Geoff Charles: How To Hire Product Teams & Increase Product Velocity | E1091

1. 0:00 – 0:39

   Intro

   1. GCGeoff Charles0:00

      (instrumental music) The founder or the first product manager should be selling the first 100 customers, absolutely. Products should sit with sales and should be in every single sales demo, and use the sales process as a way to identify pain points. You actually should be, like, a bit more professional services-oriented as a product team earlier on. If you actually find one or two design partners and you just build for them, they will love you way more than the best-in-class SaaS product that's already on the market.

   2. HSHarry Stebbings0:23

      You said before that you worked in two-week sprints. What does that actually mean in reality?

   3. GCGeoff Charles0:27

      I'll be super tactical. So you have...

   4. HSHarry Stebbings0:31

      Jeff, I am so excited for this. As I said to you before, I've been running listening to your other shows. So, thank you so much for joining me today.

   5. GCGeoff Charles0:38

      Super excited

2. 0:39 – 2:48

   Introduction to Product Management

   1. GCGeoff Charles0:39

      to be here.

   2. HSHarry Stebbings0:39

      Now, I would love to start. I always like some context. So first, how did you make your way into the world of product? Let's start there as an entry point.

   3. GCGeoff Charles0:47

      I've always been, like, very short-term focused in my career, so I just, I follow a lot of the energy, and I think that's gonna be a theme throughout this, (laughs) this chat. The first, like, energy was management consulting out of, out of college, so, um, is, is all the hype around just, um, h- how to think, how to structure, how to sell. Then I got kind of bored of, of PowerPoint presentations, so I, I, I wanted to get close to the metal in terms of big data, uh, and, and I joined a big data analytics company. And that's where I got my first foray into product, and I think that the way I did that was getting super close to the customer and understanding the customer pain points, and then, um, having great relationship with the, with the tech team and understanding, like, how do we build technology to solve those pain points? And I think the product team kind of came running from there.

   4. HSHarry Stebbings1:25

      What have been your biggest lessons in how to truly understand customer pain points? 'Cause a lot of people go through customer discovery, but I think we'll both agree, many do it badly. What is the best way to really understand customer pain?

   5. GCGeoff Charles1:38

      I think you kind of have to walk in their shoes for, for a full day. Like, what do they listen to? Go listen to that. What conferences do they go to? Go to that conference. What are their, uh, pain? What are their aspirations? Um, what does success look like in their role? What, what is their degree? What did they learn? Uh, what, um, what is the, their habits? And so, I, I spend a lot of time with, with, with customers. Um, and then it's all about just, like, asking the right questions. Oftentimes, like, product managers, they have an idea and they, they ask the question to validate their idea, and it's actually the wrong idea. And so, just ask them, like, "What does success look like here? What is the worst part of your job? What, um, what takes a lot of your time?" Um, and, and just continue digging in and digging in and digging in. And then lastly, like, when you do have a product, like, sit down next to them or have them share their screen and just watch them do work in your product, and you will see how painful your product is and how many different ways you can improve that product. Oftentimes, just PMs spend way too much time in the office, and I think that, um, that's, that's just a huge downside, uh, for your team.

   6. HSHarry Stebbings2:41

      You said that you kind of followed the energy and didn't really know where your passions lay in the first instance. That's the same

3. 2:48 – 5:34

   Prioritizing Time Management Effectively

   1. HSHarry Stebbings2:48

      for many people. Knowing what you know now and where you are now, what would you advise people who maybe don't know w- where they should spend their time and their energies?

   2. GCGeoff Charles2:56

      Figure out, like, what gets you excited. Um, I mean, you do, you do have energy throughout the day. Like, what, what is that, right? And for me, it was, it was all about building great products and seeing metrics move and, and, and winning. Like, I, I think, I think I'm a very competitive person. Um, and so figure out, like, uh, the, the right industries. For me, like, when I th- think about Ramp, for example, it's, like, probably the most competitive space. Um, it is extremely metrics-driven. I mean, everything is metrics to the point of whether, you know, it's our risk or fraud losses, or our, our conversion, or our net retention, or interchange margins. And find the industry that, that will tick that, that box for you. Um, also just note, like, what blurs your energy throughout the day. Like, what really bothers you? You know, is it, like, large meetings? Is it bureaucracy? That was for me, for sure. And so find the, the industries or the companies that don't like meetings, that don't like bureaucracy. Um, I think at, at the very least, you can actually cut down a lot of things, and, and, and that makes this, the selection process a bit easier.

   3. HSHarry Stebbings3:57

      I said there, kind of, what would you advise others? When you think about advising yourself, you know, you've had an incredible spell at Ramp, and it's an incredible journey to date. (laughs) What, what do you know now that you wish you'd known on day one at Ramp?

   4. GCGeoff Charles4:10

      Oh, man. So many things. Um, I think that the, one of the... We, we did a lot of things right at Ramp. I think the things that we got wrong were always around hiring. And hiring is probably the hardest thing to, to get right. But it's especially hard when you don't know what you actually need. Um, and the biggest, the biggest mistakes were probably on, on, uh, on, on go-to-market earlier on. You know, we, we hired people who, who had seen success and growth. And, and it's hard to disambiguate, like, h- what was your role in that growth, um, versus the company? And also, what was the go-to-market motion of that company compared to the go-to-market motion that we, we, we strive for? And so, um, you know, growth means a lot of different things. Is it, is it lead gen? Um, is it, is it performance marketing? Um, is it brand? Is it sales? Is it outbound? Is it customer success? Is it account management? Um, is it product-led growth? There's a lot of different combinations. And so, you know, people hire their first go-to-market leaders, and I'm sure you have another growth podcast (laughs) that we can, we can chat through. They often make a, uh, a lot of mistakes there. Uh, it took us a, uh, a while to figure out the right combination, especially because, you know, Ramp is, is both sales-driven and product-driven and marketing-driven. We have, like, you know, what we call p- product-led sales. Um, and so there's, there's a lot of different combinations there. So, I would say, like, be super clear on the strategy. Hire, uh, and, and hire more, um, more IC-level people who can show you the right path, and test whether that strategy

4. 5:34 – 7:39

   Evaluating and Enhancing Employee Performance

   1. GCGeoff Charles5:34

      is the right strategy for you.

   2. HSHarry Stebbings5:34

      How long does it take to know if someone's not good, do you think?

   3. GCGeoff Charles5:38

      It depends on how senior the person is. For IC PMs on my team, I basically place them in teams that are high-performing.... and I, and, and we immediately see whether they are, they're at the bar. So you, so you take basically something that is fixed, you add a variable, and you, and you, and you, and if anything changes, right, it's, it's the variable that you added, right? So that's, that's one way of just, like, making s- being able to manage performance fairly well. It's harder for senior people who you hire to also hire additional folks. That's maybe, like, where I would say, like, don't do that. (laughs) Don't hire executives that will then hire, uh, people under them because that obfuscates a lot of their performance. Uh, so be clear to the, the leaders that you're hiring, like, "You're not gonna have headcount for at least, like, six months. You're gonna have to do the job," and that's a really good way to actually assess performance. I think within three months, you should actually be able to say and figure out, like, is this person gonna hit it out of the park or is this person, uh, not gonna work out?

   4. HSHarry Stebbings6:35

      Would you rath- uh, I'm g- I'm getting off-piece but I'm enjoying the, this, like, peppering of questions. Would you rather have someone who's worked in the same category before or someone who's worked at the same stage of company that you are before?

