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Beyond the Screen: Arielle Kilroy

We recently had the pleasure of speaking to Arielle Kilroy, VP of Product at Small Improvements, where she innovates around HR tech and the future of work.

Arielle started her career as a designer and developer in the entertainment and music industries creating the first web products for movies including The Hobbit, He’s Just Not That Into You, and Harold and Kumar’s White Castle. She also worked with artists like OK Go and Amanda Palmer to build and monetize their talent as digital-led artists. Arielle then moved on to work with Sierra Club, the US’s largest environment non-profit (founded 1892, 1+ million members) as Product Head to reinvigorate their digital presence and products. During this time, Arielle won a Webby Honoree Award for one of her products.

We were excited to speak to Arielle about her work and see what the product leader, speaker and coach has been up to...

Arielle Kilroy small improvements

You studied photography and fine art before transitioning into the product world. How has your education influenced your work and how you approach new projects?

One thing that I learned specifically in art school was that there are always options. Early in school, there was a class assignment that asked us to remake an art piece in different mediums, forcing me to think about how I can create a similar experience for a viewer despite not being able to rely on my initial idea or instinct. Not only that, but I got to have the viewer experience with my classmates' new pieces. I really left that semester with the knowledge that there are almost always many options for achieving similar results.

Art school also taught me the value of testing and iteration. As an artist, I was trying to convey a message or feeling. Showing my work helped me know if I had achieved that goal. This is likely not universal for all artists, but it's definitely an experience I gained through school. It was also common to remake a piece, sometimes several times, as one learned. One can actually see this throughout art history both with individual artists and their own work as well as subsequent artists paying homage.

I know that music is a passion of yours, and you started your career working in the music industry. Why did you decide to leave, and what did the experience teach you about balancing passion with profession?

I had wanted to work in music from my tween years. It was such a 'dream come true' when it finally happened that it took me a long time to come to terms with the fact that it wasn't making me happy. The amount of reflection and mental work I needed to do to get there can not be expressed. It was a bizarre experience to be considered successful in such a sought-after field but feel anything but. The easy answer would be that there were a few key structural reasons why I left. For example, long, frequent and unpredictable evening hours that made it really hard for me to maintain relationships of all kinds. But a deeper answer would be that I believe that music has the power to change the world, but I was working mostly with the type of music that could afford to pay me, which tended to be pop. Don't get me wrong, I do enjoy some pop music and I did get to work with some amazing artists of all genres. But I wasn't getting fulfillment out of giving so many hours to something that wasn't contributing more directly to my values.

Arielle Kilroy Small IMprovements
Arielle speaking at the Product Conference Europe 2019

Congratulations on the recent launch of your personal project, Practical Product! Can you tell us a bit about the new initiative?

The idea started over a large group dinner. I was sitting next to two friends who are also product leaders, and we were chatting about how we struggle to find quality workshops to send our team members to. Most product management workshops are taught at a very conceptual level and rarely reflect the reality we see in our working worlds. We made some jokes about making our own training. Over the next few months we had more and more data that reinforced the idea, so we decided to give it a shot. With Covid-19 we've made a short-term pivot towards helping our PM community navigate the new challenges we are facing, but we'll soon come back to our workshops. We really want to train product managers we'd want to hire. There is so much more to the job than knowing agile-related processes. Organizations and humans are complex; a good PM knows how to navigate and steer both. Additionally, we wanted to do something that reflects our values. These workshops can be quite cost-prohibitive, further reinforcing the privilege that access to knowledge brings. We will offer discounts and free tickets for underrepresented populations to do our part in being good allies. Check us out at:

I heard a rumor that you don't like product roadmaps ;) What do you have against agile product roadmaps, and what alternative do you recommend for teams who struggle to adopt agile processes?

Haha, yes, it's true! I try to steer clear of product roadmaps because they usually cause more problems than they solve. I'd also argue that there isn't really such a thing as an agile roadmap since an agile process enables learning as you go, and it would be very challenging to map out future learnings and their solutions without, say, … a time machine. Roadmaps can also be a dangerous tool for a business. If a PM delivers all the functionality on the roadmap, that's generally considered successful. But did any of it deliver direct measurable impact to the business? Roadmaps often create a situation where the definition of success for your product manager in their role differs from the definition of success for the business. Now I fully understand that a true agile process is near impossible in modern business, despite what so many others say. (Note: this is a big component of the Practical Product workshops). For example, try telling your finance department to do their taxes agile. Or hiring. So any roadmap needs to reflect the reality of doing business in the modern world while allowing for the learnings, pivots, and changes that will ultimately need to happen to achieve business goals. If you must make a roadmap, I'd recommend these:

There are strengths and weaknesses to all of these, so the choice depends a lot on your product and your organization.

I'll also briefly mention that not everything needs to be agile! Waterfall is a powerful project management process that is perfectly suited for many types of software projects (infrastructure, certain security features, etc) or even parts of a larger software process (launching to customers, for example).

Arielle Kilroy Small Improvements
Photo courtesy of Small Improvements

What drew you to Small Improvements? Is there something about HRTech that captures your imagination?

I try to 'do good' with every role. I'm incredibly passionate about diversity and inclusion, and I think HRTech allows me to combine my skill set with my values. Influencing important products in peoples' professional lives to create a more equitable and supported environment for all people really speaks to me. That's how I ended up at Small Improvements. Also, the people are fantastic, so that helped the decision. ;)

Can you tell us a bit about your day to day as VP of Product? Are there any new product updates that you're excited about?

