From PM To Founder: What You Should Know

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Hannah Clark: You’ve probably heard the trope about product managers being, air quotes, the CEO of the product. And whether that phrase makes you nod your head or roll your eyes, being a PM definitely does equip you with a lot of the skills to become an actual CEO someday. But I’m sure that’s not news to you. And in fact, if you’re listening to this episode, I reckon you’ve already thought about it. But if you just need a little extra push to go all in and make the switch from PM to founder, this conversation is for you.

Dani Grant is the co-founder and CEO of Jam.dev, but before she became a founder, she was a product manager and analyst with a big dream. Make no mistake, the transition was far from seamless—she’ll tell you all about that in a moment—but it was also full of triumphant moments that have made it the best decision she ever made. And I’ve gotta say, you were really in for a treat today, because Dani is just such a wonderful person to deliver the insights you’re about to hear. This conversation was just so motivating, so inspirational, and Dani’s incredible energy is such a gift. I hope you enjoy it as much as I did, so let’s jump in.

Welcome back listeners. I’m Hannah Clark with The CPO Club. We are a community of tenacious product leaders here to share the weight of scaling your product. Our members are SaaS-focused PM’s who are genuinely in love with their work and they’re driven to help others succeed. So if that sounds great to you and you want to hear more about our community, head over to theproductmanager.com/membership.

And now we’ll get on with the show. Dani, thank you so much for making time to be here with us today.

Dani Grant: It’s so awesome to be here. I started my career as a PM, and so it’s so cool to be able to reflect with you about PM to founder and all the learnings in between.

Hannah Clark: Yeah, absolutely. It’s going to be such a full circle moment.

Tell us a little bit about your background and how you ended up where you are at Jam.

Dani Grant: My first job was at Cloudflare. I was the fourth product manager there. And when Cloudflare got sufficiently big, they did something so darn cool. They said, we want to be able to take huge risks as a company, but everyone’s really focused on the most important things for our current customers and we don’t want to gamble that.

And so they created a team off to the side, 30 engineers and 2 PMs. And my co-founder and I were the two product managers of that team. And we got to move so fast and ship huge new things for Cloudflare that could be new businesses or just totally sunsetted and forgotten about.

We got to take risks. And it was there trying to move fast and be audacious and get things out the door that we realized how much time and frustration is taken up between product and eng back and forths about what did you need me to fix? I can’t get that to happen. How did that bug happen? And we’re like, we can’t believe there are no tools for that.

And so we forked off and we created a company just to solve that. And that is now Jam. We now help 125,000 people report bugs to engineers in a way that the engineer can immediately start debugging. No back and forth necessary.

Hannah Clark: Awesome. Heroes don’t wear capes.

And on that topic, we’re going to be exploring the journey of transitioning from product manager to founder of your own startup. So obviously something that you’ve got tons of experience in doing. So can you tell us a little bit about the story? Obviously now we know a little bit about how that was incepted, but how did you know that you were cut out for starting your own business? What was that realization like and what did that first year look like?

Dani Grant: So back when I was a product manager, I thought I would never start a company because it seemed really lonely. And my favorite part of working was the team. When you’re a product manager, it’s all about the team and that’s what’s so fun. But between product management and starting a company, I did a two year stint as a VC at a VC firm called Union Square Ventures. And it was there getting to be close up and seeing other founders who they saw some thing in the world that they could improve.

And instead of waiting for someone else to improve it, they decided to take it on and do it themselves. I was just so inspired. When those two years ended, it’s like a two year program they have, it just felt like the right time to go and try and do that for a problem that we had faced.

Hannah Clark: Cool.

What were some of those challenges that surprised you during that first sort of zero to one phase that sort of came out of nowhere?

Dani Grant: Oh man. Now it’s fun to talk about because they’re all in the rear view mirror. But I got to tell you, as a PM, I was very confident about our ability to build a product. And I will tell you that this tested me fully. Probably you’ve heard of the concept of product market fit. It’s building something that is so good that people will change their behavior and their lives to use it.

It’s a really high bar. And here’s how high that bar is. Just think about you and what tools you’ve tried this year, like new products you’ve tried. Maybe you’ve tried five new products this year, 10 new products this year. Think about how many of them you are still using in your regular workflow day to day today.

It’s probably one or zero. Most things we check out, but we don’t change our lives because we’re creatures of habit. We don’t like to change. And so the bar is so darn high to build a product that not only do people sign up for to try, but they also retain. And that was a very humbling experience. To paint you a picture, we were two product managers from Cloudflare.

