EP 2: Strategic HR Leadership: Inclusive Cultures, Performance Management, and AI

Adriaan: All right, ladies and gentlemen, welcome to the Leaders in Talent podcast. I'm very excited to have Katie Evans-Reber here with me. Katie is a distinguished leader in the HR space with over a decade of impactful contributions to startups, including influential roles at Gusto and Wonolo. Currently, as the Chief People Officer at Gladly, she continues to shape organizational success through strategic HR leadership. Beyond her professional achievements, Katie finds joy in family life, sharing a journey with her wife and 11-year-old son. Katie, welcome.

Katie: Thank you so much, Adriaan. I'm so happy to be here. This is amazing.

Adriaan: Let's dive right in. You've had a phenomenal career, making interesting transitions from the shipping industry to Gusto and now Gladly. What has been a pivotal moment in your career?

Katie: I think the most influential moment was when I realized I am really interested in thinking about how we spend our lives at work. This happened early on when I was working for a financial REIT in 2008. During the financial crisis, we went from almost a thousand employees down to 80 over the course of 18 months. That was a recurring theme—being in the right moment to experience the ups and downs of the market. I realized this problem is so interesting and that I could spend the rest of my life thinking about employee experience, how we show up at work, and what work means to us as human beings.

Adriaan: What does work mean for you now, after being on this journey for over a decade?

Katie: Work is an integral part of how I identify as a person. It is where I spend the majority of my time and my "brain time." It’s a big part of my self-worth and how I measure whether I’m being successful. How I’m doing at work really influences how I feel about myself. If we’re spending our time not really caring about what we’re doing, what are we actually doing?

Adriaan: Tell me about the time when you first transitioned into a leadership role.

Katie: Listen, I'm the oldest of three siblings—I have a younger sister and brother. I’m seven to ten years older than them, so I’ve been in a leadership role since I was seven years old! I’ve always thought of myself as a leader. My first job was at McDonald’s at 15; eight months later, I was the manager at 16. I realized quickly that just being told to do something in a certain way never sat right with me. I want to be creative and I don't want to do things the way they've always been done.

I actually learned an awesome lesson about employee experience from Samantha Gadd—she’s founded Humankind and Excellent. She said that as professionals, we think we know the right thing to do, but when you are in the people profession, you are designing somebody else's experience. It is tantamount that you involve them in your process. It’s a product-led design philosophy.

Adriaan: Especially in those younger years, looking back now, what advice would you give your younger self?

Katie: I would tell myself that it was okay to feel "out over my skis." I would go back and give myself permission to just figure it out. I would relax into the moment more. Today I know that if I’m really comfortable, I’m not in growth mode. I’d tell myself to take the leap and feel uncomfortable.

Adriaan: You are now CPO of Gladly. Are there areas where you still feel you are "over your skis"?

Katie: Totally. Some days I'm still way out over my skis. The thing that surprised me most about being a CPO is that I spend the majority of my time thinking about the business and participating as a member of the executive team, rather than just leading people projects. I didn’t go to college; I’m completely self-taught. I haven't had many mentors because I’m a "songwriter"—when I’m writing music, I don’t listen to outside music because I want it to come from me. I want first-principles thinking so that what I’m building is original.

Adriaan: How do you become comfortable in a new environment, like moving from Wonolo to Gladly, while being fully self-taught?

Katie: It’s not easy. Wonolo is a B2B talent staffing marketplace for shift work. It’s very mission-driven, helping people put food on the table. Moving to Gladly, we are an enterprise SaaS company disrupting the customer service industry by creating a single "lifetime conversation" between a brand and a customer.

When you have a world-saving mission, culture is easy. The hardest thing is to create an engaging culture at a company that doesn't have that specific type of mission. To make the transition, you have to remind yourself that you don't know everything. Every company has different acronyms and revenue descriptions. You have to relearn the functions. A marketing org in a marketplace is vastly different from one in enterprise SaaS. As a CPO, if you distill it down, you're just a very senior HR Business Partner.

Adriaan: Do you remember when you finally felt, "I actually know what I'm talking about"?

Katie: There have been moments. At Gusto, I was able to convince California insurance companies to cover fertility benefits for LGBTQIA couples who weren't diagnosed as "infertile." That got picked up by a San Francisco supervisor and became a standard for workers there. But really, I’ve learned more from my mistakes.

Adriaan: Tell us about some of those mistakes.

Katie: When I moved from public companies into startups 12 years ago, it was the heyday. I went to Gusto and created a performance review process from scratch using "first principles" thinking—which I’m embarrassed about now because my thinking wasn't evolved yet.

We created a process that was non-anonymous peer feedback, self-reflection, and manager reflection, ending in a rating. At the same time, we rolled out Radical Candor. Radical candor combined with non-anonymous peer feedback was a disaster. People were leaving their reviews crying. It scales—Gusto still uses a version of it today—but it weaponized performance reviews.

Adriaan: So what is the "evolved" version you use at Gladly now?

Katie: I realized that the ultimate goal isn't to evaluate performance; it's to make sure the right people are in the right seat at the right time. For the employee, it’s about fulfillment and growth. I created a framework called ALIGN.

ALIGN stands for:

• Accountability: How you hold yourself and your team accountable to tasks and strategy.
• Leadership: Your ability to "10x" yourself and others.
• Intellect: Your subject matter expertise.
• Growth: Your growth mindset and ability to take and give feedback.
• Norms: The specific "how we work" rules of the company (e.g., using Notion, being direct, or dropping from meetings if you aren't needed).

Adriaan: Do people get a score for these?

Katie: I hate ratings. Philosophically, I don’t understand how telling someone they are "meeting expectations" is motivating. It’s a waste of time to calibrate those definitions. Instead, we do two "Align Calibrations" a year. I ask managers: What are the strengths? What are the development areas? Then I ask two pivotal questions:

1. Knowing everything you know today, would you rehire this person? (This looks at performance and org design).
2. Is this person "crushing it"? "Crushing it" is our proxy for a rating. If you absolutely have to have a rating system for compensation purposes, we can transcribe those answers into a simple "Great, Good, Needs Improvement" scale, but it doesn't need to be more granular than that.

Adriaan: Gladly is heavy on AI. What do you see happening on the AI front for people organizations?

Katie: We need to lead initiatives to bring in AI to make our jobs easier. People leaders who aren't actively exploring these tools are going to fall behind in productivity. Most tools right now are only 18 months old—they are "babies." None of them work exactly the way we imagine yet, but the commitment to exploration is what matters. Through trying, we will come to understand how AI can best serve us.

Adriaan: Katie, what is the question you would like me to ask our next guest?

Katie: I would like you to ask them: What do they think the role and responsibility of a company is in the coming years? How do they influence policy and change—or should they?

Adriaan: That is deep. Katie, I am so grateful. What is the best way for people to connect with you?

Katie: I'm on LinkedIn. Just come find me!

Adriaan: Great. Thank you so much for listening to the Leaders in Talent podcast.