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

[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.

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

[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, 

[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.

[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.

[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.

[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 

[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 

[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 

[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. 

[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? 

[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 

[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? 

[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 

[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 

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 

[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. 

[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 

[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 

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 

[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 

[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.

[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.

[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 

[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 

[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 

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.