Design the Sale

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Ryan Fennerty from General Assembly joins us to talk about selling to the enterprise when your own offerings are evolving quickly. We discuss how can the sales team can keep up, how they can evolve their sales process itself by learning and iterating from firsthand customer experience, and how they can speak the language of product without needing to learn what "kerning" is.

Ryan Fennerty is an enterprise Account Director at General Assembly. In this show, we discuss: 
  • Selling a rapidly-evolving product to an enterprise market that may not always be moving at your speed
  • Knowing how to balance "getting in the door" with a pilot, versus holding out for the big sale
  • Keeping sales, marketing, and product aligned through good communication practices
  • Creating and improving your B2B sales playbook over time

Geordie Kaytes: Hey Ryan, thanks for coming on the show. Do you want to give us a little background before we get started about who you are, what General Assembly is, and what you guys do over there?

Ryan Fennerty: Yeah, cool. So I'll start with just what GA is and why it exists. So, General Assembly, the big picture problem it sets out to tackle is essentially what everyone calls the "skill gap," and it's particularly acute in roles in technology because the traditional higher education system hasn't really specialized in helping people transition into technology careers without a lot of friction costs along the way.
So, for example, you used to have to go and get a Master's in Computer Science if you hadn't done it undergrad to enter that field. Data science, very similarly, anyone who wanted to be a quantitative researcher often was a PhD path. And so, where General Assembly started was a consumer business focused on helping people make the on-ramp into tech if they didn't have a tech background.
And so probably the first examples of that were people who knew they were analytical, didn't have a STEM background, and wanted  to become developers, but felt like their only option was law school. And so that's  how the bootcamp business got its first legs, and GA was one of the early folks in that.
So since then though, all the energy in the industry and the space has shifted towards Enterprise and B2B, and the reason is that we've had an incredible economic bull run, but then also digital transformation went from being a buzzword that everyone was keeping an eye on, to feeling like a really existential threat for companies.
They felt that every part of their — whether it was their supply chain or their go-to-market model, everything was being disrupted and digitized and they didn't have the innate skill sets. Both hard skills, just like people who are able to do things like product management, data engineering, full stack web development, things that kind of were always well known within Silicon Valley and work core roles in digital-first companies that were natively digital, like Google, Airbnb, all these large companies were like now we need to build that skill set.
And secondly they needed to understand, h ow do you get all the leaders, and the people are already in senior roles, understanding how to manage people with those skill sets as they come in, because that's not their core competency.
So anyways, in the year and a half that I've been at GA, I would say that I joined a broader business that was pre IPO as a whole, but I joined the Enterprise business which really had like one or two anchor clients that were experimenting on how to do what we call reskilling, which is repurposing and changing the roles in an organization at scale, so we're talking about a thousand people at a time.
And so I joined the Enterprise business when it was probably the equivalent of like a Series A start-up, if that. So I had a few anchor clients. We had a suspicion that like what we'd done in consumer could be grafted on to working with an enterprise directly, but that that was a model we had to test and figure out whether we could scale it.
And so, for the year and a half I've been in an enterprise sales role  we've been trying to figure out like what value do we uniquely provide to our clients? What's the best way to deliver that value? How should we price and package that? How do we find the people who believe in that value and want to buy it, and it how do we guide them to buy?
And so we've got this entire process in real time, you know, in addition to figuring out what — like in SaaS, you would say is like one of the first things you need to figure out is — what's your customer success model?
How do you make sure that once you get them into your ecosystem they stay, and they want to keep using you. Because I think one of the hardest things in B2B is, everyone is trying to get into the Fortune 500. Everyone is trying to target the same buyers. CIOs. CTOs. It is crowded. And so, once you get one, once you have their ear and you have their attention and they start working with you, you have to do everything you can to keep them in the ecosystem, because the cost of getting them to that point is so high.
This is famously why large enterprise sales technology organizations  had these big moats through sales forces, like Cisco and Oracle. They'd have these expensive sales guys who are paid $300,000 a year who just had incredible rolodexes, and were always there at the client site. And all the startups had to figure out, like, we're never going to be able to do that, so we got to figure out another way to get in front of them.
So anyways, that's the intro. My role specifically is I'm a senior sales representative on the team. And so I was one of the first people brought on to try and sell when we made the pivot to this model. There had been an existing sales team, to be clear, a lot of senior sales people had been there selling what essentially was like a workshop-type product.
But then when I joined along with a couple other senior sales people, we were the first hired in to try and see if we could all sell this new concept of what GA was in the enterprise, which is focused more on scaled-up upskilling and reskilling.

Geordie Kaytes: Okay. So the workshops used to be a little bit more one-off, and now you're doing more kind of deeply integrated with the companies that are your clients?

