Customer Success Leader
Customer Success Leader

Episode · 1 year ago

Empowering Entrepreneurs Takes Educational Content w/ Lynne Zagami


Being in and around a startup can be a stressful place, especially when you’re trying to land investors. 


Automation helps complete repeatable tasks in these kinds of situations. However, there are areas where a founder needs more specialized content and assistance.


Lynne Zagami, a former lawyer and Head of Customer Success at Shoobx, joins Eric to chat about empowering entrepreneurs through educational content. They also discuss… 


- How relationship management skills have helped Lynne shift from law to customer success


- The importance of having a responsive culture


- How to manage great customer success without causing burnout


- Why you should be answering client questions before they’re even asked

For more info, check out or send a message to

To hear more interviews like this one, subscribe to Customer Success Leader on Apple Podcasts, Spotify, or wherever you listen to podcasts.

There's a lot of stuff that we can't automate. What we can do is develop a whole lot of educational content, both around the concept of what our platform deals with and then also how those things happen in our platform. Want to create delightful customer experiences. You're in the right place. Welcome to customer success leader, where you'll learn about the successes and struggles of leaders who are passionate about their craft. Trust me, you want to stick around. Here's your host, Eric Crane. Hey, there, I'm Eric Crane, the coke founder, here at flat file, and today we're talking with another customer success leader. We've got Lindsagam me from shoe box. Helen, hi, how are you? I'm doing all right. Thank you. Are you calling from today? Just outside of Boston, in Newton Massachusetts? I Miss Oysters. Yes, I actually have started looking for lobster rolls and places that I know can do fancy take out of that kind of food, because it's almost that time. Have you been like trying to trade toilet paper for the lobster rolls? Like, what are we getting into? Levels that spars here know we're actually are. You know, fancy takeout game is pretty strong here. Our restaurant seeing a very good and my sister and I have purposely been trying to benefit some of the restaurants that we love and do a weekly dinner where we just go for it and order all the delicious thing but see food, you know it's getting to be that time and might have to risk a trip on a plane right up there. That's the one thing I missed the most about that city. Yeah, it's worth it, definitely well, thank you so much for joining us today. I like to start out these conversations with the question, and that question is how do you define customer success? So I think there's the aspirational definition for us and then there's the operational definition. The aspirational definition, I'd say, is you forming meaningful relationships with our clients that produced strong, repeatable engagement with our platform. Operationally, we're actually a little bit different. As a team, we kind of handle some of the business development activities, certainly on boarding, certainly account management, and also support. So we really see the customer from the beginning of their engagement with us as a company and our platform, through them getting up and running, understanding what that looks like and why they're moving certain information into our platform, to addressing questions that they might have about how to get the best use out of it and just that overall, getting to know them and getting to know their company and what they're up to and how they might how we might be able to support them along their kind of growth path. Got It? Well, tell me a little bit more about shoe box, like what are you doing there? So we think of ourselves as a legal operating system for startups. We work with companies from incorporation to exit, and these are companies that expect to raise outside capital, that are hiring employees and issuing them equity as incentive. So really the things that we typically think of as start up and we support them through equity management, through HR, through fundraising, governance, all of those activities, and there's a role in our software for every one of their stakeholders. And what we've really been seeing is it's really valuable to companies as they're preparing to go through a fundraise, to get their documents organized, to make sure that they have a nice clean data room to show to investors and then actually going through the investment process and coming out the other side and having kind of a ready made system for managing those investor relationships and all the information you kind of flows back and forth between them. Got It sounds like it's pretty challenging to replace what people are used to getting as a personal service with software. And I guess you know whatever your team is able to help provide your customers. How do you how do you do that effectively? So there's a piece of this which is, you know, just making sure that we are taking the elements of what people are doing now that are not helpful...

