Episode 19

A deep-dive into product-led growth & self-serve strategies — Notion’s & Dropbox’s Kate Taylor

Today’s episode is with Kate Taylor, who spent 8 years at Dropbox (leading their SMB revenue and scaled sales operation) and is now the Head of Customer Experience at Notion. Kate is full of actionable tactics on getting product-led growth, self-serve and customer service right, from how to build a tighter product feedback loop, to lessons from pricing and packaging experiments.

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Kate Taylor: [00:00:00] The front or experience is something we're trying at notion view the customer interaction as not a cost center, but actually really isn't requirement as an area of investment for us because we care about feedback and we care about hearing from customers. And so we're investing very heavily on how do we actually just help customers when they need us, whether that's making it very easy to contact us, either in the product are on the website, but we're really trying to figure out.

How do we actually make users feel at home when they open that front door? Engage with us. The concept I like to talk to the team about is coming into our living room, sitting down and having a conversation with us. How do we make it feel that easy to talk with us?

Brett Berson: [00:00:45] Welcome to in depth, a new show that surfaces tactical advice, bounders and startup leaders need to grow their teams, their companies, and themselves. I'm Brett Berson, a partner at first round. And we're a venture capital firm that helps startups, like notion, roadblocks, Uber tackle company building firsts through over 400 interviews on the review.

We've shared standout company, building advice. The kind that comes from those willing to skip the talking points and go deeper into not just what to do, but how to do it with our new podcast in depth, you can listen into these deeper conversations every single week. Learn more and subscribe today@firstround.com

for today's episode of in-depth, I'm really excited to be joined by Kate Taylor, Kate recently joined notion as their head of customer experience. She's built a really interesting career that has she put, it has been focused on finding the balance between sales and product. She started out as a rep at Salesforce in 2009, a position she landed during the recession after sending a cold email to CEO, mark Benioff.

At Dropbox, she worked on figuring out the self-serve funnel and refining the product feedback loop, as well as leading their SMB revenue and scaled sales operation. Before leaving in 2020 in today's episode, we start by digging into product led growth and self-serve motions comparing, contrasting what she learned at both Dropbox and notion.

I found this discussion to be both fascinating and timely product led growth is getting so much attention these days. But there are tons of nuances when it comes to going up market competing with sales and product planning. We also dive into how they approach product prioritization and planning. At notion.

Kate takes us through a detailed look at their system of 700 tags for categorizing customer conversations, their planning, exercises, and examples of tradeoffs they've had to navigate. We also get into how this all maps to pricing and packaging. Kate shares worries about what they learned from specific pricing experiments at Dropbox, as well as interestingly, why notions trial isn't time-based.

We also chat about how to handle a wide range of use cases and personas from how they use the jobs to be done framework at Dropbox to notions reliance on templates and community experts to help customers get started. Next we tackled the front door customer experience. The term Kate has coined to describe their philosophy of trying to get customers to engage more and not less from why customer service shouldn't be focused on getting customers off the phone to the question she asked to find more signal in their product feedback.

Kate share some really interesting and somewhat counterintuitive thoughts here. Finally, we wrap up our conversation by talking about her approach to leading teams, including why she hires for curiosity in how she tries to teach her team to ride the ups and downs of startup life. We also discuss how working for three very different CEOs in mark drew and Ivan has impacted her own leadership style.

In my view, Kate share some really tactical advice here that any founder product or go to market leader will learn tons from. So I really hope you enjoy this episode. And now my conversation with Kate just wanted to start by thanking you so much for spending the time with us today. I'm really excited about this.

Kate Taylor: [00:04:24] Yeah. I'm excited to be here. Thanks for having me. So I thought we 

Brett Berson: [00:04:26] could start super broad and maybe talk a little bit about how you're thinking about sales and customer experience has changed over the arc of your career on things that you once thought. Maybe you don't think anymore. Maybe some of the insights that you've picked.

Up from each chapter of your career, as a way to frame our time together, 

Kate Taylor: [00:04:47] you're starting to build a company you're trying to figure out who is that target market or where is the company the best fit for? Um, and at Salesforce, it was very clear when I came and I learned a lot about. How to target specific segments and what that flow should be like when, you know, working directly with a new customer, because Salesforce, like the average deal size is extremely high.

It's very Salesforce company. And in transitioning to Dropbox, when it's more product led, the model kind of flips on its head and you have to look at. What are opportunities for self-serve to lead in sales to follow. And the topic now is this like product qualified leads and how does product drive the sales funnel?

And ultimately I've ended up nestling myself right in between that, between product and between sales. Cause it's not perfect customers end up in self-serve. They may have questions. They're not quite at the sales line. And so I think ultimately if you look at the funnel holistically, You want to make sure how do you serve customers in the best way possible?

And it really depends on what that target market is, but ultimately I think from notions perspective and from Dropbox's, we don't want to leave customers behind. And so what's kind of that middle ground and finding that it was super pivotable at Dropbox and now for notion. And it's kind of the next phase that we're moving to.

Brett Berson: [00:06:02] You know, you started your career more in a traditional sort of top-down sales motion. I'm curious. What are some of the insights that you've picked up or things that you learned. That have translated really well to some of the new models that you've been working on, that Mary top-down or sales driven with sort of bottoms up product lead.

Kate Taylor: [00:06:22] I think it's easy to say a company size line is a great way to divide up customers, but that doesn't always work. So the buying process for a 10% or five person team at Nike. Might actually mirror a buying process for an SMB. And so what you really want to think about is some kind of line between team size and company size and making it as easy as possible for someone to get into the product.

And we found a Dropbox that. Really the goal of self-serve was landing teams, getting them to love the product. And then sales was about taking those teams and actually building them into enterprises and helping them understand the value of the product up market. And when we started to get that right, that was when the engine just started to click versus the traditional model where you've got.

