The Exchanges

Q You are very kind. I do want to start there with a little bit of Context and a little bit of stories in a succinct two to three minutes. Tell me, how did you make your way into the world of tech and come to lead some of the most powerful sales orgs? What was that entry point to where we are today?

A Well, sales is in my DNA. It has been in my DNA since being a very young person. I started selling ladies shoes in my father's shoe store during high school, put myself through college working at Nordstrom's, and then right out of college went into realm of professional sales, Working for ADP. ADP is one of the world's largest HRIS and payroll companies in the world, and I think ADP really was one of the first SaaS companies. So I got right into selling services, selling solutions for customers, and then in 1999, I joined this very small startup company called WebEx, helping people think very, very differently, and this very out there concept of convincing the world that video conferencing is the way to conduct work. Think about that from where we are today. I spent seven years there and finished my last three years leading North America and helping WebEx go through a very successful IPO and then a very successful acquisition by Cisco, which is where I got to meet some very special people in my life, including Eric Yuan, who is Zoom's CEO. I then got to spend seven years leading a very large part of Oracle's applications business and then joined RingCentral to help Transformed the world of PBX, moving phone systems off of premise and into cloud. I led global sales and customer success at RingCentral, and then that led me to two years ago where I got to rejoin my friend Eric Yua…

AI assessment note: “right out of college went into realm of professional sales, Working for ADP.”

Q we say about setting that culture, we actually need people to set a culture. And the question that I often have from founders is, Harry, do I hire a head of sales who will build the sales team and bring the reps, or do I hire one or two reps and feed it out gradually with more junior hires? How do you advise founders when they pose that to you?

A My lean, Harry, head of sales first, because I think a strong head of sales can do four things really, really well. First, they create that sales playbook that you asked about earlier, where the CEO is leading by example, but that head of sales goes Creates that playbook. You know, second, they can hire the team that is needed to succeed. And frequently, you know, with ambiguity on exactly what's needed. And then third, they can build the culture in sales that's needed to drive ownership. And then finally, and fourth, that head of sales can be very, very well aligned cross-functionally throughout the rest of the organization, working with marketing, helping make sure the demand gen engine is strong. Are there channel partners that need the The channel, a big part of the go to market, so working very closely in the channel and really helping keep sales fed early on. I lean this to a head of sales, but I do think it varies.

AI assessment note: “My lean, Harry, head of sales first”

Q You are very kind. I do want to start there with a little bit of Context and a little bit of stories in a succinct two to three minutes. Tell me, how did you make your way into the world of tech and come to lead some of the most powerful sales orgs? What was that entry point to where we are today?

A Well, sales is in my DNA. It has been in my DNA since being a very young person. I started selling ladies shoes in my father's shoe store during high school, put myself through college working at Nordstrom's, and then right out of college went into realm of professional sales, Working for ADP. ADP is one of the world's largest HRIS and payroll companies in the world, and I think ADP really was one of the first SaaS companies. So I got right into selling services, selling solutions for customers, and then in 1999, I joined this very small startup company called WebEx, helping people think very, very differently, and this very out there concept of convincing the world that video conferencing is the way to conduct work. Think about that from where we are today. I spent seven years there and finished my last three years leading North America and helping WebEx go through a very successful IPO and then a very successful acquisition by Cisco, which is where I got to meet some very special people in my life, including Eric Yuan, who is Zoom's CEO. I then got to spend seven years leading a very large part of Oracle's applications business and then joined RingCentral to help Transformed the world of PBX, moving phone systems off of premise and into cloud. I led global sales and customer success at RingCentral, and then that led me to two years ago where I got to rejoin my friend Eric Yua…

AI assessment note: “then in 1999, I joined this very small startup company called WebEx”

Q Do I hire a head of sales who will build the sales team and bring the reps, or do I hire one or two reps and feed it out gradually with more junior hires? How do you advise founders when they pose that to you?

A My lean, hairy head of sales first. Because I think a strong head of sales can do four things really, really well. First, they create that sales playbook that you asked about earlier, where the CEO is leading by example, but that head of sales creates that playbook. You know, second, they can hire the team that is needed to succeed. And frequently, you know, with ambiguity on exactly what's needed. And then third, they can build the culture in sales that's needed to drive ownership. And then finally, and fourth, That head of sales can be very, very well aligned cross-functionally throughout the rest of the organization, working with marketing, helping make sure the demand gen engine is strong. Are there channel partners that need, is the channel a big part of the go to market? So working very closely in the channel and really helping keep sales fed early on.