Ryan Fennerty: Yeah, what I would say is, when the original enterprise business was focused on one and two-day leadership workshops, essentially what business schools do all the time with executive type audiences, focused on — it was literally called like, "Digital Mindsets." Like, "what are the things you need to be thinking about as a leader as your company gets disrupted?" And it was a very MVP product, it was basically taking themes across every direction, from digital marketing to data analytics, and putting it into one day which was like a crash course in  what it means to be digital-first.
That was the original product. And the idea was like, we would get all these Enterprises coming to GA and saying, "Hey, can we hire graduates? Oh, by the way, can you also come in and teach us some of what you're teaching them, just so we understand?" And then that's how that organically grew into a product concept.
But then the real leap was like, the scale of the need is so high that people are coming to us and saying, "Hey, if we wanted to give you a thousand people to train in data science, how would you do it? Would you do it?" And that was when we first were like okay, there's a much bigger need, and we're going to have to create a model that looks probably a lot more like consulting and training than just training, right?
So I think our latest statement about what we are as a company — because I think one of the challenges in sales, especially when you're in a high-growth startup-type climate, is that your startup, by definition, is trying to figure out what it is you are and what you do, and so  you're selling that in real time.
And so we've had a lot of evolutions of what we are, and sometimes I struggle when people say, "What is GA?" Because we're not a training company. We're also not a consultancy like Deloitte. We sit somewhere in the middle of helping you figure out how the heck you mobilize an effort like this, then how do you execute it well, and then we'll execute it with you.
So I think now the latest thing we've been saying is, we're a "product-led professional services company."

Geordie Kaytes: So the the trainings themselves, are they customized around the exact requests of the client? Or are they pretty much some stuff that's off the shelf, that you know are curriculums that work. How does that work?

Ryan Fennerty: Yeah, I think it's a bit of both. So what we've learned, and I think anyone who's in B2B sales would probably agree with this, is  it's very important to have a view, and know what you know to be true, and be able to say no to clients. And so for that reason, when I say, do we contextualize and align to the client? Absolutely, because that's in service of making sure that we're delivering real value, and the only way you can do that is to reduce the friction cost of applying anything you've learned.
So ultimately the job to be done is to get these people knowing how to do the work, so that the next day, when they hit that desk they're doing the work. And so the work we do to customize and contextualize is more about making sure that that friction cost does not exist.
W here we do have a really strong view and have expertise is, we've created what we call "standard boards," which are industry leaders in a given discipline, from Fortune 500 through startups. They work with our network of instructors, who are people are out there doing this every day in different organizations, to come up with what we think are the core skills and the core roles emerging in a profession.
So for example, data science. When people used to hire a data scientist two or three years ago, they'd say, "I want a data scientist," and what they meant was they want a data engineer, quantitative researcher, machine learning engineer, all rolled into one.
What GA spends a lot of time doing and working with partners is to say, "There are now essentially five categories of roles that are emerging in the market, with these kinds of core skill sets. And here's what we believe are the competencies that you should be looking out for, to know that you have a generalizable standard for each of those."
And so what we're trying to do a lot is, for all of our curriculum, we have a bunch of assessments that allow us to diagnose skill level. All of that is in service of helping an organization. Once they've made the decision that  being an enterprise enabled by analytics is important,  we help them understand, within that space, what should be their strategy. And then, we identify the people that we can actually move in through skill training into those roles and competencies.
What we found in the past  was that people would come in saying like, "I want to train people in data science," and we could meet them at face value and do it. And what we'd see, without all this other wraparound work around helping advise them on strategy, governance, pinpoint the right people, was that they would put a bunch of people through, and then turn around and say, "5 were rock stars, 10 got a lot out of it, and then the others got nothing out of it, or couldn't engage with the material."
A nd that was really because we weren't guiding the client well enough to understand what value this really could deliver, and who the right people were to put in front of it. And so we had to develop all this other wraparound stuff to make sure that that was working more coherently.

Geordie Kaytes: A minute ago you dropped a "jobs to be done." Where did that come from?

Ryan Fennerty: I think that's Clay Christensen.

Geordie Kaytes: Yeah, it's a core part of design thinking.

Ryan Fennerty: That's where I first heard it. He would say, don't think of  what you're doing, think of the job to be done, because that helps clarify. I think some example he gave was from some consulting he was doing, and the place was trying to think about how to sell more in the breakfast hour, and they observed that people were drinking milkshakes on the way, and he said it was very confusing until you realized what was the "job to be done," and the job to be done was basically people wanted a sugar high while they're sitting in traffic.
So then they're like, that's the job to be done. What else could we sell to help do that job? I think that's probably — I think giving people diabetes is less of a great focus right now (laughing)

Geordie Kaytes: Was that kind of thinking, or that that way of framing things, part of the conversation as you were coming up with your sales approach?

Ryan Fennerty: I don't know in that specific way. I think what's kind of... One thing that's really interesting about GA, and something that I have never experienced because I don't think — you know, I came from Morgan Stanley, where it's just a different world, and it's not about creating and delivering products to a specific persona that you're trying to scale.
It's a different mindset in finance. It's like, you have clients that you do a defined set of things with, and you innovate within that space, so that language didn't exist. But in startups, often what you're doing is just seeing what people are willing to buy half the time, and then trying to reverse engineer, "given that they want to buy that, why did they buy that?" And then, "are there enough other people who want to buy that too that we can create a scalable engine around that to make it really a great business?"
And so to answer your question explicitly, "jobs to be done" is not discussed, as much as like, there's excitement whenever someone is willing to pay money up front for something that's a vision rather than a fully-baked product. So I guess in that sense, I would say GA has practiced the kind of design thinking mentality of, "get out to your user first and then perfect, don't perfect the model in closed-door meetings with your product managers about what's the ideal thing we think this product should be."
I think GA has been much more about, we go have a conversation, we understand how they define the problem for themselves, and then we say, "alright cool deliver against that." But what I think we've struggled with, and what I think many startups struggle with, is being very very deliberate about that question you asked, what is the job to be done? And you're probably doing multiple jobs within that, but what's the primary one to be done? And does that deliver enough value that we can build a real business around it?
One thing we struggled with — especially since we're not a defined SaaS product, we're really like  a set of wraparound services attached to training which is how we monetize the value we deliver — that gets muddled, right? And so we do a lot of things, but we're not always super clear-headed about, "what are the things that deliver the most value," to make sure we get them 10 out of 10, and the things that deliver less value, let's not sweat those as much.

