The First 100 Days of Joining a PLG Startup with Kate Donahue, Pitch

Kate Donahue: You want to get that initial context in those first 30 days? How did we get to this point? What were the decisions we made? What were the trade-offs, what is the larger vision for driving toward? Because that's going to inform everything else you do.

Trinity: Welcome to The First 100 Days, a show for revenue practitioners by revenue practitioners, giving you unscripted access and exclusive resources to help you navigate any new transitions or initiatives. I'm your host. Turn it into a win from user gems. In this episode, we're examining the first 100 days of joining a product led growth startup with Kate Donahue, Head of Product Marketing at Pitch.

I love the product so much that I asked Kate to be in this episode to give us a glimpse of the behind the scene, how pitch builds their product led motion. In case you haven't heard of pitch pitch is a collaborative presentation software. What stood out the most to me when I became a user last year is the extensive template gallery.

As a marketer, we usually have to put together a lot of decks, but with pitch, you don't need to start by staring at a blank slide. They already put together a structure, predesigned slides with tips on each slide on how to put together an effective deck. Whether it's for investors, company, all hands for sales or team building, you name it.

It easily saved me five hours when building any deck. So I convince our entire team to use pitch. Now, I just heard from Kate last week that the template gallery is now available to anyone. So if you're interested, just check out pitch.com for slash templates. All right, let's get back to Kate's story.

Since product-led growth is still a relatively new concept in our industry. I asked Katie to level set and give us her definition. 

Kate Donahue: Product-led growth is essentially where you're relying on your product as the main way to acquire new users and convert them into paying customers. So I think the traditional examples or products like Slack Calendly, newer products like Loom, where an end-user tries to software either maybe on a free trial or a freemium basis.

They start using it. They evangelize it to their peers. They get that internal buy-in that maybe team or company-wide adoption before you even get to that point of making a purchase on your own or engaging with sales, if at all, uh, compare that to the world of traditional marketing, where you are focusing on getting prospects to core checkpoints, like getting them to a gated landing page or signing up for a demo and handing them off to the sales team.

In the old world, you're thinking about marketing qualified leads, sales, qualified leads, sales accepted leads in product-led growth companies. You're thinking more of a product qualified lead. So somebody who has tried your product reach and activation stage. So they've, behaviorally hit a few checkpoints in the product, which then puts them in that qualified status where maybe they start to receive upsell materials, or they hit natural Gates within your product.

That prompt them to hopefully make a purchase, potentially even engage with sales at that point, but you're letting them really lead their own journey through your product and through the sales funnel. 

Trinity: When Kate joined Pitch, they were an early-stage startup with zero users. What were her priorities?

When she came on board, let's jump into the rest of my conversation.

Kate Donahue: I joined Pitch in June of 2019, and I was the second marketer. After our CML we're about 30 people. And at this point we had products that had just gotten to the point where we could internally dog food. It, we had zero users and we were just getting ready to. Kickoff our private beta. So at this point, my first 100 days, it was focusing on meeting the team, understanding where the product lives at that point, and then figuring out what the initial roadmap looked like, where we would be over the next month year, then defining initial product messaging and positioning based off of that, and then planning out our limited preview.

So at this point we had a waitlist with maybe 20,000. Users on it. So we had to figure out a way to organize that, how we wanted to onboard users and how we expected to collect feedback and looking at this sequentially within that feedback and figuring out who's our target audience. Who's our high expectation customer, a lot of things, a lot of level setting things to do over a hundred day period that would form the basis of the core strategic pillars of Pitch.

That we would need to have in order to launch, which we did after year-long beta in October of 2020. 

Trinity: So it sounds like there was, you had a lot on your plate, figuring it out. Didn't have users outside of internal users at that point. So maybe one thing about joining an early stage startup is just how do you prioritize?

So maybe you can double click on some of these bullets, say if someone's going to join the early day pitch, go back in time and advising to your earlier self. Like what would be the number one thing you would want them to do in the first 30 days? And why is that? 

Kate Donahue: You want to get that initial context in those first 30 days?

How did we get to this point? What were the decisions we made? What were the trade-offs, what is the larger vision for driving toward? Because that's going to inform everything else you do. So it was understanding why my presentation, software understanding. The intricacies building presentation software, where we were today, where we could get month over month.

So even with 30 people sitting down with different teams, understanding the way people work. And when I was a product-led growth company in particular, everyone's on the product team. So it's really understanding. How the product team works, how they make decisions, how really anyone else in the company can help influence that?