AI assessment note: “My lean, hairy head of sales first.”

Q the founder in, or like, you know, I remember with my media company when we sold ad slots, you know, they were bringing me in, but then it was like, Founder dependent sales, and I don't want a dependent sales model on me. It needs to scale. Is there ever a question of actually, it may be a nice fix, but it's not scalable. How do you think about that?

A Up until two years ago, I would agree with you. There are times you definitely do not, and either early times, or even in the more mature model, you don't. But giving away the Zoom secret sauce here a bit, I think as long as the founder knows how to properly Delegate and the founder can truly trust their team. I think keeping the founder in more than keeping them out is more beneficial. And the trust piece is a big part of it. We're big believers here at zoom in Covey speed of trust. Eric has given out that book to every employee in the company. We were all asked to read it. We've been asked to share things about it. And what I like about speed of trust, if Eric can trust me to make the right decisions, And I don't need Eric in every involvement, engagement, or I don't need Ryan Azuz, who is our CRO. I don't need them in every engagement to make decisions. We can make decisions a heck of a lot faster and solve for customers. You know, it really comes down to trusting the people that you bring in and them trusting you and not having the second guess decisions. You can run at a pace that others can't.

AI assessment note: “keeping the founder in more than keeping them out is more beneficial.”

Q we say about setting that culture, we actually need people to set a culture. And the question that I often have from founders is, Harry, do I hire a head of sales who will build the sales team and bring the reps, or do I hire one or two reps and feed it out gradually with more junior hires? How do you advise founders when they pose that to you?

A My lean, Harry, head of sales first, because I think a strong head of sales can do four things really, really well. First, they create that sales playbook that you asked about earlier, where the CEO is leading by example, but that head of sales goes Creates that playbook. You know, second, they can hire the team that is needed to succeed. And frequently, you know, with ambiguity on exactly what's needed. And then third, they can build the culture in sales that's needed to drive ownership. And then finally, and fourth, that head of sales can be very, very well aligned cross-functionally throughout the rest of the organization, working with marketing, helping make sure the demand gen engine is strong. Are there channel partners that need the The channel, a big part of the go to market, so working very closely in the channel and really helping keep sales fed early on. I lean this to a head of sales, but I do think it varies.

AI assessment note: “My lean, Harry, head of sales first, because I think a strong head of sales”

Q Can I ask, in terms of the process itself, like, how should we structure hiring these people? Is it like, first interview, intro, and like, are you any good? Second case study, third, final, and closing. How do you think about structuring the right process of hiring?

A This is something that I have brought from company to company, and something that I hold near and dear is, first, we talk to, you know, three to four people internally, and I identify the same three or four people as key stakeholders for whatever role that I'm hiring for, and so we do three to four interviews with internal folks that I've identified as, as the Key set of folks that we want feedback from. And then we do what we call is a stand and deliver. Candidate comes, we have no more than five to six people on the panel, but they join us either in person when that was a thing or via Zoom. They present. What's going to be telling in this is they're active listening in the process, listening to people's reactions, responses. How do they manage their time? What does their content look like? How do they organize their thoughts? You know, are they including specifics in their approach versus a generic 30, 60, 90 day plan, which we do ask them to put together, but are they engaging and answering maybe the surprise question? How do they react? Maybe when something goes wrong, technically with setup or, you know, something goes wrong and something didn't hit the way they wanted to hit. Then finally, and this is a controversial one out there on LinkedIn right now, but the thank you, you know, earlier I talked about out professionalizing The competition. This is another piece of prof…

AI assessment note: “first, we talk to, you know, three to four people internally”

Q quota, got my bonus, woohoo, how do you prevent them from going, sod it, I hit quota, I've done my job, I've got six days left of the quota, sod it, I'm just going to take it easy now because I've hit my quota. How do you still keep that fire of, I need to do more than my quota, I can do more. How do you make that work?