Geordie Kaytes: What was that like, switching from selling those one-off workshops to moving to this relationship model, where you're taking a lot more ownership of   the entire skill base within a company?  It's probably a lot more trust, a lot longer of a sales cycle, is that about right? What was that process like of shifting the thing that you're selling, and how did that affect the way you sold it?

Ryan Fennerty: Yeah, totally. So I experienced it in real time because when I joined, a lot of the sales org was still used to selling the individual product-level training, which is a very different process. It's more like, I have a manager in an organization who wants UX training for 15 people on his team, right? That's a fairly defined scope, and then there's a set of questions to just like, you know, BANT that. Do you have budget, what's your urgency, what's going to get in the way of us being able to get this done by the timeline you need, etcetera etcetera. Contract, close.
And when you move into this selling a big vision around reskilling, there's only two ways that happens. One, you go outbound and you get the right senior stakeholders, like a Chief Human Resources Officer and a CIO and a new Chief Digital Officer in a room saying, "yes, we want to do this, let's get started." So that's one path, and that's a really complex and difficult sales process for a lot of reasons.
The other path is, those folks find you because they've been looking, they've been thinking they want to do this. They've been reading, you know, McKinsey reports, and whatever Davos is talking about, it's thematic, and they're like, "we need to reskill." And then they go look for people, and then GA happens to be a name that's recognized within the space as someone who's done this work. And then, we're very fortunate in that it's a new category. There are not that many people who do it credibly with Fortune 500s, and so they tend to come to us.
But then again, we have to shepherd them down the path of where to focus first. How do we make this really tangible? How do we do that in a timeframe that our business can support? Because we can't spend a year doing consultancy for companies before they choose to do any training, because we'd go bankrupt, but also at the same time not narrowing the funnel down so much to just a small p ilot because that's the easiest way to get started, because then we can lose the bigger opportunity of tackling more at the outset.
And I'm not saying this just in a sales self-interested way. What I often see is at a lot of companies there is a lot of risk aversion, and the tendency is always to want to do the smallest pilot possible with the smallest amount of dollars, and then think about it, and then move on. But the issue is like, by the time all that happens, eight months go from the first conversation to when you end the program, and then it's kind of like, we haven't actually moved the needle for the organization. If you said reskilling was urgent, and it just took us eight months to get a pilot, you're no further along.
So I think that's a conversation I'm struggling to have, which is, I'm almost incented to get them to pilot fast, because it's like, we're working with them now, they're in the funnel. We can demonstrate real value. We're very confident that we can, and then we can grow from there. But I think in B2B and enterprise, it's very risky, because these are big complex organizations. Your sponsor and your buyers might change roles. They might attrit out of the org, you know, those are all things that are not obvious until you're selling in B2B and you realize that an eight month  timeframe in the enterprise space is like an enormity of time. The whole context can shift. The priorities can shift.

Geordie Kaytes: So how do you how do you balance that? Just trying to get in there and close a pilot, versus holding out and trying to get a deeper relationship?

Ryan Fennerty: Yeah, really good question. I don't think I have a strong answer for it. A lot of it has to do with looking for the conditions that you know exist at your best clients when they did move with urgency in a big way.
So a couple of cues you can look for is, one, do you have senior executive leaders, like SVP and above, who personally feel invested in having this happen? And that's important because they are the ones who don't sweat the details, but they are the ones who say, "Where are we on this?"
And then what you also need to have is someone who is the evangelist champion go-getter, who also feels as strongly, but are incented to push on it, because they think it gives them visibility for where they want to go in their career next as a leader in the company, or because they personally feel this challenge in their organization and they want this done for their team.
You kind of have to have those two conditions existing, or you're dead in the water. Because what I find is, it's not enough to have your champion on the other side who's really invested in making it happen, because they will fatigue. Because anything that's a new product and a new way of doing things and that's not a standard purchase requires pushing through a lot of internal barriers. A lot of them will say, "Hey, I don't understand what this is. Is it this or is it that?" I think this is a common thing that people in tech sales probably experience, because they're always selling something new right?
I'm sure people who first sold Cloud software dealt with this, trying to convince people why this was so important. And they had to find a champion on the inside to tell that to everyone else around them, who are all like, "why do we have to change?"
And then if you don't have the senior stakeholder pushing, that person doesn't have cover to stay the course, right? And so, to answer the original question, how do we balance that, you have to — to your whole point around really understanding your buyer — you have to really deeply understand what are the dynamics they're living in, because at the end of the day, it's a human being with an 8 to 12-hour work day, and this is just one thing on their plate. And so you have to think, what's their incentive to make this really happen? And those incentives are either, they believe it's going to advance their career or their profile, or it's something they really deeply believe in as important. And often we find it's both, but the second is best.

Geordie Kaytes: Do you do use any systems, processes, checklists, anything like that? Just to manage these these internal dynamics over at the client? How do you codify that, if at all?

