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 wecan'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 howthose things happen in our platform. Want to create delightful customer experiences. You'rein the right place. Welcome to customer success leader, where you'll learn aboutthe 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 mefrom shoe box. Helen, hi, how are you? I'm doing allright. Thank you. Are you calling from today? Just outside of Boston, in Newton Massachusetts? I Miss Oysters. Yes, I actually have started lookingfor lobster rolls and places that I know can do fancy take out ofthat kind of food, because it's almost that time. Have you been liketrying to trade toilet paper for the lobster rolls? Like, what are wegetting 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 andmy sister and I have purposely been trying to benefit some of the restaurants thatwe love and do a weekly dinner where we just go for it and orderall the delicious thing but see food, you know it's getting to be thattime 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'sworth it, definitely well, thank you so much for joining us today.I like to start out these conversations with the question, and that question ishow do you define customer success? So I think there's the aspirational definition forus 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 withour 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 fromthe 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'removing certain information into our platform, to addressing questions that they might have abouthow to get the best use out of it and just that overall, gettingto know them and getting to know their company and what they're up to andhow they might how we might be able to support them along their kind ofgrowth path. Got It? Well, tell me a little bit more aboutshoe box, like what are you doing there? So we think of ourselvesas a legal operating system for startups. We work with companies from incorporation toexit, and these are companies that expect to raise outside capital, that arehiring employees and issuing them equity as incentive. So really the things that we typicallythink of as start up and we support them through equity management, throughHR, through fundraising, governance, all of those activities, and there's arole in our software for every one of their stakeholders. And what we've reallybeen seeing is it's really valuable to companies as they're preparing to go through afundraise, to get their documents organized, to make sure that they have anice clean data room to show to investors and then actually going through the investmentprocess and coming out the other side and having kind of a ready made systemfor managing those investor relationships and all the information you kind of flows back andforth between them. Got It sounds like it's pretty challenging to replace what peopleare used to getting as a personal service with software. And I guess youknow whatever your team is able to help provide your customers. How do youhow 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 whatpeople are doing now that are not helpful...

