Building Traction to Capture Giants


Justin Lawson, Cofounder/CEO at JJELLYFISH (New York City/Boston), a customer development firm for early-stage enterprise startups with between a million dollars to $20 million in revenue, explains how his company enables sales teams to move beyond the warm prospects of friends and family and “hunt very large game.” JJELLYFISH analyzes sales processes, identifies customers, and then builds comprehensive, executable business sales playbooks with simple to understand, targeted value propositions that resonate with a company’s market.


Keys to building his clients’ and his company’s success include:

  • Codifying collateral and sales procedures as a foundation for sales execution.
  • Reaffirming why a client bought what they bought.
  • Ensuring congruency between how the business and its clients define success criteria.
  • Articulating services and their outcomes as a product.


Justin can be reached on his company’s website at: (two J’s) Meet with his team locally for coffee or Skype with him for an informative discussion. Or email him at: or (again, with two J’s!).



ROB: Welcome to the Marketing Agency Leadership Podcast. I’m your host, Rob Kischuk, and I am joined today by Justin Lawson, Cofounder and CEO at JJELLYFISH based in New York City and Boston. Welcome, Justin.


JUSTIN: Rob, how are you doing?


ROB: I’m doing fantastic. How about you?


JUSTIN: Good. I must say, your recording voice is really, really good. I’m going to try to keep up as best I can. [laughs]


ROB: I appreciate it. It always sounds weird when you listen to your own voice recorded, so that’s fun for both of us after the fact.




ROB: Why don’t you start off by telling us a little bit about JJELLYFISH and what makes JJELLYFISH great?


JUSTIN: I’ll definitely give you some background on JJELLYFISH and then let you know what we believe JJELLYFISH is great at.


In a nutshell, JJELLYFISH is a customer development firm for early-stage enterprise startups. To us, that’s just a fancy way of saying we help companies get out in front of, learn from, and in many cases acquire enterprise customers.


We can probably get into this, but my cofounder and I are really excited about the building phase of startups, less excited by the scale and repeatable execution. We want to build that playbook. So that’s where JJELLYFISH plugs in. Like I said, in most cases startups anywhere from a million dollars in revenue to $10 or $20 million, depending on where they are.


ROB: Got it. So you’re taking a company that has achieved some degree of initial traction—I was listening to some VCs on a podcast the other day and they were saying a half million dollars or a million dollars in revenue for an enterprise-focused startup doesn’t actually necessarily mean you’re fully at product market fit.


What have they figured out at that stage, and what are the things they often have not figured out?


JUSTIN: That’s a great question. One thing that we’ve seen is people are able to grow in some areas pretty well with friends and family. They’re able to get to say a million dollars with their network, the people that they know, the CEO just being on the street, acquiring their first 10.


But we like to come in and say, okay, you’ve done a great job of getting the warm 10 people that you know. Now try and do that same exact thing for unaffiliated customers. When we say unaffiliated, we mean people you don’t know. Can you go to a stranger that you believe is the profile of your customer and get them to buy from you in a repeatable way?


To answer your question, I think things that they’ve done is they might have a really good idea in their head about their value proposition. Maybe a V-1 of what that looks like from a collateral standpoint. But most of it still is in the founder’s head.


We want to go in there and extract all of that value and codify it so when you do hire a salesperson, there’s something to execute. That’s where we spend a lot of our time when we work with customers. Does that answer your question?


ROB: Yeah, I think that starts to unpack that problem a little bit. You’re in some ways building out the sales collateral and combining that with some plans and strategies about how to hunt very large game, if you will. People talk about the metaphor of hunting elephants versus deer versus rabbits in terms of customer size, and you’re hunting elephants, right?


JUSTIN: That’s correct. I would say our approach is more than just the collateral; I think that’s just a component of it. What we’re saying is, do you actually have a comprehensive plan that you can hire somebody on and allow them to execute with confidence?


When you start to unpack a bunch of different components there, I think one component is the sales enablement, the traditional “Here’s what we say and how we say it, and we know it resonates.”


The challenge is, a lot of people aren’t even at that point. It’s not that we can just come in and build collateral. Maybe the first thing is, let’s just set up 10 conversations with people you believe would be your customers.


And let’s sit back and actually pressure-test some of the assumptions you may have about the market to date, because there inevitably is a bit of confirmation bias going to market with, again, the friends and family. Many times, the revenue that they’ve generated from them isn’t really the market they want. They might’ve gotten their $20,000 deals here and there when they’re really hunting for the $200,000, and that takes a bit more tact and rigor.


