EP 7: On Building Trust and Retaining Talent

[00:00:47] Adriaan: All right, ladies and gentlemen, welcome to another episode of the Leaders in Talent podcast. My name is Adriaan Kolff, and I’m your host. Every two weeks, I interview leaders in talent who are making their mark on our industry. Today, I have the honor of welcoming Annie Wickman. Annie’s career started at Google, where she worked with Laszlo Bock, who was the Senior VP of Operations at the time. After Google, Annie worked at Etsy and Gusto in people operations roles, only to leave Gusto to work once more with Laszlo as his COO, CPO, and basically the C of everything at Laszlo’s startup. Most recently, Annie built out the people partner function at Forerunner Ventures Capital and has now transitioned back in-house as the Head of People at a company called Character.AI, a rapidly growing AI startup. Annie, welcome to the podcast.

[00:01:48] Annie: Thank you so much. Thanks for having me.

[00:01:49] Adriaan: So, Annie, funny story that only we know, but our listeners don’t— you had to reschedule our podcast multiple times. And I know why, because things are pretty hectic and crazy at Character.AI. Am I right?

[00:02:03] Annie: Yes, it’s been a wild ride, a really fun and rewarding and wild ride.

[00:02:08] Adriaan: Tell me a little bit more. What do you do at Character.AI, and what’s happening there right now?

[00:02:14] Annie: Yeah, well, I’m the Head of People here. I was hired in April, and in late July or early August, we went through a transaction with Google where they licensed some of our technology—non-exclusive—and took some of our pre-training researchers. So now we’re in this moment of rebuilding as a product company. Before, we had somewhat conflicting or competing missions: one to get to AGI and one to build a consumer product company. Now, we can focus entirely on the latter. It’s been a very fulfilling challenge to navigate the people side of things, like how to build this new company, get people energized, show them the potential, and manage all the operational aspects, like restructuring the cap table. Now, everyone is fully an owner in the company, and we’re figuring out what that looks like. It’s been great.

[00:03:52] Adriaan: So, Annie, help me understand this a bit better. Did Google buy your company or become a shareholder? Or am I missing something?

[00:04:03] Annie: Yeah, I’ll tread carefully here since I’m not sure how much I can share. But from what’s public, Google paid us a large sum of money to hire a handful of our top researchers, including our founders, and to license some of our technology. That was used as an investment and to pay out employees to a certain degree. So now we’re a standalone, wholly employee-owned company.

[00:04:29] Adriaan: Oh, wow. Okay. And you mentioned two different projects you were working on. Has the company pivoted or refocused on one?

[00:04:47] Annie: I wouldn’t call it a pivot. It’s more like we’ve been able to drive deeper focus on building a consumer AI product. It’s exciting. But, of course, it’s about bringing people along, as we’re only six or seven weeks post-deal. People take time to process change and understand it. Some are ready to go full steam ahead, and others are still processing what the mission is moving forward. The energy is really exciting, though—it very much feels like a startup again. It’s a lot of fun.

[00:05:29] Adriaan: So, in terms of people, what has the last five or six months been like for you? What was the situation when you arrived, and where are things now?

[00:05:43] Annie: From a people perspective, it’s been a lot of pivots. I came in to build out the team and some of the core foundations that any fast-growing startup needs—feedback, performance management, payroll providers, etc. But then the transaction happened, and we had to focus on figuring out the cap table, retention, compensation, hiring, and aligning everyone on our new mission. It’s been a journey of constant change, which is typical in startups. Now, though, we’re ready to get back to those foundations, like feedback and performance management, while also thinking about how to retain employees and keep people motivated to build a successful product company.

[00:06:48] Adriaan: I want to zoom in a bit on retention because the AI space is so competitive. The salaries being offered are wild. When you joined, how many employees were there, and what was the hiring velocity like?

[00:07:00] Annie: I think I was around employee number 90, and we were adding six or seven people a week for a while. By the time of the deal, we were just over 130, and we’re now back down to about 100, but still growing. We’re being more deliberate about the types of profiles we need to build a successful product company. There was a big focus on onboarding, and we spent a lot of time setting people up for success, which is still important. But now, we’re figuring out how to rebuild that muscle with a more deliberate approach.