A Number one, you go back to what I said earlier, you hire the right people that have personal ownership, because just because they got there doesn't mean their team isn't there, or the company hasn't hit what they hit. You have to look for people that have that sense of it's bigger than just me. So not an easy thing to go find, but it's something you should be looking for in people. That's first. And then secondly, again, going back to how you set up the comp plan, To where the deal now is so much more valuable to me than if they close it the first day of the next period, I'm going to go manufacture away to go get that deal now rather than let it delay. And I think that's where an effective comp plan can help you achieve that. Setting up good, solid accelerators, multipliers. There's ways to do bonuses either inside the plan or outside the plan, but there's ways to turn dials through that comp plan to where people absolutely want to over.

AI assessment note: “hire the right people that have personal ownership”

Q Sorry, Mitch, I'm naive. What is speed to trust?

A Understanding that I'm going to trust my team. First of all, I've instilled all of the right company's core values. Instilled that the company's mission is clear and relayed to all of my employees, not just my head of sales. And then I have to be able to take a step back and trust that they are out there making good decisions, and I'm not second guessing those decisions. And if I don't have to second guess those decisions, And they can then go make those decisions on my behalf, as I'm the founder of the company, we can move at a lightning speed where if I had to inspect and investigate every decision that is being made, it bogs us down. So that is speed of trust. I will tell you, I have never felt more empowered to do right by customer than I have the last two years being head of sales for North America here at Zoom. I know That if I make a decision, and the decision is rooted in doing something right by my customer, then I have the full support of Zoom behind me, and I don't have to go through a bureaucratic engine to go get things approved. The trust is in me to make a decision. That's a very empowering feeling that I have never been as empowered in my career before.

AI assessment note: “So that is speed of trust.”

Q Can I ask, in terms of the process itself, like, how should we structure hiring these people? Is it like, first interview, intro, and like, are you any good? Second case study, third, final, and closing. How do you think about structuring the right process of hiring?

A This is something that I have brought from company to company, and something that I hold near and dear is, first, we talk to, you know, three to four people internally, and I identify the same three or four people as key stakeholders for whatever role that I'm hiring for, and so we do three to four interviews with internal folks that I've identified as, as the Key set of folks that we want feedback from. And then we do what we call is a stand and deliver. Candidate comes, we have no more than five to six people on the panel, but they join us either in person when that was a thing or via Zoom. They present. What's going to be telling in this is they're active listening in the process, listening to people's reactions, responses. How do they manage their time? What does their content look like? How do they organize their thoughts? You know, are they including specifics in their approach versus a generic 30, 60, 90 day plan, which we do ask them to put together, but are they engaging and answering maybe the surprise question? How do they react? Maybe when something goes wrong, technically with setup or, you know, something goes wrong and something didn't hit the way they wanted to hit. Then finally, and this is a controversial one out there on LinkedIn right now, but the thank you, you know, earlier I talked about out professionalizing The competition. This is another piece of prof…

AI assessment note: “first, we talk to... three to four people internally... And then we do what we call is a stand and deliver.”

Q to help founders understand how truly great sales leaders Think and operate. And the first thing that I want to start on, actually, maybe pre-sales team, but it's the question of, does the founder need to be the person who creates the first sales playbook, or can that first sales playbook be created by a head of sales or a sales rep that you bring in? What are your thoughts?

A Yeah, founder may not create the first sales playbook per se, but they are certainly leading by example on what they want done. You know, the founder sets the bar on the type of sales culture you Caring, competitive, cutthroat, combative, whatever culture they want to infuse and instill, they're the ones that set that culture, that set their sales go to market. And I feel like, you know, the sales team's gonna have to pull the founder into a lot of early customer interaction, especially at the beginning. Eric has led by example from the minute he started at Zoom up until I was on customer meetings with Eric as we closed the quarter. I've had the pleasure to work for some founders throughout most of my career. They have all been very, very involved from the onset. Setting the tone for the sales team, I think Eric has taken that to a whole nother level.

AI assessment note: “founder may not create the first sales playbook per se, but they are certainly leading”

Q In terms of the right moment, how do you think about, and I know it's tough because it does vary again, how do you think about when is the right Time for founders to start thinking about bringing that head of sales. Is it a millionaire? Is it much sooner? How do you think about that catalytic moment for the right time?

