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'tautomate. What we can do is develop a whole lot of educational content, botharound the concept of what our platform deals with and then also how thosethings happen in our platform want to create delightful customer experiences.You're in the right place. Welcome to customer Successfullyer, where you'lllearn about the successes and struggles of leaders who are passionate abouttheir craft. Trust me. You want to stick around here's your host, EricCran Ohey there, I'm Eric Crane, COK counderhere at flat file and today we're talking with another customer success.Leader we've got limsagan Mi from shoebox Halen hi. How are you I'm doingall right? Thank you. Where re you calling from today, Jast outside ofBoston in Newton massachuset, I Miss Oysters. Yes, I actually have started lookingfor lobsteroles and places that I ou know can do fancy takeout of that kindof food, because it's almost that time have you been like trying to tradetoilet paper for the the lapter roles like what are we getting into leveldepation here? NO WE'RE ACTL! Our you know. Fancy takeout game is prettystrong here. Our restaurant seene is very good and my sister and I havepurposely been trying to benefit some of the restaurants that we love and doa weekly dinner where we just go for it and order all the delicious thing, butseafood you know it getting to be that time might have to risk a trip on aplane right up there. That's the one thing I missed the most about that city.It's worth it definitely well. Thank you so much for joining us today. Ilike to start out these conversations with the question and the question is:How do you define customer success, so I think there's the aspirational definition for us and thenthere's the operational definition. The aspirational definition I'd say: Is YouK, ow warming, meaningful relationships with our clients that produce strongrepeatable engagement with our platform operationally we're actually a littlebit different as a team we kind of handle some of the business developmentactivities. Certainly onboarding certainly account management and alsosupport. So we really see the customer from the beginning of their engagementwith us as a company and our platform through them getting up and runningunderstanding. What that looks like and why they're moving certain informationinto our platform to addressing questions that they might have abouthow to get the best use out of it and just that overall, getting to know themand getting to know their company and what they're up to and how they mighthow we might be able to support them along their kind of growth path. Goniwell tell me a little bit more about shoebox like what are you doing there,so we think of ourselves as a legal operating system for startups. We workwith companies from incorporation to exit, and these are companies thatexpect to raise outside capital that are hiring employees and issuing themequity, as incentive, so really the things that we typically think of asstart up and we support them through Equityn management through hr throughfundraisiing governance, all of those activities and there's a role in oursoftware for every one of their stateholders and what we've really beenseeing. Is it's really valuable to companies as they're preparing to gothrough a fundrase to get their documents organized make sure that theyhave a nice clean data room to show to investors and then actually goingthrough the investment process and coming out the other side and havingkind of a ready made system from managing those investor relationshipsand all the information kind of flows back and forth between them got. Itsounds like it's pretty challenging to replace what people are used to gettingas a now personal service with software, an guess you know whatever your team isable to help provide to your customers mean how do how do you do thateffectively? So there's a piece of this, which is just making sure that we'retaking the elements of what people are doing now, that are not helpful rightthat are repeatable that should not be...