We were used to, you build a product, you work really hard on it, and you launch it. And the next day, tens of thousands of people use it. That’s what we were used to. And so we did the same thing. We talked to a bunch of users. We worked really hard on the product. We launched it on Product Hunt. Thousands of people signed up.

But a week later, none of them were using it. And we’re like, oh that’s weird. So we just tried again. We made some changes and we launched again. And still the same thing, the messaging was resonating. People were signing up, but they were not retaining. And so we didn’t have anything. And so we just kept going and going.

We launched eight different attempts at solving this problem of product to end communication with a product. And this first seven totally failed. We had nothing to show for our work and 18 months in, we launched the eighth and the rest is history.

Hannah Clark: Oh, so that really is a testimony to how important tenacity is as a founder. And I think that everyone knows that, but like just hearing it and putting it in context is really key.

So in terms of transferable skills, and we’re talking about, you know, like thinking that the PM role is going to be as similar, more, maybe more similar to the founder role than we think it is. What were some of the PM skills that you were able to transfer over that maybe surprised you that they were so applicable?

Dani Grant: So when you start the company, you’re the first PM of the company, right? The founder is in the early days, the first PM. And so, things transfer so well. You’re used to interviewing users.

You’re used to listening to the voice of the user. You’re used to trying to find product solutions. You’re used to beta testing. One thing that’s very different and very shocking is you don’t have a team around you yet to support you. So, when we were product managers at Cloudflare, there was a marketing team that would go and distribute whatever it is that we had just worked on.

There was a sales team that would go and make sure that customers were successful in using it. There was a full big engineering team with years of infrastructure that had already been built to make sure the product was high quality on day one. And none of that existed. There was a support team. And so I sort of took these things for granted as a PM.

But suddenly when they were gone, a lot of different parts of the business sort of opened up to us as well, it’s yours to do. So there’s a saying that first time founders focus on product and second time founders focus on distribution. I completely understand why that is because as a PM becoming a founder, I was very focused on product, but it’s not enough to build a great product if it doesn’t spread.

And so we had to learn a lot of what the sales and marketing team at Cloudflare used to do for us, and so that was a big shock. The second is the bar is just higher when you are a founder than when you are a PM. And the reason for that is when you’re a PM in a company, that company has already achieved product market fit.

People are already using their product, and so when you add another feature, the adoption rate is quite high, even if the feature isn’t perfectly fitted to the customer. But actually to get someone to use a new tool, you do have to perfectly fit it for your customer. Even though we thought we knew how to do user interviews and to get user insights, we really had to level up.

And the one book I recommend every single founder read because it changed the trajectory of our company when we finally read it, is a book called The Mom Test. And what The Mom Test is a guide for user interviews that is so foolproof that you could even user interview your mom, the person who wants to tell you what you want to hear the most and still get actionable insights.

Hannah Clark: Yeah, that book, I feel like we’ve had it referenced on this show a number of times to the point where we should probably start giving copies away.

I think you touched on something that’s really important also is that the distribution and the scaling. So what have been the biggest challenges that you faced while making that climb and how have you approached them?

Dani Grant: I remember our first few board meetings was pre-product market fit and we would show like, here’s what we’re trying, here’s the feedback we’re getting, here’s what we’re going to try next. And everyone’s okay, cool. Then I remember we had a board meeting after we had launched this eighth iteration of Jam, and the product was growing on its own.

Because it’s a PLG product, it’s a collaboration tool, and so it just naturally grows through usage. And so we were pretty excited about that. And we go to the board meeting and they go, okay, great. And now how are you going to 10x that growth? Like 10x the rate. And I was like, oh shoot. And so we read like everything we could read on the internet.

Like every blog post that’s ever been written, how did Notion get its first 10,000 customers, how did Figma we read everything and we studied all the channels. We read this great book that I highly suggest for everyone called Traction. It’s by the DuckDuckGo founder. And it’s basically all the different channels that are available to you as a SaaS founder and how you can fully leverage them.

It’s like the book of playbooks. It’s amazing. But while we were doing all this research, what we actually saw happen is what PLG growth looks like. So with PLG, the cool thing is just by using your product, people spread and share the product when it’s a collaboration tool. And so actually the best way that we could grow our product was making our product more useful so people could use it more.

And the best investments we’ve ever made in distribution and growth has been actually focused on product. And so we did a few things. We put in like the basic product led growth sort of viral loops. If you view a Jam and you’re not yet a Jam user, it tells you, do you want to create your own jam? If you are using Jam on your own and you want others in your team to use Jam too, we’ve added a button for you.

