YouSaid · the spoken record

Sam Taylor

lines on the record: 55
first: 2022-07-20
most recent: 2022-07-20
sittings or episodes: 1
sources: podcast

Every line below is reproduced as it was said and linked to the record it came from. Nothing here is summarised or generated. Directory · Search · Corrections

“It's close to home. My wife, Kate, who you've chatted with in the past, is over at Notion, and I think that Notion has done an amazing job of unlocking and unleashing the power of their community as a way to compound not only their growing user base, but the ecosystem that they're building in terms of monetization. I think community is a huge part of what they're doing and something I'm taking notes on.”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“I think we're still fighting the potential misalignment between what I just said is the most important thing at the top of this rapid fire, which is like your genuine curiosity and customer understanding and value that you're driving for them. And the way in which sales can be perceived, particularly on the coin ops side of things, of just here for the paycheck. So how do we do away with the latter and how do we be there be a celebration of what we're learning in uncovering and the value that we're driving? So it's a perception on sales.”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“It's all about relationship building cross functionally because if you're delivering feedback or if there's things that you have conviction that you've learned that you want to be doing from a go-to-market perspective, but it's falling on deaf ears or you don't have the credibility to deliver that in the right way, you have to go deep on those relationships. At Loom, my partnership with Anik, who is our VP of product and us being on the same page around what are we learning, how are we approaching? How are we thinking about the trade-offs? How do we be in the boat together on going and building a business across our different funnels and go to market motions? That unlocks so much efficiency and speed in what we're doing. So as you're taking that approach, then your job is to also learn how to be a translator coming in. And this is probably a longer answer than the quickfire that we're saying, but a wholeheartedly believe that a huge part of success early days is being able to take what you're seeing from the customer and find the right ways to articulate it to the different parties within the company.”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“Not being intentional into the integration with the rest of the company? How do we make this be an unlock and a superpower and learning engine for the company, as opposed to it ending up being kind of an orphaned function?”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“I think with all the automation that's taking place, particularly on the mostly email side, I think there's just an exhaustion around email today, trying to find ways to cut through that noise in different more compelling ways.”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“The genuine and authentic curiosity in understanding your customers' needs is the consistent. Like how does that play into your discovery? How does that play into your approach? If you are going deep and being extremely focused on adding value to your customer, that is”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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. 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 still pushing on what is that like for us in the tens of thousands of employee organizations and how do we package up the goodness that we're seeing in smaller companies and bring it to them.”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“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 that, in my opinion.”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“You're not going to get it every single time. 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. 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. 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. I'd say if you're seeing reps on your team that are consistently getting the we're pushing and when you ask well why and how will 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”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“Ultimately, you are having to go through the process when you're doing that postmortem on why wasn't it a priority? And you could argue that that is ultimately what sales is, is how do you take something that is not a priority and find a path to making it one?”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“Did or did not end up resonating in a way that we want to learn from as a group. I think the amazing part that I've seen with our team at Loom is that who is sitting on that invite? It is not segment specific. And so we invite sellers, CSMs, whoever it may be are free to attend. We also use it as an opportunity to invite members of the product organization as well, particularly those that are building in service of our move up market so they can get more nuance and context and have the ability to ask questions as well.”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“So I'd say iterative for us as we've scaled the team just because we've moved from being, there are being four sellers a year and a half ago. We can all just sit in the proverbial Zoom room and break it down together to broader cross-functional teams. And so we put the cadence is being driven by the segment leaders. So whether it be our commercial sales leader, our enterprise sales leader. I think the person that we want driving the conversation is absolutely the deal team that was involved. The cadence with which we're doing it at this point is bi-weekly. The thing that we are really anchoring on for us is it's both deal review but also postmortem. And I think that we have to celebrate is probably too far of a term, but it's like we're all going to be making mistakes and we're not going to bat a thousand. You look at average close rates and healthy ones being in the 30 something percent range. You're not closing them all. So how do you reverse engineer why? And what are the potential things that we could have done differently or what are the things that ultimately”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“Hearing both the blemishers as well as the praises of the product on a daily basis and typically at a much higher volume than any other customer facing team. So how do we go and point these folks to the right wealth knowledge?”