...ove done, manually, artisinally, etcand letting software do those things rigt. So a lot of what we do ispreparation of HR, documentation, preparation of equity grants and thingslike that and those things oftentimes are done. You know by hand by attorneysand there's really no distinction when startups are paying for those servicesbetween the substantive legalisice rigt and paying for that versus the almostadministrative stuff of Enteriniin, someone's name and the number of sharesthey get and thenvesting schedule. BECASE Yhou Bot sort of sit in betweenthat relationship, and you K, utilizes things that are you kN kind of theseroutine based workflows that allow the attorney to focus on what theyare doingthat's important and allow the startup to have more ownership over theseprocesses and the things that they're doing and really creates additionaltransparency on both sides for each of those parties. God it so it sounds likeyou kind of need to build a relationship with both sides. The legaland the K start up side of things. Yes, and this is actually one of the biggestlearnings that we've had over the years, which is you know? Initially, we werethinking. Okay, our client based is the start up right. That's going to be theperson that we focus on the founder, the executive team, whatever that is,but really as a client service team. We support all of our uters and the mostactive user on our platform outside of those sort of founding executive teamsare the lawyers, and so we put on a lot of energy and effort over the lastcouple of years to really make those connection more robots to, and that'severything from is being more upfront about it. When we talk to potentialclients about it, to building out kind of selfservice resources for attorneyto building kind of training programs for them, so they can get comfortableon the software and it helps I actually was a corporate lawyer for severalyears for start up, so there is sort of a shared understanding there of howtricky those relationships coan be, and you know what we found is once theattorneys know they can come to us thing know where to find us. They knowwhere to find information about how to Youse Tubax they're way morecomfortable than they were. You know before they HEP on a Tine with that Godand I was wondering why he kept saying Inturnin. Instead, a lawyer and yeahLok et you from lawyer to you, know running customer success for a legalTAC SARTUPS. So this is actually the second start up where I have headed upthe client service function. My last one was a document automation companyfor lawyers and really it was a combination of loving Te, startupenvironment. I just prefer building things to performing services, but also,as I was growing up, if you will, as a lawyer, there were so manyconversations with you know, partners and more senior attorneys that I workedwith, who were like yeah you're in okay lawyer, but your relationshipmanagement skills or like off the church. You know our clients loveworking with you. Oh I wish you know. Our partners were as good at managingclient relationships as you were, and you kN W. You only hear that so manytimes 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 practicingabout a quarter of the time and the rest of my time was pent on clientservice and marketing and business development, and I was basically outdoing my job when I met the founders of shoebox and we hit it off immediatelyand started to build a relationship and then now here I am that's reallyexciting. So I mean how many folks are on the team, currently a we're a littleover thirty, mostly in Cambridge, but we've got some F. Hor developmentteamas 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 livingrooms, wherever we happen to be Yeph, Ivgot a basement and staring out thewindow here wishing I was outside today, yeah, we don't get a ton of eightydegree days here. You happen to catch me on one of them, so I got a Keepinbriefe. Exactly so tell you, I mean I love Towo a little bit more about theexperience of scaling out success and... as a function within atechnology company like what his that experience been like, as you've grownfrom. You know a handful of folks of the company now to around thirty yeahso for it was a really interesting experience, because what we realizedwas what our clients need from us. Often Times isn't so much guidancearound. How do I get this thing done in shoebox it? How do I make thesedecisions for my company right? How do I know which actions are the right onesto take and because we're in this interesting position where we don'tprovide legal, if I were not a lawfroom, we're not replacing anyone's lawyer,but we have a ton of educational content around the generalunderstanding of a lot of these concepts right like what is a stockincenttis plan? What is this eighty three B election that people aretalking about, and why should I file one right? Our clients look to us forbusiness guidance for 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 automatewhat we can do is develop a whole lot of educational content, both around theconcept of what our platform deals with and then also how those things happenin our platform. So our blog is really robust at four years now of content ongetting u kind of everything that the platform catches and then we have aself help. Library that I think at this moment is about a hundred and eightyarticle strong on just about everything that people can do in the platform aswell as you specialize content for investors for employees for lawyers,and we utilize a lot of you know. Things like we use en desk for oursupport ticketing system and we use macros and to try and capture a lot ofthose repeatable answers so that we can be as efficient as possible with thesimpler questions that we get from people, because invariably we getthings that are complicated and that take more time that we just have todedicate a fair amount of energy. To that makes sense. Yeah you want to bespending more time on those things that a machine can't repeatidly do rightexactly curious. I mean you kind of have this unfair competitive advantageright. Having been the former attorney. What about the rest of your team? Howdo you help them kind of get to this level of you know, empatheticunderstanding with your customers, who are often times dealing with thesecomplex legal issues that the average you know entrner may not understand inthat yeah. It's interesting because ire thinking on mihis a balls to over thelast few years and I've been with the company coming up on four years. Soit's been interesting kind of how this has evolved for us when I joined itwith myself and one other woman who was also a lawyer, but who went straightfrom law school into Technology Company and we've, of course hired a bunch ofpeople since then, and what we've discovered it it is. It isn't so muchthe the knowledge of you know how startup ket built corporate governancethings like that. How finance things happen? It's really a love for startupand you know a desire to support them and be embedded in that community andit's a willingness to learn the nothing bolt and logestic of thatTartup lifecycle right. How do we go from incorporation to firtire tofundraising, to more fundraising, to an exit and what are some of the growingpeans that people experience along the way and what we found is the peoplewho've been successful on our team? Have those things right, they're superhungry to learn, and they just thank start up. They're super cool and theywant to dive into that equithystem. How Dany they do that. Do you host eventslike are you you know, building out some sort of I mean flat. Communitiesare all the rage these days like? What are you using to actually help get ingintegrated in that community that you want to be a part of US hat? We do afew things we do hope. tovents. Historically, we've done a three part.What we call startup series, which is panel discussions and networking aroundtypical startup lifcycle issues, tundrysing building your team, etc, andthen we host a conference in November, which is about fundryting like theactual nets, involts of how you go...