Sales cold calling and trying to source these wall to wall deals. And these companies where you can sign up very easily. That's a really, really hard model to pursue because sales is ultimately like fighting the product itself and product adoption. So if you let the product lead and sales to follow this natural flywheel to starts to happen, and it starts to click for customers.

Can you talk 

Brett Berson: [00:07:29] a little bit more about maybe in the case of notion or, or we could start with Dropbox, what you've learned and how you've designed, how those two things click together? I guess it's both. Go to market org design and really product at its 

Kate Taylor: [00:07:44] core. Yeah. The team that I ran at Dropbox was called inbound sales.

At first, it was part of the sales org. And what we realized was it actually, wasn't a good place for it to be mostly because what was happening on the website was people had interest across a variety of different categories. Maybe that was buying, it was support needs. They want to know about partnerships.

And so that team was actually more of like, Uh, routing function. So it moved into the marketing org and we took quotas away from that team and started to make it more of a value driven, answer, quick questions, get people to the place they need to be. And that often may have been over to the sales org, or it could have been pushed them into the self-serve flow or over to support.

And I think once we were able to discover that and that interacting with customers really should be driven more on a value conversation. That was when things just started to click. And so this team ended up. Starting to get customers to the right place versus trying to force a sale and conflict with the sales team, start to be complimentary to the self-serve process.

Um, as well as the enterprise motion. And we actually started testing this. So once we got a little bit more intelligent with like how this team was operating in between go to market and product, we were starting to run experiments around holding out a set of control customers versus like in an actual variant and testing and saying, are these conversations we're having actually driving value for customers?

Let's motivate the reps on more of C-SAT or CES customer effort score and less on revenue and see what happens compared to the control. And what we were seeing is that there was a considerable lift in revenue. From reps were motivated off of having value conversations and kind of what you can call like an alley Oop, or just like a quick slam dunk question that customers had that we could answer.

And that was where we started to unlock value too, for sales, because they were saying, oh, Hey, thanks for getting this customer, the question. And then now they're in a trial or, Hey, now they're ready for a much larger discussion because they understand a basic need. It's easy to put up barriers on the site or make it difficult for customers.

Take sign up or to get in touch. And what we did was kind of the opposite, make it really easy to get in touch, help customers, and believe that that value would drive revenue and ultimately LTV. And we actually tested that to be true. True. So 

Brett Berson: [00:10:00] the models that you've been working on, does everything start as like a bottoms up opportunity?

Regardless of use case company size and you really have gotten a wave from Jane is going to sort of do outbound work on Pepsi and this person's going to do outbound work there. And the bottoms up motion is for a sort of startups and things like that. Ideally, everybody comes in through. One experience.

And then the top-down is about the expansion of an account 

Kate Taylor: [00:10:28] we've iterated on it. Notion is trying to figure out how do we have upmarket sellers doing what they do best, which is selling wall to wall deployments, getting people using and loving notion at larger companies. And then how do we enable self-serve to create almost product qualified leads for that type of motion?

So if you're a small company or a large company, You can sign up today on our site and use the product. And then as you start to use it and love it, you might end up having a conversation with someone from our sales team in the future to help you understand different features and things like that. But we want to lead with getting people into the product, understanding it, and then building that adoption and groundswell for sales to go and sell into completely honestly like.

Looking back at Dropbox, the cold by Dropbox just did not work. And we tried it quite a few times in the enterprise. And what really worked is that self-serve became a land motion for companies of all sizes. And then sales was really focused up market for Dropbox. It was companies of 250 or more. That's where sales started and notion that that line will continue to go up over time, similar model at slack.

And I think the important thing there is. That self-serve motion, which a team like mine is paired with for that product feedback loop is really helping get customers in sales is helping grow that, upgrade that adoption when they're starting to see that value. 

Brett Berson: [00:11:50] So when you look at the sales component, that really works on account expansion.

And I guess maybe potentially upsells security features administration, sort of what larger companies might like or want, how do you focus them or how do they basically know what to do in what order with what type of accounts at what point in time? 

Kate Taylor: [00:12:09] So on the sales side, a lot of it is driven through the customer need and their specific interests.

You mentioned before on like personas and use case. We're trying to really focus specifically on what that customer might need, and then let that drive the conversation. For notion, we're going to continue building enterprise features that we can best serve our largest customers today. It's still early for us and we're going to continue to grow there.

It's an important segment for us, and it's an important opportunity. So today, obviously security features and ownership integrating with single sign-on. These are things that are vital for an enterprise. And what we've actually seen is a lot of these enterprises. How may have started smaller deployments and as they've grown, these needs for our more advanced features kind of kick in.

And that's when we start to have that sales conversation, it usually happens with growth and maturity. And that relationship along the way is what enables us to have that conversation. You can take hop in. As an example started actually as part of our startup program, I believe with about 20 seats. And now, you know, Using notion and loving notion as they've grown and scaled considerably.

And so that's like an ideal use case of someone, a company that's growing significantly and finding leverage with notion and ultimately for that was a self-serve startup program that brought them in and that as they grow, our sales team is there to help them find additional value with, so to bounce 

Brett Berson: [00:13:32] around a little bit, I mean, one of the interesting questions that pops to mind is how a product and product roadmap fits into.

The strategy that you're describing, assuming you have a discrete set of resources, you could say we're going to focus a certain amount of effort on developing the early self-serve part of the product and all the things that those customers want. We could take some Reese set of resources and do all the stuff that you talked about in terms of the up market opportunities or the wall, the wall opportunities.

And so how does this specific set of ideas around go-to-market inform the way that product participation works at the company? 

Kate Taylor: [00:14:10] Dropbox? Typically when I started, we'd just basically released a team product that had centralized billing and we only did it because our user said, Hey, we need to be able to pay for all these accounts on one credit card.

And then slowly but surely we added some engineers. And one of the like Thrasher things that happened was. Pivoting every year to two years. And so we would go hard on enterprise and then back off and move to photos and then shift more toward enterprise and then back off and move toward like consumer docs.