That’s where we go in and spend a lot of our time. But it can look different, again, depending on how far the CEO or founding team has gone.


ROB: Certainly. We have some friends here in Atlanta who work on a program called The Bridge Program. They actually, in their case, get the sponsor companies to kick in some money to sponsor the program.


Your model, though, I would imagine—Is it largely aligned around that startup being your client? Is there a variable component to success there?


JUSTIN: The way we engage customers is on a project basis. There’s a monthly fee and then there is a condition element . . . if we are able to source a deal that closes, and, in many cases, we are.


But the challenge is, we can’t go in there and say, “Hey, just give us all commission,” because there’s inherently so much risk for us going into an early-stage company—same as there would be for an employee or a VC. So that’s our working model.


I think, regarding JJELLYFISH, and maybe this is getting ahead of myself, but what we do differently or well—sorry, am I jumping the gun on your next question? [laughs]


ROB: Go for it.


JUSTIN: I think one thing we learned early on, and I apologize to anybody who’s listening that is in strategy, but no founder wants to buy more strategy. Not to say that strategy doesn’t have its place, but it’s a piece of the puzzle. Selling strategy to a team that’s already so time-poor is not as valuable.


I think a lot of consultancies go in there and say, “Hey, I have a point of view. I can help you build the capabilities, but you ultimately have to do it.” I think it makes sense for consultants to do that because it scales—or at least, it scales more easily.


What we do is say, listen, we’re going to give you our point of view, we’re going to help build some internal capability, but we’re not going to assume that our playbook works for everybody—because it doesn’t. We’ll actually go in there and drive true market outcomes, whether that be interviews, whether that be discovery sessions, or whether it be coaching them and the founder on closing a deal.


We at JJELLYFISH really try to tie ourselves to hard outcomes as best we can when we work with a client. I think it just makes them feel better about hiring us, and ultimately aligns us on the highest value activity.


ROB: Interesting. I think one of the challenging things that startups have when they’re approaching an enterprise customer is they assume that the first person they talk to is actually the keeper of the truth. If they say, “Hey we need this” or “We don’t need this,” even though there may be 10 different entry points—or even crazier depending on the structure of the organization.


How do you think about this, and how would you recommend other people think about approaching this enterprise, where there may be 10 ways in, where the innovation team may not be thinking about the kind of innovation that you think they’re thinking about, and so on?


JUSTIN: It’s funny, because there’s probably so much to that question. Who is their market? Do you actually have 10 people to sell to in a Fortune 500? If you do, great. Or are there really three people? Are you selling to legal tech, where the GC is the only one that can really do it? Or are you selling to product managers or heads of product in a company that has tens if not hundreds of products? I think for us, it’s just getting really clear on who we believe their customer is.


Beyond that, getting into the discussion, it’s easy to say, “I have a value prop that I think resonates with everyone.” But the reality is the user of the software very rarely is going to be the decision-maker that can either own or dictate budget or create budget.


There’s almost two value props, or more, that you have to think about. I’m not saying create two totally different products; I’m saying, what are the incentives for each of these people?


For a user, we’ve seen more often than not, it’s the ease of use. Are you allowing me to focus on higher value work? Are you helping me get a job done? We could go to Clayton Christensen’s Jobs-to-Be-Done Framework. What are those things?


For an executive, let’s be honest: Maybe they have a contract for 3 years, or if they don’t meet their near-term priorities, they get fired. If you’re selling, “In 10 years, your company could be like this,” no one cares. I also think that it’s speed, risk, revenue costs. How do you get to a really big number that is meaningful for executives?


It’s hard sometimes to stay at that level because funders get so excited by the thing. Like, “Look at our cool thing!” What we’re really bad at is speaking the language of executives. There are so many stats out there. Salespeople—really knowledgeable about their product and really not knowledgeable about my day-to-day business.


I think those are just a few dimensions to think about when you go internally.


Everyone says it, but just shut up and listen. The most important thing is to hear what’s not being said when you’re in a room with these people. If you sit down with a CIO of a Fortune 500 company and you speak more than 6 minutes, you’re doing it wrong. I think there’s some hacks there.