...through it and where people waste money,waste time cause headaches, etca a how to fix some of those problems becauseyen, that's what our platform does right. It accelerates both the time ittakes to go through a funderase and it decreases the cost of going throughthat process. This year, we're looking at smaller virtual event, most likely amonthly series that will probably kick off in June. That you know will be morekind of intimate conversations with some breakout groups and things likethat, so that we can move the best part of our events, the networking into avirtual setting, but we also team up with accelerators and incubators inthat we provide. You know a free year of shoebox to the teams in the cocourtand through doing so, we end up going out and doing a lot of conversationsand talks around things that Kand of touch the shoebaks experience.fundrasing pap cap tables all that good stuff and we're in we kind of workingwith about thirty different programs. At this point, so between those andother sort of shoebox advocates is sort of vangelist that we have out in thecommunity. Our goal is really to just be part of those egosystems, so booksknow that yes, we're technology company, but our goal is to really empower theentrepreneur. That's Awsome, that's really exciting. So it sounds like yougot a lot going on right now and you've got a bunch of tools and technologiesto manage it as well. Where does that Technology Fail Yu? So I think one ofour biggest headaches right now or one of the big ticket things that I youknow if heu 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 filed a supportticket. If somebody had a meeting with someone, if somebody was on the phonewith them last week in one system, but the way we sort of developd this overtime is we picked up zendest really early on for support ticket we used touse, tells force for our crm. We switched over to hub spot a coupleyears back and at this moment they don't Halk to each other, except for acouple of very limited things. My dream is that theye talked to each other atsome point, because I do think it's really important to just have thatthred sixty vew of those client interactions and what we're doing tofacilitate that relationship. You know we there's a lot of stuff that we usethat we really love. I mean I definitely love, then desk. You know,we've been on a million zoom calls with clients. Lately that was a swhitch wemade as doon as kind of everybody moved home. As we said, okay, no more. Google,hang out with our clients, were all switching to zoom were all going cameraon as a team, and you know I think those are the some of the biggerdecisions that we've made, but thankfully we've been pretty good, evenat the you know, not Super Big Team, getting a lot of really good data outof our client interaction, utilizing that in a way, that's useful for ourteam and it helpful for others in our company to understand what we're whatwe're doing and what our client Youre asking us for God, it that makes sense.Are there anny sort of less well now tools or processes that you've beenable to implement there? That you just like, really want to share out? Or doyou Shata really good question? I don't think we do anything that'super unique. You know we have different sort of shared calendar that our clients can get on quickly becauseoftentimes, not surprisingly, some of the stuff our clients are doing, isbetter dealt with in a conversation or screenshare. So we try to make it supereasy for them to set those up with members of our team. Same things withfolks getting a demo of a platform, and things like that, you know and we tryto be super proactive with our responsiveness. You know, on average,almost all of our suport tickets get answers within an hour rather than youknow, sort of, like the twenty four hour standard, that a lot of people do-and I think that's just having a culture of being super, responsive andunderstanding that, like someone wrote to us because they're in need, let'saddress it as quickly as possible and that's been hugely helpful. We get. Weget a lot of positive reviews for that, all the time. That's great, so itsounds like the team is functioning...