And so all of a sudden those thrashing moments ended up compromising specific direction. And that came out in like a bunch of different ways that impacted the org. And I think as I've come to notion, the one thing that has been very clear since I joined and in the interview process was. Notion is going to be an enterprise company.

We want to build for larger companies. And so there's a balance of building features that our users need and rely on all the way to where we want to be and that balance. And there's some art there with customer feedback. Mixed with product direction and vision, but one interesting component of the way notion looks at feedback.

It's every conversation we have with a customer or prospect is tagged. We have this system of 700 tags they're used on every conversation. And are manually tagged across sales and my team, those tags actually port into our product roadmap in notion. So as engineers are working on specific features, they're actually seeing real life tallies of relevant tags on things that they're actually building for.

And that helps inform our product strategy as well as the building process and making sure that feedback loop is continually moving as I think one of the most valuable things that we've done early days. And I think Ivan was very set on. So keeping that real-time feedback loop there is important and then division of where you want to go, making sure that you're dedicated to something you can't resolve that in six months to a year, you have to stay and believe that you're in it for the longer term and in a world where there's limited resources, you have to commit.

And I think I've seen that dedication from notion and that's only going to grow on 

Brett Berson: [00:16:16] the way that you tag feedback. So is it. People taking unstructured sort of qualitative feedback and then assigning a specific tag to it. Or they're just saying, I heard this from the customer up. I heard that from the customer and it's all 

Kate Taylor: [00:16:29] structured.

So it's unstructured emails and chat conversations and call scripts. And our teams basically take that. We. Literally manually assign a task to it. And we're just starting to automate some of these workflows that actually will auto tag, but the art is actually, and has been up to this point. Now we're at sort of a scale inflection moment, but up to this point into like the manual ability to tag that, and they're very specific, I mean, 700 tags is a lot.

Could there be less? Yes. Um, but that's even a whittled down list. To be honest, there's an art in these tags being actually pretty specific. So they might be, you know, specific to not just databases. But database properties or a relational database issue, something like that. And those actually will get tagged those tags live in our product roadmap inside of notion.

And we basically built a connection so that anytime that tag is then used again at any of our tools, Salesforce in our comm. It actually goes directly onto that notion roadmap doc. And so you 

Brett Berson: [00:17:31] mentioned this just a minute ago, but then how do you take all that bottoms up feedback and squared against at the top down product vision?

What does that look like? Or what's an example of how those things come together. 

Kate Taylor: [00:17:42] Yeah. It's basically one giant partisan exercise. We did it, I think more officially than we've ever done it before this year, where we sat down, we looked at the most frequently tagged or. Most frequently requested features from our users and for notion, we're really trying to build a product that's focused on teams and moving into the enterprise.

And so we're looking at feedback like if we want to build for multiplayer workspaces, and continuing to allow people to collaborate and use notion as the hub for work, what are features that can help. Built on that use case. And so it was taking a lot of the tags and actually looking at what were most important to users.

And then there's this art component of Ivan and the vision. And then it's sitting down and looking at like, what's realistic to build this year. We planned it half years and then have kind of a longer term product strategy that is more of like vision longterm. And the product roadmap is probably more driven off of.

Tags, which again is user feedback mixed with a bit of the strategy of where we actually want it. Got 

Brett Berson: [00:18:46] it. So taking a slight turn, how does all of this map to pricing and packaging and are there areas that you see people get tripped up on most? Do you have a framework or point of view on how do you think about pricing and 

Kate Taylor: [00:18:58] packaging?

That is a absolutely great question. Um, it's actually a very top of mind for us because if I think of where customers get most confused today, it's our pricing page. And at Dropbox is actually the same thing. The page looks the most informative with all these checklists, but ultimately drives a lot of confusion on where to go from here.

And so our users are obviously driving. The direction on helping us figure out like which personas and use cases make sense in our current offering. But ultimately the feedback that we're getting is helping us figure out where should we be going? What makes sense for us in the future? Because there's a lot of different directions we can go.

Whether that's like monetizing specific components of notion. Or it's contained to elevate the different tiered pricing that we have today. And we hear users like, you know, loud and clear when it comes to like our current teams tier versus enterprise tier. And a lot of that feedback is literally coming in in real time, as we evaluate which specific path do we want to go going into the actual experiment, we ran at Dropbox around this to give you an actual example.

The pricing page will drop Dropbox, views their website as a product. And so the goal of the website is for conversion. We wanted people to start as many trials as possible, and the pricing page was one of the biggest conversion opportunities. And so it was very hard to mess with anything on that page because it could shift conversion numbers considerably.

And what we were seeing is that there was heavy drop-off for users around 30 seconds on the page. And so what we did is we started to put chat a little below the 32nd mark. And the goal there was to like catch users right before they dropped off, figure out why they were dropping off, why they were stuck and ultimately serve that back to product.

And so a short-term fix, we actually figured out was. The users are coming to the site. They have no idea what plan they're on. So when they're looking at which plan to pick, they don't even know where they're starting from. And so it was a very simple product. Fix it. If the user is logged in illuminating which plan they currently have to help give them the idea of where to go from here.

And I think. That was an awesome learning. You can quickly spin down chat on that site because now, Hey, a bunch of users were unable to convert because of this change and that, that flywheel that my team hopefully is continuing to build with product and ultimately a pricing and packaging moment where all of us internally are so focused on.

What we're trying to differentiate and build for each tier when our users don't even know what tier they're actually in. I mean, you can extrapolate that out to Netflix. If I think which Netflix plan am I on? I only know how much I pay per month. I don't know what it's actually called. We're doing quite a bit of research that notion of like, how do we learn from those types of experiences and help users naturally gravitate to the plan.