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“We literally give people a list of cross functional folks that should be on their, we refer to as a listening tour. And we also give prompts of not for each person by function, but just what are the types of themes or types of questions that you should feel emboldened to ask that person. An example of that would be like, hey, if you're talking to someone on the product side, tell me about the way that you're approaching milestones and roadmapping. How do we have inputs into those? What are the ways that you're being influenced by the customer? And how can I think about packaging up my learnings in the most effective way so it can be consumed well by you? Those sorts of things. And we make sure that that spans OG early engineering talent folks that are going to be within kind of the broader go-to-market between our PMM team, our operations team, different parts of the sales organization. I think a center of absolute unbelievable treasure trove of knowledge sits within a support organization if you have one just because they're”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“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 freaking 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, just absolutely passionate about learning as much as they can around not only the what, but the why, the why behind, the way that we're architecting and building our product or the way that we're positioning and go to marketing. I'd say very, very early on you can see the enthusiasm as well as the quality of the questions that are being asked. If you're seeing that those 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.”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“A coverage ratio perspective that aligns to the ramp schedule that we've given you, just because those deals statistically are going to be more in the six month to nine month range and you're probably not going to be having significant ARR that's retired until that point.”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“Broadly, I look at this from a segment perspective because you're going to have different deal cycles and different expectations. Our commercial business, for example, like our S&B reps are in the roughly 45-day window for average deal time, which means if you're getting your first customer conversations, there's going to be a bit of an inefficiency early and upfront as you're building that early pipeline, so to speak. You're roughly in a 2x deal cycle time frame of like within the first 90 days, you should start to see deal flow. Realistically, within the first 60 days, you should have some later stage pipeline that's sitting at pricing negotiation or aligning to the right buyer personas internally. I think for the enterprise, you're going to have a lot more extended time that's there, which means that the expectation is going to be much more on the leading indicators, like how much progress are we making in terms of multi-threading into your accounts, what early commitments are we getting in terms of PyON engagement, structuring criteria there, what is our path to you starting to put yourself in a place from”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“Absolutely. There's something ceremonial about getting through the fire, so to speak, of validating your readiness to talk to customers in front of your peers and in front of a cross-functional group. I also just think there is a huge benefit early and upfront of building a culture of coaching and being open to feedback and cherishing that feedback. We have all of our folks within the first, they usually have their first week, which is going to be much more of the company and cross-functional as we get into their second, third, and fourth weeks, very much going to be more tactical around what are we doing in terms of the motion with the sales team today. We accelerate that. So usually by the end of the second week that someone's here, they are doing a full demonstration as well as running a mock discovery. We solicit feedback from not only the folks that they are aligned to in terms of their onboarding buddies, but also a broader swath of the team so they can get feedback as well.”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“We're going back to that workflow therapist analogy earlier on. What's your perspective on the workplace today? What are we seeing in terms of trends? What are we seeing in terms of experiences that we are trying to lead people towards? And I think in our case in the industry that we're in, there's actually a pretty healthy blending right now of people understand as it relates to Loom, of sure, I can click on the icon of the desktop and hit record and get a 321 countdown. I'm going. When should I do it? Why should I do it? And how does that actually layer into modern work? How does that actually get us to a place where we're talking more about employee empowerment, flexibility, the cultural as well as efficiency benefits that you're going to get by embodying that as an organization? And so for us, we have to equip our sellers with how do we talk about the industry? How do we talk about why Loom fits into the trends that are happening today? And then ultimately, how does our product ultimately get into being in service of those things over time?”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“So, in my opinion, there's a sliding scale of 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? We're using Loom. Like, what does it mean to be a Loomate, 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? How do you lead with a bunch of cross-functional conversations so they can get to know Lumates in our case from across all sorts of different functions? A fast follow to that is product evangelism requires product knowledge. 