Above the Glass: What It Takes to Embrace the Future of Work

Written by Joy Guerin

Left: Joy Guerin | Right: Rachel Knaster

In this edition of Above the Glass, Joy Guerin, Group Product Manager at Parkmobile, sits down with Rachel Knaster, Chief Product Officer at ASAPP, to ask her about the nature of product management, healthy company cultures, and the future of work.

Tell me about your journey to ASAPP and your role there as a product leader.

I was late to the computer science game and took my first class on the subject during my sophomore year of college. Fortunately, a few incredible professors encouraged my interest in the field, so I decided to pursue it further.

I landed a job in IBM’s consulting group not long after graduation. My role was amazing because it exposed me to numerous global companies and the technology they used. It was impossible not to grow excited about building and improving software that huge, recognizable brands would employ on a daily basis.

Eventually, I moved to the Watson Group, which was still in the founding process when I joined. They were applying machine learning, natural language processing, and other AI technologies to the enterprise space, which not many organizations were doing around 2014.

It was fun solving problems that impacted millions of people with AI on an unprecedented scale. After three years, though, I wanted to transition to a smaller company and focus on building products. Someone put me in touch with ASAPP, and they brought me on to run their product team — which was just me, one of 19 people total at the company. However, in the four years I’ve been at ASAPP, we’ve raised $260 million and now have 325 employees. We’ve experienced a tremendous amount of growth, and it’s afforded me an opportunity to do what I love: helping large, messy companies solve their problems with a product I helped create.

That’s awesome. I’m an AT&T Leadership Development Program alumnus and I remember hearing about IBM’s work on Watson inside the company around that time.

Small world! It’s funny; at that point, each company we met with would freak out at the prospect of AI. They weren’t sure what it was, but a few short years later, it’s ubiquitous. People’s reactions used to be, “Should we be worried about this?” and now they ask, “How is your product different from this other group’s who just pitched to us?”

I’d love to talk more about your product management role. In my experience, the position varies greatly between companies, especially depending on size and industry. For people who are less familiar, could you elaborate on the day-to-day responsibilities of you and your team?

That’s an excellent question because product management is an incredibly amorphous role. Those of us in this field try to be adaptable, but I believe a few elements of the job are consistent across organizations and industries, such as conducting user research and interacting with customers. Product managers then brainstorm with designers and researchers to help them turn concepts into concrete ideas.

The team at ASAPP works with our AI researchers, engineers, and customers to identify the best way to solve our customers’ problems. What opportunities for impact do we see in their business performance data? How can we help them with sprint planning and backlog grooming? We ultimately own the road map to answering these questions.

It’s rare to encounter product roles that don’t have those responsibilities. However, successful product managers can also do anything else their companies require, especially amongst smaller organizations. For example, ASAPP’s product management team was historically responsible for driving end to end lead implementation because our implementation team didn’t exist yet. We have an incredible implementation team now, but the product management side is still deeply involved in other things you would think would be outside our purview, such as revamping internal employee onboarding. We train new hires how to understand and talk about the product.

Essentially, there are two halves to being a product manager: owning the product and embodying a “get things done” attitude whenever an unforeseen need arises. The first part is consistent regardless of industry, but the latter is what differs between organizations. The best product managers never fall into the trap of thinking that their role is narrow.

I agree about the need for adaptability. In my experience, the smaller the company, the broader any individual’s responsibilities might be.

Absolutely. Involving product managers with different departments creates a stronger product and culture because they become a linchpin team that understands all aspects of the organization.

I love that. What specific experiences or skills prepared you for your current role?

Besides my technical background, something that significantly influenced my development was my time as a competitive rower in high school. I was on the US Junior National Team when I was 17 and continued rowing my freshman year of college. Rowing is a physically and mentally grueling sport. You need to be strong individually, but you also need to be completely in sync with your teammates, or else the boat doesn’t go where it’s supposed to. There are no excuses for losing because you always know precisely why.

Competitive rowing taught me grit and teamwork. I apply those lessons to work: determination is necessary, but you have to push in such a way that other people want to push alongside you.

Those are my soft skills, but I acquired my hard skills in college when I learned a tremendous amount about technology within three years. The curriculum focused on building system fundamentals and having the right mindset instead of diving into coding and development before I was ready, which set me up well for the workforce.

