HRTech Interview with Kenny Freestone, Chief Product Officer at Eddy

Kenny, welcome to HRTech Cube. With over 20 years of experience in product management and development, can you share the highlights of your professional journey and what led you to your current role as Chief Product Officer at Eddy?
I’ve spent a lot of my career in product management trying to make complicated things be as simple as possible. In my first job I spent 7 years building software to teach English as a second language. When I joined Ancestry we worked to make family trees and research more accessible. While at Ancestry we launched AncestryDNA (in late 2011) which was a lot of fun to build, and was an extremely complicated project involving not just building software but also working with scientists and with shipping and manufacturing partners. When I left Ancestry after 13 years we had built tools and products that over 90 million people had used.

Building software for millions requires that the tools be easy to use. I think a big takeaway from all my experience is that software needs to be simple to use and easy to understand. I was very interested in the HR and payroll space in part because I thought the existing tools were just too complicated and there was a lot of room to build something much better. I joined Eddy in 2018 with the goal of making HR software that is simple and even fun to use.

After your successful tenure at AncestryDNA, what motivated you to transition to Eddy, and what excites you most about working in the HR tech space?
AncestryDNA was an amazing experience and we had a phenomenal team. I had spent most of my career at later-stage companies and was excited to build not just a product but a business. I love that smart people can work together and build a company that benefits its employees and the community overall.

I think what is exciting about the HR tech space is how much people need and appreciate tools that save them time and let them focus on bigger and better things. There is a lot of room to automate tasks in HR and remove pain points.

Given your experience in launching significant products like Ancestry.com’s family tree product, what key principles do you believe are crucial for successful product development in today’s tech landscape?
Its funny that the principles don’t change much when moving from ESL to Ancestry to HR tech. A key principle for us is always to listen to people—customers, buyers, shoppers, researchers—anyone who is interested. Listening helps us to get really clear on how we problem solve: knowing who we are solving the problem for, and knowing what the problem is. Once those are clear finding the solution becomes much easier.

As someone skilled in Agile methodology, how have you adapted Agile practices to fit the specific needs and challenges of product management at Eddy?
We are not agile fanatics by any means…we don’t follow any framework with any rigidity and while we do work in sprint cycles, on many projects our work might feel a lot more like a continuous delivery model. But the aspects of agile that continue to resonate include adaptability, collaboration, and a strong customer focus.

A big challenge we have at Eddy comes from the nature of the product space. We’re building an all-in-one platform that handles a huge range of work areas: hiring, onboarding, employee data, org charts, e-signatures and documents, time tracking, time off management, training and certificate management, payroll, reporting, performance management, partner integrations, and much more. Many companies focus on just one of these as their whole business. The feature footprint of what we are building is incredibly broad. An agile approach with a focus on iterative development works really well for us because it lets us build and learn in multiple areas and make consistent progress over time.

A recent example of agile practices is our recent partnership with Check to offer Clair’s on-demand pay services. As we listen to the needs of our clients and their employees, we heard a lot of interest in offering better financial wellness tools. We worked iteratively with Check and Clair to create a feature that offers employees early access to their pay—at no cost to them or to the employer, which I think is a big win for everyone involved.

How do you strike a balance between driving innovation and ensuring that the products you develop meet the real-world needs of users?
Well I think that these things don’t balance out. Meeting the real-world needs of people comes first every time. Innovation might be a nice outcome of doing that first job, but most of the time what people need in their software is not so much something new as something that actually works, and doesn’t require training to use.

This requires a lot of discipline (and investor trust) because while investors and media crave shiny novelties, what matters much more is whether the actual needs are being addressed.

What strategies have you found effective in leading product teams, especially when it comes to fostering creativity and maintaining a focus on delivering value?
Probably the most effective strategy is to build high-trust work environments and leave egos at the door. Building products is full of decisions without perfect data and information. We work hard at making sure we can debate and discuss. One mantra is to have strong opinions that are loosely held. Because of this, as product, UX, and dev teams we are able to debate, explore, brainstorm, ideate, prototype, test, and iterate with a focus on what is best for the business and the customer.

Creativity is a fragile thing that is easily crushed by egos and mandates. Our focus on building an ego-free environment creates a lot of safety and freedom to find what works—and to also reject that solution as soon as we can find something better.

What is your personal strategy for staying ahead in the rapidly evolving field of product management, and how do you continue to grow professionally?
I like to follow product sages like Lenny Rachitsky, Julie Zhuo, and Sachin Rekhi. Lenny’s newsletter and podcast is especially helpful lately.

What advice would you give to aspiring product managers and leaders who want to build successful careers in the tech industry?
Tech is a really fun and challenging space to work in. It is full of many brilliant minds and hard workers. My advice is that you belong and we need you. They say about 70% of people will experience imposter syndrome—this is normal. A favorite line from a coach I have is that “consistent competence brings eventual excellence.” Keep learning, keep working, keep growing and you’ll do great!

How do you envision the future of HR technology, and what role do you see Eddy playing in shaping that future?
HR tech is a vast landscape with thousands of software solutions competing for your attention. I expect less consolidation in HR Tech than we see in other areas. No single company has created a strong HR monopoly. The reason seems to be that businesses are so varied and do things in so many ways that HR tech evolves to meet lots of very niche needs. I think we’ll see that continue.

With that said, I think we will see significant advances in how HR continues to improve automation, especially using AI. For many companies the Covid-induced transition to remote work is now permanent and HR tech will evolve with tools for remote onboarding, virtual collaboration, team engagement, and performance management.

Eddy’s role in this future is to keep advancing and improving so we can be the simplest and easiest to use all-in-one platform for HR, payroll, and benefits.

As we wrap up, is there anything else you’d like to share with our readers, perhaps a personal mantra or philosophy that guides your work?
Thanks for the opportunity to share some thoughts!