...right, that are repeatable, that should not be kind of done manually, artisanally, etc. And letting software do those things. So a lot of what we do is preparation of Hur Documentation, preparation of equity grants and things like that, and those things oftentimes are done, you know, by hand by attorneys, and there's really no dis station, when startups are paying for those services, between the substantive legal advice right and paying for that, versus the almost administrative stuff of Enterinian someone's name and the number of shares they get and investing schedules. So shoebox could have fit in between that relationship and, you know, utilize the things that are kind of these routine based workflows that allow the attorney to focus on what they're doing, so that's important, and allow the startup to have more ownership over these processes and the things that they're doing, and really it creates additional transparency on both sides for each of those parties. Got It. So it sounds like you caind of need to build a relationship with both sides, the legal and the start up side of things. Yes, and this is actually one of the the biggest learnings that we've had over the years, which is, you know, initially we were thinking, okay, our client base is the startup, right, that's going to be the person that we focus on, the founders, the executive team, whatever that is. But really, as a client service team, we support all of our users and the most active user on our platform outside of those sort of founding executive teams are the lawyers, and so we've put on a lot of energy and effort over the last couple of years to really make those connections more robust to and that's everything from just being more upfront about it when we talk to potential clients about it, to building out kind of self service resources for attorneys to building kind of training programs for them so they can get comfortable on the software and IT helps. I actually was a corporate lawyer for several years for startup, so there's sort of a shared understanding there of how tricky those relationships can be. And you know, what we've found is once the attorneys know they can come to us, they know where to find us, they know where to find information about how to use shoe box. They're way more comfortable than they were before. They hop on a phone with us. Got It. I was wondering where. You kept saying in tourney instead a lawyer, and that we met you from lawyer to, you know, running customer success for a legal textart ups. So this is actually the second startup where I have headed up the client service function. My last one was a document automation company for lawyers, and really it was a combination of loving the startup environment. I just prefer building things to performing services. But also, as I was growing up, if you will, as a lawyer, there were so many conversations with, you know, partners and more senior attorneys that I worked with who were like yeah, you're an okay lawyer, but your relationship management skills or like off the church. You know, our clients love working with you. Oh, I wish you know our partners were as good at managing client relationships as you were. And you know you only hear that so many times before you say, okay, I think it's time to focus on this stuff. And in my last firm I actually transitioned from practicing full time to practicing about a quarter of the time and the rest of my time was spent on client service and marketing and business development, and I was basically out and doing my job when I met the founders of shoe box and we hit it off immediately and started to build a relationship. And then now here I am. That's really exciting. So, I mean, how many folks are on the team currently? So we're a little over thirty, mostly in Cambridge, but we've got some of our development teams in Europe. Got Some folks that are working on the west coast as well, although every single one of us is now working from kitchen tables, living rooms, wherever we happen to be. Yeah, I've got a basement and staring out the window here, wis she now? Was Outside a day? Yeah, we don't get a ton of eighty degree days here you happen to catch me on one of them. So anadoicated brief exactly. So tell you, I mean, I love a little bit more about the experience of scaling out success and services... a function within a technology company. Like what has that experience been like as you've grown from, you know, a handful of folks of the company now to around thirty? Yeah, so for it was a really interesting experience because what we realized was what our clients need from US oftentimes isn't so much guidance around how do I get this thing done in shoe box, it's how do I make these decisions for my company right? How do I know which actions are the right ones to take? And because we're in this interesting position where we don't provide legal advice, we're not a law firm, we're not replacing anyone's lawyer, but we have a ton of educational content around the general understanding of a lot of these concepts, right, like what is a contentive plan? What is this eighty three B election that people are talking about, and why should I file one? Right, our clients look to us for business guidance or kind of being a partner in their development as they're navigating those decisions. So there's a lot of stuff that we can't automate. What we can do is develop a whole lot of educational content, both around the concept of what our platform deals with and then also how those things happen in our platform. So our blog is really robust at four years now of content on kind of everything that the platform touches. And then we have a self help library that I think at this moment is about a hundred and eighty articles strong on just about everything that people can do in the platform, as well as you specialized content for investors, for employees, for lawyers, and we utilize a lot of you know thinks, like we use the desk for our support ticketing system and we use macros and to try and capture a lot of those repeatable answers so that we can be as efficients as possible with the simpler questions that we get from people, because invariably we get things that are complicated and that take more time that we just have to dedicate a fair amount of energy to and make sense. See, and you want to be spending more time on those things that a machine can't repeatably do right. Exactly curious I mean you kind of have this unfair competitive advantage, right, having been a former attorney. What about the rest of your team? How do you help them kind of get to this level of, you know, empathetic understanding with your customers who are oftentimes dealing with these complex legal issues that the average, you know, entrepreneur may not understand and death. Yeah, it's interesting because are thinking on its evolved to over the last few years and I've been with the company coming up on four years, so it's been interesting kind of how this has evolved for us. When I joined it with myself and one other woman who was also a lawyer but who went straight from law school into Technology Company, and we've, of course, hired a bunch of people since then. And what we've discovered it is it isn't so much the knowledge of, you know, how startups get built, corporate governance, things like that, how financings happen. It's really a love for startup and, you know it desire to support them and be embedded in that community and it's a willingness to learn the nuts and bolts and logistics of that start up life cycle. Right, how do we go from incorporation to four tires to fundraising, to more fundraising, to an exit, and what are some of the growing pains that people experience along the way? And what we found is the people who've been successful on our team have those things right. They're super hungry to learn and they just take start ups are super cool and they want to dive into that ecosystem. How do they do that? Do you host events? Like are you, you know, building out some sort of I mean slack communities are all the race these days, like, what are you using to actually help get in integrated in that community that you want to be a part of this? So we do a few things. We do host events. Historically we've done a free part what we call startup series, which is cannel discussions and networking around typical start up life cycle issues, fundraising, building your team, etc. And then we host a conference in November which is about fundraising, like...