That's going to work for them and help them activate and use the product as much as possible. So to spend 

Brett Berson: [00:21:37] a little bit more time here, how do you think about the different dimensions of pricing and the trade offs of different approaches? Right? You can. Charged for incremental features, you can charge per seat.

Some companies have a usage based model. Do you have a set of thoughts around the different tools that you have and maybe how you tend to think that they best fit 

Kate Taylor: [00:21:56] together? So for notion, our concept of a trial is usage based and for us. Everything is focused on getting users into the product activated and using the tool.

And so right now we are on a license based model, but it really starts out with a free workspace that has kind of the paywall limit at number of blocks or how much content is in the tool. And so, as we are looking at pricing and packaging, which type of model that we want to pursue, the licensed model always makes sense for us in an enterprise.

Uh, setting, just because as you think about distribution for users who are coming on and off, it's the easiest way to manage. Um, but there's a component for self-serve and SMBs at scale where usage is actually a major driver for them. So I'm not sure we've like settled. On what type of model today the licensing model is, is working well, and we're seeing users activating, but thinking about paywalls around usage or with the free product, tend to be the easiest way to drive value quickly and get users into the price.

As you 

Brett Berson: [00:22:59] think about pricing, when you start to go wall the wall, do you have any lessons learned or approaches as you move from 20 people at a 700 person company or using the product? Paying with their credit card, how that upsell and expansion has worked or how to sort of thinking about pricing for that.


Kate Taylor: [00:23:17] we've done, you know, we did this at Dropbox to these like true-up models. So you pay for a minimal amount of seats, and then you look back at the end of the quarter and say, how many people are actually using the product and those models. Those tend to work early days. It doesn't really work as you think about like counting revenue and all of that.

Like, it becomes a little bit difficult to continue that. They're trying to figure out how many people are actually gonna use this product. And so the true-up model is great because it starts to give you an early indication of how adoption is going. But. From a company like notion or a Dropbox where there's a lot of viral adoption upfront that doesn't tend to be necessarily the biggest issue because users are already using and loving the product.

So it's about bringing that all under one umbrella. And the same thing is, is in play for notion as our sales team looks into trying to bring. Multiple self-serve teams together or help it managers or engineering teams actually start to expand and use notion more. It's about bringing in all of that usage and having the conversation around why notion being that central hub is important for a company versus collaboration on a single team.

The value is really when you've got different departments in different groups using notion together. And I think illustrating that is important. That's why onboarding is important. Um, an activation, so they can see. Um, and to really understand how each group can collaborate and work together. Think 

Brett Berson: [00:24:33] about those sort of different personas, maybe in a larger company, right?

Maybe you have a, an engineer that brings in notion or brought in Dropbox to make their life easier in some way. And then you have small teams and then larger teams and then sort of a company-wide deployment. Do you think about the narrative and wants and needs and buyer psychology of all of those different constituents separately, or is somebody hiring the product?

To do a specific job in a somewhat consistent fashion over those different 

Kate Taylor: [00:25:04] personas. We use the jobs to be done framework and ultimately someone is paying notion or X product to perform a job for you. And so it's important to understand what is that journey or what are the different jobs that someone is paying notion to perform for them and by different departments, each one is going to have.

A different need. They're going to have common themes though. And I think when we've talked about our product strategy around going deep in one specific area or going wide over specific use cases, it's a real challenge to decide which one to go and in a world where you obviously don't have unlimited resources, you kind of have to pick one specific direction.

You can obviously have like a smaller team working on going deep, but trying to figure out how do you go broad and win. At a use case that's applicable and most helpful across different groups. When you have the wide adoption specifically, that notion does. And at Dropbox, it was very similar. We ended up going through quite an exercise to talk about specific buyers and their journey and how we would actually sell and bring them into the product.

And for self-serve trying to create the ability for users to identify or find common ground with and make it really easy for them to say, like, this is where I should be based on my persona. That was ultimately what we try to do with Dropbox. And with notion, we're trying to make it really easy through templates to unlock people's use case really early, so you can get in and use the product.

And when you're in an enterprise conversation, Whether that's the it manager or whatever. Ultimately, these like department heads, these different groups are the ones that have to use and love the product. And so trying to unlock what exactly they need or what they're looking for notion to solve for them there again, common themes.

And so our hope is to bring those use cases together and make it really, really clear on a broader scale, how to use the product. And then from the template side, within the product, it should be easy for these teams to start getting in motion quickly. Can you give an 

Brett Berson: [00:26:57] example of late, maybe that kind of illustrates that point.

A good 

Kate Taylor: [00:27:00] example. Right now we're trying to build out a startup program. We've had it moving now for about a year and a half. We're trying to make it really easy for startups to unlock the value of notion. In their context. So for example, you might have pitched jacks that you're trying to do. You're getting like an early product roadmap in place.

How is it when you start your workspace? Could it be that those things just exist there for you and you can dive in and actually start using them in real time for the sales team, for example, having a CRM template. That was pre-built. So when you pop into notion, oh great. CRM is already built out for you.

And so through templates, we're trying to get into these use cases so that it doesn't feel as nebulous or as much of a white space. In the sales process, you obviously try to identify those upfront. And then in self-serve you've got to like use the product to actually make your way to those. Are there 

Brett Berson: [00:27:49] other examples of companies that you've studied that have done this journey really well, that you're inspired by 

Kate Taylor: [00:27:56] you look at slack at how the use case was very simple.

It's getting teams to collaborate together and it's, it's just chat, right? So the use cases, let's get everyone together, pop into chat, everyone understand it's very, very simple and. I think what notion's trying to do is create a simple way for you to start using the product. Even though we don't just offer you chat or just offer you one single thing to do, how do we create that moment?

So you kind of say, cool, this is exactly what I'm going to use notion for. And then slowly but surely unlock and uncover other areas. We want to make it really, really simple, even though it's a really powerful tool. And I think Slack's a good example. It's just chat. It ends up becoming like. Such a pivotal part of the company.

