Lessons from Loom on product strategy, organizational leadership, and cross-functional excellence | Anique Drumright (COO at Loom)

 I thought maybe one place we could start is, I think you're about a year into being a COO for the first time after kind of being quite functionally oriented spending, I think most of your career in various versions of product management. I'm always really interested when somebody takes on kind of an adjacent role like. What has been interesting or surprising for you? 

 I don't know if this is surprising, but more confirms how interconnected product is with marketing, with storytelling and how that connects to customers. And I think it's really confirmed just how central product is to the customer experience and how the various functions support that and influence one another.

 So maybe on that point, if you were to go back and lead product again, what are like the things that you've observed in this role that might make you think differently about what you would do as a product person, if anything?

 I think a best practice that is too often glanced over is what do you wanna see in the market?

What do you wanna say to your customer? How will you explain it? In really beginning, every product review with that, you know, the first principle of what do you think the impact of it will be? But I think starting with the storytelling of what this feature, what this new offering will do, and starting much more on, on the marketing side rather than on the functionality side or even the opportunity side.

I would probably start earlier with that. 'cause I think it creates a lot of cross-functional clarity.

 What does that look like in the context of loom? 

 So I think an example is everyone's building with AI right now, and so I think initially it was like, okay, what are the capabilities we could use? What's the functionality we could use?

But really starting with how could we make this easier for a creator to connect with their audience? And what do we want the creator to be able to say and what do we want the audience to be able to say? And starting in many ways with the product marketing and how we'll explain that moment in product has been, I think, hugely helpful.

Whereas I think when I was just wearing my functionals, I think too quickly and too easily, we began with execution. And so I think it's evolved the way I think about key customer experiences. 

 And how does that connect with this idea of marketing and storytelling? becasue you're starting with the story of the value you're gonna provide.

 I think all good product management starts with it, but I think it's often something that like begins with, you know, that five minutes, this is how we'd explain it to a customer, rather than saying, this is the key moment we wanna create over the course of the next three months, the next six months. This is what we think the value will be to the customer base.

This is how we would frame it for our customer base. This is what we think the value of the business would be. And spending a lot more time on that almost product marketing moment earlier on, I think brings your cross-functional team with you much faster. Rather than making it a by the way and spending a vast majority of your effort on the product review, the feature requirements, the designs, all of that is still incredibly important.

But I think I underestimated how clarifying that best practice is in bringing your cross-functional team together. And I think it builds a better product because you're spending a lot more time obsessing about what the value you're trying to bring to the customer is. 

 And so is your sense that should be driven by the PM who's owning this thing?

Or a product marketer or it kind of depends.

 I think it depends. I think it like depends on where your team's strengths are. I also think those are really perforated lines, right? Like the line between a designer and a product manager, perforated like product manager to engineer perforated. And I do think it is a collaboration.

Ultimately, I think the product manager needs to be driving that perspective in its totality, but I think there's room for various functions to take the lead.

 So maybe when you think back to the last six months and the products that you've shipped as an organization at Loom, when you think about really nailing this idea of storytelling, is there one thing the company launched that most comes to mind, and what did that look like?

 It's like product managers and designers. We were excited about this idea of auto packaging. This idea that we could magically make a loom better with less effort from a creator and it would land better for a viewer. 'cause something that we had learned from talking to creators and talking to viewers is like, viewers really want context as to what their loom is about and creators really.

This makes a ton of sense. They really want their loom to land. Their viewers are what motivate them, right? Who they're communicating with are what motivate them. And also the number one thing that they value with Loom is that it's super fast and it's super simple. So how do we make that connection automatic?

And so we talked a lot about this idea of auto packaging and auto context, and you know, over the last few months we've released automatic titles and automatic summaries and automatic chapters. And this idea of packaging your loom automatically. What we're seeing is creators love it because it's less effort.