But, regarding how you enter these companies, one is to think about the incentives and who touches the buyer journey. It could be the user, it could be the actual decision-maker. Just make sure that your sales motion and process nears that journey that we know enterprises face.


Again, the stats are out there about the five, eight, ten people that touch the buying process. It’s just easy to overlook, essentially.


ROB: A very wise piece of advice—and I’ll let you weigh in on it—that I heard from a very experienced salesperson who sold a lot of big deals to big companies. He said one of the things that he will do is go in right after he’s got the sale done and do a debrief on why they actually bought what they bought.


He said usually maybe the three reasons he thinks they bought are true, but he finds out a bunch more that he did not realize, and may not have had any other time in the lifetime of that engagement with that customer to ask that question appropriately.


Have you had that sort of debrief opportunity? How should people think about that?


JUSTIN: I think that’s a great best practice. It’s very easy for a salesperson to just be like, “All right, the contract is signed.” The real work begins with the contract is signed. A first step of reaffirming exactly why they bought is definitely something that you need to do.


I think another piece is maybe along a similar track: Are they defining their success criteria the same way you are? For a lot of salespeople, that might be a challenge as you transition it to the account services teams. Just based on my experience, there’s an opportunity to do that better.


So, I would definitely agree with making sure you explicitly get their answer on why they purchased. It might not even be an ROI case. It might just be an emotional motivator or something with communications. It might be something out of left field.


It reminds me of something that a mentor said to me about when you’re pitching people or soon thereafter. When you’re pitching somebody or a customer, the only times that they’re paying attention is when you’re talking about them, they’re talking about themselves, or you’re forcing them to think. Putting yourself in an opportunity to do one or all of those things as often as you can is always a great idea.


ROB: Fantastic. Thank you for thinking through that. If we rewind a little bit further—you mentioned something early on—what came before you started? How did you end up starting this company?


JUSTIN: I so quickly just glossed over that. [laughs] I’ll work it backwards. JJELLYFISH was started about 2 years ago. Before that, I had met my cofounder at our previous employer. We both got hired to build out their enterprise business. I think that’s where we fell in love with “it seems like it’s hard for company to hire this type of talent, but also we really love it.”


Jen Abel is my cofounder. She’s fantastic. Before that, I spent 4 years at a company—again, B-to-B enterprise—watching them go from a million to $100 million. Jen similarly was a founding enterprise member of another B-to-B enterprise company that has since sold for half a billion dollars. Before that, I spent 5 years at Apple back when they were just getting into the B-to-B game with iPhone/iPad.


So I guess I spent about a decade in B-to-B sales before starting JJELLYFISH, and similarly Jen as well.


ROB: Very interesting. You knew her well enough that you’re quite often in different geographies that aren’t that far apart. Any specific tricks or secrets to making that work?


JUSTIN: Yeah, it’s funny. She was in New York; she went to Boston about 6 months ago. There’s a few things there. We met on the job, and within maybe 30 days we tied each other to the hip financially—which you don’t see salespeople do a lot.


It was like, “This is a hard job, building an enterprise business from zero dollars to a few million in under 12 months. Let’s just align our incentives where if I close a buck, you get 50 cents.” It’s funny because it was organic. She’s really good at things I’m really bad at, and I hope I’m the same for her. So, it was a bit organic in that sense.


But the teaming allowed us to do a lot of things at that previous employer and in JJELLYFISH. I think teaming in sales is something that is not done enough. In a meeting one person can actually listen. You can play on—there’s unconscious bias in rooms where I might have more of a connection or she might have more of a connection, or we just think about fundamentally solving problems differently.


So just [in terms of] how we work well together, I think finding your opposite that shares your values but somebody who’s energized by other things is really important.


Working with a cofounder in Boston, I actually think it’s really easy. [laughs] We’re not fans of having meetings. We connect a lot during a day for 5-10 minutes here and there, but we’re really big fans of distributed teams. I think it’s just natural based on our working style.


It’s been really a lot easier than I would’ve thought. But again, we’re a small team. I don’t know if that holds true for 20, 30, 100 people.


ROB: I love that advice about partnering and hiring for weaknesses. Even if you’re not pulling on a partner, not hiring more of yourself is typically going to lead to some good things in terms of the work that you no longer have to do because someone’s great at it in ways that maybe you’re not as great at it.


JUSTIN: Yeah, I think there’s a lot of truth there. We argue a lot. [laughs] Let’s call it how it is. We disagree on things, but we know that the outcome will be much better than where we both started. Again, I know that’s common advice, but there’s so much truth to that.


