasks and struggles. Customers won’t open up to you to tell you those things unless they trust you because they feel vulnerable in doing so. You earn that trust by truly listening and being authentic and transparent about why you’re there and how you’re going to help them.

That was the piece that greatly improved business processes at Boeing, and that became my bread and butter. We did things that saved tons of time, energy, and resources. And as we did that, every customer would sing our praises to the next one.

You truly built a champion network. As a product leader, how do you maintain the perspective that you need to be effective?

If you put the customer first, they become your champion. If you couple that with transparency and recruit them to your cause, that brings loyalty and longevity. If it’s making their lives easier and saving their organization time and money, that’s a win. It’s exciting, and that gratitude from customers was imprinted on me early on. It still resonates with me today, which is why everything that I did then and still do now is customer-led.

It’s important that customers know that you’re on their side and that you’re working toward solving their problems. If I have the ability, one thing that I like to do to foster that transparency is to make my backlog public for paying customers. They can add to that backlog, monitor the priority of what they add, and uptick things that other customers have added. Some of my favorite products today do that. For example, Rivian, the electric auto manufacturer, does that. They’re doing that using the free version of Canny.io, which is awesome!

Another thing that keeps me on the path is our amazing product management ecosystem. For example, this Leader Spotlight series is documenting so much knowledge. These insights are a new resource that’s available to countless people.

Leading with data-backed hypotheses

You want customers to use your products and understand what they do as soon as possible. How do you get your teams to focus on that as opposed to dreaming big and thinking about what the product could theoretically do?

It’s really easy to sell a dream but nearly impossible to build one, right? Experience as a developer and architect, paired with strong communication with my team, made it easier for me to focus on what we can truly do. The obvious benefit of that is that you can accurately predict the time, resources, and money needed to build things in the way that the customer expects. You can have 100 “attaboys,” but it only takes one mess-up to damage your reputation.

Not leading with what’s physically possible is a risk that you can’t afford to take. I still experiment. I like to do proof of concepts, but if I can’t even mock up the idea, how can I ask someone to build it?

With so many ideas floating around from various people, how do you communicate your POCs as something that needs to be considered and start gathering buy-in?

Firstly, I lead with a hypothesis backed by data. Those two have to go hand-in-hand 100 percent of the time these days. Data without a hypothesis is often meaningless. Without it, where is the context of the story, where are we in the story, and how does the data affect the outcome of the story? Also, if you can’t measure it, you’ll never get the buy-in to implement it. You need to have that when leading discussions with stakeholders.

With that in mind, the thing I’m most passionate about is only bringing to the table what I need. More data or more people than needed usually dilutes everything. For example, my wife and I started a side business where we did photography for 300 weddings over a couple of years. All the passion and excitement around those images is lost if you show the couple hundreds of images that are very slightly different. Instead, you could’ve had one stunning image. You don’t need multiple people to tell the same story unless it provides value.

Communicating change and empathizing with it

How do you get all leaders within an organization to buy into a product-centric mindset, if that doesn’t already exist across the board ?

It’s easier to show the value of a function than the value of a feature because customers will more often back you up on functionality. As a result, I leverage the voice of the customer and bring that into the discussion as frequently as I can. If other leaders are not going to listen to me, they should at least listen to the customer.

With that said, there have been instances where even that’s not enough, because something is broken. Sometimes you just have to cut your losses and build a feature anyway, even if not everyone has bought into it. The best you can do in those scenarios is share the true pieces that inspire your customer and leverage their excitement.

How have you built repeatability into your processes to make them more efficient?

I like to think of it as hardiness — the ability to weather change. When I was CPO at Projul, I promoted infusing the voice of the customer at every level. That was easy in the beginning because we started small, but doing it on a large scale takes more energy.

Once I identified those customer needs, I owned it. I also made sure that my developers, marketers, customer success people, and customer support folks owned it as well so that they had extra hardiness and empathy in the face of change. The reason why that was so important and why we revisited it regularly was that even in a larger company, change and pivots do happen.

For example, if you’re a developer and you’ve spent six months developing a solution, the most important thing to you is probably making that solution available. If I, as the CPO, come to you and say that we have to pull that off the table and you have to do a new thing instead, your solution is not going to make it. And unless people understand why this change is going to make the customer happier or more successful, they’re going to be hurt. They’re going to feel less valued and could potentially even try to leave the company, so aligning people with that vision has been key to my and their success.

You mentioned people feeling hurt when the organization decides to change directions. How do you communicate these pivots to minimize those personal feelings?

As a product leader, I’ve fought — sometimes for my own non-betterment — to explain why we’re not ready to move forward. I use tools to gauge how unhappy a customer might be without a feature, function, product, etc. That helps prove why some things need to move forward and others don’t.

If you don’t do this, you’re hurting not only yourself, but your team as well. It’s a long-term pain because you’re not going to create revenue down the road. Your team is going to lose trust and focus, as well as the value they feel toward what they’re contributing. For example, if my whole team is building things that get implemented and never get received well by customers, how much enjoyment do they actually have long-term about what they do? This is why it’s vital to carefully choose what moves forward and what doesn’t. Don’t push things along just to make everyone on your team happy.

Once all the pieces are in check, I want everyone on my team to confirm the goals with a “Hell yeah, we’re going to do it!” and not with a “Yeah, that sounds OK.” If there’s any weakness in the first response, then we work on that. I ask them what it’s going to take for them to buy in, because if we don’t buy in, then we’re not putting our hearts into it. We’re just wasting energy and setting ourselves up for future disappointment, and I don’t want anyone on my team to be carrying the guilt of what’s not going well. I’m a firm believer in one-on-ones as an opportunity to empower my team.

Building ANDR3W, the conversational AI

Now that you’ve moved on from your most recent position at LPL Financial, what are you working on?

I’ve partnered with Kurt Clayson, the founder and CEO of Projul, where I used to work as CPO. I’m currently leading a conversational AI product to market. We named our conversational AI ANDR3W, where the “e” is a three.

ANDR3W is pretty amazing because he addresses both incoming and outgoing phone calls. He qualifies leads, schedules demos, and answers questions — basically what an SDR would do. He can also provide customer service and replace a call center, as well as answer the phones at restaurants and make reservations. There are indefinite use cases.

What is the main value that ANDR3W brings to organizations and how do you see it transforming businesses?

The value proposition and impact are endless. It’s scalable, predictable, reliable, and cost-efficient. I think that any sales organization would tell you that the cost of recruiting and onboarding a cohort of SDRs is high because training them is time-consuming. ANDR3W doesn’t need training — he doesn’t take a break, always speaks to your company’s mission, keeps to his objective, and makes countless calls a day.

Currently, ANDR3W is making 7,000 calls a day. That was the catalyst for Kurt Clayson to bring this to market. Other companies are VC-backed and developing their own large language models, but we have some big differentiators that I’m excited about. Our goal is to be very small, very agile, and closely connected to the customer. I have broad experience in understanding the value of a bespoke connection to the customer and not just technology.

What excites you about the rest of this year and beyond?

I’m excited to see how AI will continue to drive efficiency across product development. Speaking from recent personal experience, the thoroughness and time saved from doing competitive analysis using AI is game-changing, and I hope everyone makes use of it for the right reasons — summarizing and distilling thoughts, content, and even progress as folks report to me. They used to be tasks that took forever.