...the actual nuts and bolts of how you go through it and where people waste money, waste time, cause headaches, etc. And how to fix some of those problems because, because that's what our platform does. Write. It accelerates both the time it takes to go through a fundraise and it decreases the cost of going through that process. This year we're looking at smaller virtual event, most likely a monthly series that will probably kick off in June that, you know, will be more kind of intimate conversations with some breakout groups and things like that, so that we can move the best part of our events, the networking, into a virtual setting. But we also team up with accelerators and incubators in that we provide a free year of shoe box to the teams in the cohort and through doing so we end up going out and doing a lot of conversations and talks around things that kind of touch the the shoe box experience, fundraising, preps, cap tables, all that good stuff, and we're in we kind of working with about thirty different programs at this point. So between those and other sort of shoe box advocates, is sort of evangelist that we have out in the community. Our goal is really to just be part of those ecosystems of books. Know that, yes, we're technology company, but our goal is to really empower those entrepreneurs. That's awesome. That's really exciting. So it sounds like you got a lot going on right now and you've got a bunch of tools and technology to manage it as well. Where does that technology fail you? So I think one of our biggest headaches right now, or one of the big ticket things that I you know, if she gave me all the dollars and all the time in the world, I would solve. I would like all of our client interactions to be in one place. Right I would like our entire team to be able to see if somebody failed a support ticket, if somebody had a meeting with someone, if somebody was on the phone with them last week, in one system. But the way we sort of developed this over time as we picked up zend USK really early on. For support ticket, we used to use sales forced for our crm. We switched over to hub spot a couple years back and at this moment they don't talk to each other except for a couple of very limited things. My dream is that they talk to each other some point because I do think it's really important to just have that three sixty view of the client interactions and what we're doing to facilitate that relationship. You know, we there's a lot of stuff that we use that we really love. I mean I definitely love then dusk. You know, we've been on a million zoom calls with clients lately. That was a switch we made as soon as kind of everybody moved home, as we said, okay, no more Google hang out with our clients. We're all switching to zoom. We're all going camera on as a team and, you know, I think those there's a some of the big your decisions that we've made. But you know, thankfully we've been pretty good, even as a, you know, not Super Big Team, getting a lot of really good data out of our clients interactions, utilizing that in a way that's useful for our team and helpful for others in our company to understand what we're what we're doing and what our clients are asking us for. Got It. That makes sense. Are there any sort of less well known tools or processes that you've been able to implement there that you just like really want to share out or do you should? Actually a really good question. I I don't think we do anything that super unique. You know, we have different sort of shared calendars that our clients can get on quickly because often times, not surprisingly, some of the stuff our clients are doing is better dealt with in a conversation or screen share. So we try to make it super easy for them to set those up with members of our team. Same things with folks getting a demo of a platform and things like that, you know. And we try to be super proactive with our responsiveness. You know, on average almost all of our support tickets get answers within an hour rather than, you know, sort of like the twenty four our standard that a lot of people do, and I think that's just having a culture of being super responsive and understanding that someone wrote to us because they're in need. Let's address it as quickly as possible, and that's been hugely helpful. We get, we get a lot of positive reviews for that all the time. That's great. So it sounds like the team is functioning really well.

