SALES SUCCESS IN THE MOST DIFFICULT OF SITUATIONS IN B2B SALES

Hey, before we get into the interview, I want to make sure you're checking out the other podcasts, Sales Questions, Brutally Honest Answers. And if you're looking for more brutal truth, I've got a different feed for the best of the brutal truth. So you may want to check that out. Just search for best of brutal truth and it'll come right up. Also, if you're in sales leadership, the Sales Leadership Show, where I interview the world's best sales leaders. Let's get into the interview and also check out the website at b2brevenue.com for all the training courses. Here we go.

Hey, Skyler, thanks for joining us today. As a way of getting started, give us a little background on yourself.

Yeah, thanks for having me, Bryan. So, I'll try to keep this brief. My background's a little unconventional from maybe a lot of sales leaders. But After I graduated from business school, I did that out in Europe. I came back and was having a little bit of trouble finding anybody that cared about the brand recognition of that school in Europe and changed my strategy a little bit and ended up getting connected with a couple of gentlemen who had founded a company and were actually spinning another company out of the former. It was in an accelerator. It was pre-product, pre-revenue, really not much more than an idea on a whiteboard. And I got involved with them really early on. Doing some kind of fractional work and fell in love with the environment. So I ended up spending a good portion of my early career there, about 7 years, and initially started on the product side. So led our product motions and our go-to-market and found myself in more and more later stage conversations with prospects, being a subject matter expert, doing some solutioning, particularly for those deals that We didn't quite serve 100% of their needs, but we might have had an idea of what was on the roadmap. And I was invited to lead sales after 3 or 4 years. Mind you, no sales experience, direct, indirect, really at all. So that was, you know, I'm a pretty big fan of learning by doing and had to get my feet underneath me pretty quickly, but, you know, ingested a team of 4 or 5 people, And led that for a while, did some GMing work in intermediate, like kind of took back over operations for a little bit. And I did that for quite some time. I've done some partnerships work and now currently sit as the CEO of an organization called Wishlist. So not the same firm as I started my career with, but still very much applying my B2B sales background right now.

Yeah. And what was that like with no sales experience, moving into sales and then becoming the leader of it? That must have been a Did you feel like a fish out of water, or was it a natural extension?

It's great. That's a great question. I'm chuckling because I am trying to put myself in my mindset back in the day, and I always had a lot of confidence. Anybody that knows me is— that's not something that I lacked necessarily. So I think the transition was fairly seamless. I enjoyed talking to people. I have, I think, an ability to develop rapport fairly quickly and I knew the product really well. That's what eased the transition because I had spent so much time building it and architecting it with our team. I had complete cross-functional understanding of what the implications were. I had done operational roles in the organization, so I was familiar with that sales to ops handover, which trips up a lot of young organizations. The efforts that were most difficult for me to pick up on were In hindsight, maybe glaringly obvious. One was systematic. Like, I didn't know how to set up a CRM. And if you've ever had the pleasure of trying to set up Salesforce for yourself without a consultant, good luck, right? So I made countless errors in how we structured that. We lost a lot of data. I corrupted a lot of data. So I would not say I picked that up fairly quickly. And I don't even think I'm great at that today. But systematically, I needed to spend quite some time really developing process. That took a long time for me to figure out and management as well. You know, salespeople are very different than engineers, very different than product. And I learned that very quickly that they were different. I didn't learn how to manage them effectively, but I did learn that they were different. So those are the 2 areas that took me a lot longer. And I will tell you, like, I don't know that you ever achieve perfection in either one of those areas, but it's something that is still a focus for me today.

Did you end up becoming your own sales ops person or did you hire somebody or delegate it to someone?

Yeah, that's another great question. So one of the interesting things was we, you know, in early stage organizations, you balance this like, do you build towards process or do you build towards success and then process follows because you can overengineer and for better or for worse, we fell into a bit of the latter category. So it wasn't, you know, we had some leading indicators, for success that, you know, predicted downstream results that we were okay at measuring. About 2 years into the role, we hired somebody in RevOps that helped tremendously because, and quite frankly, like that person actually had started as an SDR with us and did pretty well there, was, it comes from more of like an engineering, a systematic background. One of the reasons why they were successful as an SDR, because it's very procedurally driven. Now I promoted too quickly. That person didn't do as well as an account executive for a couple of reasons, but it was a good lesson in trying to repurpose that talent towards something that he could be much more successful in. So he moved into that RevOps role, put himself through all the Trailblazer courses on Salesforce, and learned by doing. And when I moved over to WishList, I ended up kind of pulling him along, like we'll work together for a long time because I really respected his His ability to figure stuff out. Yeah. So that's the story on RevOps. I got some help pretty quickly.