How do we make that quick aha moment with notion, but then bring you along to uncover new ways to use the product. 

Brett Berson: [00:28:45] You shared something a few minutes ago. That was really interesting about this little pricing experiment, where you dropped a chat widget on the pricing page at Dropbox to catch people and try to understand what.

Challenges they were having that then informed the way that you thought about designing and explaining pricing plans. I'm curious, do you have other sort of examples or little experiments across maybe notion or Dropbox that have led to these interesting aha moments or real insights that allowed you to change something in the way that you were building the product, selling the product, distributing the product, et cetera.

Kate Taylor: [00:29:21] Yeah. One that comes to mind immediately is. In the trial experience for Dropbox, the conversion rates, we switched from a credit card trial to a no credit card trial. And we found the conversion rates obviously dropped off. The idea was that they would be higher intent trials because they'd have to put their credit card in.

At the end. So in theory, they should be a more active space for us. But what we found was that that necessarily wasn't the case. And so we wanted to learn what needed to happen inside of that trial experience in order for you to get, to being more active, adding more files, adding collaborators sharing, what was that moment?

And so chat was actually a vital part of that product experiment to figure out. How we would kind of rework onboarding to get users faster to that moment. And ultimately for us, it was around sharing at the time at Dropbox for notion. Again, we don't really have this concept of like necessarily a. Free trial and maybe the sense of most companies and not, you know, again, a content-based trial, not a necessarily time-based, but we're actually trying something similar, coming up with onboarding to figure out what is it that users need to do in order to click in and really start to use the product more.

And so we're going to try to prompt users to take some different product actions and try to learn from those actions. If that again, creates a more active workspace. The key here is the definition of active, um, and all, all product metrics. One that would say one key learning from Dropbox was keeping metrics as simple as possible.

We used to do health scoring across like 15 different dimensions, and it was really hard to really move the needle on any health score when you have so many different factors. And so, you know, we're starting kind of with early definitions. But it's been consistent. And so what are some different ways that we can try to get users?

Those moments faster led with kind of a lighter version of almost like a superhuman onboarding experience? How do we just kind of like push you in to take some more actions? Um, because I think that's the biggest thing, especially in a product like notion, which is, can be overwhelming at first. Um, when you're dropped into kind of like a white space workspace, how do you start using it?

And once you started, it's kind of this snowball effect where all of a sudden you're adding other users. Creating wikis, you're bringing in different database functionality to run projects and things like that. And so we think onboarding is that tip that we need to get past and then help users uncover more there.

So we'll see if we're able to like uncover what those aha moments are and then ultimately product ties. Are 

Brett Berson: [00:31:52] there any other examples of those kinds of insights or things that you've learned along the way? 

Kate Taylor: [00:31:57] Yeah, I would say one really interesting one. We did a lot of retention experimentation with self-serve specifically, and then even upmarket into sales, into like, because some of the bigger companies that had smaller deployments, we would still call those part of self-serve and we were trying to rewind.

Back of what was that moment that you had to be engaged? And if you weren't engaged past X time, it just, you weren't going to renew it doesn't matter. And then ultimately focus on pre that date. Like how do we get people into the product as much as possible? And so we did a bunch of campaigns to kind of like reverse through the life cycle and ultimately found out that if you weren't active in the onboarding period, it was unlikely for you to reactivate.

And how critical this first day is, are one sort of interesting fact, and just reminding all of us of our own biases. When we're in this specific situation, sitting in San Francisco in front of our back book laptops, that's not how most of our users experienced the product. And so had specific situations at Dropbox where users were not technically active by our definition.

But when we engage with them, we actually found that it was an indispensable tool and they couldn't live without it. And it was because they were storing all their information in there and they knew it was safe and they trusted the product, even though they didn't access it regularly, they just always knew it was there.

And so it was a good reminder to like, Continue to stress, test your user base, talk to people and engage with ver a variety of different segments and really understand what value is because you can sit often in your own environment. And that's really not what your users are experiencing and for notion, most of our users, not in the U S and so it's important for us to put ourselves in the shoes of where users are sitting and what's important to them and continue to check that on a regular basis.

That's super interesting. 

Brett Berson: [00:33:39] You shared earlier that notion has this trial model. That's not time boxed. It's the amount of content versus a traditional trial. Why is that? And why does it make sense? 

Kate Taylor: [00:33:50] Certainly, we didn't want to pressure people like, oh, within 14 days or within seven days. You have to find value.

We do add time for some like on enterprise trials and things like that, because there are quite a few features in there that we want to like manage too. But for workspaces that are paying, like, we want to encourage them to use blocks and engage with the content in there. And so. We have this concept of these like free teams and using content engaging with it means that the product is valuable for you.

And the hope is then that you're going to add collaborators and others into your workspace to make it a space where innovation is happening. It's where conversations are happening. And. For us, that was the most important thing. And that model has proved to work well for a notion and it may not work for all companies, but for the way we've been structured, it's been working out.

I think though, again, when it comes to pricing and packaging, Dropbox played a bunch with free teams and there were like some different states that you could be in and we want to try to make it as simple as possible. So it's really obvious where you should be. You know, if you're an individual. And you want to be in like a free space here you are.

If you're collaborating with others, like there's a team workspace for you. And ultimately over time, like those will continue to evolve as we figure out, which kind of features are most important to the users that we feel should be in each different tier. And so hopefully we'll see pricing evolve as the product and our user base needs continue to change.

Brett Berson: [00:35:15] The interesting challenges that I've observed at notion is it's one of these small number of products. That's almost like a piece of paper. Where you can use it for literally thousands or tens of thousands of different use cases. And you often, and you were talking about this in the. Concept of getting people to use blocks and not having a time bounded trial.

And I'm curious, what have you learned about getting that go to market? Right. Particularly given that most of it is self serve, as you've been talking about other than just the sort of obvious place, which is templatizing things and giving people very specific templates to use cases. Are there other things you've learned about this sort of type of product category that can do many jobs?

