The Exchanges

Q founder. I've got us to kind of, um, should I create like word docs with like the script that I use, the core value props that I say to the different people within orgs? Should I record my calls on certain sales loft or whatever we're using? How can I document it for you coming in? So you can go, oh, I've got a treasure trove of, you know, potentials.

A I think the, I don't think it needs to be overly detailed. Like, the lift here, like, there, there's like an eighty-twenty value approach here, absolutely, of who are the folks that you've engaged with where there's just been an unlock. They get it. Like, I think in most companies, you find that there's going to be certain customers that just, that they got it from day one, they're off to the races, they're ripping. Analyze those. Don't take them for granted. Why? Like, what were the dynamics of the role the person was in, the, Phase of company that they're in. What are, what are the key identifiers that might be that map for where someone might want to spend their time proactively or pattern match what health is going to look like? And then how do you unpack ultimately your product experience, your onboarding experience, all the things that you would want? So like, how do you have the highest likelihood that someone is going to end up in that state, which you consider to be really healthy? So those usually are very, are bullet points. I think the recording of calls Is actually where the most value can be had. Um, and only because it's so rare in my experience that the founders are actually recording that and then making it available to the rest of the employee base because it's really personal and it feels intrusive at times. And it feels like, oh my gosh, like, did I even do …

AI assessment note: “I think the recording of calls Is actually where the most value can be had.”

Q So now we've hired this first person. We've gone through that process. They've accepted our offer. Fantastic. It's the first sales hires and I'm busy found. I'm fundraising as well. Uh, I rock up for first day. How do I do onboarding? What, what does that look like?

A So in my opinion, There's a, there's a sliding scale of how do you, how do you narrow eventually towards someone's core role and the core competencies of those roles? Most important thing is you are hiring someone in its most simple form, in my opinion, to be an ambassador and extension of your product and your brand. And for them to do that effectively, they have to understand what is the community that I've just joined? What do we stand for? And, you know, if we're using Loom, like, what does it mean to be a loom mate? Uh, which is what we refer to ourselves as, and I think that there's a huge part of how do you bring people in to understand the structure of the company, the mission, the values, um, how do you lead with a bunch of cross-functional conversations so they can get to know loom mates, in our case, from across all sorts of different functions. I think a fast follow to that is product evangelism requires product knowledge, and so how do we go deep on Enabling and teaching folks to be power users and have a deep understanding of not only what are we delivering from a product perspective, but almost more importantly, if we're going back to that workflow therapist analogy earlier on, um, what's your perspective on the workplace today? What, what are we, what are we seeing in terms of trends? What are we seeing in terms of experiences, um, that we are trying to lead peo…

AI assessment note: “how do you bring people in to understand the structure of the company, the mission”

Q What are some early signs that actually we hired a dud, sadly, and they're not very good? What are some of those early signs?

A I'd say you can, you can see it from a cross-functional engagement perspective. Those that are coming in that are great hires are asking really high quality questions, and they're not just asking them of their team. They're going on a frickin fact-finding mission cross-functionally, and they're building relationships to go and do it. And so I'd say those that have come in early and have had sustained success are just absolutely passionate about learning as much as they can around Not only the what, but the why and the why behind the way that we're architecting and building our product or the way that we're positioning and go to marketing. And so I'd say very, very early on, you can see the enthusiasm as well as the quality of the questions that are being asked. Uh, if you're seeing that those that are, that are treating their opportunities to be learning in a much more passive or just not pursuing them at all, those are major red flags early on.

AI assessment note: “treating their opportunities to be learning in a much more passive... major red flags”

Q I believe that founders should be the ones to create the first frameworks, to create the first stories, and to really be the creators of them. He said that actually they shouldn't be, and that it should be a sales leader, actually, that is brought in. Should it be the founder who creates the first frameworks, or is it okay for it to be brought in by a sales leader?