I think one of the, really one of the reasons I joined pitch is it's really nice to be an end-user of your own product and to be one of the target audiences. I think there's definitely a trap to fall into thinking like, what I want is what every user will want, but it is certainly gratifying seeing like the product improve and.

That's improved your workflow and having an informed opinion on the roadmap relative to even company like Periscope too. 

Trinity: So was there any trade-offs or intricacies that you discovered in the first 30 days that surprised you?

Kate Donahue: It's time management, which is challenging? And I think the first 30 days in particular while you're like, I was blown away, but the team, so there's definitely some hardcore imposter syndrome.

So two things, the team was amazing and really. Heavy hitters on like the engineering and product design side and brand design. We already had signed product designers on a 30 person team when I joined, which is just wild and unheard of. I don't think any company I've worked at before then with two to four times, the amount of people have that many product designers.

So just understanding how qualified everyone was, how like, Innovative. They were, it was really stressful in the marketing side because we want to be able to match that the other trade off, or I guess, surprising challenge in this first 30 days is that. The pitch, there's really no marketing team, no users.

So we had this blue sky opportunity to define what we wanted to do. Everyone on the initial team is pretty senior. So we were all had come from previous startups. So you've seen where things maybe went off track, or we've all had this conversation. The next time I do this, I'm going to do it differently.

So now we were in a position where we had. The budget, we needed to do things. We have the caliber of talent and now we needed to make these choices. And we had a pretty generous timeline, but with that comes like analysis paralysis. I remember having conversations with our revenue lead and talking about like our product analytics stack and how we wanted to measure things.

And we'd also previously worked together at a company where we would have wanted to make some improvements on those things. You get overwhelmed a little bit. I like the possibility of all the things you could do. So it's very unique. And previous companies, you're always inheriting decisions, inheriting technology, and figuring out like what trade-off that forces so that we were in this position where it's okay, we're a year out from launch.

We can invest in the tools we need. We can set them up, how we want to, how do we want to go about doing that? It's like very stressful in its own. Right. But it's really first world problems. 

Trinity: That sounds so nice. 

Kate Donahue: I think like all everyone wants to have like having five, four of designers and then you can set up product analytics a year before launch

Trinity: One thing you mentioned about the. Like how you feel that everyone in the new team is so accomplished so senior and therefore you feel like you're putting this pressure on yourself, trying to prove yourself. So was there any type of like low hanging fruits or like easy to achieve KPIs in the short term that you set out for yourself and communicate that with your management, that I am going to achieve this to prove your value, but also not to external audience, but also to yourself so that you feel better and accomplish more in the next 60, 90 days.

Kate Donahue: So there's always low hanging fruit or maybe it's not always, but in this case, on the document side, just like codifying things that had been discussed across teams. Unfortunately they'll set some pretty good documentation. When I joined the team has. Was on notion from like day one roadmap was in the air.

We didn't prune as well. And I think that's always a challenge it's knowledge management tools, but there was a lot in there to work from. So it was just like, how can we make these things digestible? How can we take existing user research? That's been done existing roadmap things and put it into a narrative.

People remember stories. It's like, literally the roadmap has a thousand items on it. How can we take this and put these into like initial. Product pillars. How do we start to tell the story of pitch and the nice thing with this too, is the idea wasn't until like in 30 days, I'm going to get to final product messaging or final persona research.

We had checkpoints in between. We're still a year out from launch. This is what it looks like today. And now we're going to test this with users. So it was really, let me say KPIs. Wasn't so quantitative at that point, it's given. No real users, no revenue, but it's getting to these like qualitative checkpoints with, okay, here's the draft.

One of this messaging is now going to turn into an onboarding script. So when we start our beta, you can test this with users. We can hear how they respond to certain language, what they have questions about, and we can continue to iterate in between each onboarding we're in between each phase of our beta to eventually get to that like battle tested deliverable.

Trinity: Putting it into a narrative, tell the story of the company and the products. And I feel like you could pull a lot from your background in content to make you stronger as a product marketing leader in this situation. 

Kate Donahue: Right. For sure. Yeah. I think that the background in content and became really valuable and just.

It also shortens the early on with startups. I think the more you can be a one person team on some projects, the faster you can get to where you need to be. If you don't have to do all these handoff points, that being said within the first 100 days, we did also hire a senior content strategist. And they are super helpful and also taking things into the brand narrative, starting to plot out our content plan.

So I think the early investments in content and product marketing as hires were definitely the right ones to me. 