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,”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“Of both revenue but also the input metrics that we would expect folks to do just because we were trying to build those customer learnings early on. And so I'd say don't lean too heavily into standard variable compensation just for the sake of it. I'd say give yourself the time to actually build an informed data opinion on why those targets should be what they should be and why you would expect someone to ramp at the rate that they're ramping.”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“I think variable compensation is an excellent lever at the right time. And I don't think the right time is going to be your first couple of hires because you got no data. And if we're looking statistically at someone having between 50 and 30% of their compensation tied to these outcomes and you have no idea what's possible or repeatable from an outcome perspective, that feels misaligned. I think a way that you can continue to bring folks in that have upside of some kind is how do you structure different incentives that aren't just revenue focused. Earlier on in the process as you're continuing to build that conviction of what the target should be. For me, Equip early days, we had compensation models that were very loose in terms of you were mostly base salary, but you would share an upside as you would go and perform at certain levels, but your base was enough that you should be able to live in San Francisco and be a productive member of this company. And then even early days here at Loom, it was a combination.”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“One, not having clarity on what they want early on. Like, what is the actual goal of this role and having conversations early on, I'll see it span everything from we need someone to help us figure out our entire go-to-market approach because this is going to be the first air quotes go-to-market hire. Or on the flip side, it's we want this person to come in and build an outbound motion because we got the product thing already taken care of. And by having either too wide of an aperture or too narrow, you can't have it all. So I think that you just need to have really clear conviction around what it is that you're hiring for, why, and then how do you structure both the questions that you are going to be asking individually, the filters with which you're looking at these candidates through, and then ultimately the focus areas if you have a cross-functional panel of what are the key things that you want to be dividing and conquering on in each conversation so it doesn't just end up being a repetition of the conversation before.”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“Sessions throughout that interview day. And so you're short circuiting some of the relationship building and context building, which I think is beneficial for our panel as well.”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“We're dog fooding hard, and so people are submitting looms for that to us. But then also, we get into more tactical sales management principles approach and how they would think about structuring the accountability for their team. And the flip side of it of how do you start to move us from early days squishy in terms of process to how do you help us transition and work towards not necessarily a full machine, but definitely more of a funnel view of the business. By giving those prompts ahead of time and allowing people to do it, but also time boxing, like we say, you got five minutes tops to deliver this information. We don't want this to be dissertation that you're going forth and bringing back to us. We found that that pairing gives us insight into what's this person look like in terms of polish when they've got time on their side to prepare, but also frankly with video as a medium, we just start to see a lot around the communication style skills, et cetera. And the entire panel, assuming that they pass, is able to consume those looms prior to them joining for the live cycle.”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“Go away Not in real time. And I think that that is something where if you're going to give someone the expectation that they are doing something on the fly, you owe it to them to have that be in a subject matter area that they have deep expertise and context, their existing role, existing company, whatever it may be. Many founders and many companies I see, they want to use the learning opportunity for things that they are navigating as an organization. So it's value add in terms of the conversation regardless of outcome. You can learn something in every conversation. But many times trying to ask somebody to solve your company's problems on the fly in real time is broadly not setting anybody up for success. We do something called take-homes and it sits in between the initial hiring manager screen and the on-site panel. We give folks, if you're in a sales leadership role, for example, that we're hiring for, it will probably be a couple of prompts between how do you think about building culture, building rapport, and investing in your team. Let's talk about your leadership philosophies. And of course,”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“Sure. You could have it be customer objections. We'll use Lum as an example. Someone is consistently telling us, or our customers are consistently telling us they're not comfortable recording, whatever, making something up. And we want to figure out the right way to think about our go-to-market, but also our product and our marketing initiatives to go and tackle this common objection. Like, how would you think about giving us that feedback? So it gives them an opportunity of like to set the table and deliver the feedback, but then also how do you structure a discussion around the go forward path. Now we're getting into something that would be applicable for someone that's really”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“I don't like case studies because I think they're overly structured. What I do like is the opportunity for someone to show you how they work or how they think. Depending on the phase or role that you're hiring for, if you've got someone that is going to be working heavily cross-functionally, I would include a working session with that person. And in this situation, you would give them a prompt. You could argue as a case study, but ideally it's something that's much more of a, here's a problem that we're trying to tackle. We are not going to give you a ton of information, but we want you to guide a discussion between us of like, how do we start to problem solve and work through this together? That would be one.”