There's the right amount of delight and utility. 'cause we give you your title and we select an emoticon for you. And from a metrics perspective, the viewership is going up because I have richer context. And the loom itself is more engaging. And I think that's one where we haven't been sharing about it a ton externally, but the storytelling we told internally around ourselves around hey, what is the set of features that package this loom automatically and help make creators more successful in providing context to their viewers? Really helped clarify what we wanted to put in scope of this initial push. 

 And so what did that look like when it was getting kicked off in terms of getting things off the ground, aligning around this narrative?

What's going on at the beginning before any features and functionality is articulated.

 I think we're really lucky to have a great user research in design partnership, and they also work really closely with our product marketers and product managers. And so it begins with a real synthesis and internalization of, Hey, these are the customer problems we wanna solve, and these are the new capabilities we believe in, and how did these come together?

But I do think that our product design team, especially at the initial kickoff, plays a really large portion in setting the, what's the vision of what we wanna do and why do we wanna do it? 

 And like what's the deliverable there? Is it like a multi-page doc that tries to articulate what this narrative and set of value props might look like, that then gets shared with the team and people kind of workshop it.

 Yeah, that's generally what it starts. It's the product manager starts with the PRD. The designer plays a really large role in like leveraging the UXR that already exists and really framing up the customer problem. And between the PM and the designer, they say, Hey, this is the headline of what we wanna create, and this is the feature set that we think between the effort impacting confidence rubric we're recommending. 

 I'm I really interested to learn more about what your process is for getting your arms around these other parts of the org that you didn't come up under. When you end up in the COO role, you end up having sort of this span of scope that's quite cross-functional. 

 Yeah, I think it's a very. Interesting question.

I think that the place that I always try to begin with is just re-anchoring myself because I think every function connects differently to the business's stage and the business's strategy. So I begin with trying to re-anchor to myself, Hey, what is crucial for the company right now? And like, where does this function support?

Where does marketing really need to get an A at? Where does data really need to get an A at? And just re-anchor myself on the like broader context that we're functioning under. And then from there, I just begin with information gathering. Just trying to understand what's the team currently working on? What do they think they really need to get an A on?

And just slow down to listen. I think the next kind of double click I do is with critical stakeholders. So for data, for example, what does my sales leader think? What does my customer success leader think? What does my product manager think? What do they believe should be the priorities for data based upon what they need to achieve from a business perspective?

And then from there, I try to align with the leader on do we have a shared definition of, of what we're trying to get an A on and why? And that's really like the starting point of the work is that clarity on how does this function connect with the broader business context and strategy, and are we aligned on what the priorities are?

 And is that just happen through organic conversation or have you developed some sort of process or approach to create that type of alignment? 

 I definitely go through this process. So I'm a big believer in writing down like the three things that any organization, any function really needs to be absolutely crushing at for the next three months.

'cause I think it's really clarifying. I think especially at a startup, the work, there's so many opportunities and there's so many problems, and there's such a dearth of systems. So you're building the business while you're building the product, and you're building your systems all at the same time. So there's a never ending list of things that you could improve.

And so I think getting extremely clear on what the priorities are and how those priorities support the business helps you also say no to a lot of things. And so the process that I always go through is I re-anchor myself on like, okay, what's the business strategy? What is my own instinct on what I think needs to be going on.

I then go, listen. I meet the team, I listen to what they're doing, and I really try to learn about their workflow. I then try to learn from the cross-functional stakeholders, so you could call this phase more of a traditional listening tour. You talk to your customers and then after that it's okay.

Between me and the functional leader, are we aligned and what is the refreshed set of priorities? and then from there, it's okay. What are the couple of things we can just trim and stop doing? What are the couple of things where we can be more efficient? And then a question that I often try to ask myself is like, where can I support in making the cross-functional ties stronger?

You know, when people are exhausting themselves, it's because there isn't cross-functional alignment. And the reason why there isn't cross-functional alignment is because. I'm probably not creating that signal to noise that helps everyone independently prioritize and feel like they're playing off the same plan.