How do you maintain great relationships with the other teams and shoe box product team, engineering team, marketing team. So I think as a company we're really good at being clear about what it is that sort of makes a good shoe boxer. Right. We know kind of what those values are. We know what the behaviors that work well in our team are and we do really try to hire for those things. We have really long, thoughtful and detailed conversations before anybody gets tired. And you know they their time consuming. Right. We put a ton of energy into recruiting and you know, it's paid off. We don't always agree that, you know, somebody is a great fit and that's okay and people are encouraged to be super candid about that. And I think just through, you know, having everybody kind of on this same page when they come walk in the door and having, you know, values that encourage people to be respectful and kind to each other and kind of honor people differences. Right, like my team is naturally way more chatty than our development team is, not surprisingly, right, but we have a shared respect for that and that's okay. And you know, we've build in regular interactions with those folks. Like we have a daily meeting where we talked about, you know, client issues that require some technical help, and so just those little interactions where it's like end see in your face and I'm saying hi and I'm asking you how your morning is going goes a long way. And then on our product team, our head of product is in our kind of weekly client service team meeting every week. She comes to our daily meetings, you know. So it's kind of we're still all embedded in the same all in that fabric together, and I think that goes a long way towards just creating a culture where when there are hard things to deal with, we can handle it pretty easily. Got It. That's awesome. All right. So usually when you work in customer success or services you have some pretty good stories. So I want to hear one of your best, my best stories. So I'll say like a lot of times our clients, and I say this in an endearing respectful fashion, come to us at the last minute when they're big ticket things to deal with. You here. It's okay, you don't have to cap like our soundings are busy. Yeah, so, you know, and I think visit. On the flip side of it, it's kind of one of the things that makes customer success tricky for us, which is like our founders don't always have time to just hop on a call or grab a coffee with us. They're busy people, but there's a huge opportunity for relationship building and doing our best work when they are coming up on a fund raise, you know, about to have investors looking at everything that they're doing they're about to you know, they're they've gotten someone interested in them who wants to give them five, ten, twenty million dollars and it's this hugely important moment for them and you know, whether they're doing or financing on shoe box or not, we can really shine and help them and make them feel more empowered and like they've got some control in those transactions, because typically they don't write. There's somebody standing around with a check, there's lawyers who, you know, have done these deals eighty million times before, and then there's this entrepreneur who's completely offutimes, completely green and new to that process. We've had a lot of clients to come to us and are like, I just got a term sheet and I need to get all of these things organized because they want to do something called diligence and I don't even know what that is. And so there's this like half there apy, you're going to be okay with half preparation. Why I'm going to add a third half. Those people thirds not have utilizing the platform to be really helpful in that arena. And you know, that's something that happens for us like once a month. It's not more, which is great because we're also in this place now is a company where we've got companies that have gone incorporation to exit with us, and we've got a bunch of companies that are at series B or see stage now that got onto our platform when they were three people and a pretty good idea where...