A I'd kind of call bullshit on the founder can't create it. Like, if you raised money, you started a company, and you have the capital to hire it, you're in sales. So you've already created that sales pitch. The question is, is it actually credible for folks that you are hiring that are not you, Mr. or Mrs. Founder? Can they deliver that message credibly? So I think the iteration then becomes what are the nuggets and what are the key value areas that have been uncovered during early customer wins or even losses? And then what are the ways that we want to package up those things for an early customer facing person to be able to run with? I think the ability for folks early days, so if you're a founder that's just hiring the first set of folks on your team, allowing them access to you pitching in some way, shape, or form. That can be you capturing it, or you having some sort of log of the conversations that you're doing, or actually taking the time to allow them to write shotgun on their onboarding experience, because there's so much that can be taken away from what is going to probably be perceived as Table stakes things that you've been saying for years that are actually going to be a huge unlock and highly applicable and inserted into the frameworks that that customer facing person is going to be able to reuse. And so don't discount the special sauce that you've practiced.

AI assessment note: “I'd kind of call bullshit on the founder can't create it.”

Q motion in one? Because you could have, you know, certain people in the organization saying, hey, we need the product team focused on referrals within app, within whatever, natural kind of growth tactics, much more product-led initiatives, and then you could have the enterprise rep saying, hey, we need RBAC, we need SSO, we need Yeah, enterprise requirements. Do you have that conflict given the, like, dual running of both?

A I don't say, conflict sounds like it's like this, and I think that the, the reality is, And I probably well skewed based on the organizations that I've selected into along the way, but the product leads everything. And the more compelling thing, in my view, if you're going up into the enterprise, having depth of engagement, having there be masses of folks that are gravitating towards your product, regardless of even talking to someone, and that being the statement of users speaking with their actions, That's going to fast track you through so many more enterprise conversations because of the conviction on value to the organization in the early days versus the unlock of. Are back or whatever it may be. You have to figure out a path then on. Okay. If that is the, the balancing act and you want to be doing both at what threshold as a. Product marketing and sales organization, are you all aligned on that? It becomes statistically significant if we want to put it that it's probably not even that regimented at what threshold does it tip us into? This is something that we need to be resourcing and road mapping in a more proactive way. Than what we've been doing in terms of core product innovation to date. And I think that that is always going to be. A trade off that has to be made if you were in a resource constrained environment, but ultimately it's also about like, what is your abil…

AI assessment note: “I don't say, conflict sounds like it's like this... product leads everything”

Q terms of like the product-led growth in the enterprise in tandem, when you advise startup founders today, given what you've seen in terms of what it takes to do both of them at the same time successfully, do you advise startups to not do them both at the same time? Or do you think startups can execute both the PLG and the enterprise heavier touch sale at the same time?

A I think it depends on the offering that you have, and so as an example, if I take Loom, uh, Loom has only had a sales team for two years at this point, so relatively nascent. Um, Loom has had customers and users, which we've been monetizing for more years than that, roughly four years. The product shift and strategy that we were making was moving from, you were only in previous, prior to a sales organization being here, able to Consume and use Loom as an individual. And then it wasn't until we were moving into there being a multiplayer team and company state where you're going to be expanding and looking at the use cases, but also the potential buyer personas that you're trying to go after expanding in a more significant way. And at that point, it makes sense to layer on. So if I'm reversing back what I just said, it's think about who is going to be involved in being able to make a decision of Is this applicable to me? And do I want to pay for this service? And if that individual can go and make that on their own or small teams can do it without inserting a human into the process, that will always be a more efficient path to acquisition. Uh, and so I think really when you're looking at your opportunity to move further and further up market, um, that's where you start layering in. Should we have selling capacity that is incremental and complimentary to what you have going on the…

AI assessment note: “I think it depends on the offering that you have”

Q So can you even get that data back in the pre-closed process?