And I haven't done a good job of saying, oh, no, no, no. We actually, we can pause on this because this other thing is more important. But that's generally the framework that I'm consistently trying to use. And then I'm usually like rinsing and repeating that cycle every two months or so. 

So when you think back about a cycle from like the past six or nine months, What's an example of the three goals or priorities?

Because I'm curious like at what level of altitude you think is most effective for those type of governing goals? 

Yeah, so I think, you know, the most recent example is we just hired a new marketing leader, a new VP of marketing at Loom and so as part of finding that leader, I had to really re-anchor myself as well as our CEO on what do we want this person to be really, really great at, and what does Loom really need for the next 12 months? And the level of the goals is we really want someone who's like great at growth marketing. And when we say growth marketing, we're really talking about paid marketing, we're talking about SEO, and we're talking about positioning and we want to be great at those three things.

 And that feels like one sort of functional example of getting really clear on kind of three goals. Is there an example of the cross-functional three most important things that then guide sort of everyone's work? 

 It's how we do our quarterly planning is based upon like high level like key deliverables that we want to achieve over the course of the next three months.

But then we meet every Monday to cross-functionally to review the key customer moments. And that's something that we've recently started of like, Hey, these are the five like key critical moments that we wanna achieve over the next three months, and we all cross-functionally go through that. So it's brand, it's product marketing, it's data, it's product management in sales.

And we're essentially having a staff meeting saying, Hey, these are the critical customer moments over the course of the next 90 days. Are we all aligned against them and are we all prioritizing against them? 

 What's an example of a customer moment? 

 So one of the like easy customer moments is we're releasing Multilanguage transcripts.

Loom has a wildly large international base for right now. You know, your closed captions and transcripts are only in English, so we need to be ready to support that in multilanguage. Another one is, Our AI editing suite, how do we go from how user, community and beta community to GA and how do we amplify that and make sure that it's the highest quality it can be through validation with customers as well as landing in market.

 And so for those five areas, you wind up sort of reviewing those with your functional leads on a weekly basis. 

 And what is the structure of that meeting end up looking like? 

 The structure of that meeting is we begin with, there's like a visual of what the customer journey looks like over the course of the next 90 days.

What are the key customer touchpoints of admins, of creators, of paying customers, of our free user base, et cetera. And then we go through each one of those releases. In that chronological order, you know, 'cause not a single PM is overseeing every piece. Not a single designer is overseeing every piece. And so that we can hear, okay, what's the feedback?

What are the things that we said we were gonna solve cross-functionally last week? Did we solve it? Cool. We close out that piece of release and we go to the next piece. And so it really helps us begin our week together and so that we can hear from each other cross-functionally what we need to rally around to achieve these key customer moments. 

 Why do you think alignment tends to be so difficult in companies of almost any size? I was actually talking to a CEO that we partnered with for many years and we were talking about it randomly alignment last night, and it's one of those things that intuitively makes sense, but I feel like most companies at any given time aren't in alignment in almost any facet.

Is there a reason that it seems to be so difficult to operationalize or action on? 

 This is a much more philosophical answer, but I think the reality is this, that we're humans. I'm different today than I was yesterday and the day before, and I'll be different a week from now. And I think, you know, a company is just a bunch of humans working together and so your perception of what the plan is and your belief and understanding of the plan is evolving.

And because everyone is evolving, you have to evolve the system together. I think that's why people spend so much time on alignment is it's, I think it's the reality of teams working together and I think the promised land of like alignment is when people have when the what and the why is like pulsing through you.

And it's, it, that same version is pulsing through everyone and, and you feel it as a team, right? There's like moments of Oh yeah, yeah, yeah. Like we all know the what and the why and, and we're fired up about it. The autonomy and the velocity comes with it and it's why you see people fight so hard when they're out of alignment.

