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BC Startup Sales Podcast – Selling SaaS At The Outpost with David Levy (Crittercism)

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Michael Brown

December 21, 2019
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Selling SaaS From The OutpostAnother Friday another Bowery Capital Startup Sales Podcast! This week I was joined by my friend David Levy, an enterprise Account Executive at Crittercism, to discuss “Selling SaaS At The Outpost.” We constantly talk a fair amount on the podcast about tactics of selling SaaS from your company’s headquarters but what about those of us that may not be in HQ and are Selling SaaS At The Outpost? David was the 4th sales hire into Crittercism, a first mobile application performance management (mAPM) solution, and the first hire not based in the company’s headquarters in San Francisco. He was the quintessential person selling SaaS at the outpost beginning in New York and building some serious scale for the company early on. Today his coverage is all the way up to Boston and down to Atlanta. David talked with us specifically about several components that matter most as a SaaS Account Executive not in your headquarters. Thinking about things like consistency of communication with HQ, working and discussing on the ground learnings constantly with other AEs that are in your HQ or other regions, learning from other AEs at other companies in your region, executing events and going to other smart events in your territory, and finally getting back to your HQ to meet with product, marketing, executive, and sales teams to discuss what is happening on the ground are all key to selling SaaS at the outpost. We talk about the initial days of setting up the Crittercism outpost, how David balanced selling and getting some quick wins with starting to build out some repeatability and foundation, and finally the model David believes is the best way to really maintain a great working relationship with your HQ. All in it was an excellent discussion about a generally overlooked topic that many SaaS founders don’t think a lot about when hiring that first sales person to a territory. Give a listen below and if you can review us on iTunes it would mean a lot!

You can ready the full transcript below

MB: Hey everybody, welcome back to the podcast. I am in today with Dave Levy from Crittercism Portfolio Company from my past life, good friend and he is an Enterprise Account Manager here in New York. We are going to talk today about from the outpost. Welcome to the show.

DL: Thanks for having me, Mike.

MB: So, give the listeners a little bit of a background on you. I mean, where you came from, how you got to Crittercism, any sort of background information super helpful.

DL: Cool, yeah. So, I started off my career over at Ernst & Young. So, I am actually an accountant by trade. I was in their financial services office; I was there for about 2 years. Got my CPA and then an opportunity presented itself at Crittercism, so I completely jumped ship. Went from one side to the other, to the dark side, you know, I guess, you could say I went from recording revenue to creating it. So, just been having a really good time ever since.

MB: And what was… you just wanted to make a shift away from you know being an E&Y and that world or what?

DL: Yeah, you know I always thought that you know I was more of a people person, wanted to get in front of the customer more, you didn’t do that at Ernst & Young until you are late… much later in your career and so you know that was one of the aspects that I really enjoyed, just served my customers and so thought it was a good opportunity and so I decided to head over.

MB: And do you use any element of your CPA in your day to day…?

DL: So, yes and no. I mean, it is good to have that background, it is good to understand how budgets are set up, being able to sell around that and you know kind of use the knowledge you have from your past life, it also if it comes up it gives me you know some credibility sometimes and so maybe help push things over the finish line that you know we can make this work from a budget perspective.

MB: There you go, one last question on your background. What is one thing that no one on the podcast knows about you?

DL: Oh, that’s a fun one! Well, I am a pretty avid snowboarder.

MB: Alright, man.

DL: And growing up I used to compete over… I was in a competition team in out snow, we would travel around to different mountains in the local area, Okemo, Kellington and then after a few years, I grew up and realised that you know that when you fall down it actually… it hurts, so.

MB: So, you actually had to remove yourself from the professional circuit.

DL: Yeah, yeah so, I am done with that, though I am still an avid snowboarder but no big jumps for me, nothing like that.

MB: Got it. Talk to me a little bit about Crittercism. So, you know, where is the company today? What do you guys do specifically? I mean, I know this, but for the listeners, just to have some context.

DL: Sure. So, I joined back in 2013, back then I was about employee number 25, we had 5 people on our sales team and I was including the VP and just in terms of 2014 was you know a monumental year for Crittercism. And just to give you know the listeners a background of Crittercism, so we provide mobile application performance management and so if you know you have an app and its crashing or it is lagging you know users trying to check out, make a transaction and it fails, what our software does is embedded inside of these mobile applications and it sends out a real time performance issues to their companies.

MB: Perfect and you guys are… your target customers are sort of Fortune 5… you know big brands, not really the S&B kind of segment, right?

