What a Career in Product Looks Like with Associate Director of PM at DraftKings

Product School hosted Kathryn Hill Schrumpf, an Associate Director of Product Manager at DraftKings for a #AskMeAnything session this week. Kathryn answered questions about her career journey in product, challenges she has faced, subject expertise and tech transformations, her appreciation for personalized product experiences, and the all-mighty question on feature prioritization.

Meet Kathryn

Kathryn is the Associate Director of Product of the Consumer Marketing Platform DraftKings. She has been progressively attaining higher managerial positions, from a Product Manager to ultimately serving as the Director.

Prior to her current role, she was a Product Manager of Content Personalization at ESPN and before that, she was
an APM responsible for launching two voice products on Alexa devices. Before this, Kathryn was an Assistant Product Manager of Advanced Mathematics at Cengage Learning. In addition, she graduated with a B.A in Linguistics and English Literature from The University of Texas at Austin and an M.S in Software Development from Boston University. 

“What challenges did you face when you transitioned from ESPN to DraftKings?”

I’ve gotten to work with some very cool products so far in my career.  Moving from ESPN to DraftKings, I had a lot of consistency to ground myself in, given both are sports companies (DraftKings was even more grounded in sports back then before we launched our casino products) and I had worked in personalization at ESPN before taking a personalization PM role at DraftKings.

The biggest challenges were definitely company size and culture.  Both were welcome challenges, to be sure, in that DraftKings was at the time fairly small (I think I was employee ~800) certainly compared to The Walt Disney Company which owns ESPN, and was still mostly a startup-style culture, vs. ESPN which was grounded in a culture that had evolved over time since the 1970s. As a PM, what that meant was I went from having quite formal gateposts for my products and lines of communication to a culture where networking and relationship building was essential to get things out the door.  Frankly, I loved that change, but it took a while to realize regular 1:1s with my peers were just as important in this culture as building documentation and status updates.

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“Was there a thread of common subject matter expertise that helped you make the next step up or was there not much in common there and you had to learn quickly and build knowledge up quickly each time?”

I often refer to myself as something like an “intellectual magpie” in that I love to collect bits of information from any subject that I come across and I think the reason I ultimately stayed in product management is that the job is really well suited to that approach.

There is a thread (though one I couldn’t have predicted so I certainly couldn’t have architected this path intentionally) in the subjects I’ve touched.  The part of my education that we didn’t highlight here is that I was actually in a Ph.D. program that I didn’t finish focused on medieval literature and language ethics.  Funnily, that meant I had quite a few lines on my resumé early in my career around language ethics and linguistics.  Totally unknown to me, when I was interviewing for PM roles at ESPN that’s what excited them about me as a candidate because they were starting to plan an Alexa product at that time.  From there, I had to do a quick deep dive into NLP, and further into data science and personalization, to make my more technical knowledge of linguistics stand up to the assumptions they’d had when hiring me.  Note to hiring managers: linguistics is a massive and diverse field.

From there, it was pretty smooth sailing into personalization and data science products.  My move to the marketing platform also was consistent with that thread, because it arose from a recognition that our data science products could be hugely influential to marketing technology, so having someone with expertise in that field could really boost that product development.

The tl;dr is really each step of the way I had some seed of prior experience that made me the right candidate, and it took a lot of hustle and self-study to get myself up to speed with the other parts of the job that I hadn’t encountered before.

What’s one thing which feels obvious to you, which you think the industry at large has yet to properly understand?

It’s obvious that almost everyone in technology is dealing with the most advanced ethical and philosophical questions of our time.  I think the industry overall should undergo a transformation in the next few years where ethical development is more centered in how we talk about and approach new tech.

I would love to understand the retention and engagement strategies you used or built in your product to get people to keep coming back.

Coming from the realm of personalization, I’m a big fan of personalized product experiences to increase not only retention but also positive word-of-mouth, which is a secret weapon for acquisition.  I’m an advocate everywhere I work for the responsible and structured collection of user data and doing the work upfront to make that data usable for personalized products.  If you have that basis, a PM should be able to build really exciting user experiences that meet the person where they are and help them get the most out of the product.  Something that feels “just for me” (as long as it’s not too creepy) almost always makes me love a product more, and I think as an industry we’re seeing a real expansion of personalized products as a result.