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“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 ten years, and you being able to have those relationships, but also the context of what it takes to build in the early days is actually the most important thing that you can learn and build a muscle on. And I think that if you take that ethos of really a filter that I'm looking for for early customer facing teams is can you sit at that virtual or physical lunch table and be the only person potentially that's actually in a customer facing role? Are you going to have the EQ, the product enthusiasm, and the mission alignment that everyone else does that's going to create those bonds and have a healthy culture at that point?”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“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? The biggest thing that I'm looking for there is not necessarily that this person is going to be filtering and looking at sales competencies for this potential candidate. Does this person pass the test on being able to build credibility with folks across the company? And is this person going to be able to build those relationships? And I go back to my early days, Armando Man is who hired me at Dropbox back in the day. He's been on an amazing journey since then at a few companies most recently hop in. And he sat us down early days at 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.”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“Going to be another member, like, there should be a very much 50 50 split in terms of time of getting to know one another and filling out the two-way street that is like, do you seem to be a fit and have the right filters that we are looking for in terms of your experience? But also on the flip side, like there's a decent amount of selling in the early days of why should this candidate take a risk on you and your opportunity? Like what are you on and what is your mission and what are your values? As you get through that and you find at least your early conviction of like, huh, I think we may have a mutual benefit here. That's where we start moving into a more cross-functional group. And I think I'm a big believer early days that what you absolutely don't want is for your customer facing teams, your sales team, whatever it is that you're hiring to be on an island in any way, shape, or form. And I think that that's something that can be challenging, particularly with companies that are leading with an early team that is much more product engineering and design focused. This new function being inserted into the company can be something jarring it time.”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“Scale and compound the effect of there being there versus just being potentially carbon copies of what you've already been doing. So when we get into the actual interview phase, based on those criteria, that's where I start to structure in different ways of what are the early filters that you want to be setting up. And so for some, it may be much more process oriented. In my opinion personally, spiking for product enthusiasm, curiosity, and structured learnings, because the learnings and the insights are going to be so important. And so asking questions and talking about what may have been not related to sales, but tell me about subject matters that you've been interested in. Tell me about root projects that you've been working on and the way in which you've rallied other folks around it. Tell me about times where you've had to convince people to do something that maybe they didn't think they wanted to do at first. And so I asked very open-ended questions there. I think when we're getting into the actual, like, what is the way that we want to measure this talent? Big believer that whoever the hiring manager is, whether that is the CEO, whether”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“I think as a founder, I would be taking inventory of what is the reason why you need to hire sales capacity today? Is it I don't have strong inclination around deal structure and approach and we're having a bunch of unbound interest, but we're not actually not sure the right way and the right cadence to be setting up our sales process. So do we want people that have a lot of structure? I think, and this is going to candidate profile, we'll get into the actual way to tease these things out. On the flip side, it could be, I actually just have a lot of conviction that if we increase the number of conversations that we're having, we already have strong conversion like we have like a strong ICP we're going after. We need people that can kind of triage and just handle the inbound that's coming to them. That's going to be a different set of skills. So I think looking at the founder side of what are you actually trying to remove from your plate with these hires? And what is the complementary hopefully approach of where are you getting energy in customer conversations or not? And how do you make sure that you're hiring the right profile of folks that is going to”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“I'd say the early days of knowing it is a muscle that you're building. I put it as like you decide to work out for the first time. And it feels like you're going to the gym and it sucks. You're not, you're sore, but you're not seeing any gains and you're not seeing any impact. And you have this moment of like, what the F am I doing? This sucks and I'm not seeing any benefit. Why do