...right, that are repeatable, thatshould not be kind of done manually, artisanally, etc. And letting softwaredo those things. So a lot of what we do is preparation of HurDocumentation, preparation of equity grants and things like that, and those things oftentimesare done, you know, by hand by attorneys, and there's really nodis station, when startups are paying for those services, between the substantive legaladvice right and paying for that, versus the almost administrative stuff of Enterinian someone'sname and the number of shares they get and investing schedules. So shoebox couldhave fit in between that relationship and, you know, utilize the things thatare kind of these routine based workflows that allow the attorney to focus on whatthey're doing, so that's important, and allow the startup to have more ownershipover these processes and the things that they're doing, and really it creates additionaltransparency on both sides for each of those parties. Got It. So itsounds like you caind of need to build a relationship with both sides, thelegal and the start up side of things. Yes, and this is actually oneof the the biggest learnings that we've had over the years, which is, you know, initially we were thinking, okay, our client base is thestartup, 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 mostactive user on our platform outside of those sort of founding executive teams are thelawyers, and so we've put on a lot of energy and effort over thelast couple of years to really make those connections more robust to and that's everythingfrom 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 oftraining 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'ssort of a shared understanding there of how tricky those relationships can be. Andyou know, what we've found is once the attorneys know they can come tous, they know where to find us, they know where to find information abouthow 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 metyou from lawyer to, you know, running customer success for a legal textartups. So this is actually the second startup where I have headed up theclient 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 preferbuilding things to performing services. But also, as I was growing up, ifyou will, as a lawyer, there were so many conversations with,you know, partners and more senior attorneys that I worked with who were likeyeah, you're an okay lawyer, but your relationship management skills or like offthe church. You know, our clients love working with you. Oh,I wish you know our partners were as good at managing client relationships as youwere. 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 inmy last firm I actually transitioned from practicing full time to practicing about a quarterof the time and the rest of my time was spent on client service andmarketing and business development, and I was basically out and doing my job whenI met the founders of shoe box and we hit it off immediately and startedto 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 someof our development teams in Europe. Got Some folks that are working on thewest coast as well, although every single one of us is now working fromkitchen tables, living rooms, wherever we happen to be. Yeah, I'vegot a basement and staring out the window here, wis she now? WasOutside a day? Yeah, we don't get a ton of eighty degree dayshere you happen to catch me on one of them. So anadoicated brief exactly. So tell you, I mean, I love a little bit more aboutthe 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 ourclients need from US oftentimes isn't so much guidance around how do I get thisthing done in shoe box, it's how do I make these decisions for mycompany 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 havea 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 threeB 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 apartner in their development as they're navigating those decisions. So there's a lot ofstuff that we can't automate. What we can do is develop a whole lotof educational content, both around the concept of what our platform deals with andthen also how those things happen in our platform. So our blog is reallyrobust 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 momentis about a hundred and eighty articles strong on just about everything that people cando in the platform, as well as you specialized content for investors, foremployees, 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 andto try and capture a lot of those repeatable answers so that we can beas efficients as possible with the simpler questions that we get from people, becauseinvariably we get things that are complicated and that take more time that we justhave 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'trepeatably do right. Exactly curious I mean you kind of have this unfair competitiveadvantage, right, having been a former attorney. What about the rest ofyour 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 thesecomplex legal issues that the average, you know, entrepreneur may not understand anddeath. Yeah, it's interesting because are thinking on its evolved to over thelast 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 Ijoined it with myself and one other woman who was also a lawyer but whowent straight from law school into Technology Company, and we've, of course, hireda bunch of people since then. And what we've discovered it is itisn't so much the knowledge of, you know, how startups get built,corporate governance, things like that, how financings happen. It's really a lovefor startup and, you know it desire to support them and be embedded inthat community and it's a willingness to learn the nuts and bolts and logistics ofthat start up life cycle. Right, how do we go from incorporation tofour tires to fundraising, to more fundraising, to an exit, and what aresome of the growing pains that people experience along the way? And whatwe 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 cooland they want to dive into that ecosystem. How do they do that? Doyou host events? Like are you, you know, building out some sortof 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 youwant 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 startupseries, which is cannel discussions and networking around typical start up life cycle issues, fundraising, building your team, etc. And then we host a conference inNovember which is about fundraising, like...

...the actual nuts and bolts of howyou go through it and where people waste money, waste time, cause headaches, etc. And how to fix some of those problems because, because that'swhat our platform does. Write. It accelerates both the time it takes togo 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 willprobably kick off in June that, you know, will be more kindof intimate conversations with some breakout groups and things like that, so that wecan 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 providea free year of shoe box to the teams in the cohort and through doingso we end up going out and doing a lot of conversations and talks aroundthings that kind of touch the the shoe box experience, fundraising, preps,cap tables, all that good stuff, and we're in we kind of workingwith about thirty different programs at this point. So between those and other sort ofshoe box advocates, is sort of evangelist that we have out in thecommunity. Our goal is really to just be part of those ecosystems of books. Know that, yes, we're technology company, but our goal is toreally empower those entrepreneurs. That's awesome. That's really exciting. So it soundslike you got a lot going on right now and you've got a bunch oftools 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 ofthe big ticket things that I you know, if she gave me all the dollarsand all the time in the world, I would solve. I would likeall of our client interactions to be in one place. Right I wouldlike 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 withthem last week, in one system. But the way we sort of developedthis over time as we picked up zend USK really early on. Forsupport ticket, we used to use sales forced for our crm. We switchedover to hub spot a couple years back and at this moment they don't talkto each other except for a couple of very limited things. My dream isthat they talk to each other some point because I do think it's really importantto just have that three sixty view of the client interactions and what we're doingto facilitate that relationship. You know, we there's a lot of stuff thatwe 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. Thatwas a switch we made as soon as kind of everybody moved home, aswe said, okay, no more Google hang out with our clients. We'reall 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 thatwe've made. But you know, thankfully we've been pretty good, even asa, you know, not Super Big Team, getting a lot of reallygood data out of our clients interactions, utilizing that in a way that's usefulfor our team and helpful for others in our company to understand what we're whatwe're doing and what our clients are asking us for. Got It. Thatmakes sense. Are there any sort of less well known tools or processes thatyou've been able to implement there that you just like really want to share outor do you should? Actually a really good question. I I don't thinkwe do anything that super unique. You know, we have different sort ofshared 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 aconversation or screen share. So we try to make it super easy for themto set those up with members of our team. Same things with folks gettinga demo of a platform and things like that, you know. And wetry to be super proactive with our responsiveness. You know, on average almost allof 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 understandingthat someone wrote to us because they're in need. Let's address it as quicklyas possible, and that's been hugely helpful. We get, we get a lotof positive reviews for that all the time. That's great. So itsounds like the team is functioning really well.

