The Exchanges

Q Speaking of kind of leaning in and working with you as a partner, when you think about like driving them home to actually closing, how do you think about quite a challenging element, which is balancing hitting quarterly revenue targets with longer term pipeline and sales strategy? How do you think about that balance?

A I think the balance between hitting the quarterly number and building long-term pipeline For the, if it's an early stage company who absolutely needs that, that deal, You're probably going to need your leadership and executive support as a seller on your side to make it clear in the right tone to the prospect that this is an opportunity that would really help the company at that time. Uh, but it needs to be done in a tone that works for the customer. Uh, jamming deals at the end of the quarter is always kind of obnoxious, but, uh, it happens. Uh, it does work, but sometimes there is a detrimental effect to kind of Cramming deals at the end of the quarter, uh, from a brand standpoint and from a relationship standpoint. So, uh, you know, the magic in all this is the best reps are creating ample pipeline throughout the year, and they somehow have so much, you know, they create enough pipeline that they're able to hit their quarterly numbers without doing any, anything unnatural to get those deals in, because if one falls out, they've got another that comes in. So it's around really generating enough pipeline throughout the year so that you don't put yourself in that position. Um, now is that possible every time? Probably not, but, uh, for the most part over the long run, uh, pipeline covers all soon.

AI assessment note: “generating enough pipeline throughout the year so that you don't put yourself in that position”

Q Can I ask, what are the biggest mistakes that you see startups and startup founders make when it comes to discounting?

A For most startups, if you're in with procurement and you're not selling through PLG and through the website and swiping credit cards, so to speak, and you're in with procurement, that procurement agent knows that you're a startup, knows that you are, um, really keen on that revenue and that that revenue matters, and they're going to push you harder than they might other vendors. And what they're looking for is conviction on your side that you believe in the product, That you have an understanding of the business value and the ROI that it's going to provide, and they're looking for you to make a stand. So you'll face more pressure to discount, but I think procurement is looking for you to hold the line.

AI assessment note: “procurement is looking for you to hold the line”

Q Can I ask, what are the biggest mistakes that you see startups and startup founders make when it comes to discounting?

A For most startups, if you're in with procurement and you're not selling through PLG and through the website and swiping credit cards, so to speak, and you're in with procurement, that procurement agent knows that you're a startup, knows that you are, um, really keen on that revenue and that that revenue matters, and they're going to push you harder than they might other vendors. And what they're looking for is conviction on your side that you believe in the product, That you have an understanding of the business value and the ROI that it's going to provide, and they're looking for you to make a stand. So you'll face more pressure to discount, but I think procurement is looking for you to hold the line.

AI assessment note: “procurement is looking for you to hold the line.”

Q I think one thing that I've got wrong, Kevin, as a manager, honestly, I'm young, is I try to be people's friend, and I'm not your friend. Like, I am your boss at the end of the day, and I know we don't like hierarchies or boss, but like, you, you are someone's boss, and everyone has a boss. How do you retain that hierarchy, but also trust and proximity?

A So I think the word hierarchy is interesting. I think the employee really needs to appreciate that their manager has more on their plate, that their manager is dealing with a level of complexity that they may not have to deal with, right? If I go up and if I look at my manager, Cameron, he's got more on his plate than myself. And they need to appreciate that you've got a lot going on. And when you're with them, you're focused on in their world and what's important to them. But they need to, they need to have a sense for, if I was to take your job, here are the four or five things that I would need to ramp up to have a grasp on. If they feel like you're doing the same job as them, then you're in trouble, and the hierarchy is going to break down. So I think it's about how much Work role and responsibility that we're putting at every level so that people can be their best, and how do we ramp them into the next job, and do they have an appreciation for that there is a ramp? If they do, then I think hierarchy works, and there's an appreciation. Secondly, with hierarchy, I think you're not going to exercise hierarchy every day, but there are moments throughout the year where you have to be very direct with your employees on what the expectations are, and if they're not Meeting those expectations, you certainly need to deliver that news in plain speak, and they need to know where they…

AI assessment note: “hierarchy breaks down if the leader is not available or comfortable providing direct feedback.”

Q I mean, we're gonna dive into that later. I'm gonna pepper you with questions, so have no fear. We're gonna, we're gonna fully embrace that one. Final one, though, before we do dive in. Slack is such a hyper-growth story that you're, you know, core and central to. What was your biggest takeaway from your time at Slack, and how did that impact your mindset?

A Well, I think Slack coming a little bit later had the benefit of watching other companies go before us from that, that marriage of end-user love and virality and the enterprise posture. If you think about Slack, The power of Slack comes, the bigger the team and the more employees you can get engaged on that platform, the more value they drive to their customers. So Slack from day one had an appetite to work with large teams and large customers, uh, yet they had an incredibly engaging platform. So that ability to marry end user love with the enterprise posture right out of the gates, focus on large teams and all the security controls that were necessary there. Was something that was, uh, truly unique at the time and, uh, very enjoyable. It led to, as you said, hybrid growth.

AI assessment note: “ability to marry end user love with the enterprise posture right out of the gates”

Q I think one thing that I've got wrong, Kevin, as a manager, honestly, I'm young, is I try to be people's friend, and I'm not your friend. Like, I am your boss at the end of the day, and I know we don't like hierarchies or boss, but like, you, you are someone's boss, and everyone has a boss. How do you retain that hierarchy, but also trust and proximity?