   5. GCGeoff Charles6:48

      Stage. Um, any time. I, I think the, the, the category is not that relevant. You know, I come from th- more consumer than, than B2B, and I think that's actually an advantage because you're focusing on metrics. You're focusing on conversion. You're focusing on models, like lead scoring and lead routing, all the things that, like, B2B companies have done really poor job on. And so I, I think the stage is actually much more important. Oftentimes, if you hire someone from a larger company, they come in and they, they just get shocked. Like, "Where's, where are all my resources? Like, I have, I, I've never been used to doing the work myself." Like, "What do you mean I don't have, like, 16 people just, like, supporting this one thing?" And so I would much rather actually s- uh, hire people who, who are coming from, um, uh, companies that are a bit more scrappy in terms of resources, that have gotten their hands dirty, even if they come from a different, different space. It's not rocket science. B2B SaaS

5. 7:39 – 14:20

   Focusing Strategies for Early-Stage Startups

   1. GCGeoff Charles7:39

      is not rocket science.

   2. HSHarry Stebbings7:40

      You mentioned kind of growth themes there. The one commonality in, in all 20 growth episodes we've done is that growth themes come after product market fit, and I wanted to kind of go through the different stages of company growth today. If you think about pre-product market fit, you said before, and I, I like this, but you said, you know, you have a million ideas and the hardest thing is figuring out what truly matters. How do you determine what to focus on and what not to focus on in this very, very early stage? So we're probably sub-20 people, pre-product market fit.

   3. GCGeoff Charles8:09

      So, I mean, at the early stage of, of Ramp, you know, we were about 10-ish folks, and we were just throwing everything at the wall to figure out, like, what makes people tick. The advice there is products should sit with sales, and should be in every single sales demo, in every single onsite, and, and use the sales process as a way to identify pain points.

   4. HSHarry Stebbings8:30

      Jeff, if we just jump in there, at this stage, often, there's not really a sales team. If we're pre-product market fit, it may be a founder and one sales rep. Do they just join all sales calls? Do they go to sales meetings? Just realistically for founders, what does that mean in reality?

   5. GCGeoff Charles8:46

      Yes. Like, the, the, the founder or the first product manager should be selling the first 100 customers. Like, absolutely. And that's because the salesperson is, is the, the master of, of process, of discovery, and of trying to close, but they don't deeply understand the product or even the pain points yet. I mean, they're not enabled. There's no product marketing team. They, they, they just really don't understand those things. And so use the sales process as discovery. Sit with, you know, if it's a larger customer, the CEO should definitely be there, um, and, and dig into, uh, what's working in the demo, what's not working in the demo. Where, where are their eyes opening up versus, you know, they're, they're, they're not, they're looking away? Uh, what are the questions that they're asking? And then basically just use the demo as, like, a prototype to your product (laughs) and continue. Like, that's, that's essentially your product at this stage. It's, it's, it's the demo instance and the story you can tell. And then the things that, that, they, they actually identify as like, oh, this is curious, or, like, I do have a pain point there, basically, like, run that back to your SCRUM teams. Build a prototype or build a product very quickly, and in the next demo show them that you actually incorporated their feedback. And that, I think, is also the, the piece that people miss, is you actually should be, like, a bit more professional services oriented as a product team earlier on than, like, saying, like, "Oh, I'm, I have this vision. I'm gonna build this perfect thing." Like, if you actually find one or two design partners and you just build for them, they will love you way more than, you know, the, the best in class SaaS product that's already on the market. And that's how you can win a lot of deals.

   6. HSHarry Stebbings10:10

      I get so many founders that obviously are investing today, I get so many founders that say, "I don't get it though. I did the customer discovery and they said, 'Oh, that's great,' and that's great." And people can be very polite. How do you determine between polite, that's great, and oh my gosh, this is really what I needed?

   7. GCGeoff Charles10:27

      Obviously, Ramp is free, so it's a bit easier to get the sale, right? Um, oftentimes c- customers are like, "This is fantastic," and then you say, "Well, you know, it's $5,000 a month." And they're like, "Nah, not for me." (laughs) Right? So, so that, that's one piece. Look, I think, I think it took us a, a while, uh, a while to get right, a while to, to get, um, the product that, that really wowed them. I think what we did is we were extremely aggressive in terms of making it super easy for them to switch. And what I meant by that is, like, we literally had teams say, "Give me your old credit cards. I will log in to all of your other software and I will switch your cards for you. I will sit with your finance team for a full day and I would get them se-..." So like, basically give them no reason to say no. The product is free, it's better, and you're not gonna have to lift a finger. And, and, and so just, like, be relentless there. Um, that, that'd be my advice.

   8. HSHarry Stebbings11:17

      No, I, I, I love that. Did you ever have to do that with a customer?

   9. GCGeoff Charles11:20

      Yes.

   10. HSHarry Stebbings11:20

       It's wh- I want... You did? (laughs)

   11. GCGeoff Charles11:22

       Mm-hmm.

   12. HSHarry Stebbings11:22

       And they took you up on it? (laughs) I, I love that. Okay. So, if that's kind of, like, thinking that, uh, in terms of, like, the customer discovery, in terms of internals, you've said before that you worked in two-week sprints. And I, I remember I was running, it was really annoying, I was running around Hyde Park in London, and I was like, great. That sounds awesome. How do you structure a two-week sprint? Like, what does that actually mean in reality? So can you explain, how do you plan these sprints and how is it broken up?

   13. GCGeoff Charles11:50

       So I, I've iterated a lot in terms of just product development processes and, and this is the process that I've, I've come to love.I'll be super tactical. So you have, you have a Monday leads meeting, where you talk about what is the actual plan for the next two weeks. And you alternate between tactical and strategic there. So one week, it's like the tactical two weeks, and then the week in between, it's the strategic around the next, like, couple of months. You... That's just the leads. So you align with the leads, product engineering design leads, as to what you need to achieve. On the Tuesday morning, you have a team-wide, like, scrum meeting. Uh, that basically is your five to 10 people, 10 max, where you're actually saying, "We decided this is what we're going to do," and that decision has been made. And it's all about, um, people signing up for work. So don't assign, but, but have people sign up. "Hey, Joe, uh, w- w- here are our goals. What do you want to achieve and help us achieve in the next two weeks?" And out of that meeting, you basically come back with, um, uh, the clear assignment of, of roles and responsibilities, and then any, uh, additional, like, deep dives that people need to have in terms of specs or designs or decisions, et cetera. There are no other meetings that are recurring in the, in the, in the entire product development process. Those are the only two one-hour meetings that happen. Everything else is, is scheduled if there is a blocker, or if there's a question, or if there is a, a brainstorming session, et cetera. So every other meeting is extremely gold, um, and extremely, um, well run.

   14. HSHarry Stebbings13:12

       Okay, tell me, in terms of, like, the teams themselves in these two-week sprints, how big are they, and how are tasks assigned between them? You mentioned there about, like, you choose which bits you're passionate about. How much is leader-led versus I-C led?

   15. GCGeoff Charles13:28

       I think, you know, if you, if you believe in empowerment, um, then, then a lot of it has to come from the individuals. And I think that you have kind of a, a, a social force where people are looking at their peers, and their peer's like, "I could do that, I could do that, I could do that." And they want to do more, uh, 'cause there are managers in the room, right? So, I think it's a really important culture to have people sign up and take on, take on more than to actually push these things down. And so yeah, we ha- we basically have engineers that sign up. And then we, we, we post publicly, "Here are our goals and here's who's doing what." And so the scoreboard is super, super clear. And then before the, the start of the next sprint, we basically go in and say, "This is what we wanted to achieve. What have you achieved?" And the individuals say, "I achieved this or I didn't, here's why." And, and that's essentially the scoreboard. So we also just do a lot of gratitude meeting, like, "How, wh- how has someone helped you achieve your goal?" Um, so we can continue fostering a, a culture of, of helping

6. 14:20 – 20:43

   Identifying Common Sprint Cycle Mistakes

   1. GCGeoff Charles14:20

      each other as well.