Plus, the exposure to large companies I gleaned from my time at IBM was invaluable. IBM works with almost every large company in the world, so it was a key opportunity to understand how these companies operate from a technological perspective.

Sometimes large companies can move slowly — I definitely had to learn perspective and patience when working at larger organizations. How does it compare working at a big company to a smaller one?

I’ve experienced both extremes: 500,000 employees trying to accomplish something that should be straightforward, and the 19-person Wild West version where everyone’s responsibilities are nebulous. My experience with the former makes me appreciate the pace at which ASAPP can innovate, develop, improve, and actualize ideas much more. I love that we aren’t afraid to look at our processes or systems and ask, “Is this the best way we could be doing things? Are we over-engineering? Is there too much bureaucracy?”

That’s an excellent segue to my next question. Interactions between engineering and product management teams can sometimes be complicated by organizational structure and competing incentives. How does your team effectively partner with engineering to achieve your desired outcomes?

I’ve noticed a spectrum within companies: one side has eyes bigger than its stomach, and the other is more grounded in reality. Both are necessary because if you don’t have enough appetite, you don’t grow, and if you don’t have technical people thinking pragmatically, then a lot of effort goes to waste.

Product management falls somewhere in the middle to balance the healthy tension between each side. At ASAPP, we try to have cross-functional teams that dabble in other responsibilities, so everyone understands both ends of the spectrum. Instead of saying someone’s role is X and nothing else, we have “leadership pods” where representatives from product, design, data science, engineering, and more get together with their unique skill sets to steer our product in the best direction.

This practice allows everyone involved — engineers, researchers, and the like — to feel the same level of urgency and accountability as the product manager. Instead of having one side throw requirements over the fence and say, “Here, build this,” everyone feels like they’re on the same team because each smaller group owns every part of the product, not just what they’re traditionally responsible for in other organizations.

How did ASAPP create that culture? Is it something in the DNA of the founders, or were there conscious decisions along the way to organize yourselves like this?

Everyone in the company marches in the same direction toward the same goals, even at the highest level. Our ethos is not just lip service; we really believe in our values, so I think the company exhibits a profound sense of unification. I wasn’t surprised to discover this culture when I first started, but I’m thrilled that we’ve been able to maintain our identity as we’ve grown over the past four years. Much of it is thanks to leadership at the top setting the tone and inspiring everyone else to express the same attitude.

Practically, the company as a whole is very objective-driven. For example, product management orients itself around specific goals and metrics, which allows us a breathable level of autonomy while remaining accountable to everyone else.

That’s an interesting point you bring up about accountability and autonomy. On a related note, what do you look for when evaluating product managers to join your team? Do you ensure they can handle that type of autonomy and accountability before bringing them on?

Narrowing candidates is always challenging, but I honestly believe we are very transparent with them about what we’re looking for. We never try to convince someone to join. If I reach a point when I’m trying to talk a candidate into joining ASAPP, I’ve done something wrong because it’s an intense environment with a great deal of accountability. Some applicants have made an honest decision and opted out after realizing this kind of demanding work isn’t for them, while others get even more excited at an opportunity to be part of our culture.

We ask interviewees for examples of past predicaments and inquire about how they handle situations where they have to make an impossible call. After this phase, we move on to what we call “Challenge Projects.” Each team has its own version of a Challenge Project that enables us to see not only how applicants talk about themselves but how they actually perform under pressure. They present their projects while the rest of the team pokes holes, gauging their reaction to having their actions and ideas questioned. Are they comfortable receiving feedback? How do they implement suggestions?

This is a great approach. I’ve noticed that some interviewers may place undue emphasis on whether someone fits their culture or not based on their verbal pitch, but I’m often drawn to quieter, more introspective candidates who exhibit profound thought processes that I have to discern in other ways.

Definitely. One of our Challenge Projects’ benefits is that they allow people who don’t excel at self-promotion to demonstrate what really matters — the work.

Exactly. Switching gears, I also want to ask you about how this chaotic year has impacted you. How have recent global events affected your work, and what have you done as a leader to help your teams through this period?

If you had asked me that question a year ago, I would never have known what you were talking about! I’ll go chronologically: ASAPP went remote as early as March. The shift to working remotely was significant, but ASAPP handled it remarkably well. We have an incredible enterprise engineering team that takes care of IT, and our consistently remote employees paved the way for everyone else.