It's 'cause you're always trying to get back into that tempo run. In some ways 

 When you think back across your career thus far, what are the moments where you felt that the most? 

 I think there were definitely times in my journey at TripActions where the what and the whys was so absolutely clear. I definitely felt that way, and like I would say right now at Loom, I feel that way in the sense of there's just such a belief that the capabilities of AI can be used to just further the experience of creators so intensely that there's just this excitement and a clarity of the opportunity in front of us that the alignment is much clearer and much more simplified. And I think if I were to like double click on both of those experiences, I think the way larger tech companies have evolved is you know, you have your 12 autonomous teams and they're running in parallel. But in both of those experiences, the one I'm currently having right now and the one at TripActions, we're actually running off of one plan. And there's absolutely a divide and conquer. But I think when there's too much of an effort to parallelize, then you lose that sense of alignment and that sense of broader mission.

And I think in both of those moments of time, there's only one play, you know, and that play may have three or four steps, but it is singular focus. 

 Do you think that a lot of companies can have a meaningful percentage of that time where everyone is aligned to sort of get to the top of that hill, or it's just the nature of scaling businesses that.

You have a bunch of people that are charging up their own hills and that's just sort of a constraint of bigger businesses.

 I think it's definitely possible. I don't know. I think back to my time at like Uber 2015, everyone really was trying to make transportation as easy as running water. And I would say that company when I joined was in the thousands, right? I think it was 5,000 when I joined and it, it scaled. It probably doubled over the couple of years I was there. I do think it's possible at scale now. Do I think every single step, every single day by every person is as synchronized? Probably not. But I also think if that mission is so clear, I also think you see goodness in in bottoms up ideas.

You see really hungry people pitching smart ideas, and those ideas may be executed on, or they may be like, yeah, not right now. But I think that, I do think it's possible. 

 So if you were to deconstruct, well, what's happening in Uber at that time, what was sort of the setup or the conditions or the rituals that created that type of alignment at pretty meaningful scale. 

 I think there were probably two rituals as a person who was like new to the tech sector, new to Uber, that ended up being really powerful. I think first there was like an extremely healthy all hands culture and then if you like double click on what was presented in that All hands.

It was all about rides, it was about global rides. Global drivers. And that was the exact same thing that was being presented in many ways in the regions on like the city teams and regional teams. It was all about rides. What was the best week ever for rides? Did you have the best day ever, et cetera. And so there was just everyone in the company knew what metrics we were excited about and we were obsessed with.

And then I think one of the most impressive. Onboarding experiences I ever had was 2015 Uber. I remember one of the finance leaders basically gave the economics of an Uber ride, and it was such incredible context for every single employee at the company to have. And so everyone operating from the foundation of, there's all of this excitement and these are all of the strengths in the market, but also this is very much like where we're vulnerable and why we need to be so protective of the unit.

Economics was incredibly empowering. Right? And I was just a new person an IC joining the company, but I think the repetition on the metrics as well as the context so early on enabled everyone to be an owner. 

 How do you know if you're in or out of alignment as an organization? 

 I think there's the inputs and there's the outputs.

I think the outputs, everyone instinctively knows. The outputs generally look like you're shipping slower than you were. Another output would be a lot of people are asking a lot of clarifying questions, right? I think another example is one function's moving really fast on a product launch and another function doesn't even realize.

But I think those are all the outputs of misalignment, and I think there's many different indicators. I think what I have learned is when launching a new initiative or when rolling out a three month plan, a six month plan, et cetera, you always wanna preview it. You don't want anything to surprise anyone.

You wanna get lots of informal feedback ahead of time so that critical leaders and partners. One you like heard their high quality feedback and had the opportunity to execute on it, but also that they can be partners in creating that alignment and creating that clarity and that they're able to provide way ahead of time.