ROB: In our audience we have some people who are enterprise marketing execs, we have some people who are marketing agency owners, we have some people who are more early-stage entrepreneurs. Are there any ways that you think people are marketing to try and reach an enterprise client that might be particularly ineffective? Perhaps newly so in 2018, or perhaps that isn’t effective yet?


JUSTIN: I think a lot of people get this really wrong, and it really is, at least to us, a simple fix. Point to me any executive in a Fortune 500 that has purchased anything over $10,000 and you’ve got them with an email. So many companies approach, honestly, orienting their SDRs or sales team more like email marketers than truly business sales development.


If you want to blast thousands of emails to a massive market, hire an email marketer. If you want to truly craft personalized, relevant messages (which is what we know works for executives), it takes time. I think a lot of companies do the easy route. They buy some sales acceleration platform, they get a thousand prospects, and they just have at it. They send the same message to everybody.


For us, you graduate to that. You graduate to a value proposition that has that much resonance in a market. Early on, you’re just trying to find your best five or ten customers. For us, let’s crawl before we can walk, before we can run.


Put a list together. What are 100 people that you would kill to have as customers? Let’s look at proxies within their organization. Okay, you want to sell to the CMO of whatever company. Great. Who’s in the office of the CMO? How many people do we think we can—just start there.


I’m all about putting names in boxes. I think by taking a more one-on-one approach, when you reach out they’re going to know the communication is made for them, which is going to increase the responses. Again, I think it’s just being a bit more tactful.


One thing that we always talk about with our clients is if you’re going to ask an executive for 30 minutes, they’d better know you put at least 30 minutes into crafting that email. Maybe it takes you 10, but you get the sentiment there, which is they need to immediately know it was made specifically for them, why you’re reaching out to them now, and why them specifically. Don’t say, “I saw Campbell’s Soup said something in the news.” Why me, Justin?


I think that’s really important to get to and very hard to scale.


ROB: Absolutely. That’s a high challenge, but with the size of contracts you want to sign with an enterprise client, there needs to be a high degree of trust. I think you have to start earning that from the first interaction.


JUSTIN: Yeah, exactly. You bring up a very good caveat, which is I’m not saying take this approach for the thing that has a $1,000 LTV. We specifically target, at a minimum, fifty grand. This is just the approach that we usually at least recommend starting with.


ROB: Absolutely. Any little personalization at any level, I don’t think anybody’s ever been mad at any sort of non-creepy personalization, at least.




ROB: What are a couple things you’ve learned from your experience building JJELLYFISH that you would do differently next time?


JUSTIN: That’s a good question. I think there’s two elements of this question.


One, there’s the personal side, and maybe more JJELLYFISH. I think personally, building any company or any new endeavor, surrounding yourselves with the whole mentor/advisor/coach is really helpful. I would suggest anybody starting a company to ensure they have those three people in their lives because it’ll be so much better.


I think that’s something that I didn’t do early enough in my career, even before JJELLYFISH. We’ve made a point to do it for the company, and it’s paid itself back tenfold.


Another thing, don’t get married, launch a company, and move within 12 months. [laughs] That’s a lot of moving pieces that, if you can avoid it—not the marriage part, but if you can avoid it for a little time, definitely do that.


I think more so for JJELLYFISH, something we’d do differently—there’s so much we would probably do differently. Having the information we had at that time? Maybe.


One thing is productizing a services company is hard. That’s something that we’re continuously spending time on and something we probably didn’t do enough of early on. Spending time to say, can I articulate my services and the outcomes of my services in a way that is more of a product? I think it’s much easier for people to buy and understand.


Going back to no one needs more strategy—that’s like, “I’ll come in, I’ll do a working session, and 2 hours later I’ll give you a bespoke work plan.” Like, what do you do? What can I get from it? I think earlier on, that’s something that we could’ve done better.


We just trial-and-errored it to what we have today—which, it is what it is. You don’t have to undo everything. But that’s something that we could’ve probably used more external support to do more quickly, knowing that that’s what ultimately can drive revenue for us. Hopefully that answered your question.


ROB: I think that makes sense. It’s such a challenge even for me to think through sometimes. How do we articulate our process and not just our product? To your point, to earn a high degree of trust takes more than a product, and you can have a deeper and more valuable relationship with the client.


