The Exchanges

Q Can I ask you, you know, product versus, 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?

A Companies have a lot of this. They have a B to C and startups have no data. So when you're a startup, a B to B startup, like 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 oftentimes you, you, you have PMs from, you know, the, the Facebooks 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, their, the applications they use on their phones or constantly complaining about a software product and lean into that. Cause you're not going to have data for a very long time. Only recently do we have enough data to actually, you know, run maybe test only recently do we have enough data to say, To hold teams accountable to more of a lagging metric than the leading one, but it takes, it takes a very long time.

AI assessment note: “So when you're a startup, a B to B startup, like you, you should hire people with strong intuition”

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

A 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 basically have off-sites per, per pod that are, like, 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 want to be, um, at that time frame? And, and then we, that, that is a great moment to re-energize teams so they don't, like, burn out on, like, just this, this two-week speed 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 great refresher to then, um, re, revitalize the team in the next three months.

AI assessment note: “so they don't, like, burn out on, like, just this, this two-week speed cadence.”

Q Can I ask you, you know, product versus, 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?

A Companies have a lot of this. They have a B to C and startups have no data. So when you're a startup, a B to B startup, like 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 oftentimes you, you, you have PMs from, you know, the, the Facebooks 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, their, the applications they use on their phones or constantly complaining about a software product and lean into that. Cause you're not going to have data for a very long time. Only recently do we have enough data to actually, you know, run maybe test only recently do we have enough data to say, To hold teams accountable to more of a lagging metric than the leading one, but it takes, it takes a very long time.

AI assessment note: “when you're a startup... you should hire people with strong intuition”

Q I said that 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. What do you know now that you wish you'd known on day one at ramp?

A Oh man, so many things. Um, I think that 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 in growth. And, and it's hard to disambiguate, like, 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 that we can, we can chat through. They often make a lot of mistakes there. And it took us a while to figure out the right combination, especially because, you know, ramp is, is both sales driven and product driven and marketing driven. And we have like, you know, what we call product less sales. Um, and so there's, there'…

AI assessment note: “be super clear on the strategy, hire and hire more Um, more IC level people”

Q 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 do 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?

A 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 start thinking about RAMP, and, and, and oftentimes they get excited about the problem And they're like, oh my God, I really want to 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 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 a team? Cause largely what a product team really does with the engineering 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.

AI assessment note: “We do cases that basically are, like, lateral things about RAMP”

Q of product market fit, so for you it was with the core card product, and we're at whatever that number is, 60 to a hundred 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?

A I mean, when you're a bigger company, right, you have, you now have a customer support team, you have 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 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 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 have an existential crisis and …

AI assessment note: “that's really the value of why we plan a bit, a bit longer term.”

Q shipping a new product is a massive deal, we have a brand to lose now. Do you buy that you come to a stage where, even a ramp stage, people care if you do a product that doesn't work, versus when you're a startup, I mean, kind of, who cares? You don't have that many customers, not many people will even notice. Does it matter or do people forget anyway?

A For larger companies, when you're doing a product release, it's a lot more about like marketing to 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 the market. And by the time that they get to Okay, I actually want to use ramp. I'm sold and I activate. The product will actually be much, much better than the actual product that we built and market to your customers differently than to the market that 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 huge TAM and you can separate your, your marketing strategy that way.

AI assessment note: “market to your customers differently than to the market that your customers should already be”

Q I get so many founders that obviously investing today, I get so many founders that say, I didn'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.

A Obviously ramp is free. So it's a bit easier to get the sale, right? Um, oftentimes customers are like, this is fantastic. And then you say, well, you know, it's 5000 dollars a month. And they're like, nah, not for me. So, so that that's one piece. Look, I think, I think it took us a while, um, 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 set. 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'd be my advice.

AI assessment note: “we were extremely aggressive in terms of making it super easy for them to switch”

Q Okay. Tell me in terms of like the teams themselves in these two weeks brims, 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 IC led.

A 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 social force where people are looking at their peers and their peers are like, I can do that. I can do that. I can do that. And they want to do more, uh, cause their 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, 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 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, meaning like how, how has someone helped you achieve your goal? Um, so we can continue fostering a culture of, of helping each other as well.

AI assessment note: “a lot of it has to come from the individuals”

Q I get so many founders that obviously investing today, I get so many founders that say, I didn'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.

A Obviously ramp is free. So it's a bit easier to get the sale, right? Um, oftentimes customers are like, this is fantastic. And then you say, well, you know, it's 5000 dollars a month. And they're like, nah, not for me. So, so that that's one piece. Look, I think, I think it took us a while, um, 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 set. 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'd be my advice.

AI assessment note: “oftentimes customers are like, this is fantastic. And then you say, well, you know, it's 5000 dollars”

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

A We have, you know, half the company in New York City and half the company got distributed. I think that, um, Uh, oftentimes, uh, trust is eroded if you don't actually meet in person. So we do have a strong culture of, of flying people into the New York office and, and making sure people have time together. And 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 you, if you actually haven't seen the, the, the second half of someone's body, it's harder to actually trust them. And it's harder to, to engage with, with a ton of, um, uh, of trust.

AI assessment note: “there's largely no difference between remote work and in-person jam sessions”

Q shipping a new product is a massive deal, we have a brand to lose now. Do you buy that you come to a stage where, even a ramp stage, people care if you do a product that doesn't work, versus when you're a startup, I mean, kind of, who cares? You don't have that many customers, not many people will even notice. Does it matter or do people forget anyway?

A For larger companies, when you're doing a product release, it's a lot more about like marketing to 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 the market. And by the time that they get to Okay, I actually want to use ramp. I'm sold and I activate. The product will actually be much, much better than the actual product that we built and market to your customers differently than to the market that 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 huge TAM and you can separate your, your marketing strategy that way.

AI assessment note: “market to your customers differently than to the market”