A So I think the word hierarchy is interesting. I think the employee really needs to appreciate that their manager has more on their plate, that their manager is dealing with a level of complexity that they may not have to deal with, right? If I go up and if I look at my manager, Cameron, he's got more on his plate than myself. And they need to appreciate that you've got a lot going on. And when you're with them, you're focused on in their world and what's important to them. But they need to, they need to have a sense for, if I was to take your job, here are the four or five things that I would need to ramp up to have a grasp on. If they feel like you're doing the same job as them, then you're in trouble, and the hierarchy is going to break down. So I think it's about how much Work role and responsibility that we're putting at every level so that people can be their best, and how do we ramp them into the next job, and do they have an appreciation for that there is a ramp? If they do, then I think hierarchy works, and there's an appreciation. Secondly, with hierarchy, I think you're not going to exercise hierarchy every day, but there are moments throughout the year where you have to be very direct with your employees on what the expectations are, and if they're not Meeting those expectations, you certainly need to deliver that news in plain speak, and they need to know where they…

AI assessment note: “hierarchy also breaks down if the leader is not available or comfortable providing direct feedback.”

Q Can I ask you, Kevin, you've hired some of the best across many different organizations. Comp packages are pretty hard to understand if it's your first time, and to know what's good, what's fair. What have been some of your biggest lessons on effective comp package giving when rearing?

A Well, first, your comp plan needs to be fair, and there's plenty of market data out there that you can get to understand in my end range of market to provide a fair comp plan. I think when I'm closing a candidate, I'm, I'm interested, if I'm giving them a fair comp plan, Are they really interested in about the long-term journey of this company? Because this comp plan only represents this moment in time for the next year or two. Um, if we're both successful, the company will, um, increase in size. Our jobs will be different. Our jobs will be bigger. So what, how do they view the, the long-term journey at this company? And are they excited about the company and the journey, or is it about the comp plan? Sometimes if it becomes too much about the comp plan, then that's a red flag because it is It's really about a total rewards element, which is you're, you're joining a rocket ship, uh, you're gonna love this job, and it's gonna, you know, really benefit your career overall. So that's kind of what I'm looking for, but comp plans certainly need to be fair. If you're not providing a fair comp plan, you, you can't, uh, expect to hire the best.

AI assessment note: “your comp plan needs to be fair, and there's plenty of market data out there”

Q I mean, I'm glad you said about direct feedback. I heard that you were very good at providing direct feedback, which again is something that I honestly struggle with, um, and I like to avoid conflict. What would you advise founders on how to provide effective direct feedback?

A When I think of direct feedback, I think of it in terms of a ratio. So there's the day-to-day work that we're trying to get done. There's the challenges that we're facing, and we should be enjoying those challenges and having fun with it. Uh, but there's also times where we Need to get better, or we have our blinders on, and we need to be thinking more broadly, and it's the job of the manager to, to break that news, so to speak. Uh, but it, it is a, a portion of the relationship. It is not a constant, uh, feedback loop that's happening every day. It's a moment in time. People kind of dust them, you know, sit up a little bit straighter, dust themselves off, and off we go. We're back to more of a congenial, fun, working relationship, but Again, you can't be afraid to provide that feedback, and if you're not providing it, I think the employees sense that, uh, and they are disappointed when they don't get feedback, because it's something that everybody I've worked for is looking for.

AI assessment note: “When I think of direct feedback, I think of it in terms of a ratio.”

Q I mean, we're gonna dive into that later. I'm gonna pepper you with questions, so have no fear. We're gonna, we're gonna fully embrace that one. Final one, though, before we do dive in. Slack is such a hyper-growth story that you're, you know, core and central to. What was your biggest takeaway from your time at Slack, and how did that impact your mindset?

A Well, I think Slack coming a little bit later had the benefit of watching other companies go before us from that, that marriage of end-user love and virality and the enterprise posture. If you think about Slack, The power of Slack comes, the bigger the team and the more employees you can get engaged on that platform, the more value they drive to their customers. So Slack from day one had an appetite to work with large teams and large customers, uh, yet they had an incredibly engaging platform. So that ability to marry end user love with the enterprise posture right out of the gates, focus on large teams and all the security controls that were necessary there. Was something that was, uh, truly unique at the time and, uh, very enjoyable. It led to, as you said, hybrid growth.

AI assessment note: “ability to marry end user love with the enterprise posture right out of the gates”

Q I mean, I'm glad you said about direct feedback. I heard that you were very good at providing direct feedback, which again is something that I honestly struggle with, um, and I like to avoid conflict. What would you advise founders on how to provide effective direct feedback?

A When I think of direct feedback, I think of it in terms of a ratio. So there's the day-to-day work that we're trying to get done. There's the challenges that we're facing, and we should be enjoying those challenges and having fun with it. Uh, but there's also times where we Need to get better, or we have our blinders on, and we need to be thinking more broadly, and it's the job of the manager to, to break that news, so to speak. Uh, but it, it is a, a portion of the relationship. It is not a constant, uh, feedback loop that's happening every day. It's a moment in time. People kind of dust them, you know, sit up a little bit straighter, dust themselves off, and off we go. We're back to more of a congenial, fun, working relationship, but Again, you can't be afraid to provide that feedback, and if you're not providing it, I think the employees sense that, uh, and they are disappointed when they don't get feedback, because it's something that everybody I've worked for is looking for.

AI assessment note: “if you're not providing it, I think the employees sense that, and they are disappointed”