Trinity: So was there any major changes or like differences in your next 60 days? 

Kate Donahue: Yeah. So, you know, the first digesting things in the first, like 30 to 45 days by August. So within the first 100 days, we wanted to kick off our beta.

So really that day, 60 to day 90, you're starting to reach out to users, working to schedule or prospective users working to schedule onboardings. And starting to test the script with people. So that's where people internally, a lot of excitement around, we are finally showing off our baby to people and little, they like it, or, you know, what happens when we put our product in the hands of people, will things work as expected?

What will they. Point out that maybe wasn't so obvious to us being so close to the product, because it's definitely like a big milestone moment within the company. So there was like pressure and excitement around there and it was just like, yeah, how do we get things formalized enough? So we can talk to others about them.

And then how do we structure ourselves to process that feedback? I think that was the big thing I was really focused on is making sure I wasn't the. He only store of knowledge. Now you always want to, like, if I get hit by a bus, w w who else will have these insights? So making sure we have processes for storing feedback and sharing it with others internally and making sure we were on the same page and people like that, there is, I guess, removing the bias a little bit as we get feedback.

So we can all make the decisions based off of what users have to say. 

Trinity: And that's something that sometimes like the documentation and processes to store knowledge, that you're not the only one who have that information is usually like the last thing that people will think about one day doing like user, is it use a testing or use 

Kate Donahue: it interviews?

Yeah. And I think, again, this is one of those shaped by previous experiences where I've come into companies and like here's a summary of the research. Here's what users say. And it's heavily synthesized and summarized and it's. Not so fun or insightful to consume. Sometimes like you get in the habit of glossing over it, you don't interpret it or internalize it as much as you should, which as any marketer or customer-facing person, you really want to be able to speak the language of users.

So it's really important for me to figure out a way that we could capture it verbatim as true to life as possible. So that. It wasn't me coming down from the mountain, telling others how people felt about the product, but that we could point to video. We could point to transcripts to really help make our point.

Trinity: So my understanding is that you conducted over a hundred hours of user research, like user interviews individually. 

Kate Donahue: I'd say it's about 350. If I'm just looking at what enjoyed Q has and it continues to grow. I think we did about. 300 individual onboardings before transitioning to self-service onboarding.

But then on top of that, we have feedback calls with people or support calls. Those also get tracked and logged. I think my individual record is up around a hundred onboardings personally conducted before I was able to focus on other activities. 

Trinity: So, was there anything that you did where you're like, Hmm, if I'm going to do it again, I would not do that. Was it a mistake or you thought that was a good idea and then it didn't turn out that way. 

Kate Donahue: There's always things that like, I'm sure if I looked at things closely, a billion things that I would want to change, and I was pretty happy with the onboarding experience. We had a little bit where we would.

Guide the user through the product. And then try to just like pause for moments to get the reactions, get a little bit of upfront context on their relationship. The presentations, I think the big thing early on was we started with our first users in August with more like friends and family. And while they were very lovely in friends and family users are not representative.

And not always as ruthlessly, honest as your actual users will be. And like the ones who should be informing your roadmap. So I think that was a pretty quick change we made. So from August to October, Yeah, I think 30 to 50 and hand selected people. So they were on the wait list that maybe we had a more personal connection or they were people in our investor pool and they were really helpful.

But like for the early conversations, like they would be pretty blunt about what they thought about the product, but of course they want you to succeed. So they're also going to tell you positive things. It was a little bit more challenging to get them to continue to engage with the product after. And I think it's an early-stage product.

It's really challenging to transition your actual business processes into a new tool. Thinking after months in October, once we announced the limited preview and we started pulling from, I created like an audience profile. So we had a 70, 30 split, like 70% of these people. Sort of this Typeform by like they fit within these roles.

They have this level of activity usage that they're recognizable brand. These are the people we think will be our early adopters and then 30% are people maybe outside that, not using it as often, just to see if there was a difference. Once we started to. Profile people based on like their usage of software and their usage of specific types of software.

I think we saw a stronger fit, more excitement about these, and we saw a little bit more uptake in how frequently they were using pitch. So I think like it would have been great if we could have started with that, but I think sometimes you'd need to see what doesn't work to get a sharper perspective on what you do want to do.

Trinity: That's a great idea for early products. You want to know who are the early adopters and what their characteristics are to help you with targeting too. So what are the characteristics of these early adopters for Pitch? 

Kate Donahue: Early on. We refresh the way we did our waitlist to have a Typeform survey upfront on the website.