Invite your team, right? We put like a give jam to your friends referral link and get swag to be rewarded, right? We did a few basic things. But beyond that, it was then just investing in product. And so I think that has been the biggest surprise.

Hannah Clark: You know that’s really interesting, but it makes a lot of sense. PLG only really works if the product is that great that it’s infectious.

So how can PMs who are aspiring founders set themselves up for success when starting their business now that you’ve kind of up all this knowledge from your own experience?

Dani Grant: One of the very first things you may need to do, or you may think about doing, is you probably want a team.

Because as a PM, one of the things that you’re so trained at and good at doing is bringing together the team, orienting in the right direction, and let’s go, you know? But when your founder suddenly, it’s just you and your co-founder. And so to hire a team, you might need to raise some money like we did.

And so a lot of people believe that they can raise money only after they’ve built the product and only after they have traction. But we are the counterfactual to that. We were very lucky and we were able to raise on day one. We had a working prototype that someone could try, but we did not yet have something you could actually use.

And we did not yet have users. And my advice to other founders is that if you can, try to raise before you have something because it’s actually easier to raise before there’s anything than when there’s something. Because once there’s something, you’re evaluated on that something. And if you look at all the best SaaS products out there, how long it actually took them to build it, it was more than a year.

And so it takes a long time to build something so good that someone will invest in it versus at the beginning when it’s this is early stage. It’s pre-product market fit. It’s pre-product. There’s sort of a bucket for it. So how do you raise funding? There’s a saying in VC where if you ask for advice, you get money.

And if you ask for money, you get advice. There’s something true to that. And so what I suggest to friends who are starting companies, having been a VC myself is as soon as you’re starting the company, before there is anything, figure out who are the VCs who are might be interesting and just start reaching out.

And the outreach looks something like, was just listening to your episode on this podcast about this. I really love how you think about it. I just quit my job at blank to start this company. Let me know if you ever have 15 minutes. I would just love to get your advice. And so you’re not selling, you’re not pitching, you’re compelling a call.

You’re giving them a reason. It’s because you’ve noticed them. You like how they think, you flattered them. And because of something compelling about what you’re doing, you’ve quit this interesting job at an interesting company to do something. Why have you done that? Right? So it’s compelling the conversations before you’re even ready to fundraise.

Hannah Clark: I love that way of thinking about it in that approach.

A slight change in focus because we were talking about collaboration tools, like Jam being one of them, but also just the challenges of getting started. So when you only have so much financial runway, as we’re talking about here, what would you say are the tools that are really worth investing in with whatever budget you have at the very beginning?

And do you have any specific recommendations for folks who are just scrapping it together themselves?

Dani Grant: There’s a funny story here from Jam’s early days where we really wanted to use Front, the joint email tool, but it was $30 a month. And so we did not want to spend that at the time because we were early and scrappy and had to conserve runway.

And so we made a deal, which was when we make our first revenue, we will buy Front. And time has moved on and ultimately by the time that happened, like we, we were sort of, I don’t know, our attention was elsewhere. We had different tools. So Front is the tool that got away, but we were very careful.

I think that there are a lot of startup credits out there and we utilize them a lot and they were very helpful for us. For example, we wanted to be able to send automated emails. Customer IO gives away, I think it’s a year of their platform for startups. And so it was an easy way to start. We wanted to start with Stripe.

They have a great startup deal. So we started there. There are a lot of different like marketplaces where you can find these like startup path, startup deals, but we were really like thrifting for those.

Hannah Clark: Oh, that’s a really great tip.

Okay, so a little bit of a pivot here. Let’s talk about the hardest job of a startup, which is being the first product manager at a startup, which was what you were doing for a while. So what’s your take on this? Why is this job so hard and how can PMs in this position set themselves up to succeed?

Dani Grant: Okay. So I think what you said is exactly right. When you join a startup as the first product manager, that job is a beast.

It is the hardest job in the startup. Maybe on part, like with one other, which I think is being the first marketing person, the first growth person. And why is that? Why is it that hiring the first product manager is different than hiring a first engineer? And it’s because in that moment, the founder who has just hired a first PM has to grapple with what are they actually ready to let go and walk away from and let someone else run.

And a lot of founders, myself included, don’t have that internal conversation. They’re just solving for, we need a PM, but haven’t yet figured out what they trust someone else with, what they’re ready to let go, what they’re willing to let go of. And so a lot of first PMs are super successful in whatever the company they’ve just come from.