   2. HSHarry Stebbings14:21

      Having done many of these now, when you look back, what are the biggest mistakes you think you made? And I guess if you were to advise other founders on doing two-week sprints, what would you advise them, knowing what you do?

   3. GCGeoff Charles14:32

      I think that people tend to put too much emphasis on, like, the task, the system, um, the meetings, and not enough on just, like, what do you need to achieve those goals? Um, and so... And p- and product managers oftentimes become project managers, where they'll, like, do the work f- on behalf of the engineers that just, like, simply don't want to do the, the, some of the work that, that we're putting them o- o- on, on them. What I mean by that is, um, don't write tickets on, on behalf of people. Like, let them write their own tickets. Give them the goal, not necessarily the task. Have them manage up. Like, if you, if you, if you're constantly asking them for updates or you're constantly asking them, like, what's blocking them, you're, you're disempowering them, and you're, you're, you're emphasizing a culture of, of, of, of you project managing their work. Instead, like, every single person at Ramp owns their work and manages their own project. And they're managing up, "This is the risk that I have, this is the question that I have, this is the key decision that I need you to make." Um, and that just creates a culture of just empowerment and velocity. And so don't treat your employees, uh, like babies, um, because they will become babies, or you will hire babies, or you will make, re- retain babies. Instead, like, treat them like founders themselves.

   4. HSHarry Stebbings15:40

      What do you do if they don't set ambitious enough projects for themselves?

   5. GCGeoff Charles15:45

      I think it's very clear, if you ha- if you have a core team that's ambitious and you have one person in the team that's not as ambitious as that team, you need to part ways with that person, um, because it basically lowers the bar and everyone becomes demotivated. It's fairly easy to see as long as your core initial team is ambitious. And again, like, this goes back to, like, add one variable at a time into that team so that you can actually understand what are the drivers o- o- of, of, of headwinds.

   6. HSHarry Stebbings16:13

      Do you do two-week sprint after two-week sprint after two-week sprint? (laughs) Is there any time in between? How do you structure them?

   7. GCGeoff Charles16:19

      Every quarter, we take a step back, um, and we look at, "Okay, like, what did we achieve in the last three months?" Um, we, we basically have off-sites per, per pod that are, like, uh, customer-centric oriented, and we ask ourselves, like, "Okay, like, what does, what does, what does incredible look like in the next three months? Where do we wanna be, um, a- at, at that timeframe?" And, and then we... That, that is a great moment to re-energize teams so they don't, like, burn out on a, like, just this, this two-week sprint cadence. And they also reflect on, on what they could have done better. You know, what are the changes in the process? What are the changes in terms of people? What are the changes in terms of, of, of, of, of strategy? So, we do take a step back, um, every, every three months, and that's a, a great refresher to then, um, re- revitalize the team in the next few months.

   8. HSHarry Stebbings17:05

      So if that's at the earlier stages, if we kind of move a step forward and say we do incredible sprints and we find some form of product market fit, so for you, it was with the call card product, and we're at whatever that number is, 60 to 100 people, you said then that you start planning in months for one to two quarters at a time. Why the shift to months at this stage, and how do you not lose speed with the expanded time horizon that you have to work with now?

   9. GCGeoff Charles17:31

      Yeah, I mean, when, when you're a bigger company, right, you have... You now have a, a customer support team, you have, uh, a sales team, an account management team. You have, uh, customers that are not yet sold on your product today that need to understand the roadmap to be sold on your product tomorrow. And so you need to have a bit more of a longer term focus, or a longer term, uh, goal and plan to, to make sure that you can address those needs. Um, you also need to, um...... at that stage, you have a, a bigger marketing team. And that marketing team needs ammunition to have very strong market moments. And those moments can't be like one feature here, one feature there, et cetera. They need to be an aggregation of, of features and value propositions to then go in the market and tell a differentiated story. And so that's where, uh, we- you basically just need to, like, arm them with, "Hey, here's our plan over the next, call it, you know, six months. And, and, and here's how we can tell a story within, within this product roadmap that is anchored on these, like, large market moments," um, so that you can actually go live and you can train, you know, the press team on how to tell the story to the press, video content and case studies and landing pages and conferences, whatever that is. And so that- that's now more valuable. You couldn't afford to do that earlier on. You would- you just have to- to have an existential crisis and ship as- as quickly as you can. Um, so, that's really the value of- of why we're planning a bit- a bit longer term.

   10. HSHarry Stebbings18:50

       If we're blunt, uh, a lot of, like, products and marketing need to work closely together. But product teams often will go, "Marketing are fluffy and, like, they go sponsor another event." And a lot of marketing is like, "Ugh, I'm kind of intimidated by product," especially if it's kind of engineering heavy product teams. And there's a chasm often. How do you encourage synchronicity between the two where they can work together effectively in that way, whether it's messaging for landing pages, whether it's telling press the right story and messaging? How do you create that alignment?

   11. GCGeoff Charles19:21

       We, we have a culture at Ramp where even if you're not in the team, you can, you, you can advise and leave comments, um, and suggestions to other teams. And we build in the open. And so what I, what I mean by that is, like, if you're a salesperson, you can go into my product spec and leave a comment on my product spec with your opinion. That is welcome. And same, same thing if a product marketer is designing a great landing page. You can have an engineer comment on that landing page and be like, "This- this value prop doesn't make sense to me." And what- what- what that does is, it gives everyone visibility on what everyone is working on, so there's trust. Because oftentimes, trust gets- de- decreases when you don't know what the other person is doing. It also just lets people be empowered in terms of- of- of- of giving feedback. And, um, that might slow some things down or it's, like, a bit harder to manage. Uh, but long-term, I think it, like, leads to, like, much better craft. And so yeah, the engineers understand end-to-end how to launch the product, as well as the product marketer. Product marketers have full access to all the decisions we're making on the product. They're- they sit down with us in terms of user research, and that's important so that they can actually craft a good market motion. So, there's always gonna be a tension, um, but that tension's, like, greatly mitigated if you have shared goals, like, "We want this product to be successful in the market," um, and- and trust within the teams through visibility.

7. 20:43 – 28:44

   Balancing Feedback with Product Development Speed

   1. GCGeoff Charles20:43

   2. HSHarry Stebbings20:43

      When I hear that internal feedback debate truth, um, I think to the references that I got on you, and everyone said that- that your velocity, velocity, velocity was so cool to everything you do. And then I think to Gustav Soderstrom, who's the CPO at Spotify, who said on the show, "Talk is cheap, so we should do more of it." (laughs) And I- I kind of honestly look at this, Jeff, now listening to you, and I go, they're at odds, because you're welcoming discussion and debate and leaving comments on my product specs and everyone being able to say anything about each other's work, with what was your core strength, which is speed, speed, speed. "Yeah, cute you've got an opinion, but fuck off and let me do my work," is kind of what I'm thinking. How do you retain velocity while welcoming everyone's opinion on your work?