A You're not going to get it every single time, and it's going to be, it's honestly going to depend on the relationship that you've built. I think our most successful reps are coming back in that situation where they're saying this thing pushed. And I had the opportunity and I asked why, and I got a real answer on why, and that could be. There are other things that are in the pipeline that took precedent, and here's the reasons that those took place. Uh, you get insights into what are the either. Decision making, political, whatever the dynamics are in terms of how things are prioritized at that company and you get better insight into how do we position and how do we work with that champion to move us to the top or higher up on the list that it is prioritized. Um, but that is really where you have to anchor in the relationships that you're building so you can have the candid conversations from there. Uh, I'd say if you're seeing reps on your team that are consistently getting the We're pushing, and when you ask why and how would we avoid it, and they haven't been able to go back and have those conversations, again, not saying you're going to be able to have it every single time, but if you are building deep relationships that are rooted in understanding your customer, understanding what is valuable to them, and understanding their priorities, you should have a higher hit rate on …

AI assessment note: “You're not going to get it every single time, and it's going to be”

Q How do we prevent that? Do we bring in the CPO and designers and devs into the hiring process as like a hiring panel? How do we integrate them to make it a more kind of holistic process?

A I personally, when I'm putting together panels, look for Who culturally has some of the most deep cross-functional relationships and the highest level of credibility across those folks? And how do I make sure that those people are inserted into our hiring panel? And I think the, the biggest thing that I'm looking for there is not necessarily this person is going to be filtering and looking at the sales competencies for this potential candidate. Um, Does this person pass the test on being able to build credibility with folks across the company? And is this person, um, going to be able to build those relationships? And I, I go back to my early days. Armando Mann is who hired me at, uh, at Dropbox back in the day. Um, he's been on an amazing journey since then at a few companies, most recently Hopin. And, you know, he sat us down early days at the, the lunch table, literally, because we're all in the office. He's like, The absolute best thing that you can do for your career is to sit at lunch every day with anyone other than the sales team. Go and make relationships with the product organization, the engineers, the folks that are here that are building, because guess what? They're all the ones that are about to go start a company in the next five to 10 years, and you being able to have those relationships, but also the context of what it takes to build in the early days is actuall…

AI assessment note: “how do I make sure that those people are inserted into our hiring panel?”

Q What are some early signs that actually we hired a dud, sadly, and they're not very good? What are some of those early signs?

A I'd say you can, you can see it from a cross-functional engagement perspective. Those that are coming in that are great hires are asking really high quality questions, and they're not just asking them of their team. They're going on a frickin fact-finding mission cross-functionally, and they're building relationships to go and do it. And so I'd say those that have come in early and have had sustained success are just absolutely passionate about learning as much as they can around Not only the what, but the why and the why behind the way that we're architecting and building our product or the way that we're positioning and go to marketing. And so I'd say very, very early on, you can see the enthusiasm as well as the quality of the questions that are being asked. Uh, if you're seeing that those that are, that are treating their opportunities to be learning in a much more passive or just not pursuing them at all, those are major red flags early on.

AI assessment note: “treating their opportunities to be learning in a much more passive or just not pursuing”

Q You know me, I never stick to schedule a boring shit. Um, how do you approach the product marketing challenge? Because you at Loom have the product-led growth side where, you know, end users love it in companies, but actually someone else pays for it, and so that's the problem of agency between buyer and consumer. How do you approach that today as a sales leader?

A I think it requires that you have An authentic curiosity to learn from your users, and how do you train and teach your Salesforce to take that discovery, take those learnings, and package them up both from the anecdotes and the stories that you're learning from the individual users that are finding value, and then the more broad ROI that, or impact that the business is going to be experiencing if they're making the investment at scale. And so I've used this term from my Quip days, and it was definitely parlaying that Dropbox learning to what are we doing at Quip? And, um, I refer to our early sales team as workflow therapists. Like, lay on the couch. Tell me all your problems. Like, let's understand, like, there has to be an innate reason of why has someone individually gone and signed up for your product and inserted it into their day, and how do you find the trend lines between those? How do you share those stories and make them applicable, but also Consumable, because you are learning the right vernacular that works for that company, that team, that department, and then how do you get your sellers really attuned at the different plays that you would have associated with that, depending on who you're talking to within the organization.