...really well. How do you maintain greatrelationships with the other teams and twobox product team engineering, teammarketing team? So I think, as a company, we're really good at beingclear about what it is at sort of makes a good shoeboxer right. We know kind ofwhat those values are. We know what the behaviors that work well in our teamare, and we do really try to hire for those things. We have really longthoughtful and detailed conversations before anybody gets tired and you knowthey their time consuming right. We put a ton of energy into recruiting and youK Ow, it's paid off. We don't always agree that you know somebody is a greatfit and that's. Okay and people are encouraged to be super candid aboutthat, and I think, just through you know having everybody kind of on thissame page when they come walk in the door and having you know, values thatencourage people to be respectful and kind to each other and kind of honor.People's differences right, like my team, is naturally way more chetty thanour development team is not surprisingly right, but we have ashared respect for that and that's okay and you know we build in regularinteractions with those folks like we have a daily meeting where we talkabout. You know, client issues that require some technical help, and so wejust those little interactions. Wer, it's like I'm seeing your face and I'msaying hi and I'm asking you how your morning is going goes a long way andthen on our product team. Our head of product is in our kind of weekly plantservice team meeting every week. She comes to our daily meetings. You knowso it's kind of we're still all embedded in the fame all in that fabrictogether, and I think that goes a long way towards just creating a culturewhere, when there are hard things to deal with, we can handle it prettyeasily. That's awesome right! So, usually, when you work in customersuccess or services, you have some pretty good stories. So I want to hearone of your best. My best story is so I'll say like a lot of times. Ourclients- and I say this in an endering respectful fashion- come to us at thelast minute when there are big ticket things to del it, the Tokinomisonerierhere, it's okay, you don't have to come like or foundins are busby yeah. So youknow- and I think this is on the foot side of it- it's kind of one of thethings that makes customers secestriky for us, which is like our founders,don't always have time to just help on a call or grab a coffee with us. Rithey're busy people, but there's a huge opportunity for relationship buildingand doing our best work when they are coming up on a fund raise you knowabout to have investors looking at everything that they're doing they'reabout to you know: Theyre they've, gotten someone interested in them whowants to give them five, ten twenty million dollars, and it's this hugelyimportant moment for them, and you know whether they're doing their financingon shoebox or not. We can really shine and help them and make them feel moreempowered and, like they've, got some control in those transactions because,typically they don't ite. There's somebody standing around with a check.There is lawyers who you know have done these deals, eighty million timesbefore and then there's Tha contrepene who's completely of Etans, completelygreenn and new to that process. We've had a lot of clients who you know cometo us and are like. I just got a term sheet and I need to get all of thesethings organized because they want to do something called diligence, and Idon't even know what that is, and so there's this like half berapy you're,going to be okay with half preparation, lack I'm going to add a third half thoequal thirds not have utilizing the platform to be really helpful in thatarena, 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, as acompany where you know, we've got companies that have gone incorporationto exit with us and we've got a bunch of companies that are, you know atseries B or CSTAGE. Now that got onto our platform when they were threepeople and a pretty good idea, wor they...