   3. GCGeoff Charles21:32

      You can- you empower the decision-maker. So, I actually think that, like, more data does not slow you down. I'm inundated with- with data. I mean, I- we have- I'll- I'll tell you, we have Slack channels with every single negative feedback we get from customers. Every time we lose a deal, there's a- there's a- there's a Slack. They're like, "Why did we lose a deal? Who did we lose it to? Um, and why..." You know, "Was it a product feature? Was it timing feature? Was it a pricing feature?" Whatever it is. There's so much data that's- that's happening, um, and in specs, there's so many comments. I think that that makes you better at making the decision. I think what you need to do, though, is you need to empower the person to make the decision. And when the decision is made, you need to commit, even if you disagree, and you need to align on the outcomes. If a PM gets 16, you know, thousand different, like, comments on the doc and you read all of them and you say, "I'm still going with this decision," then you commit, you hold that PM accountable to that outcome. And then if the outcome works, you can reflect back on those comments and you can change your mind. Or if the outcome didn't work, the PM should reflect back on the- the feedback they were given, and we'll have a post-mortem on it. So, I don't think more data slows you down as long as people are, again, aligned. It- it- the culture can't be like, "I just want to share my opinion because I care about my opinion." The culture should be, "I want to share my opinion because I care about the outcome and- and I'm gonna commit to that outcome." So, I don't know, short answer, uh, or idealistic is- answer if you- if you, uh, so Chris.

   4. HSHarry Stebbings22:52

      I- I totally get you. You also said in this stage, and I really wanna just double down on this 'cause I didn't really get what it meant, you said that you shifted your technology teams toward thinking about the reusability and durability of systems. What does it mean, reusability and durability of systems, and how would you advise founders on that given what you know now?

   5. GCGeoff Charles23:12

      When you're pre-product market fit, you know, it's- it's, um, it's very easy to- to- to try to build systems that, um, have extremely long shelf life. And I think you should only do that if- if they are very high confidence, meaning, like, you- you know that this system's gonna be alive for a very long time, and very high risk, meaning, um, if this system doesn't work, um, we're screwed. The rest, I think you should just, um, understand that the shelf life is probably 12 to- to 18 months and be okay with it. Once you find that product-market fit, um, then your goal is basically scaling that, as well as adding new products. And so as you go multi-product, you just need to ask yourself, "What can I reuse from the first product in terms of the second product?" Because you should typically go after a second product that has, um, you know, economies of scale in terms of the systems you've already built.... so an example for that for us was ... Our first product was cards, our second product was expense management, it was a reimbursement. Now, when you think about a reimbursement, it's fairly simple. There is an employee identity, which we already have, there is a form and a request flow, which we already have, there is, uh, an approval system, which we already had, and there's a money movement system. We had a money movement system between the customer and Ramp when they paid us back for the card, uh, we just had to switch that money move system from, from the customer to their employees. Um, and so that, that was reusability. So then we went back to all those systems and we thought, "Okay, like, how do we leverage those systems or rebuild them in a multi-tenant or multi-use case fashion?" And then the important part there is, like, just thinking slightly ahead, "Okay, like, but what comes next after that?" Like, oh, what comes next after that is probably, like, B2B payments. And so we, we re- rebuilt those systems after the first product to sustain the next product and potentially the product after that.

   6. HSHarry Stebbings24:46

      How do you know when is the right time to do a next product? I often find founders do not appreciate enough how deep their initial market is, and they have much further to run than they think, and they think about new g- products or geographies too soon. How do you advise founders on when's the right time to do a new product?

   7. GCGeoff Charles25:04

      So I think that for the majority of the company, you need to be, like, single product-oriented for a f- very long time, um, until you get to the really good market share. But as a tech team, you actually need to have an R&D department that is constantly shipping new features and new products. And so I know there's a disconnect there, but, like, h- here's, here's what I mean by that. After you find product-market fit, the, the equation really is go-to-market. The equation really is, like, your marketing, your brand, your distribution, your sales engine, your monetization engine, et cetera. That is a lot less on the, the tech team than it is on the go-to-market team. So when you're, when you're spinning up a new product after that first product, do not distract the go-to-market team until you find product-market fit. That's, like, really important. Like, what you don't want to do is, like, ask for a bunch of marketing resources and sales resources when you don't even have product-market fit on your second product. Keep that go-to-market team extremely focused, um, keep a small, small team in the tech organizations building the next product, and once growth kind of slows down a little bit on your, on your first product and the entire executive team's like, "Oh, my God, what's gonna be our next horizon?" You have it right there. You have it in your back pocket, saying, "Boom, this product is actually ready to go to market and it'll help us continue that exponential function."

   8. HSHarry Stebbings26:19

      Totally get you. How do you stop this very jerk-like shift, then, from, like, "Hey..." ... prevent that kind of jerk-like handoff from being quite so static?

   9. GCGeoff Charles26:43

      You ... What we typically do is we start at the bottom of the market with product-led growth on those products. And so there is actually no, like, sales and very little marketing. We use that to prove the business case, um, to the sales team and we continue i- iterating on the product until we can get to, like, more mid-market, sales-driven s- uh, segments. And then at that point, we can go to the sales team and say, "Hey, here's, here's the positioning that worked," and we, we leverage product marketing as well. "Here's the positioning that worked, here's the actual use case, here's the ICP, and here's the potential revenue," and then we basically train a smaller team within the go-to-market team, a smaller sales team, an account management team, to, to try to cross-sell those products or try to sell those products, and then we scale from there. So, um, that's a little bit of, of, of how we've done it.

   10. HSHarry Stebbings27:29

       I speak to a lot of founders, and we have a lot of public founders on the show in terms of public CEOs and founders, and they say, "The hard thing is, Harry, when you're, when you're a $10 billion company, you know, just shipping a new feature, it's a massive deal. Or shipping a new product's a massive deal. We have a brand to lose now." Do you buy that you come to a stage where, even at Ramp stage, people care if you do a, a product that doesn't work? Versus when you're a startup, I mean, kinda who cares? You don't have that many customers. Not many people will even notice. Does it matter, or do people forget anyway?

   11. GCGeoff Charles28:00

       For larger companies, when you're doing a product release, it's a lot more about, like, marketing to your existing customers and marketing to the market. But at Ramp, even with 15,000 customers, our marketing is actually geared towards the market, and the market doesn't even know what our product is. And so I think it's actually important to separate these two things out. When you go live with a new product, just go as loud as you can in, in the market, and by the time that they get to, "Okay, I actually wanna use Ramp, I'm sold and I activate," the product will actually be, like, much better than the actual product that we've built. And market to your customers differently than to the market. The, your customers should already be probably on a beta before you even announce it to the market. So that's, that's, I think, the advantage here, is, is you, you, you have a, a huge TAM and you can separate your, your marketing strategy

8. 28:44 – 36:52

   The Limitations and Misconceptions of OKRs

   1. GCGeoff Charles28:44

      that way.

   2. HSHarry Stebbings28:44

      When we think about new products, often OKRs determine how we think about success of them. And I, I really liked this when I heard you say it before, but you really said that we should kind of, w- not disregard them, but we get too focused on them, and that we should focus more on being product strategy driven. When we think about that, why do we get too hung up on OKRs? 'Cause they are kind of so hailed in our business. So why do we get too hung up, and why is product strategy driven more efficient?