And when I say way, we're talking about startups. So I'm talking like five days, 10 days. Give me a week or two to create the cross-functional alignment that they think they're gonna need in order to succeed. Here's a really easy example. We way amped up. Some of our growth marketing targets, and we shared 'em with the company last week, but probably three or four weeks ago, both like the marketing leader and the data leader and the brand leader were able to say, Hey, various prioritization's going to have to occur in order for us to achieve this.

And all of that leg work was done ahead of communication rather than before. So when it's communicated, everyone's feeling confident that they're going to be successful. 

 You talked about this a little bit in the context of Uber, but once you have a clear plan and folks are aligned around it, what do you think are the most important ongoing touch points?

 I'm a big believer in the end of a four week do a review. And when I say a review, I don't mean 30 people need to sit together, but it's, Hey, these are the things we said we'd get done in the next 30 days that connect with what we're trying to achieve, what's our progress plans and problems, and how would we grade ourselves? Red, yellow, green. And then I'm pretty formatted in how I do one-on-ones. And one of the key questions is, what's your perspective on your team's execution Quality. Red, yellow, green, big fan of binary questions. 'cause I think it forces clarity and like how are your big three rocks going? And so I think between the weekly staff meeting, the one-on-ones and how it connects to this like 30 day template, it really supports consistent alignment and reflection.

And are we all seeing the world the same way? And then our exec staff, Has a very similar format. I think one of the big changes that Joe and I have worked on is just ensuring that on our exec staff, we're spending most of our energy on the biggest growth levers in customer deliveries, rather than getting distracted by all of the operations that is building a startup.

 Maybe you could expand on what the overall format of the one-on-one is.

 So the one-on-ones are the standard questions of how would you grade your OKR, what is your team crushing at? How can I be helpful? And then hot topics. But I actually think the most telling questions are the top two. So the first is, What's your energy?

Red, yellow, green. And then how would you grade your execution? Red, yellow, green? Because I think both of those questions, especially in like a remote global team where you're not in office every day, give you the best indicator on how your critical leader is feeling and helps you understand where execution is falling down, and how on track are we to hit the goals that are within their domain, because very rarely is someone on track for like a great product launch, a great closing of a sales deal, and then they're red on energy and red on execution. Like how we perceive our work is the input to our outcomes. I think for me, it gives me the greatest indicator of where I can support and in diagnosing. How likely are we to achieve our goals?

 So when you think about a 20 minute or 30 minute or 60 minute one-on-one, where does most of the time end up spent along sort of that framework that you outlined?

 I do 30 minute one-on-ones. Because I do 'em weekly, I think about five to 10 minutes get spent on the first two question, the what your team is crushing at, I read asynchronously, but it's also to remind leaders that their team is crushing at things.

You know, it's too easy to look for the problems. And so that question is almost for them and not for me. And then depending on how like the kind of key goals are trending and how they grade them we may spend a couple minutes on them or very little, and then I think we generally spend about 15 minutes on the hot topics.

 And hot topics are just a catchall basket of 

 Yeah, it's generally like I am, I'm concerned on our new calculation for CAC great. Let's talk through that. How can I be helpful? We're hiring for this role. What's your take on it? This is how I'm thinking about it. We need to close scope, we need to narrow scope on this feature set so it, it is a catchall, but I think the beginning format creates focus and gives me a really good line of sight into how is this leader doing and how do they perceive their work and when they grade their execution and likelihood to hit their goals.

 What are the problems that you should be helping one of your functional leads figure out versus what they should be figuring out on their own as a functional lead if they're operating at an appropriate level? 

 I think this is such a good question, and it's one that I'm like often calibrating with myself on.

I think it depends on tenure, right? So if you have a new VP or a new director coming in, I think you're in like a trust but verify mentality, definitely for the first 30 days, but into the first 90 days, 180 days, you should no longer be there. But I think the first 90 days, you're still in a support function.

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Anique Drumright is Chief Operating Officer at Loom. She shares insights and strategies on how Loom approaches product design and strategy, how to recruit and build a high-performing cross-functional org, and how to structure effective internal meetings.