Anique Drumright is currently the VP of Product at Loom. She is an incredible organizational talent and product leader. In this podcast, Anique uncovers her unconventional break into product, her strive for continuous learning, and the secrets to managing and aligning teams for success!
Question [00:02:19] How did you break into product?
Anique [00:2:21] Yeah, so I’m a bit of, I would say a non-traditional story. Directly out of college, I was with an organization called Teach for America for 5 years. It is a nonprofit that works in high-poverty schools in the United States and high potential young leaders out of college, primarily into classrooms and you get trained and you teach for two years. I ended up spending a long time with the organization in a variety of roles. I was in Memphis, I was in Dallas and I got to this itching point where it was just really ready for something new. My brain was just hungry for something new.
I made my way to Uber and was in a variety of roles at Uber ending in a product operations role where I really began to work on the product teams and with engineers and with PMs and with designers, launching products, and just knew that I had kind of found my home. It’s just highly collaborative, the sky’s the limit. In the beginning, it’s all vision work, and then towards the end, it gets into this really exciting almost sports game. You’re like driving to the finish line and you’re like, how am I going to make it, are we going to get everything we need? And then are you measuring it. There’s just this adrenaline rush that is part of product development that I think once you experience, you’re like, yeah I want to do more of that.
Then I decided I wanted to get more into the startup area. I wanted more white paper. I knew I had experienced a ton of ownership and leadership during my time during Teach for America. And had had increasing levels of ownership at Uber. But at that point, when I joined Uber, it was like 4 or 5,000 when I left, it was well over 10. And I just wanted to be in a smaller, at a smaller company and just experience what a startup was like. So I join TripActions as a Series A company, with 40 people valued at 20 million as their first Product Manager, and then scaled the organization to around 30, between product and design with teams split between Amsterdam and San Francisco. It was crazy to go from 40 people to 1200 Series A 20 million all the way to a D valued at 4 billion.
Then I had the opportunity to join Loom. Joe and Vinay from a founder perspective, I can’t imagine working with, kinder or more enthusiastic or more dedicated founders. From a product experience, you use Loom to solve some of your communication problems, some of your execution problems in such an aha moment, that I really connected to the problem.
Question [00:05:37] At Uber you were working as a Product Ops, however you later transitioned as the first Product Manager at TripActions. How did you convince the CEO to give you that title and run the show?
Anique [00:05:54] I’ll just begin by saying during my time as a product doing Product Ops at Uber, I was lucky enough to work with a product manager who gave me a ton of autonomy. I was able to gain a lot of hands-on experience about what did it look like to run a team and how do you shoot vision? How do you seize opportunities? How do you size problems, and we’re just given a lot of autonomy? I knew that I had taken my time to learn and could do it. Then with joining TripActions, I was lucky to find founders who placed big bets on people, and they placed a big bet on me and I returned their investment over and over again. But it took both me placing a bet on myself, taking ownership of my own learning, taking ownership of all the opportunities in front of me, and also other people placing a bet on me. And then me returning that with performance.
Question [00:08:01] Tell me the story about what makes Loom so unique and why you are experiencing such incredible growth?
Anique [00:08:06] When I first onboarded Loom, I spent 30 days doing both internal interviews and customer interviews. I must’ve talked to like 50 or 60 people in these first 30 days. The number one thing that users love about us is our speed and simplicity. So it is so quick and so easy to record a video message and send it. And then I think one of the richest aha moments of using loom is yes, that speed and simplicity, but then the next one is you get validation that someone watched it, that someone left a comment that someone left a reaction. It’s both like it’s a combination of the usability, the reliability, and then also like those critical moments of communicating, we give really good feedback on that just makes it a really rich product experience.
The way that we are approaching the problem is when you are communicating with video, there are varying levels of formality that you want to communicate with, sometimes extremely polished, sometimes very casual, and we want to make it extraordinarily easy to be successful anytime you need to communicate with a video message. One of the things that I quickly learned in managing like a remote team, in working across time zones was how important video messaging is to make that culture successful and to make your team successful because you just lose so much if you’re only relying on those two working hours you have or a perfectly written email that people are going to take the time to read for 45 minutes and digest. Loom just makes all of that so much more for sure.
For anyone who works on product teams, especially like now in this hybrid remote world, or like across time zone, every single person has experienced the pain of, I have design feedback and I’m just not able to express myself adequately over Slack or via an email or this thing is going wrong, and I want to help us debug it. So let me record a loom, so I can quickly achieve that. Those pain points are so real to anyone working on product teams.
Question [00:11:36] During the pandemic, there are more and more people that need to rely on this type of asynchronous communication. How has that impacted your roadmap and internal work?
Anique[00:11:49] We have seen explosive growth. The level of investment that you put in product quality, security, stability, and speed, I think definitely increases as you put more load on a platform. I also think it’s become clear that people are really using our product as a quick messaging product, as just, video messages sending back and forth. So just continuing to invest in that speed, in simplicity has been really important to us, but this has always been the vision of loom. It’s just that the outside landscape is like catching up really fast.
Question [00:12:58] Do you see Loom as a standalone product as a platform, or is it more of an add-on to other platforms?
Anique [00:13:08] So I say this as an and statement, right? So we want to be everywhere that you work in everywhere that you communicate. There’s a reason that our desktop recorder just always sits on your desktop, right? You can click into it and get it going with literally two clicks, the same with the Chrome extension. We seamlessly embed into Slack, into Notion, into the email. If you want to use our home, and you want to get recently shared Looms, your library of content that you store your training in that will be available to you, but we will also always prioritize working in tandem with existing channels of communication.
Question [00:14:45] How are you structuring product teams, because it’s not just product managers, right?