So if you really want, like you could bypass it and still be on the waitlist, but to get on the priority list, we just asked a few questions. What kind of tools do you use both presentation, software, other workplace software, how often you make presentations, how often do you make presentations with other people?

How many people is your role? So it was a pretty. Intuitive split focus more on business people. So early on we're product for teams, primarily we made the choice to focus on teams of smaller companies under, I think under 200 employees, people in either marketing or product management or entrepreneur roles, more like.

Business-oriented, less emphasis on engineers early on the sun might make it in that 30% split. Uh, we focused on people who are using at least two presentation goals. We, our hypothesis was one of the values of pitch is that you. Don't have to compromise. Like you have to do with legacy tools. You don't have to jump between whether you want to collaborate or whether you want it to look nice.

So if we could find people who extensively had that pain point, we thought they might see a good fit and pitch early on. We also focused on people who are using. More modern tools in their workplace that was like notion or Figma people who have been able to successfully adopt newer business software.

And then people who made presentations at least once a month and with other people. And I think this is actually something that was. Informed a little bit by those early conversations in our beta, we start asking like, what are you using for presentations will stay because we didn't have that information on our early users.

And yeah, we can just let them vent to us. And they would tell us like, Oh, I use Google slides because of this, but then I have to use Microsoft this and keynote because I want it to look really nice, but then nobody else can edit the keynote file. So we learned through people's grievances, like who might be feeling the pain enough that they would.

Still be pretty happy with a beta product. And at least if not be able to fully transition to it, at least see the vision, see where we are going and being able to provide solid feedback that we could funnel back to our product teams. 

Trinity: Yeah, my update, my next alpha user research question to just tell me, what do you hate about X and just let that go

Kate Donahue: Honestly, people love to complain and complain. Super insightful. That's my key quote here. I don't know. Did you pay attention to the launch? Hey, email service. So their list basically wrote me an email about everything you hate about email and people would go off. At one point lead. We played around with different things during our beta of our recruitment, like how to get people engaged enough to.

Hop on a call with me for an hour. One of the things we did at one point with a certain group was just before even letting them schedule an onboarding, Hey, if we were to give you access to pitch, how would you use it with your team? And I received a lot of emails back and people would really outline.

Here's why things aren't working today. Here's what I think your tool will do. Here's what would make me really happy. And not only is this like, just gold on the marketing side, especially when you can get people's real language in writing it also. I think it created this value exchange where it's like they had to work really hard to get access and really show their excitement.

So when you do give them access, like they want to be good citizens and get feedback and then use the product. Like they recognized that there was some sort of exclusivity. And access to pitch. So we tried to use some of those psychological leavers to our advantage experience.

Trinity: Now, if you were to create a cheat sheet for a marketer or a product marketing manager, who's responsible for a product-led growth launch, what would be on it?

Kate Donahue: A few, I think key things really focus in on it's spending time, understanding your customer's ecosystem of tools. So it's not just like competitive research is always part of a product marketers job, but I think you need to go beyond that.

What are the tools that they use maybe on a consumer basis, on a business basis each day? What are the tools that they love? And what can you learn from those? Especially in the case, if you're like we're competing against incumbents that are not so modern, not so product-led. So while there's definitely things like.

On the core user experience. We want to understand that people do from those. We want to understand what features they're shipping. More importantly, we want to see the tools that people love. Day-to-day like what's setting the bar for their expectations on what software should do. So I think like having that kind of bigger picture view is really important.

And then I think, you know, being as customer-facing as possible, whether that's getting to interact with customers directly or partnering closely with peers and support and user research is. Big regret from previous roles where I didn't do the groundwork of speaking with customers outside of like customer marketing opportunities.

And it was big investment here, like sitting down with it, but it was just so important to shaping my language, taking my world view, really building empathy with users when the product needs to sell health. And like, when you need to put your self really in the shoes of your customer, like you have to do that by living alongside them.

It's almost this like, Anthropological exercise in understanding what drives them, understanding what frustrates them. And just the more time you can spend hearing those words coming from them directly, it's going to make everything else. You do so much better. The final thing is. Investing the time in understanding product analytics.

So if you have a product qualified lead, or activated user definition, knowing what that is, understanding how marketing can or will support that, if you've figured out what growth loops might be, or have those hypotheses, just understanding how you can support people, getting to those points, helping people get to that kind of time to value that time to sharing.