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When you interview an Engineering Manager, what do you expect them to know?

 This is a great question because I think a strong team overall is the only way for a PM to be truly successful while also getting to love their job.  When I interview an engineering manager, I rarely do a technical interview with them; I rely on my engineering counterparts to do that.  So I focus very much on how collaborative we can be together.  I have enough of a technical background to like a highly collaborative relationship with my engineering team.  To that end, I’ll often talk through a hypothetical product scenario and see if we naturally get to a point of collaborative brainstorming together.

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How do you conduct Customer Research at Draft kings and how often?

We actually have a varied approach to customer research, and teams that focus on that in collaboration with Product.  At previous jobs, I’ve sometimes been more central to the actual planning and execution of user research so it’s been great having partners here who have real expertise in this area. 

We do customer research through surveys, online discussions, wireframe trials, and (pre-COVID times) even in person in rooms that were designed for user research in our offices.  I’m sure I’m even forgetting some of the kinds of research we do – there are so many!  In terms of how often, it’s honestly constant; our research team maintains a roadmap just like we do in product, where theirs is the research deliverables that they’re creating for us, and we advocate to get that research prioritized on their roadmap.  I love having those deliverables on hand when working with a designer or building a product spec because it gives very direct guidance for where to take the product.

How do you get members of other teams and higher management excited about your product?

 I’ve been lucky so far in that the products I’ve worked on have been by their nature exciting and core to the business priorities each year.  I do maintain 1:1s with many of my peers around the company though and frequently appear in company lunch-and-learns, product demos, new employee onboarding training, and occasionally company all hands, to share what my teams have been working on so that I can ensure as broad a swath of the company as possible knows the cool things we’ve got in the pipeline or have already released. 

The big benefit I see there is that creates a natural pipeline for ideas originating from all over the company, widening our impact.  So really for me, getting people excited is all about showing up and telling them why what we’re doing will make users’ experiences better or stakeholders’ jobs easier.

Can you walk us through your experience with launching the voice products on Alexa devices? what was the requirement source for them and how did you measure the success?

My time working on Alexa products was so wild, and honestly, a bit of a blur because in many ways we were building the car while driving it – the car in this case being standards for developing this kind of product.  At the time Alexa was quite a new product on the market and users really hadn’t yet established patterns of use that we could build our own product off of.  To that end, our measurements of success were quite basic – how many active users did we have (MAUs and DAUs) as well as % of sessions with or without logged errors.  I’m sure these days product success for Alexa or any voice skills can probably be defined with much more granular clarity, which would be very helpful for PMs in that you may find you have more control over that measure of success than we did (back then it was heavily tied to the success of Alexa products themselves).In terms of requirements, I actually read two books when I started that job that helped a lot, even though one was a bit outdated and talked more about voice for telephone customer service lines.  I definitely used both of these to guide my approach to writing requirements.  I’m actually struggling to find them on Amazon right now because there’s been an explosion of guides since then, but if anyone DMs me I’ll go check my bookshelf and follow up with those titles.

Side note: it’s so funny saying things like “back then” to refer to 2017 like it was so long ago – but that’s life in tech

The gaming industry is rapidly evolving, and from your perspective, and I often felt regulatory bodies are not opened to some of the newer technologies, for example, cloud services has been taboo.  What are your thoughts on moving technologies in the gaming space?

Mobile gaming is both a very new (legal) industry in the US and highly regulated which means product management goes hand in hand with close observations of constantly evolving regulations.  I greatly admire all of the companies who are trying to get into the space, particularly those building utility services like geolocation that make my life and those of other PMs in the industry easier.  I’m not sure what the future will hold because the industry is in such a state of flux right now, but I’m hopeful that over time regulators will start to establish norms that allow the industry to grow organically and with less uncertainty.

what kind of products Draftkings is working on to differentiate from your competitors? The growth in betting in North America is amazing how do you cope with that? 