Right? One job might be a Wiki. One might be an Evernote replacement. One might be a product planning and the list goes on and on and 

Kate Taylor: [00:36:08] on. One of the biggest things I've seen at notion that's different from any place I've worked or any company that I've really seen is the power of the community. We have an amazing network of ambassadors and consultants that have to preach how to use notion and almost do all of this viral marketing for us.

And that started early days with notion. We found ways to connect with different communities internationally and bring in a consultant program so they could help teach people how to use the product. And these are people who are now running their business, teaching how notion works across YouTube, in their own communities.

They're actually creating templates and selling them themselves. I think the word of mouth power for notion has come through really, really passionate people who have figured it out and then are spreading the word in one to many settings. 

Brett Berson: [00:36:57] Can you give a couple examples of maybe how you've leveraged or deployed these folks that know and love the product to help solve?

Some of, it might be some of the customer success or might be traditionally at an enterprise company, kind of professional services 

Kate Taylor: [00:37:13] started early where these informal meetups, where we found these very like passionate users were holding meetups in a variety of different countries and setting up seminars and get together for people who are passionate notion to talk about it.

And out of that sort of spun this ambassador program. And ultimately now we have. Actual like consultants and people who work directly with notion. And so there's a bunch that we can do to help those consultants and ambassadors reach their local areas. And so we have lots of viral marketing that's happening there and we're also starting to create more communities ourselves.

Um, so that's more for champions groups for specific sets of user types, like teams, users, and self-serve users. How do we connect them together? As well as our enterprise users working through our customer success organization. To help really understand that adoption. So I think there's high touch around customer success all the way down to the lower touch, like one to many community management and unlocking some of these almost professional service community outside of notion to do a lot of this onboarding at scale.

And we're seeing it work. It's really, really powerful. I actually am even using some of our amazing ambassadors and consultants to help with training and onboarding for any like new employees that we have. I find that. There's some very passionate and honestly expert level folks who are in our community that we can leverage even internally more ourselves.

Brett Berson: [00:38:39] That is such a cool idea to have people in the community they're so knowledgeable and so talented that you would want them to literally help train new employees. It's such a brilliant idea. 

Kate Taylor: [00:38:49] Yeah, it's pretty cool. We've started to work on some different programs. I mean, notion can, you can do some very powerful things with it.

We do like a spotlight on that sometimes internally, and I'm continually amazed at the depths of which people use notion to run their life in a personal context and deep and work. And so how do we continue to like, Even like help our employees understand that connecting them with real work that users are doing through our ambassadors or with users themselves.

It keeps us tapped into, again, the real work that's happening with notion versus like what's in our heads. As we sit here and build product tangibly, how people find value in the product. 

Brett Berson: [00:39:25] Switching gears a little bit. One of the things that I often notice is that most companies think that the grass is always greener.

So if you talk to a CEO of a consumer company, They'll tell you about how easy life seems in the B2B space, dark to a B2B company. They see a company just growing virally. And while that seems a heck of a lot easier, I, and the reality is I think no matter which path you go, it's, it's quite difficult. But on that note, I think you hear a lot of companies that have a more traditional go-to-market function may be a little bit more up market, really interested in layering in or utilizing this concept of product led growth or self-serve adoption.

And my sense is most of the time they screw it up or it doesn't work well, I think it's, the grass is always greener in the inverse, right? You have companies that are bottoms up and they're like, well, we'll just layer on a direct sales team and they'll do million dollar ACV deals. And wildlife will be really easy in practice.

It's actually quite difficult. I'm curious if there are things that you've seen work or things you've been interested in recently, when you think about a more traditional go to market function. Adding in some sort of self-serve bottoms up product led growth type approach. 

Kate Taylor: [00:40:37] After the fact, I think it's really hard to do the reverse.

I can't think through one that's figured out, Hey, like this is working really well in enterprise. We're going to go down into do self-serve and that's a bias for the companies that I've been a part of. It's really hard as a, for an enterprise team when you start with a self-serve motion, because your product's always in theory, cannibalizing itself, and you're competing often against yourself.

And so it actually be really interesting to go through the reverse experience because I definitely think you're right on the grass is greener side from the sales team. We're consistently competing as ourselves between the enterprise and team product. And what we should be doing is making it really clear for customers.

If you're of this certain size, and these are your needs, this is the product for you. So there really shouldn't be sort of competition with self-serve. And if anything, it's like, how do we create a healthier funnel? So that it's very clear that where you start and where you grow too, with the product, you talked a 

Brett Berson: [00:41:35] bunch at the beginning, kind of about the inverse, or we were talking about a second ago, which is when you're more down-market and moving up.

Do you have any other thoughts or traps around what often goes wrong there? And one of the things that I've noticed across so many companies is this is an area that is both quite tantalizing and is an incredibly efficient way to screw up the company. And there are many, many examples. I think, of downmarket products that have tried to go up market and.

My sense is that they don't get the interplay between go to market pricing and product. And all of these things have to be in sync and they just think, oh, you have a new sales team, or you have a new pricing model and boom, we're selling. We go from 20 K deals to 200 K deals or what have you. But I'm curious as you sort of studied the landscape of this, trying to move up market.

Are there other traps or things that you've noticed along the way that tend to trip people up 

Kate Taylor: [00:42:32] again with the sales team around the self-serve side and what should they be doing versus what should self-serve be doing? What happens is if the self-serve side starts to take off, you might back off of the enterprise feature development or you make shift away and start to build more on self-serve, but we're taking sort of an opposite approach, which is.

Self-service taking off. That's great. Even though self-service going well, if this is where we want to be, and we're actually dedicated to it, we need to continue building out functionality that supports the enterprise. And ultimately this will go down market and benefit all users and. It's that dedication factor when one starts to win, do you then shift resources or kind of course, correct.