A I'm a data junkie. I love data. I think data leads us to really, really good, well-founded decisions. However, this is one of those rare times where I think feeling over fact might work. You know, there seems to be a tipping point where the CEO can no longer address certain things at the same time. Questions from customers, demand from prospects, Market conditions. And then as you get to a certain point, right, more complex buying decisions that need a great seller who can navigate the company's processes. I think it does vary and depends on contract size, right, on what the average deal size or ASP. I think you can make it past a million ARR, but then once you get past that, at least from what I see, it's time. I think you have to bring that head of sales.

AI assessment note: “once you get past that, at least from what I see, it's time.”

Q Now I'm with you. Okay, so we've got the profile, we've got those characteristics, we know how to uncover them, and yes, Mitch, I found them, I've done it, you as the advisor have helped me so much, now we need to onboard them. What should the ideal onboarding process look like for the new reps we've hired, and how should I structure that as the founder?

A Onboarding is such a critical part of a seller's journey. From a seller's journey perspective, you could only have two outcomes from onboarding, beyond ready to sell. It's number one, that they know in their head And their heart that they made the right choice for them to sell it at your company. So infusing that they know in their head and their heart that they made that right choice. And then number two, do they know how to be successful with the product or service and the processes that they have available to them at the company? It's interesting. There's a balance in onboarding. Onboarding new sellers needs to be a balance between enough product knowledge and skill master. You know, at Zoom, we have a month long onboarding process for all of our newest sales hire. Each week we focus on a topic. It's either product, it's either sales process, role-specific knowledge. We have done this now virtually for the past 19 months, and as you have seen Zoom's amazing growth, you know, we have grown not just in number of customers or revenue, we have grown, our company has doubled in size, and you know, our sales team has doubled in size. We have had to onboard remotely hundreds and hundreds and hundreds of people So doing this meaningfully during a remote experience is not an easy task, and we have done extremely well. I actually just did a session, what I call voice of the rep. I do …

AI assessment note: “we have a month long onboarding process for all of our newest sales hire”

Q Can I ask, in terms of the tasks, the processes, the duties, what would you expect new hires to perform in those first few months to set the foundations for them being successful in their role?

A Yeah, good question. So we definitely define what a seller should be able to do in a very clear, 30, 6090 day plan. And we spend a lot of time with our sales managers, ensuring that they Hold their teams to those plans. So if I'm a founder, I'm going to define what 30, 60, 90 day looks like, and then I'm hoping I'm going to have a head of sales because then she will infuse that with all of those reps. But these include things like prospecting, how to run proof of concept, how to truly do account planning, how to plan for a territory, how do you do a territory plan and territory management of that plan, product and pitch certifications. We do a lot of certifying here, and I did certifying when I was sales rep number 10 at WebEx, all the way to, you know, leading a thousand here. Really understanding the corporate pitch, the corporate story. Storytelling is a big part of it, and then we spent a lot of time on pipe creation and pipe conversion, and I think the biggest piece is you have to have these things documented out and know between enablement team and the sales management team who's doing what and why.

AI assessment note: “these include things like prospecting, how to run proof of concept, how to truly do account planning”

Q quota, got my bonus, woohoo, how do you prevent them from going, sod it, I hit quota, I've done my job, I've got six days left of the quota, sod it, I'm just going to take it easy now because I've hit my quota. How do you still keep that fire of, I need to do more than my quota, I can do more. How do you make that work?

A Number one, you go back to what I said earlier, you hire the right people that have personal ownership, because just because they got there doesn't mean their team isn't there, or the company hasn't hit what they hit. You have to look for people that have that sense of it's bigger than just me. So not an easy thing to go find, but it's something you should be looking for in people. That's first. And then secondly, again, going back to how you set up the comp plan, To where the deal now is so much more valuable to me than if they close it the first day of the next period, I'm going to go manufacture away to go get that deal now rather than let it delay. And I think that's where an effective comp plan can help you achieve that. Setting up good, solid accelerators, multipliers. There's ways to do bonuses either inside the plan or outside the plan, but there's ways to turn dials through that comp plan to where people absolutely want to over.

AI assessment note: “you hire the right people that have personal ownership... how you set up the comp plan”

Q Sorry, Mitch, I'm naive. What is speed to trust?