   3. GCGeoff Charles29:11

      Yeah, so OKR is just a way to, uh, measure performance, right? And this, uh, objective and then, and then key re- key result. The, the reason why I, I don't like the framework is that it doesn't actually talk about strategy. It just gives a goal and then it just tells the team, like, "Go hit this goal." But there's no thinking on the exec level about, like, how we can actually achieve that goal and why that goal is important. And you spend a lot more time, like, debating what's the right metric, is this, like, achievable, is this not? And then you have teams trying to, you know, sand back some of the metrics so that they can look good to the rest of the organization, it becomes, like, a very political game. When, in fact, what you should be talking about on a quarterly planning perspective or goal setting perspective is, like, what truly matters for our business and how do we actually achieve that thing, which is the strategy? And so I- I'll give an example. Like, it, it'll be very easy for me to tell the product team, like, "Ah...... hit X dollars of revenue in this segment (laughs) . And then we can debate like, "Oh my god. Should it be, should it be, should it be X, should it be Y?" But like, we don't know. Like, I mean, there's so many things we don't know. Like, we're, we're so immature as a business still, even, even, even through... with a, with a ton of revenue. And so instead I say, "Well, okay, the strategy is, uh, it's e-commerce, and the strategy is, um, it's, it's cash flow conversion." And so we wanna build, we wanna ship a product that solves that problem in three months and get 10 customers, and that's much more specific and that's actually a, a delineation of product strategy and that should be the goal. And, and at that point, um, it's much more clear what we need to get done and there's a lot less debate, uh, around the goals themselves.

   4. HSHarry Stebbings30:41

      So you say there about kind of less debate around the goals themselves and less on the metrics themselves that you care about, but they determine success. And I, I've seen you say before, "I just care about how we're going to win." Same, but what is winning? Winning is dictated by setting a finish line and hitting that finish line, so do you not need to set them to know what winning is?

   5. GCGeoff Charles31:04

      I think winning can be derived... So there's, I think there's like leading and lagging metrics, right? And you wanna, you wanna win on your lagging metric, but you really wanna focus on the, on the, on the leading metric. I think setting goals on lagging metrics like revenue, market share, NPS, that's, that is, um, that is not gonna be clear to a team on how to actually change those metrics. I actually much rather focus on the leading metrics, which is like, how many customers did we get on this new product? How many, um, features did we ship in this specific segment? Um, how many logos did we close, um, with this specific strategy? Those are much more leading rather than the, the lagging ones which is, which is revenue. Um, and so-

   6. HSHarry Stebbings31:47

      I prefer, I prefer value-based metrics, which is like, how many transactions did we drive on a per customer basis? What's the usage on a per weekly basis? What's the card spread within orgs within the first 30 days? Like, that for me is the most valuable because it actually shows in that revenue retention over time, it shows you sort of, um, way more than like how many new logos did we get. That can go up or down. Do you see what I mean? But if you sh- do value-based metrics, for me, it, it just says so much more.

   7. GCGeoff Charles32:17

      The question really is around metric setting, is like, can I as a team in a two-week sprint move this metric? And if I can, it's a great metric. If I can't, it shouldn't be part of really our, our goals. And so oftentimes you have such a la- lagging indicator. It's like the, the S&P 500 stock price. It's like, you're, you're not gonna move that (laughs) in a quarter. Like, quarterly earning calls of publicly traded companies, that's the outcome of, like, the work that happened a year ago. And so you're not gonna build a team on that because th- they're gonna work super hard, they're gonna see the stock price change, and they're gonna be like, "Oh my god. Like, the work I'm doing is not valuable." But no. That was the work you did 12 years, 12 months ago. And so I agree with you in terms of value-based metrics, but I actually care a lot more about the, the actual correlation with what I'm doing today and the metric that I'm holding my team accountable for.

   8. HSHarry Stebbings33:03

      I, I, I totally get you there and I understand also it's hard with a lot of value-based metrics. It's still pretty tough to move them within a two-week sprint period. Like, that's not easy to do. When you, we said about kind of product strategy, uh, you've done a brilliant framework before. I did just wanna dig in on a couple, which is like, you said number one is goal, what do you wanna see in the world. If we start there, can you have many goals? What makes a good versus a bad goal?

   9. GCGeoff Charles33:29

      Each team should probably have one, maybe two goals. And then as, as a tech organization or as a, or as a product team, we try to sensi- synthesize those and aggregate those into like three, maybe four. A good goal is it's clear, it's, it's achievable, it's motivational. I mean, everyo- everyone kind of knows this, that the, the g- the, the perfect example is like, you know, putting a man on the moon by, by this date, right? Um, that's, that's a great goal to have. Um, there's, there's a, there's an outcome, it's measurable, it's motivational.

   10. HSHarry Stebbings33:57

       And what's a bad goal? Where do people make mistakes with goals?

   11. GCGeoff Charles34:00

       If you see yourself repeating the same goal for like many quarters at a time, um, it's not motivating. Um, and so s- something that's more like a vision or mission statement, um, should not be a goal.

   12. HSHarry Stebbings34:13

       Can I ask you, on number two, it's hypothesis. What was Ramp's hypothesis and how did it change?

   13. GCGeoff Charles34:21

       So our, our hypothesis from the start was that finance teams were equipped with tools that did not work for them and that incentivized them to spend much more time and, uh, spend too much money. Because of that, their employees suffered by, uh, having to jump through hoops for expense reports and having to understand accounting speak to even, like, submit those. And everything was just backwards. It was backwards in terms of control, it was backwards in terms of incentives. Um, and so our hypothesis was how do we give, uh, a product and a solution to finance teams that help them spend much less time managing expenses and made the right decisions for their business in terms of spending less? That hypothesis, you know, was, was kind of our, our positioning statement around like the card that helps companies spend less, uh, which was a great anti-positioning against the, the status quo. I think that over time, you know, we, we fine-tune those hypotheses. So for example, for, for the, the first version of our product, it was all about like receipt hygiene, like, finance teams chasing people down for receipts, and so we just doubled down on just that hypothesis. What if Ramp became the bad guy? What if Ramp, um, automated the receipt collection process and the finance team was actually the good guy and just pointed to Ramp saying, "This, this, it's Ramp's fault. It's not me. I'm trying to be the good guy." Um, and that hypothesis worked, worked fairly well. There's other hypotheses that might have worked as, as well as that, but, um, that, that was kind of the, the, the initial take on it.

   14. HSHarry Stebbings35:41

       Do you think startups get hypotheses right?

   15. GCGeoff Charles35:44

       I think oftentimes PM are enamored with their solution and they're not actually good at defining the hypothesis that led them to that solution. And they just, they just ship this product and the product doesn't work, and then they, they have to go back and say like, "Why didn't it work?" And, and they'll, they'll, you know, they'll have a bunch of excuses, right? "Oh, d- you know, it's..."Uh, the- the- the design isn't good, the marketing isn't good, the sales team isn't selling it, the engineering team cut scope, whatever it is. But a lot of times, the pro- the reason why the product didn't work is because your hypothesis was wrong and, and it's hard to actually reflect if you didn't write down that hypothesis ahead of time. What is your, your belief, uh, about the customer, the problem, and the solution that will make this successful? And if you, and if you write that out then you can actually reflect back and, and learn a lot more. And you can also just be hypothesis-driven in the sense of, like, hey, like, it's not- I'm not a, I'm not a bad PM because I had the wrong hypothesis, um, uh, ide- I had the hypothesis, I learned it, I tested. You're a bad PM if you don't learn from your failures (laughs) and you blame others. Uh, so take responsibility for the hypothesis that you've made and then make sure that you're, you know, you're winning more often than not, let's put it that way.

9. 36:52 – 42:11

   Learning from Post-Mortems in Product Leadership

   1. HSHarry Stebbings36:52

      In terms of learning from your hypotheses there, postmortems are a crucial part of any product team. H- what've been your biggest lessons in terms of how to do postmortems well as a product leader?