Well, you're always going to have your traditional funnel. Marketing is not going to get away from camp that you really need to be able to tie what you're providing from. A marketing or education standpoint to onboarding standpoint, like how it translates to product behaviors and the more you can tighten and refine that it's more efficient for you.

It's more efficient for the company. It's also, you're delivering what your user actually needs versus what you as marketing think like what checks the boxes from a traditional marketing point of view.

Trinity: This 100 days is sponsored by user gems, a software that helps companies identify buyers that are more likely to buy a product. Use the jams, tracks your current and past customers for job movements so that when they switch companies, you can sell to them again. And based on your sales and product usage data, it also finds prospects that are similar to your existing customers.

According to reviews and G2 crowd. And I quote, use the gems is a prospecting miracle. If you in a revenue roll, check out user jams dot huh?

Let grows. The product has to sell itself. Like Kate said. In this context, the product team is also part of the revenue team. So I asked Stephan, our CTO and Co-founder, to join me in this episode. Fun fact, Stephan and Christian, my co-host and CEO are identical twin brothers, Stephan. Welcome to the show. What are your thoughts about what Kate shared? 

Stephan: Thanks for having me. Yeah. This episode was especially interesting to me since we are currently also working on a. PMT motion. And it's a great to hear insights about how pitch did exactly this. So successfully. I think Kate's situation is, is very special because when she started at pitch, they had zero users and they were.

A year away from launch. So the goal that you had at the beginning was not necessarily product marketing, but rather use acquisition for user testing and user acquisition, actually for the waitlist. And I think this, this makes it so interesting just to see that her. First hundred days when she initially started, uh, probably very different from the first hundred days when the product got launched.

So it also shows that you can have several first hundred days at a company depending on where the product currently is. 

Trinity: Thing is, she mentioned like 20,000 people in the wait list, which was incredible. So they definitely did a lot of legwork upfront, including the user research that she said that they did a hundred or 300 hours of user interviews.

That's just incredible. 

Stephan: It's a super high number. I think she said that she alone did 100 hours of user onboarding and user testing. And I think. It also shows how, what a huge product-focused pitch had right? From the beginning, as she said, they were a team of 30 and nine of them were product designers, two product marketers, and the product wasn't even launched by them.

Trinity: Yeah, we definitely learned from this interview, like I, myself specifically, because as you mentioned, right, UserGems is rolling out a new product where it's a bottom up where individual sales reps can sign up for free, like to start. And I learned from this interview and that's why we set up a lot of user testing would have to do a lot of calls with potential users to get that feedback.

Versus in the past, we would have say, Hey, let's this launch it. And then learn from that kind of like the whole thing, move fast, break things and iterate. But I think now that users, especially in our space have such higher expectation of software and you only have one chance to make a good impression.

Stephan: What really stood out was the whole thought process behind the use of testing that the way Kate described it, that they selected users based on their experience, but also based on the tools that we're using to really get the user state that they thought might be the power users of the product, but also to try to get some users that might not be the power users to see how they use the product and how the product.

Might be improved for those users. And I think it was great how she said that they went about to, to get more feedback from the users. Even before the user testing, they asked questions, like, what do you expect from Pitch? What is some functionality that you would like to have even before that? So the product for the first time that we're already asked to give feedback.

And I think this is a really good idea, because then those are users that are not biased in any way that they can just think about what they would like to have in a product. Also focus on what is something that you love about a product? What is something that frustrates you?

Trinity: I think that's the part I really liked. Like what do you hate about blank? And that's great because when you hate people just go on and on about it. So maybe we should send out, like, what do you hate about prospecting? What do you hate about. Finding leads that will buy your product and let's go.

Stephan: it would probably be interesting to send out some emails. Like what do you love about prospecting and what you hate about prospecting and really compare the answers and see what is actually more useful and might turn out. It's more useful to hear what people have. 

Trinity: If you're listening to this episode right now and you on LinkedIn, I'll probably start a LinkedIn poll or it just like.

A random status. What do you hate about prospecting? Let us know. We want to help. Yeah. 

Stephan: Th that the question is what's the best way to, to find out on how to help use us. And I think that Kate really gave a great overview about how pitch did it and. I'm still very impressed, how they developed the product that they had, that many people working on a product even before it went live. And this really just works. If you do a lot of user testing and it shows in the product that they did it.

Trinity: Are you going through a major transition within your organization or your career? Do you have a first 100-day journey to share recently on the past? If, yes, I want to hear from you email me at podcast@usergems.com.

And if you're looking for the ultimate revenue leader, cheat sheets, sign up to receive them at usergems.com/podcast.