Yeah. And what's it like becoming a sales leader without having that 5 or 10 years in the field or even the DNA of a salesperson? Sounds like your DNA is much more on the product entrepreneurial side, which has a lot of sales I think sales, a lot of sales for better or for worse is rooted in pretty straightforward metrics.

So what helped me get over imposter syndrome or really settle into the role was also having individual success in seeing deals through from open to close, closing larger business and demonstrating to the team that I was an expert in that capacity. That really helped me settle in and develop some authority with the team, even though the background on paper wasn't there, the results were coming in and that really had spoken for itself. That's why I had a fair amount of leeway from leadership overcoming some of the innate nature of being a director of sales that I just didn't possess. So I think that really helped over time. The other awkward component, Brian, was that I didn't hire— I hadn't hired any of the team myself. And that was uncomfortable, certainly. And over time, that changed almost 100%. You know, that was a gradual transition. But I do think, you know, when you take over a sales team, that requires maybe more intentionality than I gave credit for at that point to really understand where people were at and develop that personal relationship. I was a little hardheaded. Looking backward.

And was it bidirectional, meaning that the reps didn't really buy into you and you didn't buy into them? And it's kind of that, you know, the fingers pointing both ways.

Yeah, probably. You know, I, for better or for worse too, and I got coached out of this at a young age, but I will bring it up. I was a very— I was a young leader too. I mean, we're talking I think I was 24 when I stepped into that role and, you know, everybody on my team was at least 5 years older than me. And I don't know if in hindsight if that actually affected anything, but certainly like my brash attitude didn't help in a lot of circumstances and maybe I was overcompensating. I don't know, that's for a psychologist to tell us. But I think there certainly was some tension with certain stakeholders and we also had very different sales styles. As I said, I was very disciplined with My knowledge of the product. I didn't care about going and playing golf with people. What I cared about was understanding what they were trying to accomplish, what their pains were, and delivering value. And it was fairly straightforward for me when we engaged with the prospect as to whether we could do that or not. And if we couldn't, then I wasn't gonna sit there and spend $100 on a steak dinner and take you out to golf. I just didn't care. I needed to move on to the next one. So methodologically, there was some real differences and You know, ultimately that's a learning. You've got to establish a culture as a sales leader of folks that buy into your system, buy into your methodology and will kind of fall in line. It is a little bit of rank and file in sales at some point.

And how big or how complex was the sale dollar-wise, number of people involved, timeframe?

Yeah, at that point our ACV was probably Probably between $15K and $20K. Sales cycle was fairly lengthy. It was tied to a lot of fiscal year budgeting. So depending on when you first engaged with the prospect, you could very well need to nurture that account for 9, 10 months. And that involved multiple stakeholders, very, very difficult. And obviously, I appreciate that nuance now. Beforehand, it was like, well, Why aren't they making a decision as quickly?

I've got a quota to make.

Yeah.

Don't we know?

Not helping me in Q2. But we did learn over time. We did a little bit better segmentation of our clients and understanding how each variable affected time of the deal, deal size, and complexity. I wouldn't say it was an overtly complex sale. We dealt with the number one issue we had with that piece of HR technology was urgency. And that's a very difficult, we could probably spend hours on that topic alone. But that was more important than like the technical complexity or the stakeholder management or anything else.

So you're selling to HR, is that true?

Selling to HR, still selling to HR. I said I would never do that again, but I, here I am. I think HR is a very misunderstood function within any business and there's a very large variance in terms of how that audience is respected and treated within organizations and thus the output and the way that they think about problems. And it's really important with HR to get to that understanding as quickly as possible. So the know your audience becomes particularly acute here. We spend a lot of time on rapport building, grounding yourself within their roles because titles in HR are meaningless. You gotta understand, like, is this person a functional Are they a systems person? Do they just fire people? Like, how does the organization think about their value creation? That gives us an indication of how we can equip them to have internal dialogue, things like that. So it's a tricky one, certainly, but once you're in it, it's, I don't know, there's some level of like magnetism. I came back.

Well, I gotta Imagine it's one of the harder personas or departments to sell to because they're the nice people, right?

Yes, they're people people. I mean, that's why they're people people. I will tell you that there are different perceptions in this space.

There are.