Ryan Fennerty: Yeah, I think most B2B organizations would have something like they would call their "Sales Playbook," and within that you would define who are the key personas in your sales process, that are important parties to helping — not just sell the client, actually I think this is misunderstood about sales a lot.
One of the most dangerous things that happens to a sales org, especially in B2B, are false positives. They are people who are really intrigued by what you're doing, but will spend tons and tons of time with no urgency to act. And so they'll want to do lots of meetings and they'll want to keep following up, but they're really not — they're not even aware that they're not in a position to buy, sometimes.
I've had this happen — this was early training for me as a salesperson — I get into these sales processes with people who I genuinely really enjoyed, and we were so aligned, and we'd have mind meld, and we'd even be co-developing proposals together. And they were new to buying in their organization, they didn't even know how to buy. So when it finally came to it, they would they would look at me and say, "I really thought we had the green light here, but I'm getting told there's no budget."
And so the point being that, in sales, and the reason why you have playbooks, and why you have personas, is because it's as important for a sales organization to qualify the person they're talking to to make sure, are    they telling you the right things that tell you that they're going to be successful with what you have to offer, and that they feel the need for it deeply enough to make this work, as it is about like trying to convince them to buy?
I feel like so often, the traditional view of a sales person is someone who sells you anything, they'll sell you the Brooklyn Bridge, right?  That's the traditional view. In practice, I actually find great sales organizations are incredibly good at finding the people who are ready and want to buy from them. They spend all their energy on getting stuff that is just going to be a real waste of their time out of the funnel, and the ones who really will get a lot of value from them, they find a way to get to them faster.
And so to your previous question, about how do you balance getting the pilot in versus getting the bigger thing, the way I think over time to do that well is to know: what are the conditions that lead to someone being a buyer in a big way of your product? What are the conditions that lead you to believe this person could be, but they're not ready now, so let's get a pilot? You just have to create the evidence you need to gather at each stage in the sales process to make that decision.
And there's no data, there's no precision to this. I think over time organizations can get better at it. The more they're really good at being deliberate about putting those in place, but I think the reality is most organizations really struggle with it, specifically large B2B-type sales processes, which are lumpy and highly consultative. I think in SaaS, all this is easier, because you have so many data points. You can look for themes, and be more brute force about it as an enterprise.
You have to just be much more consultative with your team, asking: are we getting the indicators that tell us that this is the type of buyer who we should stick it with, because we can deliver value in a real way, and the conditions exist for them to be able to act on that? Versus: this is someone who Is not ready, and we should just get them into a pilot.
So every good  sales org will have a Playbook that defines who the personas are, what their sale process should look, like ideal state, and then how you qualify whether to keep spending time with this prospect. If you're in a sales organization where that doesn't exist, and they're not actively building it and asking for you to help build it, that's probably a big red flag. That means you're in a boiler room. They're giving you a call list and they're hoping you sell stuff.

Geordie Kaytes: You mentioned the sales organizations not necessarily having data or anything, but they good ones improve their playbook over time. How does that how does that actually work? Like, what does that process look like to to feed the real world back into that Playbook, and make it better over time?

Ryan Fennerty: Yeah, so even in like complex, lumpy B2B, I think not having the data there is like malpractice. GA definitely collects all the data.
I think what's really hard, to the point you raised to the very beginning, is: how do you actually look at that data for real signals, given that's much more of an art than a science because of the number of data points? But the data is still very important to tell you things like: what is the average deal cycle? How is that trending over time? How many touch points did it take for us to get to different phases?
And every sales process, the core management tool most will use is  Salesforce, right? That's like an industry standard. I'm sure others exist. But every time I've seen, it's been Salesforce. And your pipeline is where you have all of the different opportunities you're working on related to a client, right?
And those are often categorized by: "prospecting," meaning like these are the earliest stage conversations, very high level. Then, "qualification." Then, "active discussion."
So "qualification" is like, we've had our first call, I think these folks like are saying the right things and the right people are involved, so we should keep talking to them, but they're still question marks. "Active discussion" is when you're going back and forth and saying, "I think there's alignment here. We really like that. We have some more questions here." It's like a give-and-take. And then the goal of active discussion is, through that you guide them through a process to come to a proposal, and then after proposal, contracting, and then close, right?
And so the way people manage data and a B2B sale — even if there's only, say, 30 data points in a given salesperson's funnel at any point, because that's the number of opportunities sitting in that stack, that's actually still a pretty rich database for someone to aggregate and understand: who are the types of clients who are at each stage of our funnel? Are we seeing any patterns? What are the things they're buying? Is their focus on data products, UX, or product? 
What's often hard for startups, is that themes about what they should care about only become obvious in retrospect. So, you're always kind of playing a little bit of a catch-up game. But we're collecting all this data now around the health and the speed at which things are coming into our funnel and moving through it, so we can understand like are we focusing our attention on the right people. When we have the right people, are we efficiently helping guide them to buy well, and then also what are they buying, and what are the themes around that, and then who are the personas  involved in the buy?
So we collect all that data, and build our internal view of what we should be doing.

Geordie Kaytes: And what do you do with that internal view? How does this data become actionable, and what are the steps that  you take to turn it into change?

