Insights from a CHRO: Smartsheet’s Kara Hamilton

For Kara Hamilton, chief people and culture officer at Smartsheet, the thread running through her career–from finance and business operations to HR strategy–has been about understanding a company’s culture, from the inside out.

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It was an adventurous early career jump from real estate to teaching English to students and business people in Japan that led to her first tech job at the U.S. subsidiary of a Japanese tech company called Sophia Systems.

“I didn’t speak Japanese but I had cultural knowledge,” says Hamilton. While at Sophia, she discovered that she loved tech–and the human innovation needed to support it.

“It’s been very much a journey of one opportunity leading to another,” says Hamilton, who joined Smartsheet in 2012 to lead the finance, legal and IT teams before taking the lead HR role in 2016.

During her time there, the company has grown from 30 to 1,500 people, providing a collaborative work-management platform to some 84,000 customers worldwide and earning kudos as a best place to work in Seattle and Boston. Prior to that, Hamilton held various operations-related roles at four other tech companies.

“You don’t always know where things are going to lead, but they’re going to lead somewhere,” she says. “Being both open to your path and intentional on your path is a balance that is important. If you’re too intentional, you might miss out on something that presents itself that’s equally exciting.”

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HRE: You’ve said that the difference between an OK team and a thriving team is creating an employee experience that people feel connected to. How is that playing out in Smartsheet’s people strategy?

Hamilton: We have spent a lot of effort on talent acquisition and our employer branding [as a once-] tiny company where nobody knows what you do. We considered ourselves a secret in the Bellevue [Wash.] area because we had customers all over the world and, yet, people in our own community didn’t know who we were. We need to hold a high bar and have clarity on their expectations of what that role is going to provide Smartsheet, but, we also need to show our best selves and who we are to that candidate.

We really want to make sure that their journey [through the employee lifecycle] is a fruitful one. We want them to feel like they can spend a good chunk of their career here. Those [lifecycle] programs are things like educational and development programs, training programs and internal mobility. When someone is a high performer, if they have interest in another area, we want to make sure that they have new opportunities for meaningful work.

We’re also on this journey of, how do we build in meaningful corporate-social-responsibility programs along with learning and development, along with maturing our diversity, equity, inclusion and belonging, and career pathing?

I’d be remiss in not mentioning the foundational elements of having a strong purpose and having core values. We’ve created what we call our Values in Action Playbook. It not only lists our six values–honest, supportive, driven, innovative, authentic and effective–but also talks about borders: What does it mean to bring those values to work every day, and what are the cultural “motions” that go along with that?

Being supportive is one of our values, and we describe that as being kind and helping each other succeed. It’s a very specific kind of being supportive. It’s about bringing your best self to work and really realizing that we’re one team, so how am I going to work with my colleague to make sure that that they succeed? That’s my duty and the cultural motion that comes out of it.

HRE: How does your Values in Action Playbook build and improve workplace culture?

Hamilton: We have monthly meetings for all the new employees who have joined us, and we discuss the values and the action framework [from the Playbook]. We are all called, no matter what our role is, to do continuous improvement, making the organization the best it can be through your own expertise and experience.

The action framework is five steps–observe, ideate, research, recommend and execute–and we think of that as a circle. If I observe something, I have a responsibility to think about how to make it better and to research the options of what might work. You get with other people and learn things that we all do in a silo. You recommend solutions and work up a plan [if it’s worth executing]. We don’t ever stop.

HRE: You’ve talked not about best practices but “next” practices. What trends do you think will impact the future of work and how should HR respond?

Hamilton: One of the things that we’re thinking about a lot is honoring different tracks in career progression. That takes two forms. On one hand, it’s honoring people leaders and their role, which is very important to the organization. We want people leaders to create healthy and effective teams–that becomes the main focus of their work.

Then, on the other hand, we want to make sure we’re honoring people who want to stay as individual contributors. They are benefiting the organization through their deep expertise, through solving hard problems for us [and providing] technical leadership rather than people leadership. We’re intentionally creating career-advancement paths, so people managers and individual contributors can both have progression.

Careers are longer now, [and] there’s time to grow in different directions, to build one set of competencies and then go to a different discipline. If we can keep this high performer on our team, that helps with our retention and we keep their skills and experience within our walls. So, you’ve got loyalty and retention, but also there’s a different set of competencies. If you apply it to a different problem set, you’re getting a new lens.

When someone at Smartsheet transfers from customer success to, let’s say, the product team, they’re bringing all the knowledge of how they work with customers. They know how customers use our product. They have to learn some things about product management, but we can teach that. Then we’ve created this connection and value and we’ve actually extracted the value they’re creating, [and they have] an opportunity to be an ambassador.

There are five generations in the workforce. I’m pretty excited about Gen Z coming into the workforce. They’ve had access to technology since they were babies, and they’re coming in with the expectation that [their company] will be thinking about equity. They are already a very diverse generation.

They think of work as, it’s what I do, not where I do it or when I do it. I think HR professionals will be well-served to think about flexibility as being another type of autonomy. We want to trust people to deliver. We’re making sure that we’re broadening that [definition of autonomy] and are responding to a workforce that is going to feel more fluid in how they do their work.

To nominate yourself or another HR leader to be interviewed in Insights from a CHRO, email [email protected].

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Maura C. Ciccarelli
Maura Ciccarelli is freelance writer based in Southeastern Pennsylvania. She can be reached at [email protected].