Join a startup and the founder doesn’t trust them and they’re not able to succeed because either they’re totally micromanaged and who can succeed in that. Or they don’t have the trust to actually make moves. And if they suggest a big swing for the company, the founder doesn’t yet have the trust to say yes, go.

So we have a first PM now at Jam. She’s amazing. Her name is Maya. She’s incredible. And importantly, she did not start as a PM at Jam. She started as an engineer. And over the first two years that she was at Jam, we built trust about her quality bar and her bar for craft and what good looks like. And we built like a joint language for how we talk about building product.

And so when we needed a first PM, I already had that trust with her to be like, I know what you’re capable of. I know what you ship when you ship high quality. And I want you to bring that mindset that we’ve already agreed on to your work as a PM. And so she crushes it and I trust her and I can step back and she can run.

If you’re the first PM, the question for you is how to succeed. It’s how do you build that trust with the founder? And so my advice for anyone considering taking a first PM role is to actually just ask the question to the founder who’s interviewing you and say, I know that this job is a huge change for the company. I know that in order to succeed, we need you to be able to trust me and to trust my judgment. How should we build that?

Hannah Clark: Just to zoom in a little bit on what that would take. So in your case, obviously it was a matter of quality, a matter of being able to build that trust, which was over time, right?

Like it was had to happen organically. So let’s say we’re starting at the interview and you’re interviewing someone who’s a candidate for your first PM role. Maybe we want to put ourselves in the role of the person on the hot seat for that job. What kinds of suggestions would you have as far as stories to tell or skills to present that can help to build that early foundation of trust before we even get to the point where we’re building rapport?

Dani Grant: If you think about building trust in any relationship, it’s a lot of communication and speaking the unsaid things and saying here are where my boundaries and limits are, and accepting that and understanding how to work around that.

I think that as the person who’s being interviewed to be the first product manager, you can ask questions like, Hey, what in product do you feel ready to let go of and you don’t want to deal with and you want me to fully take off your plate? What do you not feel ready yet and we should collaborate on? Or what do you not even want me to touch?

And that conversation is super important and it builds that trust and it lets the founder know okay, they can take these things off my plate, but they don’t feel like they have to take the company roadmap on day one. I can trust this relationship. Another question you can ask is something like, what does done and ready look like at your company?

So when I say this product is ready to ship, what does that mean for you? And the reason why that’s so important is because that means something different at every company. If you think about like obvious examples, like Facebook in the early days, they just wanted to ship an experiment. They had such a volume of users.

Their strategy was just get stuff out the door. But if you think about a company like Linear or Stripe, their whole brand and their moat is the perception of craft. They can’t do that. Or the company, like, why should they even exist? They exist for craft. And so that conversation is super important. I think that when you’re being interviewed, surfacing these conversations help the founder imagine what you will be like in this role.

It just starts you actually collaborating and working together. I think that would be the best way to sell yourself.

Hannah Clark: Yeah, I love that advice. And I feel that’s also applicable also to something like a performance review situation in which maybe you need to retroactively recoup some of that trust as well. So, yeah, those are great tips.

Before we wrap up, I do want to hear a little bit about the light at the end of the tunnel. Like the payoff portion of being a founder. Because we’re talking a lot about how difficult it is and the challenges. But what’s the best part of being a founder?

Dani Grant: It’s like being a PM. It’s talking to users. This morning before this, we brought together users all over the planet who are all building products and companies to share what they’re building and people like shared demos of the products that they’re building. And there was this like great discussion in the chat. And it’s when you meet the people who are doing things that are so darn inspiring, and you get to help them in this like little way.

It’s like this one tool that they use, you see what they’re able to run and do with it. And you get to meet these inspiring people from all over the world. It’s holy moly. It’s it’s just the best thing ever.

Hannah Clark: Well, this has been such a fun conversation. I have to say you have just the best energy. I can only imagine how great it must be to work for you. But if we can’t work for you, where can we follow you online?

Dani Grant: First, I love product feedback. So if you’re jamming, if you’re using Jam at Jam.dev to report bugs to engineers, just email me, stream of consciousness. I want to hear it all. I’m Dani@jam.dev.

Hannah Clark: Awesome. Well, thank you so much for joining us, Dani. This has been such a pleasure. I really appreciate being on the show.

Dani Grant: I’m such a fan of yours. Thank you so much for having me.

Hannah Clark: Thanks for listening in. For more great insights, how-to guides and tool reviews, subscribe to our newsletter at theproductmanager.com/subscribe. You can hear more conversations like this by subscribing to The CPO Club wherever you get your podcasts.