The Exchanges

Q You, you mentioned value also. Quite a few times here. When we think about connecting value from your solution to the customer needs, what do you think are the biggest mistakes that you've seen founders and early stage teams make from many of your mentoring days and sessions?

A I think it's how making sure that the value is proportional to the investment that we require for that company to be successful. Like value is such a broad term, but sometimes you could say, yeah, of course this provides value. Like this is a solution that Provides day to day value for, uh, my end user, but an aggregate is not enough business value or is not a strategic business outcome that warrants the amount of money that have to spend to invest in a solution like that. Um, and it seems really simple, but it's not, it's not obvious. And I think like, you know, as I think about my career, the one, uh, you know, common thread through all the companies that I've worked at is that every company, we spent a lot of time trying to reorient people, people around value selling. Like Slack, it took multiple years. When we arrived, you know, the PLG motion, one of the deficiencies of a PLG motion is that, you know, value isn't really necessarily rooted in the sales process early on. You're trying to help facilitate the process. Um, so we had to sort of connect value selling to what a PLG motion looks like and connect the two, and it takes time. It's not obvious.

AI assessment note: “not enough business value or is not a strategic business outcome that warrants the amount”

Q Okay, so if we use that as a start point, we now know where SEs sit in the process. We know when to hire them. I need to hire them now. I got five to seven, and you're gonna help me hire my first. Thank you so much. How do I structure the hiring process for an SE?

A Uh, it's pretty simple. Like, I, I believe that, uh, you need to have, you know, a process that helps you get to know that person, of course, as well. There was something that we did at Slack. Which we haven't yet implemented at Rippling. I'm not sure if we will, uh, which is, uh, sort of a chronological interview. And it seems like it's a lot of time to spend, but we would spend an hour and a half going through a person's background job by job to understand their motivations, why they joined a company and why they left the company. You know, especially if you're in a lot of interviews, it's really difficult to get to know somebody and really get to know their motivations and the work they've done and whether or not Uh, you know, their resume is actually reflective of the impact that they've had over time. Um, so that was a really helpful exercise. That's not just unique to SEs, but that's something we did and I thought it was really effective and helped us get to know and hire really great people from basically zero to 200 across the board. And then you also want to have an opportunity for the demonstrate the craft because there's very much like part art and science in this role. Like you, deep expertise is important, but what's also important and what makes SEs the most successful is if They also are great presenters and can articulate value, so you need to give them an oppor…

AI assessment note: “spend an hour and a half going through a person's background job by job”

Q You, you mentioned value also. Quite a few times here. When we think about connecting value from your solution to the customer needs, what do you think are the biggest mistakes that you've seen founders and early stage teams make from many of your mentoring days and sessions?

A I think it's how making sure that the value is proportional to the investment that we require for that company to be successful. Like value is such a broad term, but sometimes you could say, yeah, of course this provides value. Like this is a solution that Provides day to day value for, uh, my end user, but an aggregate is not enough business value or is not a strategic business outcome that warrants the amount of money that have to spend to invest in a solution like that. Um, and it seems really simple, but it's not, it's not obvious. And I think like, you know, as I think about my career, the one, uh, you know, common thread through all the companies that I've worked at is that every company, we spent a lot of time trying to reorient people, people around value selling. Like Slack, it took multiple years. When we arrived, you know, the PLG motion, one of the deficiencies of a PLG motion is that, you know, value isn't really necessarily rooted in the sales process early on. You're trying to help facilitate the process. Um, so we had to sort of connect value selling to what a PLG motion looks like and connect the two, and it takes time. It's not obvious.

AI assessment note: “in aggregate is not enough business value or is not a strategic business outcome”

Q I totally agree with you in terms of getting more and more data from every interview and instance. I do want to move to post the hiring process now. We've got this incredible SE. We're very excited to have them in our startup. I've never onboarded before, though. Fuck. What's the ideal onboarding process for SEs, and how do I structure it?

A It's, I think, pretty simple. You obviously will have some sort of product training, depending on, you know, what stage of growth you're at. When we were at Slack, we sort of built it from, from scratch. They had Uh, some well-documented like product documentation, et cetera. We use something called work ramp. Um, there are many tools like it, uh, to walk, uh, a candidate through like a six week process where basically they have some self-service training to go through. They get exposure to a lot of customer calls and they get a lot of exposure to the ideal customer profile as well. And sort of a blend of both, I think is critical. Like it can be done in a lot of different ways. I don't think it takes a number of months to, to get somebody ramped depending on the Uh, the technical depth of a product, but, and it's very easy to just to put together, you know, a product training and enablement and onboarding, customer training, enablement and onboarding, and you want them coming out, understanding and feeling confident in how to present and demonstrate the product and confident in understanding the ideal customer profile and who the buyer is.

AI assessment note: “walk a candidate through like a six week process where basically they have some self-service training”

Q Zach, is outbound dead? Because in terms of sense making, you have to get them through a certain stage of the funnel to get to sense making. Is traditional outbound dead, do you think?