it? Maintaining the perspective on how do we push our teams? How do we push the collective company to continue making the investment? And how do you start to set more incremental milestones for what success looks like? And I think if you're focused just on output metrics around what have we closed, these deals”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“We're going to need it, and it's a muscle that you have to build over time. In my experience, that's a 12 to 18 month runway of actually getting the learnings, getting the motion, and getting the fruit of that labor, so to speak. And so going back to your original question of should you do both or are they at odds? They're not at odds, but you have to treat them as completely different go-to-market motions, as you're resourcing it from a PMM positioning perspective, from a rep accountability and activity perspective, and then ultimately the way that you are structuring the evaluations that come from it.”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“It's a completely different motion for your organization. And that may sound very obvious, but let's unpack with what that means. You have assumed intent on the inbound side. You have assumed value, especially if you've got users that are engaging, utilizing your product at work already versus outbound, like, no clue. Maybe, maybe they're using us. Maybe there's some indications of where you want to be outbounding, but typically you are moving from team level, end user and department level engagement being the driver of the YU why now approach as you're moving into outbound you as an organization need to be much more opinionated on here's why you should have an initiative that's aligned to what we're doing here's the impact that you should be experiencing and we would be delivering for you and then how do we make sure that ultimately we're delivering on that as a team and so i think from an outbound motion perspective we've already started to do this at loom of like we're in the early innings of experimenting and building that motion not because we need it because we know that some”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“Unlocks the right type of customer, and how do we have agreement then as an organization on what is the ICP that we're willing to go after? And the reason the ICP thing, in my opinion, is important is you're going to get a lot of inbound interest, particularly from very large enterprises, many of whom are in regulated industries that you are not even remotely close to equipping and servicing in a realistic way. And so I think having very defined filters of what you will or won't entertain as a collective company, as a guiding and North Star for you is important in my opinion.”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“At what threshold does it tip us into? This is something that we need to be resourcing and roadmapping in a more proactive way than what we've been doing in terms of core product innovation to date. That is always going to be a trade-off that has to be made if you are in a resource-constrained environment. But ultimately, it's also about what is your ability to go and capture a market? And I think for us as we're really trying to carve out a category here at Loom in terms of the way that people are interacting with video at work, we feel that there's a huge opportunity for us to grab market share by going into the enterprise and influencing larger organizations and the way that they're working, not only because we're trying to force our way in, but we're in a fortunate and privileged position that they're coming to us looking for that. So I think as we look at and as we can stack up, here are the common themes and threads that voice of the customer that our sales organization and insights that we're delivering back. How does that build conviction and therefore the roadmap that we want to build towards of what”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“Conflict sounds like it's like this. The reality is, and I'm probably well skewed based on the organizations that I've selected into along the way. But the product leads everything. 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 our back or whatever it may be. You have to figure out a path then on, okay, if that is 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.”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“View that our team is on the hook for two things error and insights and the insights are almost as important, if not more important, the earlier you are on your go-to-market journey because that helps inform where do you want to resource and how do you want to go to market more broadly, how do you build conviction in the right ways. So I've personally seen that having folks that are more excited around just customer learnings, feedback, interactions and first principles like inquisitive thinking and then being able to take that in a structured way and translate it to the CEO, but also to your product lead. If there's a marketing person that's there, how do you get them on the same page? There's so much more value, in my opinion, on how do you get the cross-functional company bought into the voice of the customer. And that may not be a quota caring rep that can deliver that if that's the most important thing to you early on.”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“In my view, the answer is C, neither potentially. And the reason for that, it depends on what you want. Are you at a place where, let's say that you're a pretty niche product and you have a pretty solid value prop and it's very clear who the buyer persona is? And it's like, we need folks to be triaging an inbound queue and possibly outbounding into this narrow thing that we were building in service of. You can make the argument, let's get some junior resources in and let's start seeing if you can scale to the next level if you're just having more customer conversations. More times than not in my experience, and I draw on both Loom as well as Quip in this case. There's a blend early days of are your first customer interactions support, more customer success oriented because you're helping them figure out the value that's there? Is it actually sales? Like, do they know what they're getting with your solution? So with these early hires, and I still repeat this and my team, if they listen at some point, are going to go, oh man, there he is saying it again. But I really.”