...incorporated with us. So it's reallyexciting to be able to do that stuff with them. It's great yeah. I mean Ireally want to know. I want to see metrics on what time of day thatinitial message comes in every single time at like UNM, two am average. We doget them in the middle of tne night for sure you know we're because we're onthe east coast. We monitor our support channels from nine N to ten PM EIHT entime seven days a week, and we consider you know that fix toten on call and ouron calln shifts are routinely duzsy, especially from our west coast client,because you know people are doing things in the evenings the end of theday or whatever. Interestingly, a lot of our stuff come to like Tuesday,Wednesday Thursday, because people are just theyre warming up they're in itthey're tackling big things, and you know that's when all of our calls andfemails come in, and you know our team just routinely is Wam on those day gotit. How do you help break up some of that potential? Burnoutso I've been incustomer success before, and I know that, especially when you just reallywant to serve your customer. Well, it can be hard to see like where thebounds 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? Howdo you like manage that balance where you want to give the customer greatexperience, but you ast want to make sure that your team doesn't necessarilyburn out on trying to do that. Yeah I mean we've got a couple of kindof theyre like products that operate is really pells. If you will so in thevery beginning, our onboarding process was entirely manual entirely done byour team, which was not a lot of fun. HEC just put it that way, and so, eventually, a couple years ago, webuilt smen automated on, like it's a shoebox workflow, just it's related toonboarding activity, as opposed to you know, doing some option, grants orhiring someone, and so there's sort of this automatic floor that put in on youknow where we can get involved and what we can do. You know we can supportpeople through on boarding. We can educate them as to what needs to be putin the system and why it's important and what, through the end goal, is westopp short, however, of reaching and grabbing their documents and doing itfor them? Also, you know the legal advice. Piece is really a helpfulbuffer for us. We get clients all the time who are like I'm going to do thisthing. Is this a good idea or I'm debating doing these two things,curously advice, I've gotten! Is it right, you know and will say look.We've got all sorts of contextual or Kive of General guidence that you canpartake of. We can tell you generally speaking what we we see our client do,but no, I can't tell you how to make that decision. I'm sorry and and we'resuper clear about that and I think our clients get it to they're like I know Iknow it' just you know and well heare, it's more fun to talk to you guys thanit is my lawyer and like okay, that's great, we appreciate it, but you stillneed them. So take this information and go tack tothem say then you sign your email jd right, exactly it's almost tricky, sometimes where I'mlike. Do I tell them, or do I not tell them that I'm actually awayre exactlyso? I really thankful for all this thoughtful advice and charing yourexperience with thats a do like to ask a final question. Just what is the bestpiece or set of advice? You've gotten related to customer success, Thas farin your Cuer, so this one is Super Dorky and actually came when I waslawyering as a first year associate, which is for any of your listeners, whoare also attorneys will know, is like the worst year of your life as a lawyer,because you come out of law, school and thinking. You're Super Smart, you'vejust learned everything and just pass the bar, and it turns out you knowabsolutely nothing and you're, basically religated to doingsrecretarial work and when you're working in a big firm to a lot of times,if you're communicating out to client your email get reviewed before they getsent out, and I was working with a...

...colleague of mine who was reviewing anemail I was sending out to our client, which wis at aventure capital firm andhe said to me. Okay, this is great. You've covered the point, but the stuffyou've provided is going to trigger this other question about now. XYZneeds like you've got to just add in the answer to that question too. Inhere, you've got to put the potato on the fort, and I was like what is thatand he was like. Oh you know some eighty five year old partner Ha taughtme this. When I was a first year in Blah Blah Blah like you got to just doit for them anticipate their needs and then do the next step d. like that'sridiculous and then, of course, you know a million years later, like no,it's actually perfect- and I have honest, O God- threatened our team-that one of these days, I'm going to like, go to an SC designer and havethis like etched on a sign somewhere to put in our office because it's totallya way of life for us. Now, it's like what are they asking us? You know whatDar these people need. Let's think about other things that they might needto know because oftentime, our clients will ask us about oranges, but theyactually need to talk about an entire fruit, salad and you know and behavethat way have that be kind of a Armato. If you will, that is amazing. I'mprobably GOINGTO steal that. So thank you. soally fight. We really appreciateyour time to day limb. Just surmind, everyone, theeing, that's Linza, Gamifrom shoebox and T is stelld s Hoob xcom. If you want to learn a little bitmore about, let ther do it. So thanks you all for listeningin and we'll catchyou next time. You depend on the fastest time to value.For your customers, so why I let data onboard and Sel you down: Stop emailingspreadsheets, creating CFT, templats or spending a practiky transfers, createcollaborative secure workspaces with your customers and their data savingyou time, while providing a memorable, onboarding experience. Oh and there'sno code required, you can go to flat file, dot, IO SLASHTHF leader to learnmore and get started for free. Thank you. So much for joining us forthis episode. Customer Success leader is brought to you by flat file ifyou're a fan of the show and want to help to share these conversations withothers. Leave us a rating on Apple Podcast, just tap the number of stars.You think the show deserves. That's it for tyday catch you in the next one.

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