A Understanding that I'm going to trust my team. First of all, I've instilled all of the right company's core values. Instilled that the company's mission is clear and relayed to all of my employees, not just my head of sales. And then I have to be able to take a step back and trust that they are out there making good decisions, and I'm not second guessing those decisions. And if I don't have to second guess those decisions, And they can then go make those decisions on my behalf, as I'm the founder of the company, we can move at a lightning speed where if I had to inspect and investigate every decision that is being made, it bogs us down. So that is speed of trust. I will tell you, I have never felt more empowered to do right by customer than I have the last two years being head of sales for North America here at Zoom. I know That if I make a decision, and the decision is rooted in doing something right by my customer, then I have the full support of Zoom behind me, and I don't have to go through a bureaucratic engine to go get things approved. The trust is in me to make a decision. That's a very empowering feeling that I have never been as empowered in my career before.

AI assessment note: “we can move at a lightning speed where if I had to inspect”

Q How do you think about making the teams work so well together? Because you can often find the kind of Siloed. And then often, if you tie quota or achievements to certain things, they'll just focus on theirs and fuck enablement, whatever. How do you make them communicate efficiently?

A I mean, a big part of it is bringing them in. And what I mean by bringing them in is ensuring that, you know, they're sharing each other's plans. They're sharing each other's strategies in each other's meetings. And look, we don't like to just do meetings to have meetings, but you have to involve your cross-functional teams to With you, if you're going to be successful, I meet regularly every single week with my peer on the solution engineering side. I meet regularly every week with my peer and customer success. I meet regularly with my specialty sales leader. They are part of my quarterly business reviews. I'm part of their quarterly business reviews. So it isn't just I'm working on my thing. You're working on your thing. I know we both depend on each other. You have to really, really engage and bring them together and ensure that they're working that way together.

AI assessment note: “bringing them in is ensuring that, you know, they're sharing each other's plans.”

Q In terms of the right moment, how do you think about, and I know it's tough because it does vary again, how do you think about when is the right Time for founders to start thinking about bringing that head of sales. Is it a millionaire? Is it much sooner? How do you think about that catalytic moment for the right time?

A I'm a data junkie. I love data. I think data leads us to really, really good, well-founded decisions. However, this is one of those rare times where I think feeling over fact might work. You know, there seems to be a tipping point where the CEO can no longer address certain things at the same time. Questions from customers, demand from prospects, Market conditions. And then as you get to a certain point, right, more complex buying decisions that need a great seller who can navigate the company's processes. I think it does vary and depends on contract size, right, on what the average deal size or ASP. I think you can make it past a million ARR, but then once you get past that, at least from what I see, it's time. I think you have to bring that head of sales.

AI assessment note: “once you get past that, at least from what I see, it's time.”

Q Can I ask, in terms of the tasks, the processes, the duties, what would you expect new hires to perform in those first few months to set the foundations for them being successful in their role?

A Yeah, good question. So we definitely define what a seller should be able to do in a very clear, 30, 6090 day plan. And we spend a lot of time with our sales managers, ensuring that they Hold their teams to those plans. So if I'm a founder, I'm going to define what 30, 60, 90 day looks like, and then I'm hoping I'm going to have a head of sales because then she will infuse that with all of those reps. But these include things like prospecting, how to run proof of concept, how to truly do account planning, how to plan for a territory, how do you do a territory plan and territory management of that plan, product and pitch certifications. We do a lot of certifying here, and I did certifying when I was sales rep number 10 at WebEx, all the way to, you know, leading a thousand here. Really understanding the corporate pitch, the corporate story. Storytelling is a big part of it, and then we spent a lot of time on pipe creation and pipe conversion, and I think the biggest piece is you have to have these things documented out and know between enablement team and the sales management team who's doing what and why.

AI assessment note: “these include things like prospecting, how to run proof of concept, how to truly do account planning”

Q Now I'm with you. Okay, so we've got the profile, we've got those characteristics, we know how to uncover them, and yes, Mitch, I found them, I've done it, you as the advisor have helped me so much, now we need to onboard them. What should the ideal onboarding process look like for the new reps we've hired, and how should I structure that as the founder?