A Well, I, I, I do think it's amazing that we still use email to try to capture people's attention and how many LinkedIn messages I get with zero to little detail about a service that somebody is trying to provide or offer to me. And it's just, it boggles my mind. I'm definitely not the kind of person to call those people out on LinkedIn because I think that's, everybody's just trying to do a job and it's a really hard job. I don't think outbound is dead. I think outbound has just has fundamentally changed in terms of the methods that you need to use to engage prospects. And you have to take like a, uh, a multi-channel approach to that. You can, and it's as simple as, or can be as simple as, you know, creating different forms of content to capture people's attention in the way that they consume information today. Um, I've kind of thought about this in the past. It's kind of like a, a TikTok style approach to Uh, to selling. Like, you know, you and I, you know, we're gonna get off this podcast, or whenever you take a break, you're gonna look at your phone and consume about 16 different pieces of content and articles, and probably read half of those articles. Like, we don't have time to consume long-form content in the way that we did, but we're selling as if people have time to read these elaborate emails and pour through our website. We've got to capture their attention where the…

AI assessment note: “I don't think outbound is dead. I think outbound has just has fundamentally changed”

Q Zach, is outbound dead? Because in terms of sense making, you have to get them through a certain stage of the funnel to get to sense making. Is traditional outbound dead, do you think?

A Well, I, I, I do think it's amazing that we still use email to try to capture people's attention and how many LinkedIn messages I get with zero to little detail about a service that somebody is trying to provide or offer to me. And it's just, it boggles my mind. I'm definitely not the kind of person to call those people out on LinkedIn because I think that's, everybody's just trying to do a job and it's a really hard job. I don't think outbound is dead. I think outbound has just has fundamentally changed in terms of the methods that you need to use to engage prospects. And you have to take like a, uh, a multi-channel approach to that. You can, and it's as simple as, or can be as simple as, you know, creating different forms of content to capture people's attention in the way that they consume information today. Um, I've kind of thought about this in the past. It's kind of like a, a TikTok style approach to Uh, to selling. Like, you know, you and I, you know, we're gonna get off this podcast, or whenever you take a break, you're gonna look at your phone and consume about 16 different pieces of content and articles, and probably read half of those articles. Like, we don't have time to consume long-form content in the way that we did, but we're selling as if people have time to read these elaborate emails and pour through our website. We've got to capture their attention where the…

AI assessment note: “I don't think outbound is dead. I think outbound has just has fundamentally changed”

Q have been asked that before. Uh, but I, I, I want to ask, you know, you spent time at obviously Salesforce, you mentioned that, but also Slack, where you worked with many incredible people, Maggie being one of them. Incredibly tough, uh, question, but if you were to take away a single biggest takeaway from each of those experiences that really impacted your mindset, what would be one from each?

A You know, I thought about this. I, I think, uh, you know, the one common denominator across all of my experiences, uh, is the quality of people. And I would say also, while I've worked at some really successful companies, there's some companies that didn't love, live up to expectations. And I've learned just as much from those experiences as I did from Slack, Salesforce, and Box, et cetera. So, um, and I would say the common denominator is I've always followed great people. And, uh, that is a good proxy for understanding whether or not the company is going to be successful and is on the right trajectory is the quality of people you're surrounded with. And that's a common thing that I solved by followed throughout my career.

AI assessment note: “the one common denominator across all of my experiences, uh, is the quality of people”

Q Did you know they were super high quality straight away? One of the biggest mistakes I make in hiring, I fall for people who are good at selling themselves and then they're not actually that high quality. And then actually some people are quieter, but really high quality. And I miss them often.

A Yeah. Uh, that's, that's a really hard thing to do. And I think like it takes, you know, years of experience being around a lot of different people, making some good hires, making some bad hires. Um, but you know, I think about like the advice that I give to folks earlier in their career is to go someplace where you're surrounded by people that are smarter than you, but also people whom with you think you can collaborate effectively. Um, because the people that you work with are really what makes, make every single day tolerable. Um, it's all about the people. It doesn't matter how fast the company is growing, how great the technology is, how big the total addressable market. If you don't feel like you're learning from the people that you're surrounded with, then you're in the wrong spot.

AI assessment note: “advice that I give to folks earlier in their career is to go someplace”

Q have been asked that before. Uh, but I, I, I want to ask, you know, you spent time at obviously Salesforce, you mentioned that, but also Slack, where you worked with many incredible people, Maggie being one of them. Incredibly tough, uh, question, but if you were to take away a single biggest takeaway from each of those experiences that really impacted your mindset, what would be one from each?

A You know, I thought about this. I, I think, uh, you know, the one common denominator across all of my experiences, uh, is the quality of people. And I would say also, while I've worked at some really successful companies, there's some companies that didn't love, live up to expectations. And I've learned just as much from those experiences as I did from Slack, Salesforce, and Box, et cetera. So, um, and I would say the common denominator is I've always followed great people. And, uh, that is a good proxy for understanding whether or not the company is going to be successful and is on the right trajectory is the quality of people you're surrounded with. And that's a common thing that I solved by followed throughout my career.

AI assessment note: “the one common denominator across all of my experiences, uh, is the quality of people”

Q Did you know they were super high quality straight away? One of the biggest mistakes I make in hiring, I fall for people who are good at selling themselves and then they're not actually that high quality. And then actually some people are quieter, but really high quality. And I miss them often.

A Yeah. Uh, that's, that's a really hard thing to do. And I think like it takes, you know, years of experience being around a lot of different people, making some good hires, making some bad hires. Um, but you know, I think about like the advice that I give to folks earlier in their career is to go someplace where you're surrounded by people that are smarter than you, but also people whom with you think you can collaborate effectively. Um, because the people that you work with are really what makes, make every single day tolerable. Um, it's all about the people. It doesn't matter how fast the company is growing, how great the technology is, how big the total addressable market. If you don't feel like you're learning from the people that you're surrounded with, then you're in the wrong spot.

AI assessment note: “advice that I give to folks earlier in their career is to go someplace”