AI assessment note: “package them up both from the anecdotes and the stories... and then the more broad ROI”

Q motion in one? Because you could have, you know, certain people in the organization saying, hey, we need the product team focused on referrals within app, within whatever, natural kind of growth tactics, much more product-led initiatives, and then you could have the enterprise rep saying, hey, we need RBAC, we need SSO, we need Yeah, enterprise requirements. Do you have that conflict given the, like, dual running of both?

A I don't say, conflict sounds like it's like this, and I think that the, the reality is, And I probably well skewed based on the organizations that I've selected into along the way, but the product leads everything. And the more compelling thing, in my view, if you're going up into the enterprise, having depth of engagement, having there be masses of folks that are gravitating towards your product, regardless of even talking to someone, and that being the statement of users speaking with their actions, That's going to fast track you through so many more enterprise conversations because of the conviction on value to the organization in the early days versus the unlock of. Are back or whatever it may be. You have to figure out a path then on. Okay. If that is the, the balancing act and you want to be doing both at what threshold as a. Product marketing and sales organization, are you all aligned on that? It becomes statistically significant if we want to put it that it's probably not even that regimented at what threshold does it tip us into? This is something that we need to be resourcing and road mapping in a more proactive way. Than what we've been doing in terms of core product innovation to date. And I think that that is always going to be. A trade off that has to be made if you were in a resource constrained environment, but ultimately it's also about like, what is your abil…

AI assessment note: “the product leads everything. And the more compelling thing, in my view”

Q Final one for you, and it's just us on the line, so it's all cool. What's the number one, what's the number one reason why enterprises don't buy Loom this quarter?

A Well, I think broadly we're in a macro environment where everyone is just looking at spend across the board. If we take that off the table, I think that we at Loom are still in the very early innings of Showing up as a enterprise initiative, and when I say that specifically, it's we have so much momentum and goodness that's happening across the organic growth that we're seeing, the early customer base that we have, and this is always going to be that chasm crossing that we're going through, and so I'd say for us today, it's how do we actually educate on this category, and then how do we lead folks to understanding The value that they're going to be receiving, particularly in the enterprise. And I think for us, we're, we're still pushing on. What does that look for us like for us in the tens of thousands of employee organizations? Um, and how do we package up the goodness that we're seeing in smaller companies and bring it to them?

AI assessment note: “it's how do we actually educate on this category”

Q I'm fascinated to hear when we think about Salesforce and Dropbox, two such iconic companies, if we were to isolate like one or two takeaways for you from each, what would you say those are that really shaped how you think today as a sales leader?

A So I think Dropbox With it being a decently early pioneer, if we want to call it, on the product-led side of the house. I think the, the early learning for me, particularly as we were building the direct sales motion in tandem with the product-led side, is security is not enough. You need to find more value than just security when you're thinking about a consolidation plane. I think the learning for me along the way was we were really trying to take the density of user engagement And our, our de facto was going and selling to IT or CIOs around how do we roll this up and how do we protect the house, so to speak. Um, which when you put it in those terms, like, you're basically positioning your service as a liability as opposed to a value add. Uh, and effective in certain ways, but, you know, in a, a environment where I think that we have to make sure that we are continuing to Align with the goals of our customers, align with the impact, and particularly on the future of work side of things, like what are we doing to enable a more effective and efficient workforce? And so I think for me, really taking that lens, particularly when I went to Quip, which was my next opportunity, um, and really focusing on the workflow and the day-to-day engagement and impact, and then how do you roll up that positive, that additive Um, experience as a core part of your value prop. That was a key take…

AI assessment note: “That was a key takeaway for me for Dropbox.”