Ryan Fennerty: Yeah, so that that data feeds in a couple directions. So ideally, marketing would have that data, and be able to make real time views about where to focus their efforts to drive more speed in different parts of the funnel, right? Marketing is by definition focused on the top of the funnel, and so that data I think is increasingly being used by marketing to understand things like, " What's clearly trending?" Or, "data is very popular. A ton of organizations are very focused on data and AI and implementation in the enterprise." So, are we making sure that, in the key channels we choose to be in, where we think our personas are, are we focused on those, and we are we taking the insights about who's interested in finding like-minded organizations to reach out to?
Then the second piece on the data is — and this is something we're updating now like in real time — is just like, "do we have a coherent way of guiding people to buy in a way that provides insights and makes us look really credible and like experts?" And so the specific example is that is after folks have said they're interested in thematically what we do, we've had one or two or three calls when we zeroed in on a couple of populations in the org — let's say actuaries — they're really interested in doing something with their actuary population around upskilling in data science. The data we're using now is trying to say, "what is the most efficient way to get the information?" We need to create a credible proposal for them that gets them to be able to buy and get started with us.
And In the past we've done something called a working session, where we literally physically go to their site and we bring some subject matter experts in the room, and we have a structured agenda around taking an existing curriculum and mapping it to what we think aligns more closely to their needs, and then making sure the right stakeholders are in the room to get a verbal agreement that this is great, and then to name any sort of obstacles we should be thinking about before we close.
And so that's increasingly how the data is being used, is to map that more bottom-of-the-funnel process and just make it much more efficient for the client and for us, so we can be really effective in helping them buy.

Geordie Kaytes: And so let's talk a little bit about the team itself, the sales team. Is GA bringing a few people into the room, different specialties, or is usually just you shepherding them through the process, or how does that work?

Ryan Fennerty: Yeah. So the way we're set up is, we have salespeople who we call "Account Directors." We don't call ourselves Account Executives, but that's probably the closest corollary at your average SaaS firm. We're called Account Directors because we do, by design, tend to work more like an agency model, where a clustering of really large clients feel what we do really deeply and want a strategic partner. So everyone tends to have a couple of anchor clients who have very much committed to reskilling in a big way, and it's multi-year relationships.
And then another big part of our work is to bring in new clients into the GA ecosystem. And so that's more what you would call a Hunter role than a Farmer role. But all GA salespeople are hybrid Hunter-Farmers, which is a bit of an unusual model. Most organizations separate those as two different roles; one's called an "Account Manager," and their job is to take an existing client and grow business within that account, and the Hunters are the ones who take leads and work them to close. We're a hybrid model in how we're set up.

Geordie Kaytes: So, why is that?

Ryan Fennerty: Great question. I think one was just the fact of being an early-stage startup that was being created in an existing organization, rather than a newly-funded startup in search of unit economics, right? This might be just a factor that we grew out of GA consumer. So it's not like we've raised a bunch of funding and could have a big burn rate and at some point raise another round when we got traction, and just fund ourselves however we wanted.
I think part of this was that GA broadened senior sales headcount without having established a top-of-funnel marketing engine that could support the headcount. And so what happened over time — and I think this probably happens with other startups — is you had a couple big clients who wanted to keep working with you, there was a lot of business to be done, so you're putting your salespeople in front of that because it was a way to keep them, and because there was obvious revenue in front of you, and you needed someone smart and consultative to go get that revenue.
And then meanwhile, they're trying to build the funnel. And so new stuff would come into the funnel and they'd have those same sales people also work on those, and so I think that's the origins of why that structure exists, which is imperfect, but I think that's the reality of how a lot of — anything that's not raising funding to create the ideal structure, and then has a runway, probably might look like that.
I suspect a lot of people that start their own business and privately fund it probably look like that. I'm sure everyone who has created their own agency or consultancy, it looks like that, right? You have a couple anchor accounts to fund your growth for a few years, and then you hire people in and you jump on any new business that comes in, and then over time you start separating those activities.
So anyways, that's how we're currently structured, mostly because of how we started, just the dynamics of how enterprise started out. And then now we're at the point where I think we're recognizing that, because our core business really is much more of a strategic consultancy model where we monetize through scaled training, that there's always going to be a world where your senior-most salespeople are focused on Fortune 100 clients that have multi-year, multi-million dollar relationships and all the new stuff coming in the funnel tends to be like one-offs or smaller engagements.
And so, I think we'll start seeing more sales resources that just focus on those, or more junior sales resources who focus on that stuff to get trained and ramp, so that they can take on the next big clients that become multi-year, multi-million dollar engagements.

Geordie Kaytes: And you think the training with working with these smaller, one-off accounts translates well to working with the Fortune 100?

Ryan Fennerty: I think it does in the sense that it helps you understand our products, and the core training, because I think one thing that's fairly complex about GA is that there are like six different disciplines, all of which have four different program formats we can deliver, all of which are customizable. And so you can just imagine someone coming into that environment having to ramp.
And then also it's daunting because when I sell digital marketing to an organization, I have to talk to the Chief Marketing Officer, or at least someone who's their expert on their team around digital, right? So I have to know enough to be able to have that conversation. I don't have to be an expert, but you have to get past the litmus test of talking to the SME on their end. Same thing in data. So...

Geordie Kaytes: So you've got to know a little bit of everything so you can talk intelligently to everybody on their side.

Ryan Fennerty: Yeah. And so I think having people work on one-off trainings that are much more of a product sale is actually a good way of getting them ramped up on product knowledge and to understand our products, when they work, when they don't, what are they like. 
I think it's difficult doing professional services, in a way, because especially in this training version, it's one of the hardest sales. There's so many human elements involved that it's not like — maybe I'm not giving selling software enough credit, I'm sure this is true for that too — but when I sell a group of 30 people a program that in 10 weeks will take them from basic Python to deploying machine learning algorithms in their Jupyter Notebooks, there is so much stuff around it that you don't appreciate, which is critical to the success of the product, that you don't know until you've done it. Like the firewalls on that side, communicating with the participants in time, people who want to drop out partway through. There's all these things that you have to as a salesperson learn how to build a mental map of how to deal with those when they arise.
So I think the product sale is very important, and then you can be taught the bigger picture B2B account relationship management enterprise sale.

