The Pavilion Podcast
The Pavilion Podcast

Episode · 2 years ago

Ep 5: Scaling Customer Success Teams from Scratch feat Anna Elwood

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Ep 5: Scaling Customer Success Teams from Scratch feat Anna Elwood

Bo. Hello everyone and welcome to the revenue collective podcast. I'm your launch host, Justin Welsh, member of the Los Angeles Chapter of revenue collective. In inside of these episodes we're going to feature ideas in conversations that are inspired by ongoing discussions within the revenue collective community across the globe. Inside of the RC slack channel. There has been some talk recently around scaling customer teams from scratch, and that's exactly what we're going to speak about in this episode with our guest vp of customer success in sales at teachable, Anna lwood. And before we dive in with Anna, a few notes. If you're out there listening and you want to join revenue collective, visit revenue collectivecom and Click upply now. The second note is that this podcast is coming to you from our sponsor, gone, the number one revenue intelligence platform for remote sales. We are thrilled to announce a strategic partnership in which we will be bringing you the best events, content, research and spaces to engage with your peers. To kick it all off, they are sponsoring the revenue collective podcast. We will bring you new stuff every month, so do not miss out stay uptodate on the latest collaborations at Gong Dot io RC. Okay, let's kick it off with Anna Lwood. Our guest today is Anna Lwood. Anna is currently the VP of sales and customer success teachable, a platform that enables creators to monetize their expertise in build their businesses. Prior to teachable, Anna was the global head of customer success at no tell. She started her tech career as vice president of operations at ZAC DOC, a healthcare technology company, at the beginning of a better healthcare experience focused on empowering patients. Annam was one of ZOCDOC's earliest employees, joining the company at employee seventeen, in serving three markets, helping build it to over six hundred employees and serving users nationwide. Anna, so good to be talking with you. It's nice to set with you this great so Anna, you and I have worked together in the past, but I would love to learn more about what you're up to you today. Tell us a little bit about teachable in your role. They're currently sure. So teachable, which you vary sacinctly described, is about a five year old company. We actually were recently acquired by Hot Mart, which is a Brazilian based company doing the similar things that we do, but but three years older and much larger than we are. Our growth to date, or rather maybe up until about six months ago, was largely from kind of a singular marketing acquisition strategy and a lot of organic word of Mouth Growth, and that marketing exquisition was centered a lot around live digital of events that would attract creators and have...

...them begin to use our platform. As we've grown, it's been important to obviously maintain the growth rates, which is also meant that we've had to diversifire acquis and strategy, and so I joined to one which are our customer care team, which is about twenty people or thirty people, as well as build out a sales and post sales experience that will not only support some of our highest value customers but also adds by diversifications that were looking for in continuing to grow our business. Great now, I know you've built out these, you know you've built these really massive customer facing teams over the last decade of your career and I know everyone sort of has a different approach when building teams and I know you're maturing some of the teams. They are teachable. How do you think about building your teams? Is there a particular type of employee or set of skills that you're looking for when you're staffing up your teams? A teachable yeah, I think that the type of person that you hire, some of your first hires, and I know that you probably observed this to Justin both at Stott up in your role since then, is very different than the highers that you make later on. And I've referred it, and I'm totally listing from other people. I've failed to remember whom exactly. Probably said this first that I was pretty too, but the difference between athletes versus experts and the early days you need really kind of drew up rations individuals who can do a various set of things. When I first started at Doc doc, my role included cells ups work and marketing and office management work, and when I think about a very new team, I think along those dimensions very much. So it's not only an individual who's going to be kind of being an individual contributor, but also will be contributing to the building out of that team or that process. The other thing that I think is important in this is true for me, and not just the individuals that I bring on to help me build something, is I've got a roll up my sleeves and be in it and I have to very frequently be actually doing the work to understand what it is and how it operates and what works and what doesn't work, and then quickly, as much as I can, pull myself out of the weeds and observe how it's working. Think kind of longer term, and so, you know, the process of kind of doing the do and observing, doing the do and observing. I think it's a really critical part bringing something from from zero to something. The other thing is in scaling something, the early days are all about, you know, the MVP or the minimum viable product when you think about even toolings or process or systems. But at a certain point in time that minimum will no longer do, and being able to know when that happens been very quickly pivoting and focusing on building something that can last long term. Yeah, I you said something really interesting in there that kind of Pique my interest, which is like this athletes versus experts, or how you...