A Onboarding is such a critical part of a seller's journey. From a seller's journey perspective, you could only have two outcomes from onboarding, beyond ready to sell. It's number one, that they know in their head And their heart that they made the right choice for them to sell it at your company. So infusing that they know in their head and their heart that they made that right choice. And then number two, do they know how to be successful with the product or service and the processes that they have available to them at the company? It's interesting. There's a balance in onboarding. Onboarding new sellers needs to be a balance between enough product knowledge and skill master. You know, at Zoom, we have a month long onboarding process for all of our newest sales hire. Each week we focus on a topic. It's either product, it's either sales process, role-specific knowledge. We have done this now virtually for the past 19 months, and as you have seen Zoom's amazing growth, you know, we have grown not just in number of customers or revenue, we have grown, our company has doubled in size, and you know, our sales team has doubled in size. We have had to onboard remotely hundreds and hundreds and hundreds of people So doing this meaningfully during a remote experience is not an easy task, and we have done extremely well. I actually just did a session, what I call voice of the rep. I do …

AI assessment note: “Each week we focus on a topic. It's either product, it's either sales process, role-specific knowledge.”

Q How do they say it wrong? If you were interviewing me, what things would make you go, oof,

A Yeah, it's a good follow on. I feel like it's more of you get some of the flippant answers. You get some of the generic answers. The gold is in the second and third level questions too. You know, really asking them the meaning, like share how that happened. Share what you felt like when perhaps that deal didn't go your way or back to, you know, personal ownership. Share with me when you were at the end of a closing period, month, quarter, fiscal year, And you were already well past your number, but the team needed the extra deal. So share with me what you did, how you acted, how you acted around others around you to pull them up with you, and then getting the answers that are people are coming across. You can feel if they're being genuine or if they are being textbook or flippant. People that quote a lot of things from books, and here I am talking to you about speed of trust, but I feel like when I did speed of trust, you heard me come across, I hope, feeling genuine about what I take away from that and how I apply it. Those are all things that I look for.

AI assessment note: “you get some of the flippant answers. You get some of the generic answers.”

Q How do they say it wrong? If you were interviewing me, what things would make you go, oof,

A Yeah, it's a good follow on. I feel like it's more of you get some of the flippant answers. You get some of the generic answers. The gold is in the second and third level questions too. You know, really asking them the meaning, like share how that happened. Share what you felt like when perhaps that deal didn't go your way or back to, you know, personal ownership. Share with me when you were at the end of a closing period, month, quarter, fiscal year, And you were already well past your number, but the team needed the extra deal. So share with me what you did, how you acted, how you acted around others around you to pull them up with you, and then getting the answers that are people are coming across. You can feel if they're being genuine or if they are being textbook or flippant. People that quote a lot of things from books, and here I am talking to you about speed of trust, but I feel like when I did speed of trust, you heard me come across, I hope, feeling genuine about what I take away from that and how I apply it. Those are all things that I look for.

AI assessment note: “You get some of the flippant answers. You get some of the generic answers.”

Q I mean, in this respect, you've known Eric for 20 years. You are a very wise, seasoned sales leader. When you're hiring twenty-five-year-olds, thirty-year-olds, you name it, and you don't have that long-term relationship, and they're less It's bluntly mature. Is it difficult to scale that incredibly deep trust that one has with, you know, for longer, more mature people? Do you know what I mean? Is it hard?

A Yeah, no, it's a great point, and of course, you have mechanisms and processes put in place. There are guardrails that if guardrails are reached, then they're triggers people having to help make those decisions, but there are less guardrails here than I have seen before, or the guardrails are set up So thoughtfully where we just don't get bogged down in a lot of bureaucracy. So it's a great question. And yes, we've got plenty of sales reps that are early on in their career, but I feel like even giving them the ability to know that we trust them to go run their processes, know that we're here for them. And we are definitely a leadership team that rolls up our sleeves and gets Intimately involved, but no, they feel they are trusted to, again, do right by customer. But of course, there will be times and places where there are checks and balances, but, you know, we're very careful not to bog ourselves down in that too much.

AI assessment note: “giving them the ability to know that we trust them to go run their processes”

Q Now, you're going to be my advisor here. Hypothetically, I'm this young, first-time founder. I'm hiring my sales team, and I've got my sales team. How do the best founders set sales culture? Is it about repeating missions, and how do I know what's the sales culture that I want, and then how do I instill it effectively?