DL: So, you know our technology really stands across all different verticals, across all sizes of companies, you know we work with everyone from startups to you know some of the large enterprises out there like the Ebays and Netflixs, the LinkedIns, the Yahoos. But then we also work with some great startups in the area Hinge is a great New York start up that we work with. So, and really everyone between, anyone where you know it’s a high value business to consumer, a business to employee application so it could be important for revenue reasons, for brand reasons or for if it is an employee facing app like a planner cell device or if it for field cells rep, you know these apps need to be highly performing and there is a high cost of failure associated with them.

MB: Sure.

DL: So, yeah, I mean, like we were saying before you know 2014 was the… you know a monumental year for us. Today we are monitoring over 30,000 apps, about a billion multi active users on our platform, we added about 70 application developer partners which is extremely important to have especially when you are out in the field. We raised our ASP, our average selling price at a 93 percent and we raised 30 million dollars, so yeah some fuel in the tank for growth.

MB: Excellent, that is great to hear. So, we are going to talk today about working from the outpost, the concept that we are talking about is you are not in headquarters; you are probably the first hire in sales in this separate office. This consistently comes up a lot with sales people, they want to understand how to act, how to react, what they need to do to really be effective in their role. And so, I thought I would bring Dave on today to talk a lot about this, so maybe give the listeners a little bit of background; when did you first set up New York? You were obviously the first person to come on to get that off the ground. Just kind of set some framework of sort of when did this start and how big was the company, things like that.

DL: Sure and I love that you called the outpost by the way, it reminds me of “Game of Thrones”, like when “we are North of the law.” So, like I said we started back… I started back in 2013, I was the first remote sales hire in New York, we did have reps that were back in California that were working the North-East region so we were fortunate enough to have a couple of customers set up in New York which was extremely helpful. But, you know at the end of the day and also at the same time you know when I started we also had another rep start down in Atlanta so we started two remote hires at the same time.

MB: But you had essential sales office, they had made the decision to move towards more of a kind of regionalized approach you get hired in pretty small business though right, at that point.

DL: Yeah, relatively absolutely and so I think you know the first goal is to get a resource on the ground there, then you want to set up a bunch of meetings, you want to get in front of people, start selling your product. Once you start getting some traction, expand, get some local technical resource and so six months later we hired ourselves a sales engineer to come and help out with a lot of the demos and a lot of the technical resources a the local level which was critical as you are growing your business and obviously you know we cant be flying over our asses all the time.

MB: Sure. I mean, just to dig in right into these sort of tactical of it, so you have this office, you are set up, well, what are the kind of first things that you talk about sort of setting up meetings. How did you sort of think about the first 30 days? And then maybe to expand upon that, what did you need to sort of do in those initial days to really not get fired you know like what… it is obvious that you have to win business but kind of maybe give the listeners a little bit of thinking around, okay now you are in that role, what do you really need to do?

DL: Right, now that makes sense. So, you know as you said obviously sales is a results trigger so if you are not closing deals you know HQ or remote you know that might not be a good fit but you know taking the consideration that you are remote you know one of the first thing that you need to do is take advantage of living in your Geo. You know this is a huge advantage you know unless you are living near HQ and you also working at territory you are going to be you know calling in from remote and so if you are living in your own Geo, take advantage of it, network within your Geo. I was going to meet ups, meeting people who I am selling into, I also I remember within the first few months you know while I was still squatting at AOL Ventures back in the old days you know we threw our own meet ups so I brought on 20 to 30 people, I invited… we had our CTO fly in, you know it was a great event. There is no substitute for having your prospect and your current customers talking, your current customers saying, well here is the ROI I have gotten from Crittercism. And so even if you don’t do a meet up just get in them for dinner, doing something like that. You know another aspect in networking is you know finding reps at other companies that are selling into similar roles as you.

MB: Interesting.

DL: And so you know so obviously were it to be one of your competitors right, some sort of complementary product; building those relationships and just working at the street level on, on ways that you can work together.

MB: And do you just cold outreach them or how do you…? You just had a network that you just started to build and then…

DL: Yeah, just had a network you start to build, you find people on LinkedIn and if he is another account executive in your area and he is selling it to similar people and you could show that you are doing the same thing and that you can help each other out there more than likely than not or at least you know take a call.

MB: That makes a lot of sense.

DL: You know even meeting people for coffee, you know sometimes people don’t want to do a whole new fancy meeting in an office, just I like to say, hey want to meet at Starbucks, something casual like that and you know a lot of the time that will work and get them to at least meet with me.