Can you really do both at the same time? And I think it's those trade-offs in those moments that are difficult and it's the dedication piece that often can shift in a world where you don't have unlimited resources and you have to make a decision. So switching 

Brett Berson: [00:43:28] gears a little bit and talking more about customer experience, basically every company wants to be customer obsessed or care about the customer.

You don't hear a lot of companies say, you know, screw the customer. We don't like them. But I think that you've kind of really put this idea of customer experience, customer obsession, and institutionalized it. And you kind of have this idea of front door experience that you've mentioned in the past. And I was hoping you could share a little bit more about how you.

Operationalized customer obsession in the work that you've done. 

Kate Taylor: [00:43:54] Yeah. Good question. The front door experience is something we're trying at notion. We view the customer interaction as not a cost center, but actually really as a requirement, as an area of investment for us, because we care about feedback and we care about hearing from customers.

And so we're investing very heavily on. How do we actually just help customers when they need us, whether that's making it very easy to contact us, either in the product are on the website, but we're really trying to figure out how do we actually make users feel at home when they open that front door?

Engage with us. The concept I like to talk to the team about is coming into our living room. Sitting down and having a conversation with us, how do we make it feel that easy to talk with us? And for me, I'm actually looking at trying to put more ways to get in touch and hear more from people. So we can continue to drive that product intuition internally.

What are other 

Brett Berson: [00:44:45] practices or things that you do, or maybe things that you say often. Around this idea of customer obsession or putting the customer first, 

Kate Taylor: [00:44:53] I think it has to come out in practice. So if you believe that putting customers first, having conversations with them, ultimately drives LTV and increases the actual dollar value of that customer.

Then interacting with them should be a no-brainer. And instead of trying to avoid customer conversations, how do you make it easier for them to find the information that they need? And so there's just a bunch of different things, early days. We were very, very focused on engaging with every single user on Twitter.

We would get back to every single person. And we still do that today. I think customer obsession has to come from the top down. I think. From Ivan's perspective, he's always been very focused on reading direct feedback every day from our users to drive what's in his head and where he thinks notion is going, spending 

Brett Berson: [00:45:42] time with customers, maybe you yourself or your team is what are the types of questions that you ask that you find gives you a lot of 

Kate Taylor: [00:45:50] signal on the initial interaction that we have.

We try not to end the conversation. The goal is, and to get them to stop talking to us, it's actually the pivot around and figure out like, Tell me why that feature is important to you, or tell me more about your workflow that would cause you to ask this question. It's not just a simple link to a help center and close out the conversation or a link to our buy page or sign-up page is focused on.

Tell me more about this. Why is this important to you? Tell me more about your business and what you're hoping to accomplish. And again, the goal is there is just to help identify more of where notion could drive impact or how we could change the product. To drive more impact in the future. It's this feedback loop and making users understand that what they're talking to us about is actually critical to the company.

And that's this concept of hospitality, living room front door, where we want them to feel like they're part of the process with us and they should leave every conversation feeling like they made an impact. 

Brett Berson: [00:46:50] Really interesting insight. It kind of inverts what the role of customer service is all about.

How did you all figure that out or did it just intuitively come. Rick is normally when you think about customer success and customer service, you know, a traditional organization has metrics around how do you get someone off the phone? They would coach a rep and say, you're spending too much time to resolve a given issue.

And so you've obviously done the inverse and some curious about the origin story. 

Kate Taylor: [00:47:15] It's back to the community concept. So the team I actually took over was not called the customer experience. Um, it was actually called community at first. It was a little confusing for me because I was like, community is a marketing word.

Right. And I was like, no, community is what we're building at the company. And we believe that. The team that's driving. Those conversations is actually the foundation of that group, of the community of notion users. And I liked that concept a lot. Changing the team name was just a tactical thing, but the spirit of it and the spirit of the word community is something that I think every new Tino should have not only on my team, but across every org.

It's around this idea that. Helping one user it's gonna help them unlock some certain value with the product, help them understand notion, but they're part of larger communities and different areas. And if you believe that writing the best story with that user, then allows them to go tell someone else that has been a common thread from day one, with notion, 

Brett Berson: [00:48:16] given you so much feedback, coming from so many different places, as you just outlined this really cool system you have of organizing and tagging and sorting.

Can you maybe tell us the story of a trade off, around feedback that you had to navigate or figuring out who to build in what order, and I know you'd have higher level product strategy, and then you have all this bottoms up feedback, but it might be interesting to share an example or talk a little bit about how those trade-offs happen.

Given this sort of ecosystem that you've built around the product development. That's 

Kate Taylor: [00:48:50] a great question. Especially right now, we've put out a lot around just notion spending most of our time around engineering and product toward reliability and performance. And that has meant we've had to have trade-offs, but we believe that that's the most important thing that we can spend time on as our user base continues to grow.

And so other features that users might request all the time in the best way possible. Like we haven't been able to get to those quite yet. And that's a tough thing to kind of share with people where we're getting. Questions about improving the way that docs might be working or permissions. It's like, Hey, like we're dedicated to this area.

And that means that we can't work on other things. It's this like ruthless prioritization that I think our head of engineering is really strong at. And honestly, I think users respect because they want to see us improve and performance and reliability. And we're already starting to see new signs of that.

And so that's just like a real life example of where we'd love to get better. And we're actually putting the fire power behind it, despite all the asks for things. That would make notion cooler, but maybe not operate as fast as we want it to, 

Brett Berson: [00:49:50] to end our time together. Just bouncing around and talking more broadly in terms of the way that you run teams, you hire and lead teams.

And on the hiring front, one of the things that you mentioned is that you tend to orient around curiosity is like one of the number one things you care about and hire for and was interested in having you talk a little bit about maybe how you suss that out or what you're looking for and why it matters to you.