How do you maintain great relationships withthe 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 whatit is that sort of makes a good shoe boxer. Right. We knowkind of what those values are. We know what the behaviors that work wellin 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. Andyou know they their time consuming. Right. We put a ton of energy intorecruiting 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 areencouraged to be super candid about that. And I think just through, youknow, having everybody kind of on this same page when they come walk inthe door and having, you know, values that encourage people to be respectfuland kind to each other and kind of honor people differences. Right, likemy 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 wehave a daily meeting where we talked about, you know, client issues that requiresome technical help, and so just those little interactions where it's like endsee in your face and I'm saying hi and I'm asking you how your morningis going goes a long way. And then on our product team, ourhead 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 ofwe're still all embedded in the same all in that fabric together, and Ithink that goes a long way towards just creating a culture where when there arehard things to deal with, we can handle it pretty easily. Got It. That's awesome. All right. So usually when you work in customer successor services you have some pretty good stories. So I want to hear one ofyour best, my best stories. So I'll say like a lot oftimes our clients, and I say this in an endearing respectful fashion, cometo 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 arebusy. Yeah, so, you know, and I think visit. On theflip side of it, it's kind of one of the things that makescustomer success tricky for us, which is like our founders don't always have timeto just hop on a call or grab a coffee with us. They're busypeople, but there's a huge opportunity for relationship building and doing our best workwhen they are coming up on a fund raise, you know, about tohave investors looking at everything that they're doing they're about to you know, they'rethey'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 shineand help them and make them feel more empowered and like they've got some controlin those transactions, because typically they don't write. There's somebody standing around witha check, there's lawyers who, you know, have done these deals eightymillion times before, and then there's this entrepreneur who's completely offutimes, completely greenand new to that process. We've had a lot of clients to come tous and are like, I just got a term sheet and I need toget all of these things organized because they want to do something called diligence andI don't even know what that is. And so there's this like half thereapy, you're going to be okay with half preparation. Why I'm going toadd a third half. Those people thirds not have utilizing the platform to bereally helpful in that arena. And you know, that's something that happens forus like once a month. It's not more, which is great because we'realso in this place now is a company where we've got companies that have goneincorporation to exit with us, and we've got a bunch of companies that areat series B or see stage now that got onto our platform when they werethree people and a pretty good idea where...