The growth in betting has been such an amazing thing to have a front seat for.  I joined DraftKings in 2018, in the months between the launch of their SB and Casino products, so I’ve gotten to see the evolution of the industry at a very critical time.  It takes a real spirit of collaboration and consensus at the company that we’re invested in the product’s success and here to help each other to get through it.  There are certainly unexpected busy times when growth opportunities appear, and it becomes very much about pitching in where you can, offering expertise where it’s helpful, and supporting morale for those who are working even harder than you are.  But then once those times ebb and things are back to (relatively) normal, taking a break to breathe and reset.  It’s tempting in a rapid growth industry like this to feel like you’re sprinting for years but that’s not sustainable; you sprint around the times when it will have the greatest payoff, then rest, recuperate, and go back to a maintainable pace during times of BAU hyper-growth.In terms of differentiating ourselves from our competitors, I think we have an outstanding commitment to a great product experience with a focus on the US sports fan or mobile gaming customer.  Users in the US are different from those in Europe so it’s useful to be a US company when US gaming is taking off.  I think it says a lot that I was hired as a PM of data science (with a real commitment to personalization) for this company back when it only had ~800 total employees; the user experience is absolutely core to the value we bring to the table.

What kind of tools or processes from PM field that I can apply to my professional development as I progress to start a company then eventually manage a portfolio?

I’ve never started a company myself so I can only speak from my experience in product management but I do know people often compare being a PM to being a mini-CEO.  My dad was a CEO when I was growing up and I think that rings true to what I remember of his job.  In particular, a PM has to be able to balance creativity and vision with hard metrics, cost/benefit analyses, and resource allocation.  Being too tied to one side or the other can be catastrophic for a product portfolio, either for a PM or for someone leading an entire company.  The other thing I think I’ve personally had to work on as a PM that I see great CEOs doing is finding strategies for synthesizing others’ expertise into thoughtful decisions. 

You can’t be the expert on everything, so figuring out what others are good at and educating yourself enough in their field to grasp what they’re saying will allow you to connect the dots and drive collaboration either with your team or in your case with your employees. 

Finally, I’m guessing you’ll be seeking outside funding at some point for your company; PMs have to be very good at articulating potential value to stakeholders and company leadership to show the valuable engineering resources are using their time wisely – that skillset should certainly translate to building great conversations with VCs or other investors.

Is there anything you have learned about managing feature prioritization when satisfying different business units with competing business needs? Does it ever just come down to gut feel or have you found a robust process that works for you?

Wow this is the toughest challenge that I consistently face working in product and I wish there were a solid solution to it.  Alas, I’ve asked every mentor I’ve had in the industry and everyone struggles with this.  I can share the strategies I’ve adapted to make it less painful though.  

First off, if you’re lucky you have more exciting opportunities coming in than you could possibly do robust business cases for.  I’ve found myself in that position many times, and there are three possible solutions to it that I’ve used in different scenarios:

(1) use your gut to narrow down which opportunities have the greatest likelihood of high value then do the detailed case on those;

(2) put the burden of the initial definition of value on the stakeholders who are making these requests;

(3) delegate to a member of your team – this works especially well if your company will hire a product analyst to pair with you. 