...hire people. I've always kind of called it builders versus optimizers. There are folks that come in and they can be both an individual contributor but feel like they're also driving company and product direction, but feel like they're also wearing multiple hats. You know that that's generally where I feel more comfortable, versus pulling levers to get one in two percent better. Those are those are optimizers who come later in the business and as you're scaling or building a business from scratch, it's so important to get those builders, to get those people that can do so many multiple things and do it with the right attitude, the right positivity, the right skills, their learners. Where do you find people like that? Like, how do you find people early on who are ready to go on a really long and challenging journey with you when you're building something from scratch? Yeah, I don't know if there's necessarily always a singular place where they're found. As you know, Justin I have like a really unique background. I studied the art. Many of the teams that I have built aren't the kind of classic especially, you know, even thinking about some of my business operations, are not analytics groups, they're not necessarily you know, post MBA's or x bankers, and I think it's because what I try to find is not only someone that has, you know, the intellectual capacity and curiosity, but also individuals who can menage ambiguity really well, who are comfortable with not having a lot of structure and direction. I think one of the reasons why I think guy have thrived in many ways and some of these pet companies is because, coming from an arts background, you don't have a lot of structure and I'm very comfortable in that environment. I found them in a lot of different places. Frankly, I find that, now that I've met and worked with a lot of really great people from from my past roles, I find them for my history and for my network. Yep, that that for me. When it comes to getting a team off the ground, I go to my I go to my sure things, right the folks on our network, the people we know in revenue collective, our previous employees. You know, I've had a lot of success hiring early on, just going going to the well. That always brings me water. So you know, I know that that's a huge opportunity. When when you're getting started and when I worked with you, you ran customer success teams. I noticed now that you are running sales as well, which I think is great and I've always felt in you know, I think of people like you are, I think of our friend Megan Bowen, I think about great executive leaders in my opinion, can flex and they can flex from CS to sales and potentially vice versa. I see that less. So what something really surprising that you learned when you took over the sales and revenue teams? A teachable yeah, well, I would say that I can't say I took them over. I've started to build it and it has definitely been a learning process, but not in like necessarily massive ways, because I think building a team there are more similarities than there are differences, and we've already spoken about many of them. Of the similarities,...

...the things that I have observed in the sales team is that, unlike some of the teams where I've built kind of larged prophecies, you know, customer support or in maybe a tier two or technical support, or even some of these data operations teams where work comes to an individual, I've relied a lot on, you know, developing intrinsic motivators for them. You know, it's like the why behind what you do. That's like the first and foremost thing that I've found will really get people going and help them understand what they should be doing and why they should be doing it and how much they should be doing it and perform at a consistent level. And I'm only about, you know, four to six months into this on the sale side, but it is very clear to me that it's a very different profile of person who, understandably, will take on a sales role because the work doesn't necessarily come to you. Some of it is easy, you know. I've been involved in closing deals that I felt like it just falls on my lap, but surely often, you know, it's a struggle and I certainly saw this firsthand in my roles and working in organizations that have a large sales culture. But I really understand and really beginning to embrace the importance of Extrinsic motivators, you know, around compensation and Commission plans, which has been, I think, a good learning for me. Do you find it challenging, and I'm just thinking through you know, my own career where I've run revenue teams right that, that's that's all I've done. I've never managed a customer success team. I've dabbled in marketing, but it must be challenging to flip back and forth between motivating or leading customer success folks and then going in motivating in leading salespeople. What are some of the challenges with having to do both of those things? Do you rely on your management team to do that, or do you take a sort of a roll your sleeves approach to that as well, like you described earlier? Yeah, so the customer support side and the service side is a relatively established team and, like I mentioned, this is more about maturing it and transforming it and I'm so grateful to have come to teachable and have had a bunch of leaders there that I can really rely on. My first, you know, three to six months was spent mostly focusing on that team, making sure all the right people were in the right seats. They we had a strong road map envisions for who we wanted to be and where we were going, and most of my time now has been the rolling up my sleeves and, you know, really being neck deep in the sales world. I try to avoid jumping back and forth to frequently because I find myself really under supporting everybody in circumstances like that, but they're absolutely have been times where I've left our customer team to kind of their devices right now where we have had record numbers across the board in every aspect of our business because of the...