   2. GCGeoff Charles37:03

      A lot of documentation, um, blame, like, n- no blame. Um, I think it's actually, like, y- y- you need to have curiosity. You need to engage with, with questions. You need to have a, a fairly cross-functional team that everyone that's affected be present so that you build trust, uh, with those teams. Oftentimes, you know, when you screw up, it's not the engineering team that, that is affected, it's the customer service team, it's the s- the account manager that had to apologize to the c- to the customer. And so, uh, bring those teams together, share the data, be up front with the facts, um, then open up discussions around, like, what could we do better? What are some other ideas or hypotheses for what we could do better? And then take action items that are very clear, um, and timely, uh, to address those things so that the postmortem doesn't happen again. I think that's the most important thing is, like, screwing up once, it will happen. We will screw up all over the place, and we have. Screwing up twice on the same problem cannot happen.

   3. HSHarry Stebbings37:57

      Product reviews, remote versus in-person, how do they differ?

   4. GCGeoff Charles38:02

      I mean, we have, you know, half the company in New York City and half the company kind of distributed. I think that, um, uh, oftentimes, uh, trust is eroded if you don't actually meet in person, and so we do have a strong culture of, of flying people into the New York office and, and making sure that people have time together. And it- so if you have that, then, like, there's, there's largely no difference between, between remote work and, and, and in-person jam sessions. Um, but if you don't, if, if you actually haven't seen the, the, the second half of someone's body (laughs) it's harder to actually trust them and it's harder to, to engage with, with a, a ton of, um, uh, o- of trust.

   5. HSHarry Stebbings38:39

      I totally get you and I agree with you. So many people meet me and they're like, "Wow, you're, you're actually quite big. You're not small."

   6. GCGeoff Charles38:46

      (laughs)

   7. HSHarry Stebbings38:46

      Uh, I always find it very entertaining when people see, uh, me in person. Uh, I do wanna ask, the third thing in product strategy, now we've got our goal, we've got our hypothesis, and the third was right to win. Why are we uniquely positioned to do this? And the honest truth is, like, is anyone really uniquely positioned to do something? When you think, like, Google, Facebook, in this case Stripe, anyone could allocate a insane amount of resources and come and take your lunch. No? Am I wrong? How do you think about that?

   8. GCGeoff Charles39:17

      The reality is, like, it's very hard for large companies to, to actually innovate. Um, and you can see this with, like, when you're launching a second product at your, in your company. It's, it's, it's hard. And you're just, you're a small company and it's still hard. I mean, think about, like, if you have a huge company and a huge go-to-market engine and you're trying to launch a new product, like, it becomes exponentially harder. And w- why is that? You have, um, you have board expectations, which are very short term focused, you have, um, a go-to-market team which is incentivized with one business model, you have an understanding of one specific customer profile, and then you have, like, one core, uh, DNA of, of, of engineers that are all, like, incentivized to, to, to build organizations under them. And so it's hard to just, like, break all that. You need to break, sometimes, the, the, the actual business model. You need to break the go-to-market motion and focus on a new customer. You need to break an engineering and product and design, uh, org structure to create new teams. And that's really, really hard. And so you've s- you've seen that, you know. Um, uh, y- yeah, how, how has Amazon actually been able to launch financial products? Um, it's, it's been hard. How has Salesforce actually been able to make, um, their acquisitions super successful? It's hard 'cause they do seat-based, um, uh, incentives. Whether it's, like, Facebook trying to enter the B2B space, whether it's Stripe trying to actually go from, like, developers and SME to finance teams in, in, in the enterprise, it's hard. And we actually haven't seen that much success.

   9. HSHarry Stebbings40:36

      Can I ask you, who makes you more nervous? Is it, like, incumbents or is it startups? 'Cause it's like, your AmEx could actually integrate AI pretty well and play into the next generation of especially, like, expense management well. I don't think Concur will, but AmEx I can see doing better. But like-

   10. GCGeoff Charles40:53

       So I, I, I, I think if, if we weren't in the B2B, like, fintech space, I would say incumbents. And you've seen that with, like, Microsoft Teams and Slack. Right? It's like a, it's like a perfect play of, like, I can build something that, like, is pretty much a copycat and I can distribute that way better than you can in this ecosystem. So that's, that's scary. That said, there isn't a incumbent B2B spend management company that is actually even close to, like, a Microsoft level of, like, innovation and, and velocity. So I'm not really scared of the incumbents at all. And, like, AmEx is, like, it does not know how to build software. It is an incredible company with an incredible brand and an incredible card and merchant product, um, but they're a far cry away from, from being a SaaS company. So I would say, I would say, um, um, um, new entry, um, and, and specifically, um, folks that are going after, again, like, a very pointed solution and find a new, a, a, a new entry in, in the finance, um, space. And so that's why we take a, we, we, we, one, like, keep a very close eye on, on, on new players, we invest in new players, we acquire, uh, you know, acqui-hire, uh, great talent, um, and we actually use that as a testing bed to figure out, like, what's working and we include that in our product strategy.

10. 42:11 – 53:37

    Overcoming Challenges in Product Strategy

    1. HSHarry Stebbings42:11

       Competitive landscape is one risk that one always faces regardless of business. Part of the product strategy, like-... thinking process. Eh, number six was risks, which is why would we fail? When you think about that, talk to me about how do you know when to give on a- up on a product and when it's a fail? And how do you think about that core segment of why we fail in the product strategy session? I love the statement here, "Double down or pivot is hard." What does that mean?

    2. GCGeoff Charles42:41

       At Ramp, we've, we've shipped a lot of things and I don't think we've been, like, particularly good at, like, taking things down. Um, and the framework that I have around, you know, do you actually, like, s- sunset the feature or the product or do you keep it? Is one of, like, what is the cost of keeping that up? And I think until, until very recently, we were able to hide the complexity of, of new features, and we only opened it up for certain segments, um, of, of, of customers. I think if you get to a place where you're, you're clutter- cluttering your application, or you're adding a lot of complexity and that, like, reduces the stability, then you should really think about, like, sunsetting these features. And so, for me, I would much rather have a lot of features that we can turn on and off based on the segment and based on the needs and continue testing, rather than, than, um, deprecating. I think in terms of, like, doubling down, you know, we, we should, we should be very clear on our- around how confident are we that the next hypothesis that we have will pan out, and how, how much effort will it be to test that new hypothesis? And oftentimes, you know, the first hypothesis was, was your, your, your main one, and you might not have a second one that's as strong. And that's- uh, if that's the case, then, like, don't double down.

    3. HSHarry Stebbings43:50

       What was a really h- strong hypothesis you had that turned out to be wrong?

    4. GCGeoff Charles43:54

       One of the hypotheses we had was that we can embed, like, a financial product directly in our, in our, in our, um, invoicing products, and it'll just, like, have massive take-up. And, and the hypothesis there was that the person paying the bill had the authority to take a loan to pay the bill. That was the wrong hypothesis, in the sense that the person paying the bill oftentimes, it's a clerk, it's, it's a, it's a, it's an, it's a, it's, um, an agent that just is more of an operator than necessarily, like, a big decision-maker in terms of, like, your financial, um, your financial decisions. And so you n- actually need approval from, uh, more of a CFO, uh, strategic finance person to understand, like, eh, should I pay f- an interest rate to actually extend that payment? And so we had the wrong hypothesis in terms of, like, the actual target segment, which then made our product... We had to essentially shift our product to increase the val- the, the take-up of that.

    5. HSHarry Stebbings44:45

       When we think about, like, hypotheses in product, so much of it, for me, comes down to this kind of age-old question of, like, art or science in product. When you reflect on the, is it an art, is it a science, we mentioned that kind of when do you pull a product, again, slightly art, slightly science. How do you reflect on, is product more art or more science?