A I mean, some of it comes from what your product or your service is and who you're touching. And founders are very in tune, right, with, and hold that, that product, that service, that market, you know, very close, near and dear. But then I feel like, look, they need to understand their product fit, their market fit. And then I think that determines, you know, what they want to do with their team and what type of team they want to bring in. Some of it has to do with their competitive landscape. Who are they competing against? You know, what does that competitive landscape look like out there? Some of that has to do with, you know, geographic boundaries. Where are their customers most? And that will determine a little bit on culture because selling, and I've had an opportunity to lead global sales teams, different cultures around the world. I think there's a lot of different factors that they have to take in mind as they then want to determine, you know, what that culture looks like.

AI assessment note: “I think there's a lot of different factors that they have to take in mind”

Q I mean, in this respect, you've known Eric for 20 years. You are a very wise, seasoned sales leader. When you're hiring twenty-five-year-olds, thirty-year-olds, you name it, and you don't have that long-term relationship, and they're less It's bluntly mature. Is it difficult to scale that incredibly deep trust that one has with, you know, for longer, more mature people? Do you know what I mean? Is it hard?

A Yeah, no, it's a great point, and of course, you have mechanisms and processes put in place. There are guardrails that if guardrails are reached, then they're triggers people having to help make those decisions, but there are less guardrails here than I have seen before, or the guardrails are set up So thoughtfully where we just don't get bogged down in a lot of bureaucracy. So it's a great question. And yes, we've got plenty of sales reps that are early on in their career, but I feel like even giving them the ability to know that we trust them to go run their processes, know that we're here for them. And we are definitely a leadership team that rolls up our sleeves and gets Intimately involved, but no, they feel they are trusted to, again, do right by customer. But of course, there will be times and places where there are checks and balances, but, you know, we're very careful not to bog ourselves down in that too much.

AI assessment note: “of course, you have mechanisms and processes put in place. There are guardrails”

Q but I'm going to ask it anyway because I'm too intrigued. I'm a founder setting quota now for the first time. I'm ambitious. I see huge market. I see huge opportunity. How do you think about how to set a quota that is both ambitious, but also achievable where people are not feeling completely terrified or demotivated if they don't hit it? How do you think about that right balance?

A Sales reps want to feel like they are winning. They want to feel, they want to go home at night, and they want to sit down at the dinner table and look across at their family or significant other and feel like they won today. And it's really important to set up the rule of the game, be it quota, to where they can not only achieve, but overachieve. A lot of that then dovetails, Harry, into the comp plan, because the comp plan can then be an equalizer for But I feel like a sales rep has chosen this profession because they are the ones that are the 10 Xers. They want to win. You have an opportunity when you set up quota and your comp plan to ensure your number is achievable enough where people can go beyond the number and get into multipliers and accelerators. Sales reps are going to feel like if I'm just doing everything I can, I'm coming to the end of a closing period And I just don't see the finish line. There is an innate feeling emotion that will say, you know what, I'm going to give up and I'm going to go attack it again the next period. But if I'm going into that closing period and I'm right at the number and I see at 110%, 120%, 150%, there is a another, you know, echelon for me to get to. I'm going to run through walls. So I think it's a great question you ask. I think it's a really important one is setting up the rules of the game for people to You're going to make a bet…

AI assessment note: “ensure your number is achievable enough where people can go beyond the number and get into multipliers”

Q but I'm going to ask it anyway because I'm too intrigued. I'm a founder setting quota now for the first time. I'm ambitious. I see huge market. I see huge opportunity. How do you think about how to set a quota that is both ambitious, but also achievable where people are not feeling completely terrified or demotivated if they don't hit it? How do you think about that right balance?

