Running the Enterprise Playbook: Land and Expand, and More with Envoy's Head of Enterprise Sales

Hello everyone, welcome to SaaStr Scale 2021. We are thrilled to be joined by Sarah Lash, Head of Enterprise at Envoy. Sarah has a great session for us in store today. We have 20 minutes with her and we do have plenty of time for questions, so please make sure to start brainstorming those and feel free to drop them in the Q&A section at the bottom of your menu. Sarah is going to be talking about running the enterprise playbook, land and expand and more, something I know we're all really interested in learning and hearing more about from her experience at Envoy and beyond. So please join me in welcoming Sarah. Before I let her dive into the content, she's going to start off with why the data matters for this session. So Sarah, can you quickly tell us what people can expect from your presentation today?

Absolutely. So one of the things that I've accomplished in my first 6 months at Envoy is growing the enterprise team from 5 account executives to 17 and hiring a second sales leader. Besides the critical matter of having enough sellers, one of the reasons why this was such a critical metric for us to look at was when I joined, I went from about -15% quota capacity to greater than 15% above quota capacity. So it's really ensuring that we have the right folks in place and a protection on those forecasted numbers. To make sure that we've got a healthy sales force ready to go and, and conquer that opportunity. So I'll tie that back a little bit, but overall I really looked at this as it's an and, not an or strategy. And so many times organizations focus on starting in the land and expand, or starting at just discover and defend. So bottoms up versus top-down selling. But the key really is for successful growth and how do you optimize to do both? The land and expand is super important and really ensures that kind of tactical success and base business of a run rate. I really work to encourage our reps to target getting to quota 70 to 80% of these transactional or run rate deals. So part of that is understanding and evaluating what that metric is. Is it sub $100K? Is it sub $50K? Is it even sub $20K? Based on how the business is selling. It allows you to penetrate multiple departments, multiple locations. Many organizations have decentralized procurement, but that transactional-based engine is the foundation. But what happens as you get to scale is that's not fully scalable. And so ensuring that you're targeting the right messaging and value proposition and value selling at the C-level bringing those cross departments together. Now that might lengthen your sales cycle, but it should also increase your average transaction size, but also provide a stickier customer in that sense. And so by adding in this top-down sales motion and making sure that you're not just reliant on those big deals, it gives you a smoother forecast, it gives you smoother quarterly attainment, but it really allows that rep to take that business from 70 to 80% transactional and get to that over 100%, or that's when you start to see reps at 130, 150%, maybe in certain quarters because they're overlaying those chunkier deals. Now, many times reps are really good at one versus the other, but it's our job as leaders and as companies to work to enable and provide that balance. And whether that's through systematic approach, whether that's through onboarding or training or utilizing different solutions, for account planning or other metrics to get the team focused in that manner. And so I am in that process of kind of looking at that at Envoy and how we can work to do both. But the key for me is always looking at hiring for growth. Hiring is one of my favorite activities. Over the 20+ years I've been in the tech sales industry, I calculated that I've probably done close to 10,000+ interviews, whether that is on-campus recruiting for SDRs or senior executives. I love those first conversations and really understanding how can this person add to our company, or how can we add to their career? And I love that feeling within that first 5 minutes of an interview when you just know that you found that perfect fit. But I look at hiring in 3 ways. What are my immediate or current needs? Ultimately, be aware that I might have to backfill, whether that is for internal promotion or attrition, that I have to get ahead of that game. I have to be prepared with either internal candidates that I might be able to move up a level, develop those relationships, ensure that I know them and their performance before that interview. Even if I don't have positions posted or positions open, I'm constantly pipelining. I do a lot of Zoom coffees right now. I used to do them in person, but it's exciting to constantly talk through and understand who's in the network, who's looking for opportunities, who may not be looking for opportunities that I can develop relationships with. And that way, when attrition happens, either positive attrition, negative attrition, I'm prepared to ensure, or I know if I'm going to pull positions forward a quarter or two, I've got a network of candidates ready to go. My midterm needs are really, as I look at what is my current year of hiring, I know I'm likely going to double my sales team again next year. So what are the type of things that I need to do to ensure I have the right folks in place? So one is risk tolerance. As we grow the business, there's never going to be 100 perfect candidates out there. So I have to balance the team and understand maybe they have SaaS experience, but they don't have the same segment experience, but they're really ready to take that next step. Or maybe they have the segment experience, they've been selling to big enterprise organizations over the last 10 years, but they don't have SaaS experience yet. How can I balance those two types of hires along with a traditional SaaS hire to get that broad, diverse team with different types of experience levels that can build upon each other and fill in each other's gaps. The thing that we sometimes forget about though, when we're hiring for growth is retention. What can I do to ensure I'm coaching, I'm developing, and I'm showing my existing team that it's not just about the new folks that I'm bringing in, but that I'm committed to their growth, to their development, and to their career. To ensure that they'll have a long-tenured opportunity with Envoy as well. And then I think about my future. So if I'm growing my team, what future leaders am I going to need? What types of more senior reps may I need? And how can I continue to pipeline or hire maybe above my current