Geordie Kaytes: What's the the additional skills that you think that people have to have to learn once they've got that baseline selling those one-offs? What what sort of skills do they pile up on top of that to be able to intelligently sell to those bigger accounts?

Ryan Fennerty: Yeah, great question. So selling the one-offs is I think exclusively about building product depth and learning the contracting process. Two non-trivial things to learn. That's just the experience of going through the process of going through  procurement with an enterprise, having to get through legal, having to get an MSA in place, all stuff that honestly looks very similar if you're selling a $30,000 engagement versus a million-dollar engagement. It's a very similar process. It's very laborious. That's partly why most people who do enterprise have to get a certain ticket value, because you're doing all the work whether it's $30,000 or a million.
The things that they would have to learn then to do the really large sale are much more about — I would think it's much more about moving from being focused on selling an individual product and qualifying whether this is the right product that fits them, to the pure consultative sale of understanding, "Do these buyers know what it is they need to solve? Do they understand their path to solve it? And do they have the right stakeholders at the table to be able to act on that?"
And so that's I think the difference from moving from a product sale, where the box is a little more constrained for something that's like, "I'm selling a data science training," because usually the conversation is with them saying, "I think I want to do data science training," right? And so that's where you're starting the conversation. Your job is to say, "do you have the right number of people, do they have the right skill sets, are we on the right time frame, do you have the budget required to do this?"
When you're doing the big enterprise consultative strategic engagement type selling, it's much more about talking to a different set of stakeholders, often SVP and above, and credibly guiding them through a set of questions. Which is like, "do we understand?" We're naming a lot of big problems. Can we help them coalesce around one of the most acute things we need to solve now, what are the different paths to tackle them, is GA a fit for how to tackle that, and then coaching them on process to get the right stakeholders the room, where one part of the solution might be that sale that's the product sale, right? Like, one part of that conclusion might be we need data science training for these 30 people.
So, I don't know if that was the most articulate explanation, but that's the  difference between consultative selling — helping people to find a problem they need to solve and how they can go about that and then how that might fit into specific solutions — versus someone starting at a much later state in the process, and saying, "I want to do X," and you helping them figure out whether X is a fit for them.

Geordie Kaytes: So this consultative selling is something that you, just through experience with clients, experience with the product, you get just a better intuitive sense of how to match those those problems and solutions together?  Do you think it's specific to GA's products and clients and ton of stuff you have to learn, or do you think it's more of  a general sales skill?

Ryan Fennerty: I think it's far more the latter. I think this is very common. Consultative selling is about being really good at structuring your conversation to get the information you need to guide the process further, knowing that you have a limited amount of their attention to do that.
And then the second big part of consultative selling, which I think  people who have really succeeded in consultative selling in lots of contexts can probably graft that skill to many places. It's why they're very valuable, because ultimately what they become is masters of hearing cues from a buyer, helping guide them to clarify their thinking, and then challenging their notions when there's a space to challenge them constructively, which I think is a very hard thing to learn to do. Most people are like, "oh they're interested in buying, let me just tell them yes to everything so they'll buy."
Probably one of the first things to learn is how to tell clients "no" at important moments, like, "you're not going to be successful with that approach," or, "if you're trying to buy us because of X, that's a wrong reason to buy us, and I would suggest someone else instead." I think that's the moment when a lot of sales people come into their own, when they're able to do that.
And then the last big piece around consultative selling is being incredibly good at structuring and guiding a buying process. Naming the steps. If you think of yourself, if you were sitting at a company and you had to buy a big piece of tooling, you've never done that before, right? Or maybe you  have, but it's been a few years, because you don't upgrade your CRM like all the time, you do it like once a decade, right? So think of that salesperson. That salesperson has guided many other people to successfully buy it. So what they bring uniquely to the table is an ability to help you think through how to buy from them.
And so ultimately my takeaway is that a lot of what makes a salesperson quite good over time, and why experience does play some bearing here, is once you've had lots of conversations with people like them, you kind of see the like normal distribution of things that people think about, and so then you become a really good consultant in helping them think through it.

Geordie Kaytes: And can you — how does one share that experience with the rest of the sales team? Is that is that possible? Is that something that you can get outside your own head and give to the others on your team to make them more successful?

Ryan Fennerty: Yeah. I think the healthy routines are, usually a sales team will have a fairly frequent cadence as a group, constantly keeping themselves honest around who the personas are, are they still the right ones, is the pitch were using the right one, are we communicating our value accurately, and is it being received well? Because that stuff, that's not static. It changes constantly because, especially in technology, everything changes so rapidly that you've got to constantly  update those narratives, as the product evolves, as how the client perceives the space and the category evolves.
And then the other thing is the Playbook, how we guide the sales process, all those need to constantly be tweaked. And that's not a single salesperson sharing, that's literally about bringing your sales force together with marketing, and ideally with product and customer success, to say, "What are we learning? What's new? What's changing? What stays the same?" I'm constantly going through that feedback loop. I think organizations that don't have that —  and GA, to be candid like hasn't always had that, and it's trying to implement that much more effectively now — but that feedback loop allows you to create the flywheel of people saying the right things, and then if it's not working, that starts getting communicated back.

Geordie Kaytes: How do you structure those feedback conversations?  It sounds like this amazing world where product is talking to sales is talking to marketing and they're all talking to each other and learning about what's working, what's not.