...current environmental climate, and I'm having to move myself back into that world briefly to help make sure that they're well supported. So, the context switching, I don't think of anybody a huge amount of service. I try to limit it as much as possible and I found that really the best work that I can do is kindling with my sleeves and spending with dedicate, dedicated time that our sales team needs and then, you know, starting to hire actual leadership to help leave this with me. Individuals that have come from deep sales experience and management experiences before teachable and we just brought somebody on a couple weeks ago to help me with that right now. Congratulations. Thank you. Yeah, I'm very excited because she's also a female and love to perpetuate females and sale. Awesome. I know you've been doing it four to six months, you know only but if you were talking to a founder or a CEO and they were contemplating putting sales leadership responsibility on the plate of their current customer, success or support leader. What might you tell them from your experience? Are Some of the key indicators at this person might be successful in taking on that additional responsibility? Well, I'll have to see if I'm successful in doing this myself, but I can rely the lively answer that question. What I would say is we're talking a little bit about that the context switching side. You heard that. Potential reminder is my calendar. You know, while I try to minimize this, I think you need to bring somebody on who's very adaptable, who can move from one thing to another. And if it's not just from team to team, then you know, as they're discussing earlier, it's from looking at a bird's eye view versus rolling up their sleeves and doing the work themselves. I think they have to have a very little ego. I've been learning a lot as I've been going. That something I'm very comfortable with. I've jumped from industry to industry and, like I mentioned, didn't come from, you know, necessarily a corporate experience or even started experience. My first took on my role at Bostock and being able to learn on the fly and quickly and comfortably. I think is really critical. And then I think the other part is being able someone that has a track record of hiring strong talent and ideally may be talent from different types of teams, which is an indicator of them understanding what's unique about one role versus another and an indicator that perhaps they can easily flex. I'm in understanding a revenue and sales team. That's great. Yeah, I think I think there are some some certain skills and I think definitely being able to put your get your hands in there, rolling up your sleeves in really understanding process and people is just a huge indicator of someone to be successful. And you know, as I think about and I mentioned you've been your guest on the show here we had Megan Bowen, who started in sort of the customer success or customer support facing roles and then moved...

...on to lead really great, great sales teams. I think about myself when I was younger and immature and you know, I think, boy, I look to my sales leader and you know, they didn't sell my products. And I've hear I've heard people say if you haven't carried the bag, you shouldn't lead the sales teams. Now that I'm older and more mature and more experience, I think that's a load of a load of blowny. What would you say to that person who said if you haven't carried the bag, you shouldn't leave the sales team? I would say, because I would agree with you, I don't think that that necessarily an accurate view of the world. I would actually adjusted and say if you aren't willing to carry the bag, then you probably shouldn't lead a film, because the willingness is, you know, an open mind to understanding what the real situation is. I have myself observed situations where, you know, leadership is making decisions for a sales organization with like really a false understanding of what the reality is, and that doesn't help anybody, let alone the in the entire business and, you know, the future for that business. So having an open mind and being humble, I think, is the most important part. What I will say is that a personally, I learn very much by doing and I had, you know, some great opportunities at the tail end of my time at SOC DOC to be heavily involved in some of our larger commercial field LETHEL systems and it was a huge learning for me. The deals that we're talking about now are vastly different. You know, these aren't three million dollars. You know, these are nine hundred or a thousand dollar contracts and in order for me to really understand what that self processes like and that purchasing process for our customers, it's been really important for me to do it myself. I am the worst at it in my team and I think my team really loves to see that, but I certainly can help support them and lead them to, you know, ultimately what we are hopeful to achieve longer term with the vision of our teams. Yeah, I've I've worked with you long enough to know that if you put your mind to it, you're probably going to be the the best at it. So I think teachable is in very, very good hands. So, first of all, congratulations. It's amazing. It's a great company. Now I've I've spent a lot of time exploring teachable on my own is as a content creator and really excited to see that they have an incredible leader in place. And you know, we're nearing the the end of our time together here. Before we do that doesn't I'm just going to say that I think I know that you were exploring teachable and I know you ended up with a different platform and of great respect for that, but I just want to say that I don't believe that you're done your exploration phase. We're just letting on you try the current last form that you're using, but know that we will be coming back to you and sometimes I'm to see how that's going. I believe I will be a teachable customer in the next six months. Any think...