Kate Taylor: [00:50:15] Curiosity is something that I've found. You can't teach someone that either have it or they don't. And it's one of those things where you can bring in people with actually very different backgrounds who have curiosity. They can apply that to a problem and actually solve it in a really interesting way.

So a practical example of this interviewed someone for a sales role several years ago, and this person has. Six months of internship experience that was like completely irrelevant to technology. And before that they were actually a barista and I was trying to figure out, like, tell me more about becoming a barista.

Like, why did you choose this? What was that about? And ultimately it sprung out of a deep, intense love of coffee and how coffee beans were harvested and brought in and like how actual coffee was. Round and the art and science, like behind all of these things and went on like a 20 minute deep discussion about his love of coffee.

And like at the time I didn't even drink coffee, like now after three kids by inhaled coffee. But at the time I was just like this guy, I want to apply this, not to coffee, but to tech and bring him in, you can apply that curiosity to customer conversations or like prospect conversations. This is going to be incredible.

That person actually, I. Kept on my teams during my time at Dropbox and was incredibly successful non traditional background, but had this inherent DNA that just made him integral to the team and a foundational member that was pivotal for Dropbox. Longterm. You think 

Brett Berson: [00:51:43] curiosity is a horizontal skill that if somebody is curious, it tends to translate to much of what they do.

Or have you found that curiosity can be quite localized? Meaning somebody is very curious about coffee, but really nothing 

Kate Taylor: [00:51:58] else. It's probably an indicator, but I think obviously there are other things you'll want to look for. The biggest thing in a startup environment to me is being able to ride the waves.

I try, especially with. People earlier in their career to teach them to not go into the highs and lows or peaks and valleys, because that can often happen. Right. It's easy to get sucked into in times are amazing. Or like when times are low. And I found as the folks who keep that even keel component going, and you can ask for that through like how they've handled projects or stressful times by going deeper and layering questions, you can assess what happens when they fail at something or their stress, or how do they kind of bounce back from that.

In terms of the 

Brett Berson: [00:52:41] idea of teaching people to ride the wave, the ups and downs. How do you teach someone to do 

Kate Taylor: [00:52:47] that? A lot of it is by example, to be honest, I try to keep high energy with the team at all times. And I try to be really, really honest if something is not going well, we'll talk about it. I try not to let it visibly thrash me as the leader.

And I openly discuss like, Hey, this is, this might be a low time for you. Let's talk about it. Or Hey, like you're crushing it right now. You're like right on this ride up to the top. Let's take this in for a second. I asked the team a lot to reflect as well and write down experiences. People ask me, what's your favorite memory from your time at Dropbox?

Honestly, it's like hard. I feel like I blacked out for like components of it. And if I look back and there's one thing I wish I would have done, it was documenting each quarter. What were key things I learned. And so encourage the team to reflect the more fires you go through the. Better your career is going to probably be, cause you're learning.

And if it was really easy, they wouldn't have to pay us. So it's those kinds of things of, I think ultimately it's my responsibility to teach them these things 

Brett Berson: [00:53:44] to wrap up. I thought. It would be great to hear a little bit about what you've learned from the different CEOs that you've been around. I think what's really interesting in your journey is they seem like very different people in terms of mark and drew and Ivan.

I mean, Ivan and mark seem quite different. And so I'm curious when you think across the different types of folks that you've worked with or worked for, are there specific insights or concepts that. You have been heavily influenced by and show up in the way that you. Run teams, the way that you set strategy, the way that you solve problems, 

Kate Taylor: [00:54:21] where you worked in the office, which I guess now kind of feels far away a year past the start of COVID Marc Benioff was amazing in the proximity.

He wanted to be to actual customer conversations like his office and what they called exec row. At the time he was right next to where all the business development reps and sales reps were calling customers. And at that time, cold calling was still a practice that was out there. And so he was just constantly around like how people were pitching and talking about the product.

And that gave him a lot of energy. I always found that was like a very interesting strategy that anytime he was walking by, or he was in the vicinity, he was like absorbing the energy and the conversations. And I just, I thought that was amazing for me as I think about like how I set up the team. One. I love sitting in the pod.

I learned so much from having casual conversations and joking around with people and creating this fun energy. Like I love the quiet office thing, but yeah. You might also find me annoying. Cause I'm that leader who's trying to like get everyone to talk and like mix it up a little bit. But I think that I got that from early days at Salesforce of like that energy is palpable and it brings up the room.

There's obviously time for deep focus work, but I tried to limit my meeting time and do as much as I can from my desk. To be around with the team. The energy totally resonated with me from the early days. And then withdrew in a rush. Dropbox was incredible at supporting its people. It was one of the most amazing places to work from day one, the benefits, the way that we kept employees engaged and focused on.

Each other and supporting through life journey. I think of like when I joined Dropbox 2012, I was like 25 at the time, just getting kind of like engaged. I had my whole where I am now, which I didn't even know at the time was going to be happening. Dropbox supported me through that entire journey from phases of like eating in the office and hanging out with everybody till 11:00 PM.

All the way to, I'm leaving at four to be with my family and the entire time they were there supporting me no matter what. And that's a pretty incredible journey to be on. And we'll be forever grateful to the way that they have structured the company and continue to do so today. And then I've been, it's early.

Haven't been a notion for too long, but what I was really drawn to with Ivan. Was just relentlessly listening to customers. So my team owns like Twitter engagement side and responding to every single customer is very hard. We have a lot of Twitter followers and I haven't read it every day. He never fails.

And I find that the way he built that product feedback loop, it took us years to get that going at Dropbox. It honestly, it was really hard. It's hard to like back out of that. If you can do that from day one, It's inspirational and I'm continually taken aback just at how much I've been prioritizes our customer base and having these listening posts around in our various communities.


Brett Berson: [00:57:04] Well, thank you so much for spending the time with us. This was fantastic. 

Kate Taylor: [00:57:07] It was great to be with you all. And thank you so much.