MB: Sure.

DL: You know some of the things that you might not even be thinking about is networking with your own internal team. I known that sounds like it is pretty obvious actually if you are at HQ because you are around these people all day long, you are sitting next to them, eating with them, but when you are remote you are kind of excluded from that, you are on your own, you are on your own Island, so it is really up to you to reach out. You know when your at headquarters I always make it a point to meet with engineering, to meet with product, to meet with marketing, to meet with the other sales guys, just to get you know a fresh perspective. You know I tell them what it is like on the frontlines and what I see and then I go back and I get this new perspective which is extremely helpful.

MB: And how… just because communication comes up a tremendous amount. Are you… just maybe your day to day is predominantly in your CR… you are out at meetings and stuff but as it relates to HQ communication how do you handle that and then when do you actually go back really? Is it once a quarter, once a month? How do you kind of think about that?

DL: Sure. So, we have our own communication system, we use that to chat so we are on that all the time and I am calling… I have a direct line with my VP I just… I can call him up at 7 in the morning, 11 at night, we have a great relationship. Same with the other rep that I work with that’s out of the Boston area. So, it is really just picking up the phone and calling them or messaging them or have chat. In terms of going back to headquarters, we usually go back semi annually for a sales kickoff, just get the whole sales team together, get everyone talking where I get the products, partners come on board, they talk to us. So, that is always a nice bonding experience.

MB: So, you will go back… you will basically only go back probably twice a year and try and line up as many meetings with company folks as you can?

DL: Exactly, right.

MB: Got it, got it, that makes sense. You know you talked a little bit about the tools you use, you talked a little bit about kind of the first 30 days, you know you have to kind of play that selling into the market and networking the heck out of you know really building bridges. You talked a little bit, but I want to dive in a little bit more on this, you have sort of a Boston rep and you said that when you first started well, you had a rep in Atlanta, do you work with them at all or how do you kind of think about the entire East Coast, the kind of region, how do you think about working you know either collectively with them or not with them on particular accounts or business? Do you sort of get up to Boston more frequently or down to Atlanta more frequently? Just how do you think about that as kind of as a person in a new geography?

DL: You know absolutely, I think it is important you know when the first things you do when you enter to a new GO, it is really important to understand who your customers are, where you are successful, where you are not successful. So, look at who your current customers are, if you are you know in the app world not all companies value a user the same, if we are not successful in a particular vertical, you know you are only one person out in the field, you know you are not going to be… don’t waste your time setting up meetings with that. So, it is really important you identify where you can be successful. You know really from there you want to leverage your network like we were talking about earlier so whether that is your investors, or your great investors like Mike, whether it is also your own customers so. And you know you mentioned it, the rep down in Atlanta so Turner Broadcasting was… is a customer of ours so they headquarter down in Atlanta but then they have groups like CNNMoney for example, truTV, they are all based in New York and so we were working with some of their divisions not others, we ended up setting up a meeting through networking with the folks down south setting up meetings in New York and, you know, building more business like that.

MB: And so, is that the Atlanta rep reaching out to you and say, hey we have an opportunity here or is it you going to them or is it just kind of collective knowledge that…

DL: I think it goes both ways and in that scenario I was probably eyeing that brand, I was like, “Oh, they are up in New York, let’s set something up.” And he is like, “Absolutely, let’s go for it.” So…

MB: And so, the Atlanta rep will come up to New York and you…

DL: So, in that situation I would just probably manage the account up in New York and then of course tie back to the folks down in Atlanta, but a lot of time these companies will operate in separate divisions and so, I will actually work the accounts.

MB: Got it. Talk a little bit about how things can go wrong in these situations, you know sort of missed deals or missed accounts. Was there ever any… you kind of talked about a lot about the communication, I think that is super important, but is there some sort of gotchas to watch out for and things that you should really, really think about as an AE in a geography that you know you have seen go wrong or you have coached other younger AEs on you know that kind of thing?

DL: Oh yeah, I think it goes back to what we were talking about before where it is really understanding where you are successful and where you are not. You know, for example, New York; the first things you think of are media companies and financials. You know financials wasn’t necessarily where we should be targeting 2 years ago, now we 100 percent want to be you know full speed ahead there and you know at the time it was just for security reasons you know being a SaaS provider, sometime there you are hesitant, also the sales cycle is much longer and so, you need to be spinning your wheels long time going after these accounts where you are not going to have any traction. So, it really needs to be the appropriate time in order to do that and you know we have reached that for financials which is great and now would be more of an appropriate time to go after them.