[00:07:50] Adriaan: How do you handle the balance between quality and speed, especially in such a competitive, fast-moving space? What’s your take on that?

[00:08:08] Annie: I’m a big believer in speed and iterating. I think there’s a quality bar things need to pass, probably around 70 or 80 percent, and then you push it out and iterate. Of course, some things—like payroll—need to be perfect. But most processes can be continuously improved.

[00:10:55] Adriaan: You’re competing against Meta, OpenAI, Amazon, Google—all giants in the space. How do you compete with that? Do you even try to compete on salaries?

[00:11:14] Annie: We do compete, but the advantage of being a startup is that people often leave companies like Google or Facebook because they get frustrated with bureaucracy. At a startup, they can actually make an impact. So we lean into that. People find meaning in their work when they know how it connects to the mission, and they feel empowered. That’s key for retention. Trust is another big one—people need to trust their leaders and managers. We can’t compete with Google on cash comp, but we can compete by offering potential through equity and the unique experience of working at a startup.

[00:13:10] Adriaan: You mentioned building trust. How do you do that from a leadership perspective?

[00:13:17] Annie: It’s hard, and it takes time. You have to be open—no question is off-limits. Presence matters too, not just being a floating head. I try to sit down, eat meals with people, and get to know them. You also need to be careful not to make decisions that erode trust, like taking away a benefit without a clear explanation.

[00:14:52] Adriaan: Is there a proactive way you do this, like a process around it?

[00:15:01] Annie: It’s about being thoughtful as a team and talking to your people. When you’re considering changes, like removing a benefit, you have to get feedback and make sure people understand the reasoning. It helps ease people into the change and ensures you don’t make decisions in a vacuum.

[00:18:11] Adriaan: I had an experience where we didn’t communicate transparently, and it eroded trust completely. I promised myself I’d never do that again. Now, I’m open with my team about financials, potential layoffs, everything. It was hard, but it built trust. When we had to lay off 50% of the team during COVID, people comforted me because they understood the situation. It’s something I’ll always stick to.

[00:19:46] Annie: That’s amazing. It’s about treating people like adults, right? If they have clarity, they can accept difficult decisions. That’s a testament to your leadership.

[00:20:06] Adriaan: What trends are you seeing in the industry right now, especially with companies like Amazon announcing return-to-office mandates?

[00:20:17] Annie: That’s the big one I’m watching with interest. I don’t see a blanket return-to-office mandate working. Your top performers who don’t want to return won’t, and what are you going to do—let them go? I think companies should focus on the people who need to be in the office, like younger employees who are craving in-person connections. We’ve implemented a hybrid approach at Character.AI, with three days in the office. It works for us, but it’s hard to enforce office time, so we’re trying to make it fun and appealing for people to be there.

[00:24:13] Adriaan: Six months into Character.AI, what excites you the most?

[00:24:13] Annie: Our potential. We have an amazing team, and the space is constantly evolving. I’m learning a ton, which is incredibly motivating. I also love building from the ground up, and we have a lot of building to do.

[00:24:57] Adriaan: If you could give advice to your younger self, what would it be?

[00:25:10] Annie: I’d say trust your gut more and don’t stress so much. I’ve made most of my career decisions based on gut feeling, and it’s worked out. Also, believe in yourself more—have confidence in your abilities, and take on challenges that feel a step ahead. It took me longer than it should have to feel that way, but I’m there now.

[00:26:05] Adriaan: Do you feel confident now?

[00:26:13] Annie: I do. Of course, there are always moments of doubt, but overall, I feel confident.

[00:26:24] Adriaan: That’s great. Annie, this has been such a pleasure. If people want to connect with you, is LinkedIn the best way?

[00:27:55] Annie: Yes, LinkedIn works great. Thank you so much—this was really fun.

[00:27:59] Adriaan: Thank you, Annie!

[00:28:07] That’s about it. I hope you enjoyed it. If you did, please like, share, and subscribe. Bye-bye!