Ryan Fennerty: Yeah. I'm naming the ideal state, like let's be real. You've worked with many product organizations. They're just slammed, constantly. Like, this is hard.
It's funny too, culturally, salespeople — because we're all, you know, I guess stereotypically extroverts — we prefer human interaction of being in a room whiteboarding and talking this out and recording notes. Product are like, put it in Jira, please. (laughing) Right? And it's just funny because  that's just a giant cultural gap that I don't think is understood.
I think product finds it really painful to be in a room with sales, where they all like to hear themselves speak and they're all like, "I think clients want this and that," and I can just see their faces and he's like," oh God, this is such a waste of my time."
But if you do some prior thinking, and you structure it and you put it into Jira, it's like, "thank you for the feedback. That was really helpful." And salespeople are like, "not another fucking Jira process where I have to write the Next Great American novel about what I'm observing." They're like, "nah, I'd rather not do it."
So I am not answering your question directly, but I'd say like these are just two cultural tendencies that happen across product and sales where I've seen miscommunication happen. It's just, even in the mode on how people want to communicate, is very different.

Geordie Kaytes: So have you found a solution for that? Have you figured out how to kind of balance those, and get people talking to each other?

Ryan Fennerty: Yeah, we haven't found the silver bullet, but we're compromising. The pendulum has swung. I think product felt really strained a year ago. And so there's a recognition that we really needed to  step up and help them, because they were really asking for help and feeling overwhelmed.
And then I think the pendulum swung, where sales was feeling like, "alright guys, we all live in Jira now. I think we were not that big an org. We should be talking to each other, you know?" And the way to structure those conversations to be effective is to keep them short, limit them to 30 minutes, 40 minutes at most. Have a structured, uniform sequence of things you discuss, with expectations for what's recorded and what action steps happen after.
So to be concrete, I would say 30 minutes where every part of the org comes in with one or two appointed ambassadors. You just share: what's a  new thing we learned from a recent sales process that we think is worth listening to, and why? What's our evidence for why this is something new to pay attention to? What's something that we should keep doing because we have evidence about it? And what's one thing to just put in the parking lot as a thing to think about? Like, a customer insight, that the buyer persona seems to be shifting, or we're noticing that a new competitor is positioning this a little differently.
Just that stuff, just doing it that simply and having a clear action owner who's like, "If we think it's significant, here's the action we're going to take in the product roadmap," or marketing is going to take action, or we're just going to monitor it. That stuff allows you to create a really efficient, structured way of taking qualitative notes on the pulse of what's happening. So that's just one, for product and sales and marketing to have more communication around the core messages and value-add, how that's being understood in the market.
I think the second one that the sales org needs to do is, especially in B2B where you have long-cycle enterprise sales, is it's called the "deal autopsy." You sit down and you understand,  for ones that you won but especially for ones that you lost, why did we lose? We didn't qualify this well, we were beat on price, were we beat on features, you know what I mean? That's really important hygiene to have, because it's the only way you can really understand what the sales process looks like at a very detailed level, and what we can generalize from what we just saw. Like: who ultimately was the champion who made this happen? Who's the one who signed the contract? Who's the one who blocked it? How do we get around them?
If you don't do that, you're losing opportunities for people to take that and then apply it in real time as their sales process are happening. And also this is something that GA hasn't done a great job on, but it's starting to do now. In the past we were very focused on just hitting our numbers. And I think there's a tendency in startups to — where the targets are really high and they're trying to grow really fast — that some of these things feel like nice-to-haves rather than must-haves, and they get deprioritized.
But I think my sense is that in organizations that are trying to find product-market fit, it is so critical to do it — not just so that you get the data to feed into the org to do things, it's literally to keep everyone aligned. Otherwise, you could have sales people out there telling seven different stories about who you are and what you do.
But I feel like there's so many parts of this puzzle that... So, product marketing, and then marketing, and then sales, and then product, and often when we talk about user-centric behavior, it's always in the product org. The marketing org often uses it because they're the ones who ultimately own, "who are the key personas we're trying to reach, and with what message?" And then they also are supposed to be architecting the buyer's process from, "how do they think about making the decision to buy," and "how do we guide them through that," to then the salesperson ultimately being the person who knows how to find that person at the right time in their consideration phase and then guide them to buy, and buy well.
And so that's the theory of action about how this is all supposed to work. In practice, it is mayhem as far as I can tell. We define the personas, but then when you're in the trenches, it's kind of like, "Yeah, that's a theoretical persona. Right now. I've got four people say they want to buy, and like none of them look like our persona." You know what I mean? 

Geordie Kaytes: Yep. Yeah, and there's like a few things in there. So part of it is, I think obviously personas and segments have almost certainly have very different buying processes. Right? So what works for one persona might be totally radically different for another persona, and yet we often shove them through the same sales process because that's the way our CRM is designed.
There's no way to skip this step even though it's totally irrelevant to Persona B, because you know, what do we do? We just do we put a blank in the CRM? So I  think that's a thing a lot of people struggle with, is a lot of over-structuring of these sales processes, which is kind of the opposite of just letting everyone go loosey-goosey and do whatever the hell they want.
If you go too far in the other direction, you end up with these totally unnecessarily complex and multifaceted and structured sales processes that don't allow people to work the way that reflects the way the customers want to buy, but then the flip side you've just got these... If you've got customers who are coming in and when you say that you hit them at the right point of the consideration phase, I don't know if the old style kind of four-phase sales funnel approach is even the way that a lot of especially complex B2B sales works anymore.
It's not you know, unless you're getting — I think enterprise, like doing a hundred million dollar data center installation probably still works like that. — but when you're you're talking about products in the in the four to five figures range, or maybe even like low six figures, the the the decisions are being made in the insanely complex, multi-person manner bouncing between a bunch of different people with different levels of understanding of the problem and the solution and what's out there. And there's just — it's yeah, as you say, it's chaos. And it's chaos because it's a natural human system that we're trying to put some controls on, and design thinking is literally designed to do that. Right?
That is the tool that we have to deal with complex, insane human systems. It's to observe them, pull out commonalities, try to create loose enough guardrails around the common behaviors to account for them, but also understand that we're going to be dealing with a confusing and dynamic and almost random system that we're going to have to be able to adapt to and in the end if we fail to adapt to it, then they're going to go somewhere else and spend their money somewhere else.