MB: So, really, running those vertical market audits in the geographic you know audits and seeing exactly what works and what doesn’t and then being smart enough to not do something stupid and go after an area where you are just never gonna win any business.

DL: Exactly, it might be extremely appealing to take a meeting with a big brand, you are like wow! I got a meeting with this company, that’s amazing. But, you look at the business model and you look at our past history it seems like it could be one, two, three to six months of wasted time and so in a sales persons day everyone knows the most valuable resource is time and so if you are better off cutting the cord early then six months time will go and you will realize that well, yeah I already knew that this wasn’t going to work out and I went after it anyway.

MB: Sure. How do you think about… well, a lot of this connection between account management and sales starts to come up in geographies, how do you kind of handle existing accounts? Are you constantly seeking budget and talking to HQ about you know kind of keeping not only the funnel flowing and sort of new customers being one but also do you sort of keep in touch with the existing customer base? I know it is not as simplistic as just, “Thanks for buying my software, see you later.” So, maybe just expand on that a little bit if you can.

DL: Yeah sure, so you know we are a SaaS platform. So, you know subscription after and… you know, there is not much risk in terms of switching for the other person so it’s very important that our customers are successful, that they are happy and getting what they want so you know that’s a huge part of our business and we all follow up after you know we finish up the deal, I will follow up with the customer you know a month after to see how everything is going, you know I will try to put some plans in place, you know we want to get these features in by this, we want to achieve these goals and you know I think that from any SaaS company out there I would strongly encourage you know customer success to be the top priority of yours because you could be bringing in 10 million dollars in ARR but if you are losing you know 3 million in ARR every year then it is coming out…

MB: Yeah, it’s hard. But, you are not then after that one month specific to your geography, you are not really… I mean leave that sort of to your customer success team and the account management folks or…?

DL: So, right now our sales reps are handling our customer success teams.

MB: So, you are highly active with talking to them?

DL: Correct.

MB: Got it.

DL: It is I mean it is also something that we are exploring as a customer success team but at the end of the day you know I know the customer very well and I am able to you know up-sell them on some other things potentially in the future but yeah of course a customer success team if that is another approach.

MB: Sure. Last question before we break and you give final sort of tips and tricks, often times we talk a lot about budget and your own capability in a particular geography, I don’t know exactly how Crittercism worked, were you sort of assigned a budget for marketing or events or things like that to do these meet ups or what’s kind of the best practices for you know brand new AM and a brand new enterprise account manager in a geography thinking about, hey I have to spend some money to win some business, is it as simple as just going to HQ and really saying, hey I need 10,000 dollars to do something. How did you sort of build that relationship and really grow this kind of meet up concept that you had?

DL: Sure. So, you know I think when you go back to headquarters, you are developing those relationships, you are really building trust with your team and especially when you are out in the field, you know they are not seeing you everyday so you know they have to be able to trust you from the beginning. So, you know maybe if you don’t have any prior statistics on the ROI of an event like that you know you tell them I am going to get these people in a room together, I am going to get these customers, these prospects and you know I think it will really pay off in a whole… make a splash in the market and you know you try it if it doesn’t work then you will for the next time you know and if it works that’s great, you know let’s do some more.

MB: Got it, makes sense. Any final tips, tricks, words of wisdom for the young SaaS enterprise account managers that are entering new geographies?

DL: You know, I would say at the end of the day you are out there on an Island. So, one thing that you should really try and do as well is leverage any channel partners that you can.

MB: Oh nice, okay.

DL: So, for example, there are many development shops in the New York area, their job is solely to create mobile apps for potentially the top Fortune, you know 2000 companies and so, even though developing these relationships might take a long time, it is a longer process because you are going from the partner and then getting introduced into the account. If you can get that going you know even if it takes you know six months, a year to get that going the rewards they could reap from that will be great.

MB: And that is something you do pretty early on?

DL: Right. So, you try and do that alongside with the direct selling. It is very tempting just to you know forget about the channel partners and go directly for the account. But, a lot of the times they have full trust, a 100 percent trust in your development partner and so, if we can get in there, that’s an easy way into the account.

MB: Excellent, makes sense. Thanks a lot, Dave for coming in, any last words?

DL: No, no. Thank you for having me. This was great. Good luck to all you account executives. It might seem sometimes that you are all by yourself, but there is a whole team around you and it’s a good time.

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