A Sales reps want to feel like they are winning. They want to feel, they want to go home at night, and they want to sit down at the dinner table and look across at their family or significant other and feel like they won today. And it's really important to set up the rule of the game, be it quota, to where they can not only achieve, but overachieve. A lot of that then dovetails, Harry, into the comp plan, because the comp plan can then be an equalizer for But I feel like a sales rep has chosen this profession because they are the ones that are the 10 Xers. They want to win. You have an opportunity when you set up quota and your comp plan to ensure your number is achievable enough where people can go beyond the number and get into multipliers and accelerators. Sales reps are going to feel like if I'm just doing everything I can, I'm coming to the end of a closing period And I just don't see the finish line. There is an innate feeling emotion that will say, you know what, I'm going to give up and I'm going to go attack it again the next period. But if I'm going into that closing period and I'm right at the number and I see at 110%, 120%, 150%, there is a another, you know, echelon for me to get to. I'm going to run through walls. So I think it's a great question you ask. I think it's a really important one is setting up the rules of the game for people to You're going to make a bet…

AI assessment note: “if you set it too high, people will give up and wait”

Q I find is like very often we both know enterprise contracts can take nine months, 12 months, 18 months to sign. If I'm a founder with my new sales team and we're in enterprise, three months in, four months in, they haven't sold anything, but it's just a process. How do you know if they're good or it's just a very long process and how long do you give them?

A So that's a big question. It depends on a set of key factors. Average deal size, selling model, what your selling model is. It does depend on the overall quota being set. Like, you know, what is the quota and are you running a quarterly quota? Are you running a six month quota? Are you running an annual quota? Are you running a monthly quota? I think it also depends, Harry, on what's shifting in the market. It seems like the one whale deal that a rep sells to make their number. Look, too many reps will put all their eggs in, you know, one basket. And if that basket turns up empty, they're hosed. Their team is hosed. In some cases, the company can be hosed. So there has to be mechanisms to balance, you know, how many, I'll give you a baseball analogy, right? How many triples and home runs do you have versus managing the singles and the doubles at the same time? You know, also, I think, you know, many companies are land and expand and retain, right? That's their model. Smaller price points to start the expand along the way. So I think that is also another factor in this and small wins along the way, but larger wins are going to take six to nine months. But I think there's a lot of dependencies there.

AI assessment note: “It depends on a set of key factors. Average deal size, selling model”

Q to help founders understand how truly great sales leaders Think and operate. And the first thing that I want to start on, actually, maybe pre-sales team, but it's the question of, does the founder need to be the person who creates the first sales playbook, or can that first sales playbook be created by a head of sales or a sales rep that you bring in? What are your thoughts?

A Yeah, founder may not create the first sales playbook per se, but they are certainly leading by example on what they want done. You know, the founder sets the bar on the type of sales culture you Caring, competitive, cutthroat, combative, whatever culture they want to infuse and instill, they're the ones that set that culture, that set their sales go to market. And I feel like, you know, the sales team's gonna have to pull the founder into a lot of early customer interaction, especially at the beginning. Eric has led by example from the minute he started at Zoom up until I was on customer meetings with Eric as we closed the quarter. I've had the pleasure to work for some founders throughout most of my career. They have all been very, very involved from the onset. Setting the tone for the sales team, I think Eric has taken that to a whole nother level.

AI assessment note: “founder may not create the first sales playbook per se, but they are certainly leading”

Q I find is like very often we both know enterprise contracts can take nine months, 12 months, 18 months to sign. If I'm a founder with my new sales team and we're in enterprise, three months in, four months in, they haven't sold anything, but it's just a process. How do you know if they're good or it's just a very long process and how long do you give them?

A So that's a big question. It depends on a set of key factors. Average deal size, selling model, what your selling model is. It does depend on the overall quota being set. Like, you know, what is the quota and are you running a quarterly quota? Are you running a six month quota? Are you running an annual quota? Are you running a monthly quota? I think it also depends, Harry, on what's shifting in the market. It seems like the one whale deal that a rep sells to make their number. Look, too many reps will put all their eggs in, you know, one basket. And if that basket turns up empty, they're hosed. Their team is hosed. In some cases, the company can be hosed. So there has to be mechanisms to balance, you know, how many, I'll give you a baseball analogy, right? How many triples and home runs do you have versus managing the singles and the doubles at the same time? You know, also, I think, you know, many companies are land and expand and retain, right? That's their model. Smaller price points to start the expand along the way. So I think that is also another factor in this and small wins along the way, but larger wins are going to take six to nine months. But I think there's a lot of dependencies there.

AI assessment note: “So that's a big question. It depends on a set of key factors.”