With (1), you could miss a diamond in the rough; with (2) you may dry up your ideas pipeline by putting too great of a burden on stakeholders to get heard; with (3) you’re demanding extra resources, which not every company can provide.  So each has a time and a place. Now in terms of really making that final prioritization decision, in the best-case scenario, your company has articulated some accepted means of translating many KPIs into one master KPI to prioritize off of – the “all roads lead to revenue/ profit/ MAUs” approach.  In that case, you identify the KPI(s) that you expect this product change to impact, get some estimate of how much movement it’s expected to create, then translate that to the KPI that everything ranks against, like revenue.  Life, however, is hardly ever that clean.  An only slightly less quantitative approach is to define the company or team priorities for the year that you’re dedicated to moving, and prioritizing the projects that will move those KPIs specifically – this is commonly realized in the “OKR” approach.  So say you have a project that will absolutely skyrocket user acquisition this year, but the acquisition is not one of your OKR key results nor does it translate directly to one, you may not do that project despite its objective value.  Finally, the gut approach is one that PMs do frequently fall back on and it’s not a bad approach or something to scold yourself for.   The thing we often forget is that as the person closest to the development of this product, you put a lot of work into knowing its ins and outs and its impact on users so by definition your gut not uninformed.  It’s just nice when you can take that knowledge of the product and translate it into measurable, and ideally stack-rankable value because then you can keep your personal gut biases and potentially narrow perspective in check for the good of the larger company.

ps: Hope you enjoyed my almost Tolstoy-esque response to what was a fairly simple question. Definitely one of product management’s great unanswered questions right there

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What do you look for in a PM during interview?

his depends a lot on the level of the PM because the range from Associate PM to Senior PM is wide in terms of expectation, but setting aside the question of skill and maturity which has the most variation, there are a couple of qualities I always look for and that I’ve seen as many experienced candidates as inexperienced fall short on.

The first is creative problem-solving.  I’ve learned as a PM, you’re going to have to solve different kinds of problems at least monthly if not more frequently than that, and often the problem you’re solving is not only new to you but new to your company or even industry.  I like to see that someone can think through a problem they’ve never seen before and propose varied approaches to thinking through the problem and examining potential solutions.

The second is collaboration.  Can you be an excellent PM who is not particularly collaborative?  I’m sure that’s possible and even the norm at some companies.  Where I work, collaboration is absolutely necessary.  That’s not to say you have to be all that extroverted or charming – I’ve been very charmed by people who I can tell don’t work well with others, and had excellent brainstorms with true introverts – but you need to be excited about an open exchange of ideas with your peers and colleagues.

The final quality is an interest in learning.  Often when interviewing a candidate I’ll see that they’re seriously impressive either in quantitative skills or creative skills, but need work in the other side of product management.  Even if they’re strong in both, I know PMs rarely specialize for their whole career – for example, the products I’ve worked on are incredibly varied.  So I care a lot less about what someone already knows than how teachable they are and how interested in things they haven’t yet been exposed to.

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What career pivots/opportunities would you advice current PMs to take to reach a similar position as yours today ie. going from PM to Associate Director?

I think being open to career pivots has been one of maybe two or three top factors that have lead to my own rapid growth in my career.  To that end, I hate to suggest particular career pivots to aim for, because I wouldn’t want to suggest that any career pivot that speaks to you wouldn’t be useful.  I have an illustrative tale for this from my own career:

When I was just a product assistant, I stepped in to manage a portfolio when my boss retired.  I loved it and by all accounts was good at it; I was convinced the next step was to become a PM myself.  The problem was, I was told that to get that role I really needed to do a couple of years in marketing, sales, or content development then pivot back but what I loved were portfolio management and tech and I absolutely loathed marketing.   You probably see where this story is going.  I leaned into opportunities that let me work more with tech but with a less sure path to a real PM title, pivoted several times, and ended up in the job faster than I would have otherwise because I followed opportunities that I loved and wanted to work hard at. 

Eventually, the opportunity presented itself to work with marketing again but this time with marketing tech which I knew was an exciting and critical field for my company so I took the chance.  And here I am today building really cool marketing tech.

The moral I take from this is that following opportunity that you’re excited about is more important than following the “right” path.  I went with what was interesting to me, not with what I was told would give me a sure outcome, and as a result, I’ve not only advanced quickly but also can honestly say I’ve never had a job I hated.

Do you have any final advice for aspiring Product Managers?

 if you’re aiming to be a product manager, take whatever opportunities arise to learn.  Just because something isn’t in the traditional checklist of PM skills or tools doesn’t mean it won’t be useful.  What has been most useful to me in my career has often been something totally off the grid, which helps me bring new and exciting perspectives to my company’s products.

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