need to ensure that I've got that person in place, ready to sell Envoy when I'm ready to move somebody into a strategic account manager position, or when I'm ready to add another senior leader in the business. And so through networking programs, retention programs, and just kind of looking at that base of talent overall, that's really how I grew with amazing recruiting and management team, our team from 5 to 17 in 6 months. And so the image you see here are actually some of our envoys that have joined the team in the last 6 months. Now, once you've got that great team in place, we need to think about how we are strategic with those team members. So account planning to me is a huge opportunity to think about how we can have that cross-departmental commitment and participation. It's not just the account executive that has to focus on what are those accounts and how we're going after them, but how can you do that with the BDR, with the CSM, the customer success manager, with your partner network, with marketing for account-based marketing and have that joint strategy that has accountability reviews, that has assigned goals and targets to it, but really working to customize and develop that process that works for the team. Not every organization is going to be at the same stage at the same time. And so, for instance, at Envoy, I'm starting to target strategic account planning for expansion. Accounts. I want to take our top 20% of our potential opportunity expansion and really focus on what I can do there. I'm setting some ARR targets and some goals on how many account plans each rep needs to do, how many each frontline manager will be reviewing, and how many will be reviewing at a cross-functional level, assigning a specific portion of our expansion ARR growth for the coming year to that account planning to track, measure, monitor, and use data to kind of hold ourselves accountable for that. I think there's a lot of opportunities with cross-functional development and leadership, especially as we grow into some more top-down, discover and descend sales approaches. Data, territory development, and understanding how you're creating equitable, opportunities, but also covering the market in the right way. And so I have 7 years of experience of selling data analytics and a portion of that time in sales operations to understand territory development and really figuring out the best approach for this. So first off, you can't measure, balance, or manage that if you don't know what you're looking for. So I like to look at what is the market opportunity, what is our total addressable market, What is our ideal customer profile in that market, or where might there may be more opportunity? What are the metrics that you're using for this to develop that territory? Is it organizational size, the number of employees? Is it organizational revenue? Is it a specific industry? Is it a specific vertical? How are you looking at that to then balance that across territories? Sometimes in smaller segments, you know, you do things in a geographical sense, You've got 4 people covering New York City and 1 person covering 5 states in the Midwest. And so that doesn't always work the same in enterprise. A lot of times you'll start that way and figure out how we can kind of tier and grow. How do you— how often do you reevaluate that for change? One of the things that I think through is how can I keep it stable for the team, but also for the customers? We don't want to continuously change account managers. And so as I know I'm hiring at scale for next year, I'm working to develop all of the territories that I will have and really clearly communicate to my team. You might be covering two territories to start. This is going to be your permanent opportunity. This is your babysit opportunity. And I think that clear communications and overcommunications to the team for those rules of engagement is really key. One of the other items is no data on account size, shape, etc. is perfect. If it was, let me know what you have out there because I'd love to hear it. But what you have to do is you have to choose what is going to be your single source of truth for that data so that you know that that is always what you're going to be leaning on to ensure that that's what we point things back to. And don't waver from that. I really encourage if issues come up for the cross teams to try to resolve that on their own. The more that they are invested into finding resolution that works for them, the happier they're going to be. Really try to only utilize leadership or ops for final engagement decision-making when absolutely necessary. One of the things that I learned in my time in sales operations was I will never make everybody happy, but I will likely make everybody unhappy. That's not a fun position for anybody to be in. If they can make those decisions on their own, then they'll feel accountable to that and really comfortable. And then I mentioned earlier, geographic versus named accounts. When you're getting started, kind of spreading the masses and just handling it on a geographic sector is going to be the easiest way. But as time goes on, it's super critical that you start to focus your sales reps' time, their sales energy, their sales calories into the accounts that matter. So when do you start tiering? When do you start cutting territories from a geographic sense to maybe 50 named accounts or 20 strategic accounts or even 5 flagship or lighthouse accounts. And so looking at that and the priorities of the business are really critical for that sense, and then making those decisions, possibly even adding in account managers that handle that transactional sale so that the enterprise account executive can focus on that top-down selling and partnering together. For me, it's all about what is my leadership vision and values. When I joined Envoy, one of the things that stuck out to me was just the organizational values and how much they aligned with what my leadership vision, what my personal values were, and defining who I was and being able to really stick to it. If you talk to anybody in the industry that's worked with me in the past, they're probably going to say a similar theme about myself. I'm an over-communicator. I lead with integrity. I really like to enjoy myself. I want the team to have fun. I'm a cultural builder. I'm a brand ambassador. And so for me, tying in this leadership vision, making sure my team knows what I'm about really helps me communicate with them, question them in a positive learning environment to ensure that we're all rising together for success. And so my top takeaways on this enterprise playbook are: it's top-down