Anique [00:14:50] Correct. Definitely not just Product Managers. I always tell everyone who is new to product is to have a deep, deep understanding that you are useless without great collaboration. You need to have incredible relationships with your designer and engineering dudes.
So both Loom and TripActions or B2B to C products. Obviously we’re selling in a B2B way, but ultimately we are delivering value to an end customer to an end-user. I have found it most intuitive to really follow that end-user experience when designing product organizations because I think it generally aligns with incentives. You’re thinking about the journey of the user rather than kind of segmenting it out because if you do that, I think you can create a disjointed product experience.
Question [00:16:17] How do you go about hiring PMs at Loom?
Anique [00:16:21] I definitely believe in a rigorous interview process, that’s, cross-functional, I think it’s super important to standardize your interview process just because you calibrate and you can catch yourself up on like how you were judging quality candidate to candidate. I’m a huge believer in having an assignment because it shows you how someone works, how invested they are. Then I think in terms of the qualities that I hire for, I hire for grit, I hire for results and I hire for curiosity. When I say grit, it’s really a combination of like leadership and grit. I think that you have to be curious as a Product Manager, you have to be a tinker. And understanding how products work, what’s going on in the geopolitical world, what is going on in kind of the investor part of Silicon Valley, etc…
But I also think that you need to have a track record of delivering results. You need to know what that feels like and what it takes, and that the last 20% can often be messy. That habit or that practice of delivering results is the same, whether you work in product, engineering, in education. It’s a muscle, and it’s a commitment to completion that you want to hire with a strong track record of, and on the grit and leadership piece, ultimately you’re inspiring teams. You need to help inspire teams to do their best work and achieve a greater goal. I definitely hire for that leadership curiosity in results background.
Question [00:18:09] Are there any specific education or non-experience requirements, or do you go more based on the skills that you’re looking for?
Anique [00:18:18] I think at a startup, I do try to hire people who have experience in product, just because it is a less formal environment. There isn’t an associate PM rotation that you’re going to do, that you would generally do at a Facebook or a Google, and because there’s no associate PM experience, I do expect product managers to come in with a background in product experience, and then depending on your needs, you make different decisions and trade-offs on seniority.
In terms of assignments, I’ve done both. And I think there’s merits to both. One type of assignment is you take the business that you’re working at and you give it a nebulous problem and you test someone’s approach to carving out like assessing the problem and opportunity space and what that solution would look like and what the prioritization was follows.
The other one is to give like just a totally wild assignment and you can see how someone breaks down problems and opportunities, and, push them to create, a product for a grocery store, right? Like how would you design the best bag checkout system, right? And the goal in all of this is how do you digest problems? How do you prioritize? And I think it’s really important to get a taste for that. And as well as someone’s communication skills, both written and verbal during the interview process.
Question [00:21:02] What’s on your bookshelf and how do you learn these days?
Anique [0021:04] I definitely listened to a ton of podcasts, I think it’s such a great way to take a walk and also be learning and be just hearing from others. One thing that I definitely think is true when learning, is that often times people gravitate to other success stories, but you can learn a lot from other people’s failures. And so listening to that human story and others’ experience in growing companies and products, I just find that very inspiring. So I try to listen to those a few days a week. Then the regular business book is sometimes fun. I think the ones I have on my bookshelf right now are What You Do is Who You Are by Ben Horowitz, a second book Option B by Sheryl Sandberg. It’s great to get inspired by great leaders stories, but I do think it’s not only curiosity about what’s happening in the business world and within the product environment, but I also think just curiosity on how you can continue to grow as in person and continue to manage yourself and your own emotions and your own communication is equally important. So I try to kind of balance both of those learnings.
I’m currently recommitting myself to my yoga practice. So I’m currently on a 30 day cleanse, which I think is very good for the new year. My product team has started having watercolor happy hours. So we’re doing, we did one formal watercolor class, but now we’re in a formally building our watercolor skills, and just some cooking. So my learning on the side has been really much more joy based.
The other thing that I’m actively learning, that’s both personal and connected to work is just communication and how people communicate, and how effectively people communicate. It’s obviously important day-to-day as a Product Manager, but it also is like the heart and soul of the Loom product is you be the best communicator you can be. That’s been fun where it’s kind of combining something that I’m both naturally and personally very curious about, but also gets to be reflected in the product.
Question [00:24:05] What other tools or products are part of your product stack?
Anique [00:24:10] Google sheets, for sure. Slack, Loom absolutely, Figma. Those are our general go-to is a fair amount of Intercom.
Question [00:24:32] What type of advice would you give to your younger self before you even broke into products?
Anique [00:24:39] What would you say first and foremost, there’s always going to be people who you can learn from. I think everyone should take the opportunity to learn and really nurture that relationship and say thank you, let them know that you are learning. Make sure that when they give you an opportunity, you’re over-delivering on that you do what you say, you’re going to do it by earlier than you said you were going to do it by. I think really nurturing those opportunities is huge.
One of the mistakes that I have made and continue to make and will always be getting better at is, a core skillset that I rely on is grit and hard work, that’s really important, and that’s propelled my career, definitely. But that only takes you so far. So make sure every once in a while you are pulling your head up and you’re aware of the market and you’re aware of how things are changing. Sometimes when you’re earlier in your career, you can hold goals too tight, and then you lose perspective. I think that mentorship piece is hugely important.
And then the other pieces definitely rely on your work ethic and being committed, but don’t be afraid to like, pull your head up and, and make sure that you’re still driving towards what you want, in the style in which you want to do it right. How you do things does matter, it’s just super important to continue to build perspective regularly.
We’ll be back next week with our final episode of The Product Podcast with Justin Bauer from Amplitude with even more of the latest insights from the Product Management world. Stay tuned for more!