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“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 it right? Who am I to say that I'm the expert on XYZ thing? But again, it's that objection handle, that positioning, that extra question that founder asked along the way, which you've built the muscle memory for by getting your company to the place that it's in because you have been in sales the entire time. You just may not actually unlock and think that that is something that can be used by someone other than you.”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“I don't think that needs to be overly detailed. The lift here, there's like a 80 20 value approach here, absolutely, of who are the folks that you've engaged with where there's just been an unlock? They get it. I think in most companies, you find that there's going to be certain customers that just, it got it from day one, they're off to the races, they're ripping, analyze those, don't take them for granted. Why? What were the dynamics of the role the person was in? Phase of company that they're in, 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 bullet points. I think the recording of calls is actually where the most value can be had. And only because it's so rare in my experience that the founders are”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“Well, 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 were 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”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“And a challenging opportunity from a where do we start and why? And I think for us when I look at frameworks, it's whether it be vertical specific, whether it be persona specific, how do we start to layer in applicable stories? I think storytelling is such a key part to sales. So how do we have relevant stories that our customer facing teams, regardless of their quota carrying? Like, are they adept at being able to tell the meaningful stories from our user base, our customer base, et cetera? And then also, how do we then look at the different types of plays, if you want to put it that way, or frameworks for are you going to have more of a bottoms-up, adoption driven play? Are we going to have a more tops-down initiative because we're actually aligned with power and we're attached to a more strategic undergoing at the company and Loom is going to be a vector or in service of that strategy. And those are the sorts of things that we need to capture in terms of what are the elements of health for those pursuits and then what are the right frameworks to be.”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“I don't love playbook as a term because it sounds rigid. And from what I just described to you around the types of conversations that are moving the needle for us and are leading to like the true great understanding of our customers, I hear playbook and it's, let me follow the steps, let me regurgitate these things. Let me ask this line of questioning. And that doesn't actually incorporate the most important part of it, which is listening and then making moves along the way based on that. To flip it around, I refer to it as frameworks. I apply this when I'm hiring a new leader on the team, a new rep on the team is bring the frameworks that have worked effectively for you in the past. Playbooks are not going to be a one-to-one, hey, I can rip and replace and take over there. So when I think about frameworks for us and what that means for our organization, Loom, Dropbox, Quip, I've had both the blessing and the challenge of horizontal tools that can be used by almost anybody at an organization, which is an amazing opportunity from a TAM perspective.”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“We're using. And so for us, it's really how do you ask open ended questions around why someone has taken personal initiative? And then how do you go through that fact-finding mission to figure out how does that play into the existing culture and workflow of the team?”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“I think there has to be a first principles of why were you compelled to go through and sign up and just see what they say. Leave it super open. And then also, I think the next piece is particularly when we are using data effectively as our sales team, which means that we're trying to talk to heavily engaged users. I'd like to ask what's preventing you from sharing or forcing other folks at the company from using this? Or they may flip it on their head and be like, no, I'm singing Loom's praises. It's all over the place. Like we have to go and make sure everyone's using this. And then we go, okay, let's ask why are you needing to do that versus the product being able to expand in its own way. And so I think for us, we start to learn the cultural idiosyncrasies that are really important for how do you change behavior. That informs then what are we doing in a proactive state as sellers to bring the right cross-functional groups into the fold, the right use cases that we want to be anchoring on for a pilot group? What are these success metrics that we want to set up as a part of this sales process that”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source
“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 or impact that the business is going to be experiencing if they're making the investment at scale. So I've used this term from my quip days and it was definitely parling that Dropbox learning to what are we doing at Quip. And I refer to our early sales team as working.”
2022-07-20 · The Twenty Minute VC · 20 Sales: The Biggest Challenges Building Outbound Sales Teams and How To Overcome Them | How The Best Sales Reps Do Customer Discovery | 2 Elements Sales Teams Are Always Responsible For | Sam Taylor, VP Sales and Customer Success @ Loom · IDENTIFIED FROM THE TRANSCRIPT · source