selling and bottoms-up selling. It's not one or the other, and having the ability to lead to do both is really key. Recruiting and retention— don't just hire for scale, make sure you're developing your internal team to advance as well. Territory planning, account planning, tiered reps, Think about that in a strategic approach in advance so you know when you have to pull the trigger for those next steps. And then lastly, make sure your vision and values drive it all together. It's super critical to be on the same page with your team, with your organization, and with your company so that you're aligned on all of your goals. And with that, I see we've got some questions in the chat. I'm going to stop sharing my screen so that I can properly answer them. And I'm excited to kind of see what, what we've got. So jumping right in, um, see, there's a great question here. How are you dealing with the great resignation? What is your target retention percent for account executives? So we're all, you know, myself included, I did change roles about 7 months ago. I think it's important to understand what are your team's priorities, what's important to them, and how can you work to develop them, or maybe have honest conversations about, you know, there not being an opportunity or something in that sense that you can plan for it. My target retention is going to be around, you know, less than 15% of the team. I factor that in for growth as well. I look at retention as an overall attrition, so there's positive attrition moving up within the organization or promotion or lateral moves and ensuring that I have a plan for that, but I'm constantly pipelining to make Sure. Over 10,000 interviews. Wow. Do you have a go-to interview question that tells you the most about a candidate? Yes, it is a frightening experience to think that I've interviewed over 10,000 people, but it's also exciting in that sense. One of my favorite questions to ask is I just try to figure out if they're a curious individual and why and what drives that curiosity. But one of the things that I've been doing to learn that and understand that is on my initial hiring screen, I'll actually start with their questions for me. I think that initial hiring screen, especially right now in this Great Resignation, is as much of an opportunity for the organization to vet out candidates, but for candidates to vet out an organization. Flipping the switch on them and having them ask their questions first really allows me to understand their curiosity, their knowledge, and just kind of, are they really into having this call with me, or are they just interviewing because they want to see what's out there. I also like to ask people, you know, what's their favorite book they recently read, even if it's not a business book. It just tells me a little bit about them in that sense. And then I always love to ask just what are they personally working on right now. I think development is a great area of focus. I also think development is not necessarily what you're not great at, but what are you great at that you gonna get really great at. One of the next questions that I see is, how do you get legacy reps or leaders to adapt to change? I think this is one of the most critical things that we do in our roles today, because sales as a segment has just changed significantly. And ultimately, I think it's about trying to communicate early, often being really clear with the intention and the why. And really working to ensure, if necessary, having one-on-one conversations with potential laggards and hearing them out as to maybe why this change isn't good for them or isn't exciting. One thing I learned early on, I had a manager that I would roll out something that I thought was super exciting in a group setting, and that manager would actually question in that setting things that you know, they didn't necessarily agree with. And I realized that that was a resource for me to start prepping and presenting that change to them first. So I would hear those questions so that I'd be ready to either pivot what I was looking to roll out or prepare to answer them. And so how can you utilize those in an appropriate fashion? I see a question, um, from Vishal. Should there be separate leaders managing land and expand sales motions. I've seen startups drive expansion through customer success function. At this time, at the stage that we're at, I don't have separate leaders managing either. Over time, what I have seen successful is adding in those either inside or account manager level reps to an enterprise sales organization that are maybe handling some of those transactional motions. I do think there is huge opportunity and partnership with customer success to have that foundation of passing insights and opportunities over to the seller in order to ensure those expansion opportunities are capitalized on. I try to not have that customer success manager as the seller though, because I think the trusted relationship that they have is really key to ensure that there's the right kind of value from that position there. And one of the last questions I see is, "What are some of your tactics for pipelining candidates?" So I'm happy to give all of my secrets away, but I do participate in quite a lot of networking groups. I look to see who I can meet, engage, and network with in there. I was living predominantly on the East Coast for a number of years. I was in the Washington, DC area for just over 20 years, and I moved out to the Pacific Northwest, to Seattle, 4 years ago. And one of the key realizations I had was this amazing network of people that I was hiring for, especially in an office position, was no longer available to me. And so I've really worked to diversify my network, uh, whether that's through meetups, whether that's through introductions, asking people I know for referrals. I do a lot of personal time on mentoring and coaching, but through that, it gives me the opportunity to get additional candidates and conversations going. Anybody that reaches out to me over LinkedIn that's expressed, you know, interest in opportunities, I try to at least have an email conversation, if not a quick phone conversation with. And so I think it's just important to put yourself as that leader out there. And I really encourage my managers to do the same thing. Well, I know we're getting to time, and so I really appreciate the opportunity to share, you know, my best practices with you all on building an enterprise org to scale and taking things from not just a land and expand, but to a top-down sales motion as well. And so thank you everybody for coming and look forward to hearing from anyone in the market.