    6. GCGeoff Charles45:05

       It's funny, like, I, I, so I, I have a, a standard scientific process for product development that I've, like, tried to apply across the entire teams. And yet, like, different teams perform in very different ways. And so that kinda shows you that, like, it is more art than science. And I think art is a big part of, of what we do at Ramp when we th-... Our biggest advantage is actually, um, it is velocity, but it's also the, the design experience of our product, and how, how, um, delightful it is to, to finally work in a solution that is much more consumery in terms of, of its design than typical B2B SaaS. And that takes a lot of creativity, and so I would say, you know, I spend a lot more time on, on the art part of product, which is, uh, which is almost like painting on a canvas in terms of, of, of prototypes and designs and, and, and flows. And I think that's, that's a, that's how you build great products, is really spending a lot of time with an empowered design team, testing and iterating with our, with the customers.

    7. HSHarry Stebbings46:02

       Can I ask you, you know, uh, product versus pr-... Art versus science is similar but different to, like, intuition versus data. You said before that all of Ramp's success was intuition in the early days. How do you think about that and the question of intuition versus data?

    8. GCGeoff Charles46:20

       B2B companies have a lot less data than B2C, and startups have no data. So, when you're a startup, a B2B startup, like, y- you, you should hire people with strong intuition, or at the very least, like, strong ideas that they can, um, very quickly invalidate, um, with more qualitative data than quantitative data. I've, I've, uh... Oftentimes, you, you, you have PMs from, you know, the, the Facebooks and, and, and Googles of the world that are actually just good at testing, um, and, and moving metrics. But their intuition oftentimes isn't actually, um, locked into customer research and, and, and actual customers. Hire people who have, who are able to listen, who have a strong sense of what's a good product. Like, they're actually, like, snobs when it comes to, like, their, their, their, the applications they use on their phones, or they're constantly complaining about a software product. And lean into that, 'cause you're not gonna have data for a very long time. Only recently do we have enough data to actually, you know, run an A/B test. Only recently do we have enough data to say, to hold teams accountable to more of a lagging metric than a leading one. But it takes, it takes a very long time.

    9. HSHarry Stebbings47:23

       Can I ask you, in terms of design, as you mentioned earlier, kind of ge- creativity, the beauty of creativity. I had, uh, Jean on from Plaid, the CTO at Plaid. And he said that AI will most profoundly impact product by reducing the importance of UI. Do you agree with that? And how do you think AI changes really how product works and is consumed? (laughs) Which is a tough question.

    10. GCGeoff Charles47:52

        I, I, I definitely agree with that. I mean, when you think about m- a lot of the SaaS products out there, it's, like, reports, it's tables, it's forms, it's dropdowns, it's buttons, all of which are meant to, like, help you achieve the goal that you have. But, like, realistically, like, you can list out the actual jobs to be done of your customers pretty cleanly, and there's not that many of them. And then you can definitely use AI to do that. And so an example of OnRamp was, like, we had a huge table of, like, all of your card transactions, and you would go in and you would just approve the transactions that were in policy. Like, you can leverage AI, now we do, where we can just flag magically, like, the things that are actually out of policy or actually fraudulent. And we can actually have much more of a conversation-based approach to, to what the customer is doing. So, 100%, I think the, the software is gonna look a lot less like tables, graphs and dropdowns, and a lot more like, like a conversation, or at very least a UI that is extremely dynamic, that abstracts the data that you actually would need to see, and just gives you the actual raw intelligence. And I think hopefully we spend a lot less time, um, uh, in, in more tactical work and much more time in strategic work.

    11. HSHarry Stebbings48:54

        ... I clearly just quote prior guests who I think are smarter than me. But Glen Coates, who's VP of product at Shopify said, "The day the founder relinquishes the title of head of product or CPO is the day the company dies." Do you agree with that statement?

    12. GCGeoff Charles49:09

        Yeah. I, I, I listen to that and, and, and love that. Um, I, I don't agree. And, and again, this is the Shopify, you know, obviously, you know, T- Toby's like very involved in, in the product surface area. At Ramp, I think we, we have, um, a f- slightly different approach. I think that the, our, our founder, Eric, is very focused on our vision, very focused on our brand, very focused on our marketing and our story and our positioning in the market, um, and has a, a very strong sense of, of what we want to be as a company, and a very s- very high bar for who we want at the company. How we get there, I don't think that it's necessarily super important for the, the founder to, um, to have the strongest opinion. I think that they need to shepherd, uh, the culture to get there. They need to hold the teams accountable for high velocity. They need to be able to opine on what looks good and what it doesn't, what is a good decision and a bad decision. But you need to have an empowered, uh, product team and tech team that actually calls the shots in terms of the sequencing. We've done well with, with kind of our RCTO, Karim, uh, wearing more of that, that product hat, um, and I think it's, it's, um, um ... Yeah, I think it's worked well for us so far.

    13. HSHarry Stebbings50:17

        You mentioned the people that you bring into the organization, especially being someone like Eric and Karim, you know, really focus and have done so well. Given the focus on velocity that you have, how do you ensure that the people you bring in have the same centricity towards velocity that you have?

    14. GCGeoff Charles50:34

        Yeah. How do you, how do you hire people with ... that have a, a, a strong sense of velocity? So, look, the, the first one is, like, look, what's their motivation? So I, I ask them, like, you know, "Why are you interested in joining Ramp?" And I think that, um, that the answers I look for is, like, "I was ..." Um, "I wanted to move faster." Um, "The company was too big." Um, "Things were moving too slowly." Um, "I like Ramp's velocity philosophy and I wanna know what it feels like." Um, "I like building and shipping things." Like, those are all, like, strong signals. Then the second thing is, like, do they actually have that experience? Like, have they actually tried to push something through? So you go deep in their profile, like, what's, what's ... How, how have you had impact at your previous company? And then you go deep, like, what was something that was getting in your way? And you see them react. Like, di- di- did you, did you confront that? Did you address that? Did you, uh, influence that? And then finally, like, people who were ex-founders that might not have succeeded, or, um, uh, early engineers that, that, um, have been coding for a long time that, that, that just wanna build great things. And I think you find that DNA, um, that, that really helps. So th- those are, those are some of the things that we look at.

    15. HSHarry Stebbings51:35

        When we think about the process now, you said number one before, did you have impact, background, and go in-depth. Totally agree. Number two, second round, do you put in the work, take-home exercise. What's included in the take-home exercise? What d'you want to see? Is it on your company? Is it on their old company? Is it on a different company? Can you help me on that one?

    16. GCGeoff Charles51:57

        We do cases that basically are, like, lateral things about Ramp, so they're about something that we would never do, so that we never really, like, steal people's work. But something that is, like, somewhat relevant to Ramp, so that the person can actually, uh, start thinking about Ramp. And, and, and oftentimes, they get excited about the problem, and they're like, "Oh, my God. I really wanna work at this company." And so it helps them just start understanding a little bit of our space. Um, but typically it's about, you know, a, a, a, a new product that is working or not working, and what they would do about it. What I look for there is just, like, did the person put in the work? Are they super clear? And are they able to, like, influence, uh, a, a team? 'Cause largely what a product team really does with the engineering and design team is, like, they're the ones advocating for something and influencing teams. And so if you can't influence me that this is a good idea, um, you're not gonna be able to influence the team.

    17. HSHarry Stebbings52:42

        Got it. And I like that in terms of building the excitement around the space. The third step was, can you think deeply on the spot? What does that mean, and can you unpack that stage for me? How do you test thinking deeply on the spot?