...they incorporated with us. So it'sreally 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 metricson what time of day that initial message comes in. Every single times itlike one am, two am average. We do get them in the middleof the night, for sure. You know we're because we're on the eastcoast. We monitor our support channels from nine am to ten PM eastern time, seven day of the week and we consider, you know, that fixto ten on call and are on call. Shifts are routinely busy, especially fromour west coast client because you know, people are doing things in the evenings, the end of the day or whatever. Interestingly, a lot ofour stuff comes to like Tuesday, Wednesday, Thursday, because people are just they'rewarming up, they're in it, they're tackling big things and you knowthat's when all of our calls and emails come in and you know, ourteam just routinely is swamped on those two. Got It. How do you helpbreak up some of that potential burnouts? I've been in customer success before andI know that, especially when you just really want to serve your customerwell, it can be hard to see like where the bounds are between thisis acceptable and showing the customer the best path and this is far too muchand you are doing way too much. So how do you how do youlike manage that balance where you want to give their customer great experience but youalso want to make sure that your team doesn't necessarily burn out on trying todo that? Yeah, I mean we've got a couple of kind of they'relike product that operates really spells, if you will. So in the verybeginning 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 asopposed to, you know, doing some option grants or hiring someone, andso there's sort of this automatic floor that's put in on you know where wecan get involved and what we can do. You know, we can support peoplethrough on boarding. We can educate them as to what needs to beput in the system and why it's important and what's through. The end goalis we stop short, however, of reaching and grabbing their documents and doingit for them. Also, you know, the legal advice piece is really ahelpful buffer for us. We get clients all the time who were like, I'm going to do this thing. Is this a good idea? orI'm debating doing these two things. Here's the advice I've gotten. Is itright? You know, and we'll say look, we've got all sorts ofcontextual or kind of general guidance that you can partake of. We can tellyou generally speaking what we we see our clients do, but no, Ican't tell you how to make that decision. I'm sorry, and and we're superclear 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 tomy lawyer and like, okay, that's great, we appreciate it, butyou 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 whereI'm like, do I tell them or do I not tell them thatI'm actually a lawyer? Exactly. So I really thankful for all this thoughtfuladvice and sharing your experience with us. I do like to ask a finalquestion. Just what is the best piece or set of advice you've gotten relatedto customer success thus far in your care so this one is Super Dorky andactually came when I was lawyering as a first year associate, which is forany of your listeners who are also attorneys will know, it's like the worstyear of your life as a lawyer because you come out of law school ofthinking you're Super Smart, you've just learned everything, you just pass the barand it turns out you know absolutely nothing and you're basically relegated to doing secretarialwork 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 getsent out. And I was working with...

...a colleague of mine who was reviewingan email I was sending out to our client, which is a venture capitalfirm, and he said to me, okay, this is great, you'vecovered the point, but the stuff you've provided it is going to trigger thisother question about now Xyz, and he's like you've got to just add inthe answer to that question to in here. You've got to put the potato onthe floor, and I was like what is that? And he waslike, Oh, you know, some eighty five year old partner taught methis when I was a first year and Blah, blah, blah, likeyou gotta just do it for them and to sipate their needs and then dothe next step. And I was like that's ridiculous. And then, ofcourse, you know a million years later, like no, it's actually perfect.And I have honest to God, threatened our team that one of thesedays I'm going to like go to an SC designer and have this like etdone a sign somewhere to put in our office, because it's totally a wayof life for us now. It's like what are they asking us? Youknow, what are these people need? Let's think about other things that theymight 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, youknow, 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 today. Lyn. Just remind everyone listening that's Lendsagami from shoebox and is spelledshoob xcom. If you want to learn a little bit more about what they'redo it. So thanks you all for listening in and we'll catch you nexttime. You depend on the fastest time to value for your customers, soI let data on board and sell you down. Stop emailing spreadsheets, creatingCSB templates or setting up FTP transfers. Create collaborative, secure workspaces with yourcustomers 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 IOCS leader to learn more and get started for free. Thank you so muchfor joining us for this episode. Customer Success leader is brought to you byflat file. If you're a fan of the show and want to help usshare these conversations with others, leave us a rating on apple podcast. Justtap the number of stars you think the show deserves. That's it for today. Catch you in the next one.

In-Stream Audio Search


Search across all episodes within this podcast

Episodes (28)