...about that? Of Cool. Well, listen, you got your a guest. You're going to jump into the quick fire five and you might have just closed a closed a new deal. So, as I mentioned, you're very good at the the sales. So give yourself some credit. So we love doing the quick fire five. It's really simple. It's five questions we get top of mind real answers from executive revenue revenue leaders like yourself. So are you ready to dive into the five? Sure, awesome. What is Anna Lwood's most controversial perspective on business today? So I think it's very of the moment but fits with other moments as well. But I'm not a fan of you know this prospecting outreach where we, you know, apologize for covid right now. I think that it's just a waste of time and it's not necessarily helpful in actually getting people to engage, certainly as a customer myself. I know there's a lot of discourse right now in that topic, but I personally am more interested in understanding, like why someone cares to read out to me to begin with. Not feel bad for the fact that no one in a global pandemic like that's just a natural and to be expected situation. I agree. What's a song that amps you up for the Work Day every day? What's something that you listen you to get pumped I don't listen to music for my work day, but I definitely listen to music to get pumped up, especially when I'm running, and I've been listening to Paul Simon's late in the evening on repeat, also because I am, you know, very committed to making this my new Karaoke Song. Nice. I don't think of Paul Simon and pump up in the same sentence, but you will. You do it. I have not so for folks who who are out there in contemplating the revenue collective. What's been your favorite experience to date in the group? Far, in a way, the fashion on site that I attended back, I guess it was in the fall, that focused a lot on executive compensation and equity and just a real honest and transparent discussion and sharing about how we all should be thinking about how we are valued as individual and I know that that was, you know, and on site, but I also know that those documents and resources have remained available and I've used them and leverage them. That have been in valuable to me. Same here. Hugely Valuable, absolutely leverage at that. I like the reading and s one with Toma's tongue's I little over my head, but I truly enjoyed listening to him go through that. But what's something that you consider yourself to be world class? And World Class? I think that I can to have an engaging conversation with almost anybody.

I just don't always want to, but there are moments where I, you know, just like want to meet a new person and if that's just like going to a bar and picking some that's completely different than myself and, you know, engaging them in a quick conversation, I find myself able to do that pretty consistently and they seem to have an enjoyable time to great lastly, give give the audience your life motto or guiding principle that they can take home with them today. I've been told that I make decisions very much on like morals and values, and I think that's probably true and I've observed that there are instances where I think people have probably taken advantage of that, and I'm not really bothered by it because I very much think that my career and my life is a marathon and not a sprint. I care more about being a really good person with high integrity than, you know, winning every single day, based off of how someone might define winning. And I guess the other I guess principle it was with in that is, you know, just the idea that you should be treating everybody with respect and as you wish to be treated as well. But there have been more people than I that have held that as a principle and certainly that have actually claim that. But yeah, now I love it. Respect integrity and playing the long game, I think. I think these are great so I appreciate you sharing that with the the audience. It's been great chatting with you and it's been a while since we've we've chatted, so it's great to catch up with you. Tell everyone how they can get in contact with you, should they want to reach out to you. Sure I'm on Instagram and twitter and claimed at Anna Lwood. You can get me there. I'm obviously on Linkedin. You probably ask me about my flat handle for revenue collective and I'm just Anna outwood and my seat and I'm very open to talking with anybody about any of these topics and more so, please, please, please, along the lines of, you know, my kind of guiding principles. If I can be of help, I you know, really want to, because I also think that that will be paid for and some time in my future. And it was so excellent happening on the show. I'm glad that we got to connect again and I'm sure we will be connecting in the next six months, maybe three months, maybe even sooner, because I am not super satisfied with my other solution. So good, good, here. This is actually my ultimate purpose of coming on the spot for you and my husbands fought amazing and so great to talk to you and we'll catch it a little bit. Thanks so much. Okay, bye. Thank you. By.

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