We've just rolled out two new big updates:Pulse SurveysandRetention Analytics. Pulse Surveys are an important part of creating excellent employee experiences so it's nice to see it added to our offering. Retention Analytics is a first-of-it kind machine learning product designed to help HR know where to focus their attention. It analyzes a bunch of data to predict where turnover might be likely. This way HR can talk to employees and address any issues before they decide to leave.

Arielle Kilroy Small Improvements
Photo courtesy of Small Improvements

What are the most significant differences between B2B and B2C product development?

The two biggest differences are volume and expectations. In B2C it's much easier to A/B test. The nature of B2C generally allows for a larger audience of users and therefore a larger pool of testers. In B2B you need to be much more creative to test, but it is possible!

The nature of the relationship is also different because in B2B your customers are hiring you to do a specific job after likely evaluating several options. The relationship tends to be longer term. There is an inherent agreement that you won't be disrupting key business processes day to day that you have to respect.

How do you see the importance of user research and testing for B2B products? What does your user research process look like?

User research and testing for B2B is just as important as for any product. If you are not constantly doing these activities, your product will stagnate, and the market will notice. We can all think of the slow death of some wildly successful products. I've personally seen some of these, as have most PMs this deep in their career.

Our process varies a bit depending on what we are trying to learn, but we follow a process that is loosely based on The Lean Startup (if you have not read this book, go read it now) and a continuous discovery and development methodology. This means that we always have several ideas in various stages of discovery while having different features in development. We test ideas many, many times, each time increasing the level of investment as our confidence grows. This might mean that we test several versions of a drawn prototype until we have high enough confidence that the value proposition is something that solves the problem we are trying to solve and delivers value customers would potentially pay for. Then we test iterations of higher fidelity prototypes until we see if we can hit our success metrics before moving to code. Because this relies a lot on qualitative testing (again, we are a B2B), we usually combine it with some other types of data, like in-app experiments to judge potential audience interest, surveys, etc. We follow a 'good enough' quality orientation working towards Earliest Usable Products and Earliest Sellable Products, which means we don't chase perfection. Successful feedback from customers looks like this "This is great! Are you considering adding XYZ to it?". If you aren't getting requests, you've over built.

Small Improvements
Photo courtesy of Small Improvements

As VP of Product, one can imagine you have to manage multiple teams, priorities, not to mention personalities. What do you consider to be the role of culture and how do you facilitate alignment on your team?

SaaS businesses are product led, so in my experience it means my team and I can have an outsized impact on the culture. I try to and expect us to lead by example. There are of course times where we all don't bring our best selves to work, but the lead by example model still applies. It just shifts to asking for patience and understanding.

Culture is set from the top, so it's part of my responsibilities to set it. It's also important that the organization both supports me and holds me accountable for walking the walk, not just talking the talk. This applies to everything from ensuring inclusive hiring practices, supporting employee growth, reinforcing data-driven decision making, empowering teams to own their work and more. Culture is much more than cool benefits and swag.

You're very passionate about diversity and inclusion and take an active role in D&I initiatives at Small Improvements. What can people in positions of privilege do to create cultures of inclusion in tech and design industries?

Wow, I could write several blog posts on this. I'll start with four tips. Never ever accept "not a cultural fit" as a reason to not hire someone. This is lazy hiring. It's exclusionary hiring. If someone doesn't believe in the values or processes of your company, then name it specifically. If you don't relate to a person, that's not a good reason to not hire them.

When you review a CV and you don't see something on there, just ask! Not everyone has the same background/network/etc to know exactly what you are expecting, especially for early career roles. Privilege breeds privilege, break the cycle!

Look at your leadership, look at your managers. It is statically impossible that you can't find qualified diverse candidates for these roles. If your mid and top levels are mostly homogeneous, then look at your promotion paths, your recruiting paths etc. There is so much data out there that shows that certain groups are promoted or hired for their potential, and others have to demonstrate experience. Break this pattern!

Lastly, we focus a lot on employee D&I, but remember your users. How accessible is your product? When you refer to customers, internally and externally, how do you represent them? Pronouns, photos, etc all contribute to creating a world that caters to certain groups and not others. Make product inclusiveness a KPI.

Arielle Kilroy Small Improvements
Photo courtesy of Small Improvements

And finally, many of us are still working from home, waiting out the pandemic. Do you have any tips on managing remote teams?

Keep your 1:1s. If you don't do these weekly, start now. Without the face time, it's impossible to know how they are doing. I personally don't like operational 1:1s, so I'll recommend to all the managers out there to keep a focus on the person and not the to-do list. We have a 4 point agenda in my 1:1s that have served us well so if you are not sure where to start, try these:

  • What went well last week?
  • What did we learn last week? What would we do differently with hindsight?
  • Check in on professional development
  • Anything else?

You'll notice that I use "we". I also use 1:1 time to reflect with my team members on my victories and learnings. Perhaps they will learn from it, perhaps they will have suggestions, either way, it keeps the feedback going in both directions. I'll tie this back to leading by example!

Thank you Arielle!!

Know someone you think we should interview next? Let Maya know:

Arielle Kilroy's headshot courtesy of Sonni Frej

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Written by

Maya Guice


Maya Guice







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