Ryan Fennerty: Yeah.

Geordie Kaytes: Well, awesome. Well, Ryan, I know I've kept you for a good long time now, so I think we can we can wrap it up.
Is there anything that you want everyone to know about GA, about yourself, before we wrap it up?

Ryan Fennerty: No man, thanks for the opportunity. In the future. I'm interested in hearing more of your thoughts as you do this around — given everything you heard, because there is a lot of complexity here — taking this whole mindset of user-centric design to a sales process, where you think the biggest opportunities are in that.
Because in my gut. I feel like it's a really important insight, and a thing to explore. And a lot of the sales processes do feel like we're all following a similar playbook. And so I'm interested to see where this goes, and as the structure evolves, how that question gets answered, or what you start learning as you talk to people.

Geordie Kaytes: Yeah. I've got some suspicions, but I think it's it's just... It's an interesting thing to kick around because you talk about sales talking with product, and product, going out there and hopefully doing their user research and evolving the product.
And sales is doing that in a way, right? They are talking with people. They are the front line, and understanding what people are saying, how people want to buy. But the process of actually organizing that thinking in a structured way, and organizing not just the data, but actually the process of going out and getting it in the first place, I think product has a lot of really well-established processes and principles around that.
And sales, it's very... You know, obviously getting the sale is what we're concentrating on. We're not necessarily concentrating on learning right in the moment.

Ryan Fennerty: Yep.

Geordie Kaytes: That's I think what I'm trying to understand a little bit better, is: "what's the opportunity to learn while you're selling?"  And that just can feed back into a design thinking process around understanding the buyer, understanding the buying process, and evolving not just the product, but the way that you sell, around that in a really rapid iteration way, so it's not just, you know, every every six months to a year we look back on our sales process and say, "hey we could have done this better."
Think about two-week releases for the sales Playbook, right? What if we could do pull requests and update the sales Playbook as fast as we update product code? That's something that I think could be an interesting way of rethinking the way that we approach selling and the sales process itself.

Ryan Fennerty: Yeah, that's really cool. I love that idea. I feel like ultimately what you described is what everyone says is the job of a start-up writ large, to understand in real time what value they're delivering, take those insights and feed that into the engine so that they can scale most efficiently. The observation on the ground is that like that is an aspiration, the reality is far messier. And it might be interesting, in the spirit of design thinking, to understand the most common root causes for when people wanted to do this, what gets in the way.

Geordie Kaytes: Absolutely. Yeah exactly. That's exactly what I'm going to be trying to nail down. But it sounds like GA has evolved hugely in the last, you know, even since you've been there. So I'm sure it's going to keep changing and keep on improving over time.

Ryan Fennerty: Yeah, no, it's been... I think when you're in the furnace, executing in a start-up on the ground, it's hard to have some distance from it, and think about it. But yeah, you're right, like in a year and a half it's actually pretty remarkable how much transformation has happened. And yeah, I don't know. It's really fun. And it's really challenging. But I definitely think it could be less challenging if you're successful in your endeavor here, because it would allow organizations to direct their focus and their resources on the right places much faster. I think it's the source of a lot of burnout and a lot of failure at startup places.

Geordie Kaytes: Exactly, and none of this is rocket science. People are  doing this well, they're just not doing it fast. And they're doing it intuitively, and not in an organized way. So you end up with these people who are these sales geniuses, who take their sales orgs and make them ten or a hundred X, but, all that information, all the way of doing, that lives in their heads.
And that's not ideal, because you have to pay these people so much money. And great companies with great products that could potentially get out there and do really cool stuff  just can't get traction and get sales because the don't have and they can't afford a million-dollar a year sales leader who is  crushing it at another B2B sales company, and just has no interest in joining a little startup to help them completely reorganize their sales process around the way their customers want to buy.
It's the idea that it's... Why can't startups afford amazing sales thinking, right? Because it's expensive. And if you can make it cheap, because it's just  a better way of thinking about building customized sales processes and customized communication flows within the organization, if you can make that not the purview of a 25-year-experience VP of sales, but if you can make it just something that you grab off the shelf and then run internally, that to me feels like it could change a lot of companies.

Ryan Fennerty: Yeah, very cool man. Awesome. Well, yeah good luck editing, and yeah, editing out some of my... I think I only dropped one F-bomb.

Geordie Kaytes: No, I'll keep that in there so I can get the explicit tag. Thank you so much for giving me so much of your time. 

What is Design the Sale?

Success in complex B2B sales isn't an accident — it's by design. In this show, you'll hear from leaders in sales, marketing, design, and technology about the latest tools, methods, and ideas behind winning sales processes.