Faces of HR

Faces of HR: Kristen Kenny on Empathy, Building Culture & Instilling Values

In undergrad, Kristen Kenny studied teaching and business management. She was still considering her options one summer when she started working as a Recruiting Coordinator at Fidelity Investments. Although she had found the role via a temp agency, Kenny would soon find out that there was nothing temporary about her serving in HR.

Kristen Kenny

Suffice it to say, Kenny enjoyed the work so much that she returned each summer, and after graduation, ended up joining the company full-time. After a few years working at Fidelity, a colleague invited her to join the team at a high-growth startup and that’s where her passion for HR and high intensity environments was set aflame. Since then, she has served at 10 high-growth startups and been involved in four IPOs.

“I join companies before they’ve designed HR, recruiting, and leadership and development initiatives, and I get to build them from scratch,” Kenny recently shared with HR Daily Advisor. “As a very growth-focused person, I feel fortunate about how much choice I have had, and continue to have, in my career.”

Currently, Kenny is Chief People Officer at EngageSmart, which offers vertically tailored customer engagement software and integrated payments capabilities to improve mission-critical workflows.

Over the course of her 20-plus years in HR, Kenny has prided herself on focusing her efforts on start-up companies to build infrastructure around HR/recruiting operations and business expansion – and EngageSmart is no exception.

I’ve enjoyed building out my talent management team, and working on implementing leadership and development, and figuring out succession planning and performance management,” Kenny says. “An area I’m excited to continue growing is our support for our employees that are parents and caregivers. We strive to embrace our team members as whole people, so implementing programs that support our employees in their family lives has been a priority. In the past year, we’ve significantly improved our maternity/paternity leave policies and established a subsidized care.com membership for all employees, both of which have proven helpful to our employees.”

In our latest Faces of HR, meet Kristen Kenny.

Who is/was your biggest influence in the industry?

I respect and appreciate Daniel Pink. His book Drive presents a compelling model for reframing how we think about motivation. It really altered my perspective for the better. I’ve been following his work for the last several years, and it’s been a significant inspiration to me as an HR professional.

What’s your best mistake and what did you learn from it?

At one point I took on a new role at an organization where no one knew me. Prior to joining the team at CarGurus, I was always referred to organizations and had existing contacts. It was uncomfortable to start at a new company and not know anyone—in some ways, it felt like a mistake at first, because I was out of my comfort zone. Ultimately, though, it was a valuable learning experience that helped shape my career today. I learned the value of building my brand from the ground up and developed my ability to hit the ground running in a totally new environment with no preexisting connections. The experience also drove home for me how important it is to always work on expanding my network. Having an expanded network has helped me to not only build out my own teams in HR, but also help other teams as well.

What’s your favorite part about working in the industry? What’s your least favorite part, and how would you change it?

I genuinely love working in a field that, at its best, prioritizes empathy. I think the challenges of the last few years have really put a lot of people to the test, and it’s been easy to become frustrated and overwhelmed—but I’ve also seen some incredible examples of people rising above to help one another.

I become frustrated with the HR industry when people lose sight of that core value of empathy. If I could institute a change in this industry, it would absolutely be to increase the value we place on empathy. We’re all human, and we’re all doing our best, and how you treat others affects them. Approaching everything with that frame of mind, from a meeting with an employee to designing an entire initiative, would go far.

It sounds like through your experience you really care about people, and you want to help them feel safe and comfortable, which is important in the industry. Please elaborate here.

Helping people feel safe and comfortable is incredibly important and is a huge priority for me, especially in my position. Throughout my career, I’ve found that one of the most impactful ways to make employees feel safe and comfortable is through company-wide initiatives and programs that benefit employees in the ways that matter most to them. Each employee has different priorities, and that is incentive enough for us to have robust offerings—so that there’s something meaningful for everyone. That’s why we’ve worked to implement changes that can help people across the board. For example, our Care.com membership helps our team members across all stages of life and with all kinds of family structures find support in caring for their loved ones. To me, this program embodies meeting people where they are to provide resources that make them feel safe and comfortable.

Opportunities for mentorship are also key, and I’ve noticed that opportunities to connect with a mentor or mentee are expanding. I look to my mentors often, both as it relates to my career in HR and in relation to broader growth and development, because those are the people who have helped me forge my career. At the same time, I’m looking at who around me I can help. I’ve been blessed with many great opportunities, and I try to make sure I give back by mentoring others. 

Whether a team member stays with the company for decades or continues their career elsewhere, I want to have been able to make a tangible difference through a project or initiative, whether it directly improved their career development or supported their life outside of work.

How can company leaders make HR a value within their organization?

I think one major step you can take to cultivate a community that recognizes the importance of HR is to recruit people who see its value right from the start—sort of perpetuating the value of HR, through HR. For every role across the organization, we must evaluate how each hire aligns with our company values. Do they understand our values?  Do their passions and interests reflect those values? This is critical: employees need to be passionate and understand a company’s priorities in order to work there effectively.

Where do you see the industry heading in five years? Or are you seeing any current trends?

Keeping track of trends can be overwhelming, but I think it’s crucial for anyone working in HR to pay attention to evolving needs and sentiments, both from a hiring perspective and from an employee perspective. It’s key to be adaptive in responding to changing social, economic, and cultural conditions.

It seems almost too obvious to say at this point, but the pandemic has really shifted the landscape permanently and, I think, for the better. It’s all about asking, “How can I make life outside of work easier?” When we were in-person, we could offer low-cost perks like dry-cleaning services and enrichment events. And now that we’re remote, there are versions of those things that can still be meaningful and engaging while increasing value for employees. Flexibility and ample time off are essential. Having empathy for everyone’s personal situation is important, and again, it doesn’t cost a thing.

What are you most proud of?

As a person who really thrives in high growth, rapidly developing environments, I’d say I’m quite proud of my ability to come into a situation where there’s still a lot in flux and start putting key HR infrastructure into place. Once those things are in place, it allows me to focus on what I find most fulfilling: building company culture and instilling values. At the end of last year, I hired a senior director of L&D and talent management. He’s been taking on a lot of important initiatives, in addition to what we’re working on together, and it’s all quite exciting—both the initiatives people actually see, and those behind the scenes. I’m also proud of our work to support our employees who are parents and caregivers—these programs fulfill a need for both our team members and their families.

Do you have any advice for people entering the profession?

In addition to emphasizing the importance of empathy, I would tell them that creativity and responsiveness are significant virtues. For example, the companies I work with are often still growing and as a result don’t always have the resources to offer the robust compensation and benefit packages that they are endeavoring to be able to. But that doesn’t mean I can’t demonstrate their importance to the company, and fairly compensate them.

One of the most important strategies to retaining employees is giving people the tools and autonomy to drive their own careers and encouraging an entrepreneurial mindset. Let them know that you want to uplift them, not hold them in place. Create opportunities for growth, and work to eliminate barriers for employees.

I would also encourage them to model the best aspects of the company they represent in their own day-to-day interactions. For example, I’m a single parent to a four-year-old, and I emphasize to new hires how my leadership team has never questioned me if I say I have to sign off, or if I need to change my schedule to address a family situation. Our employees get to see that kind of work-life prioritization happening in real time. Knowing we’re serious about our values can make a big difference. They’re not just hearing us say that work-life balance or mental health, or whatever the issue may be, is important. They’re seeing us make choices according to that belief, and we’re encouraging them to do the same.

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