    18. GCGeoff Charles52:54

        So yeah. The, the, the final round is, is you, you meet, um ... There's, like, a product engineering and, and design interviews, and, and half of it is, like, fit and half of it is case. And we basically just throw a, a ton of different cases at them. Whether it's a case around, like, a system failed, what do you do? Or, um, customer's complaining, what do you do? Um, or a product shipped and it, it, the metric moved this way, what do you do? And you just start, start addressing basically, one, like, are they framework oriented? Like, do they have a strong framework for how they think? Two, um, are they able to, to, to ask the right questions and engage with you to get to the right outcome? And three, are, are they actually, um, able to get to the, the root, the, the root problem or cause very quickly that helps them just get to, like, 80/20 in terms of the solution?

11. 53:37 – 59:36

    Quick-Fire Round

    1. GCGeoff Charles53:37

    2. HSHarry Stebbings53:37

       I, I, I love that in terms of the 80/20 to the solution, and I agree totally. Uh, can I ask, can we move into a quick-fire? So I say a short statement, and then basically pepper you with questions. Does that sound okay?

    3. GCGeoff Charles53:49

       Sounds good.

    4. HSHarry Stebbings53:50

       So, tell me. You're a long-distance runner and a runner. What are the similarities between running and product?

    5. GCGeoff Charles53:56

       It's long and hard. You have to do, like, short distance as you go through this long distance, so two-week sprints for a, a marathon. Um, it's very metrics oriented, so, you know, you know how you're pacing and you know how you're doing. Honestly, it takes repetition. Um, you won't get the first practice right, you won't get your first run right. But if you put in the work every day, um, you'll get through it. It comes when these things compound.

    6. HSHarry Stebbings54:17

       I love running. Like, one of my favorite things in the world. What do you do, what do you tell yourself when your legs just say, "No more. Nah. I'm done."

    7. GCGeoff Charles54:25

       Slow down slightly, uh (laughs) , and, and also just, I think aim for, like, n- more near term goals. When you're tired, just reduce the goal that you have. So your legs might, like, feel tired if you're thinking about, like, "I have 15 more miles." But how do you feel if it's just like, "Okay, just get over this hill, just get over ... just get to that tree"? And I think if you do that, if you break down ... You know, it's, it's hard to think about, like, how does Ramp become a $100 billion company? But it's much easier to say, uh, "How can we crush this, this day? How can we crush this quarter?"

    8. HSHarry Stebbings54:52

       I totally agree with you. I always think just get to the next mile, and like, just get to the next mile, next mile. And then I always do positive visualization. I picture myself at the end, and think how good that will feel. That's a really helpful one. Not enough people do positive visualizat- so I have an espresso and a biscuit at the end, and I see myself in that moment, and that is like, goodness will come.... (laughs) if I finish. And if you don't, you're shit. You're stuck halfway through a course, empty. That sucks. Okay, most important skill to build early on in your career in product?

    9. GCGeoff Charles55:24

       You gotta spike at one thing. Um, either you deeply understand technology so you're an ex-coder and you know how to code, either you deeply understand business equations, you're an ex-VC or you just read, like, 10Ks for fun, or you're just a, a deep snob when it comes to product design. Like, pick your poison. Ideally, all three. Um, but you need to spike in one thing so that you can come in and you can build a lot of trust with that team.

    10. HSHarry Stebbings55:46

        What would you say is the biggest mistake founders make when hiring product teams?

    11. GCGeoff Charles55:50

        They don't let go, um, uh, in terms of the how, um, and they're not clear enough in terms of the, uh, what.

    12. HSHarry Stebbings56:00

        How do you advise them on how to let go?

    13. GCGeoff Charles56:03

        I think the moment that they join, um, be very clear with them, like, "For the first month, I'm gonna micromanage you and I'm, and you're gonna shadow me for everything that I do." And then the moment that you know that they got it, you need to step away and empower them and let them make mistakes. Oftentimes, they either, like, give everything and then but they don't let go and so the person's super disempowered, or the person actually doesn't have any of the context to make the decisions. So be, be the super micromanager the first month and just signpost that with, with your hire, and then step off and step out and be very clear on the outcomes you're trying to drive.

    14. HSHarry Stebbings56:33

        What one piece of advice would you give to a product leader starting a new role today?

    15. GCGeoff Charles56:37

        You know, the founders are probably, um, very anxious, so overcommunicate. Overcommunicate, overcommunicate. When I first joined as, as the, the first product, uh, person at Ramp, I was giving, like, weekly updates on here's exactly what we've done, here are the decisions that I've made, here are the trade-offs that I've made, here are the key things I need your opinions on. And I overcommunicated constantly to the leadership team, and that builds a lot of trust. So, uh, make sure that you're, you're, you're sharing what's in your mind with, with them in a way that is, is very actionable for them to opine on.

    16. HSHarry Stebbings57:08

        As a leader, do you think you can force your team to overcommunicate with you? What I mean by that is I hear you and I'm like, "God, I would love it if everyone in my team sent a little update at the, every Sunday saying, 'This is what I did. This is what I achieved.'" Can you implement that in your team?

    17. GCGeoff Charles57:25

        I have, yeah. Monday morning, the first thing everyone on my team tells me, what did they get done last week? What are they gonna get done this week? What are the key decisions that they're going to make? And what do they need my help on? And it's public, and so everyone on my team can read each other's, um, goals and outcomes.

    18. HSHarry Stebbings57:38

        Would you like to be a CEO in the future?

    19. GCGeoff Charles57:40

        I don't think so. (laughs)

    20. HSHarry Stebbings57:42

        (laughs)

    21. GCGeoff Charles57:42

        I can't... I, I have very little patience with, um, uh, r- you know, fundraising, no offense, and, uh, and I'm, I'm not a very strong marketer. Uh, I'm a builder, I'm an operator. Maybe if I find, you know, people who can compensate for that, but I think that, um, where, where I shine and what, what I love doing is, is building great products. Um, and I think that CEOs oftentimes get, you know, the majority of their time is spent on, on telling the story, on being great at the press and, and great with investors. And, and I think I would, I would, I would, I would get fairly stretched and, and not super happy. But I'm glad that, uh, we have people like that that I can work with so that I can just focus on the shit that I wanna do.

    22. HSHarry Stebbings58:24

        Final one for you, Jeff. When you think about company product strategies that you see, which one are you most impressed by?

    23. GCGeoff Charles58:32

        Maybe surprising for me to say, but I think Apple continues to crush it, um, uh, from a product strategy perspective. And what I mean by that is, you know, they have a level of craftsmanship, a level of, of, of delight in brand that just has incredible loyalty to their customers. And they've also just had this compounding effect of, of the ecosystem that they've been building that continues to just drive so much revenue. I mean, when you think about, like, the iOS ecosystem and the monetization on, on applications, when you think about Apple Pay and the Apple Card and the Apple Wallet, um, it just continues to compound, and you see that in the public markets. So, um, I'm super impressed with, with that company and their, their ability to continue to innovate, even at that scale. And honestly, they, they've, they've rarely missed and, and they're still absolutely, um, winning the market today. And so, I, I hope that Ramp continues to have that level of brand loyalty and, and that compounding effects of the ecosystem that, that we're building today.

    24. HSHarry Stebbings59:26

        Jeff, as, as I said, I loved your prior interviews.

    25. GCGeoff Charles59:28

        Thank you.

    26. HSHarry Stebbings59:28

        There were so many things I wanted to double-click on today. Thank you so much for joining me.

    27. GCGeoff Charles59:32

        Mm-hmm.

    28. HSHarry Stebbings59:32

        And I've absolutely loved this.

    29. GCGeoff Charles59:34

        Thanks a lot, Harry. This was fun.

Episode duration: 59:36