This is a theme that’s been coming up repeatedly with some different types of companies, different types of agencies that we talk to: how they’re able to take what could sound like more of a commodity offering—or at least undifferentiated in the eyes of the person who is evaluating it. I don’t know if there’s even any difference. If you’re differentiated but the person reading doesn’t understand how, I’m not sure that that’s different at all.


JUSTIN: Yeah, that stems into another problem that we definitely had. I shouldn’t say this about myself, but just trying to sound smart and using the B.S. buzzwords. Trying to distill it down to something your grandma would understand is so hard. That’s why sales copy and copywriters are worth every penny. Getting your solution down to that level of competence is really important.


That’s something we continuously focus on, especially when customers are looking to us to help them with that. No one wants to be the McKinsey, the management consultants that internally might not be good at managing consultants. [laughs]


Distilling it down to where your grandmother would understand, I think that’s really hard to do. It’s funny; we were sending some of our early sales collateral of how we position our business, and people that have been in sales for 20 years, that have sold billions of dollars, were like, “What are you talking about?” [laughs] I was like, all right, maybe this isn’t as good as we thought.


Again, being very clear and not trying to oversell—because people read through that so fast—is just important.


ROB: Got it. What else is coming up for JJELLYFISH that you’re excited about?


JUSTIN: For our business, we’re lean, trying to keep it lean, but we’re growing. We brought on a few more people this year. The first year was, can we get through a year? Will people buy our stuff?


Now that that’s happening, we’re getting more people coming to us and finding people that are like minded, that are excited by this early-stage sales and customer development. If you’re that person, call us. There’s no shortage of early-stage companies and early-stage products that need that type of help organizing the path to traction.


That’s been really exciting for us. We have all good business stuff, more projects this month than we did last month, and that continues. For the business, it’s great that people are finding value in what we do. That was one big assumption that we spent 2 years validating.


Continuing to share our time with likeminded people internally and then working with awesome founders and getting to learn from them has been really exciting.


ROB: Is there any interesting trend of particular categories of unmet need when you’re talking to some of these enterprises? Is there a class of problem that’s not being solved well right now?


JUSTIN: I think there’s more the macro challenges of bound deficit. You talk to any founder, they’re going to be like, “I don’t know how to hire good salespeople. I don’t know where to go.” That is such a massive problem.


It’s also funny—if you’re hiring your first salesperson to build the business beside you, stop putting up job descriptions that are like “$50,000 OTE” or “$60,000 OTE.” Clearly people aren’t putting enough thought into that profile of person.


I think salespeople can do a better job of articulating where in the company or product maturity they get most excited. We don’t do that as salespeople. It’s just “I’m a sales guy, I take a thing and I sell it” or “I’m a saleswoman, I take it and sell it.” I don’t know if I believe that the person you want to hire for zero to $3 million as a salesperson will be excited by going $10 to $30 million.


Again, that’s just something at a macro level that I think has been a challenge. I think that trend will change. We know companies that at this point are more willing to hire contractors and external support as well to find that expertise, all the way from Google down to startups. I think that will continue to increase. Luckily, we’re trying to position ourselves as that fringe firm that can help with a very specific set of problems.


I might have one more in me for the trend side, if you wouldn’t mind.


ROB: Got it. Justin, when people want to get in touch with you and with JJELLYFISH, how should they find you?


JUSTIN: That’s something we don’t do a good job at—I would say Two J’s, which is a whole other story, and if you reach out to me I’ll give you the full background on the name.


We’re more than happy to share a meal, share a coffee with anybody locally, or just do virtual coffee on Skype. If there’s any value that we can add to people, 30 minutes or an hour with perspective, that’s time well spent for us. We always learn things on those discussions. or (again, with two J’s!) is the best place to reach us.


ROB: Super. That is a very generous offer. I think you’ve given us a very different lens to think through here today. I think there are shared challenges here that we can all learn from. Thank you for taking this time, Justin, and sharing your experience. We look forward to seeing so much more from JJELLYFISH.


JUSTIN: Thanks for the time, thanks for the invite. I look forward to speaking again soon.


ROB: Thanks, Justin.

Thank you for listening. The Marketing Agency Leadership Podcast is presented by Converge. Converge helps digital marketing agencies and brands automate their reporting so they can be more profitable, accurate, and responsive. To learn more about how Converge can automate your marketing reporting, email, or visit us on the web at

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