We have offices in California, New York, and Buenos Aires, so the cross-functional teams I mentioned earlier were able to adapt their operations reasonably quickly because they were already spread out. However, certain adjustments as a product manager have been difficult. I’m accustomed to frequent meetings, but back-to-back Zoom meetings can be taxing. It went smoothly from a technical standpoint, but the emotional shift was jarring.

I don’t think there is a simple solution for overcoming that mental adjustment. I’ve noticed that people who have strong relationships at work have gotten closer,. Some attempts have worked better than others; we’ve tried virtual happy hours and activities where we run through competitive analysis or product critiques in groups of people who don’t typically work together. We’re trying to keep everyone connected, regardless of how often people engaged with each other in the office.

Feedback has been generally positive. Someone on my team commented that work is a welcome distraction from many of the things going on. ASAPP is incredibly fortunate to have grown during the pandemic because enterprise companies need viable software now more than ever, and we make an effort to support employees who need it.

What steps would you recommend for engineers who are interested in transitioning to product management? I know some engineers who expressed their curiosity, but they weren’t sure how to make the change.

Related to what we discussed earlier, the first step is to understand what the role is, particularly at the company you’re applying to. This step requires learning all there is to know about the company’s product itself and the more flexible aspects, such as what other duties the product management team takes on.

Step two is getting involved. Reach out to someone on the team and ask if you could shadow them or observe a project in action. Product managers love having engineering partners who view their jobs in a new light, and you’ll get a taste of what the work is like. Even if you decide the role isn’t what you want after all, you’ll be a better engineer for it because you’ll understand how the business aspect of development works.

I want to return to a point you made about people outside the tech industry not understanding AI. Some people fear that AI will automate jobs away from humans. As a product leader, how do you think about leveraging AI to empower rather than replace human skills?

I love questions like this because it gives me a chance to talk about how ASAPP is fully focused on making humans better at their jobs. We often discuss the future of work, and I believe ASAPP is a major player in developing AI that learns from what people do, identifies what works well, and makes suggestions to improve what doesn’t. Automating people out of work is not our goal.

Instead, we focus on customer interaction software. Technology severely underserves the three million customer service representatives that work in the US, which results in an annual attrition rate of 40% to 100%. ASAPP seeks to learn from these people to improve their capacity to do their jobs and maybe even open better career opportunities. It’s something that we’re passionate about, and it means we get to spend time with our users instead of trying to take over.

That’s an inspiring perspective. I know that people who work in customer support and service roles sometimes feel pushed to the side when they’re really doing some of the most important work. Having tools to make their jobs easier is terrific.

I agree, customer service jobs are stressful, and the pandemic has only made things worse. You can sometimes expect multi-day wait times when trying to get large companies to answer your questions. Agents were sent to work from home without the necessary tools to succeed in the world’s rapidly changing environment, so we feel fortunate to provide these tools and make a tough job more manageable for those who do it.

I’d love to hear about how you keep your knowledge and skills up to date. What books and resources do you recommend for people interested in product management or AI roles?

AI is a rapidly evolving field, so I advise keeping up with publications and conferences that cover new developments. As for product management, a book I highly recommend is Crossing the Chasm. It’s actually about marketing, but every successful product manager needs to understand how positioning and marketing products works. Another is The Mythical Man-Month, which discusses the product management and planning and execution sides of work. I had so many “Aha!” moments reading that one.

The third book I’d recommend is one ASAPP’s CEO distributed to everyone a few years ago called Endurance. It’s about Ernest Shackleton’s expedition to Antarctica, so it’s packed with stories about leadership, grit, teamwork, and other insights regarding the more intangible aspects of product management.

Finally, would you say you have a secret superpower or X factor that has bolstered your success, and how did you develop that skill? How would you recommend others identify their own superpower?

It’s hard to be humble with this question, isn’t it? Some feedback I’ve received from colleagues is that despite whatever stress I’m dealing with, I never let it affect my mood or take it out on anyone else. You should never let your negative emotions rub off on someone else — that’s how toxic work cultures come to be. It’s important to be tough and decisive, but you have to do it in such a way that it makes everyone around you feel better about the situation. That kind of attitude doesn’t come naturally, it takes work, but I’d say it’s my biggest strength when guiding my team.

With grit, determination, and adaptability, anyone can transition into different roles of the tech industry and thrive as the global workforce evolves.

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