...they incorporated with us. So it's really exciting to be able to do that stuff with them. It's great. Yeah, I mean I really want to know. I want to see metrics on what time of day that initial message comes in. Every single times it like one am, two am average. We do get them in the middle of the night, for sure. You know we're because we're on the east coast. We monitor our support channels from nine am to ten PM eastern time, seven day of the week and we consider, you know, that fix to ten on call and are on call. Shifts are routinely busy, especially from our west coast client because you know, people are doing things in the evenings, the end of the day or whatever. Interestingly, a lot of our stuff comes to like Tuesday, Wednesday, Thursday, because people are just they're warming up, they're in it, they're tackling big things and you know that's when all of our calls and emails come in and you know, our team just routinely is swamped on those two. Got It. How do you help break up some of that potential burnouts? I've been in customer success before and I know that, especially when you just really want to serve your customer well, it can be hard to see like where the bounds are between this is acceptable and showing the customer the best path and this is far too much and you are doing way too much. So how do you how do you like manage that balance where you want to give their customer great experience but you also want to make sure that your team doesn't necessarily burn out on trying to do that? Yeah, I mean we've got a couple of kind of they're like product that operates really spells, if you will. So in the very beginning are on boarding process was entirely manual and entirely done by our team, which was not a lot of fun, which just put it that way. And so eventually, a couple years ago, we built from an automated on point, like it's a shoebox workflow, just it's related to onboarding activity as opposed to, you know, doing some option grants or hiring someone, and so there's sort of this automatic floor that's put in on you know where we can get involved and what we can do. You know, we can support people through on boarding. We can educate them as to what needs to be put in the system and why it's important and what's through. The end goal is we stop short, however, of reaching and grabbing their documents and doing it for them. Also, you know, the legal advice piece is really a helpful buffer for us. We get clients all the time who were like, I'm going to do this thing. Is this a good idea? or I'm debating doing these two things. Here's the advice I've gotten. Is it right? You know, and we'll say look, we've got all sorts of contextual or kind of general guidance that you can partake of. We can tell you generally speaking what we we see our clients do, but no, I can't tell you how to make that decision. I'm sorry, and and we're super clear about that and I think our clients get it too. They're like, Oh, I know, I know, it's just you know and will hear. So it's more fun to talk to you guys than it is to my lawyer and like, okay, that's great, we appreciate it, but you still need them. So take this information and go talk them to say, then you sign your email jd right. Exactly. It's almost tricky sometimes where I'm like, do I tell them or do I not tell them that I'm actually a lawyer? Exactly. So I really thankful for all this thoughtful advice and sharing your experience with us. I do like to ask a final question. Just what is the best piece or set of advice you've gotten related to customer success thus far in your care so this one is Super Dorky and actually came when I was lawyering as a first year associate, which is for any of your listeners who are also attorneys will know, it's like the worst year of your life as a lawyer because you come out of law school of thinking you're Super Smart, you've just learned everything, you just pass the bar and it turns out you know absolutely nothing and you're basically relegated to doing secretarial work and when you're working in a big firm, to a lot of times, if it's communicating out to client, your emails get reviewed before they get sent out. And I was working with...

...a colleague of mine who was reviewing an email I was sending out to our client, which is a venture capital firm, and he said to me, okay, this is great, you've covered the point, but the stuff you've provided it is going to trigger this other question about now Xyz, and he's like you've got to just add in the answer to that question to in here. You've got to put the potato on the floor, and I was like what is that? And he was like, Oh, you know, some eighty five year old partner taught me this when I was a first year and Blah, blah, blah, like you gotta just do it for them and to sipate their needs and then do the next step. And I was like that's ridiculous. And then, of course, you know a million years later, like no, it's actually perfect. And I have honest to God, threatened our team that one of these days I'm going to like go to an SC designer and have this like et done a sign somewhere to put in our office, because it's totally a way of life for us now. It's like what are they asking us? You know, what are these people need? Let's think about other things that they might need to know, because often times our clients will ask us about oranges, but they actually need to talk about an entire Frud Salad and, you know, and behave that way. Have that be kind of a our motto, if you will. That is amazing. I'm probably going to steal all that. Thank you so real. I find I really appreciate your time to day. Lyn. Just remind everyone listening that's Lendsagami from shoebox and is spelled shoob xcom. If you want to learn a little bit more about what they're do it. So thanks you all for listening in and we'll catch you next time. You depend on the fastest time to value for your customers, so I let data on board and sell you down. Stop emailing spreadsheets, creating CSB templates or setting up FTP transfers. Create collaborative, secure workspaces with your customers and their data, saving you time while providing a memorable onboarding experience. Oh and there's no code required. You can go to flat file DOT IO CS leader to learn more and get started for free. Thank you so much for joining us for this episode. Customer Success leader is brought to you by flat file. If you're a fan of the show and want to help us share these conversations with others, leave us a rating on apple podcast. Just tap the number of stars you think the show deserves. That's it for today. Catch you in the next one.

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