I remember I met a woman out in Santa Barbara one year who actually came from a legal background and had found herself in HR. And she said something to me that struck struck me pretty deeply. And she said, listen, you're overcomplicating what HR's value prop is to the organization. Our value proposition is making sure we don't get sued. And I hadn't, you know, by their own employees or former employees. And I hadn't thought about it in that respect. But of course, like procedurally and a lot of the policies that are driven, a lot of the structure, a lot of the trainings that are done across population sets, there's absolutely a legal component to all of that. I think the reality is, so I'll give you one like snippet. One like psychographic piece of information that indicates how an organization views HR is reporting structure. So whether the HR director or whoever the senior-most person is reports to the CEO or CFO tells us a lot about how that organization thinks about their folks. And if it's the CFO, that's an uphill battle because that tells me that they think of their people as line items on the OpEx portion of your P&L, and that is— or your budget. That tells us something very different than an organization who reports up to the CEO where maybe it's more culturally focused or whatever else. So certainly, you know, certainly a difficult one, but one that is rewarding once you can crack it.

Yeah. So you're looking for the Netflix and not—

Yeah, if every company was a Netflix or a Zappos, we would be in great shape here. You know, the CFO companies also, there's some macroeconomic conditions that were favorable for us. You know, there's certain headwinds now, of course, but the labor dynamic is changing really, really rapidly and organizations are certainly being forced to adapt. Now, the interesting thing is across HR technology, there hasn't been a lot of strength in establishing metrics for success of a lot of these programs. And that's, you know, ultimately what a lot of CFOs want to see. You know, what's the ROI? The last organization I went with, the whole industry moved towards, we can't prove ROI, so let's create a new metric. We're going to call it value on investment, which is like, that feels valuable. So you can manufacture these data points or talk tracks, but at the end of the day, we still have to demonstrate value. And I think So I think like we're very understanding that the CFO is a part of our— whether they're not a part of the buying process, they're a part of the renewal process. So we're very focused on how we can deliver data in a proactive manner to suggest what we're actually doing.

So I mean, given that the dollar amount wouldn't imply that was that sophisticated or complex of a deal, but the persona that you're selling to in the department does.

Yeah, they have pretty fixed budgets.

Totally.

You know, the— when you look at the sales funnel, the first components are fairly straightforward. You want to get to know people, rapport building. You want to understand, like I said, where they situate within the organization. The hardest part is, for me, the mid to late stage, and it gets back to urgency. It gets back to how do you get to the economic decision maker? How do you get to a decision in general sometimes? Like the problem, fairly easy to identify, the solution fairly easy to like correlate back to for value creation, but is it as important as other initiatives or is it as important as other departments' initiatives? That's where it becomes more challenging and more nuanced. And certainly I wouldn't say we've solved that 100%, but we have a lot of motions that we run to either manufacture that, better communicate it, or to weasel our way in there for the right stakeholders.

And was it money or was it time from the priority standpoint?

In terms of what the organizations, like what got them to move?

Yeah, because I got to imagine, you know, getting interest like you described, They have the problem, you have a solution. They like the educational process, the conversations, they see the possibilities, but they've got 401, they've got all these other things, health insurance, wellness, all this other stuff battling for their attention and their budget.

Yeah. Yeah, it's well said that, you know, there are table stakes. In benefits, you know, for— you just mentioned really the 2 big ones we see, retirement and healthcare, are non-negotiables really anymore. So I think like whether it was time or urgency, whether it was time, we've spent a lot of time trying to think about how you lower perceived switching costs because a lot of HR technology— so if you think about an HRIS system or a payroll system, Those can often be 12 to 18 month implementation cycles, really long time. And a lot of times knowing these buyers, 6 months into implementation, you're like, why did I choose this vendor? And we're 6 months in, we've got another year to go. Sunk cost fallacy, but like, you know, you can't undo that decision. So we have to really be intentional about talking about what's actually required from their— perspective or their team's perspective during implementation, that's certainly helpful. The other element is that at least on the timing side, we have inverted our mentality such that we don't think that we can create urgency, but our job is to stay top of mind so that when urgency hits, we are there to provide the solution. So that is much more of a nurturing mentality. It's more of a long play, but if you have enough volume, those numbers still absolutely work out. So that's also been very, very helpful of like, it's a no for now. That's really what we say. And then it's our job to just stay in touch, providing value with information, not just the check-in emails that we all hate, actually providing value, market insights, product updates, whatever else, so that when they're ready to have a more concrete discussion or when the executive team has that discussion again, that they associate that problem with Wishlist.

Now, that sounds like a very thoughtful approach from a 24-year-old first-time sales leader. How did you come up with— because I got to imagine most 24-year-old sales leaders, it would all be KPI-based instead of any kind of empathy or understanding of the market or their perspective. It would have been just pound the phones or the email.

Oh man. Yeah. So I think there's 2 ways I could answer that. So one might be unconventional, but I— so if you go back to my undergraduate studies, I went to the University of Michigan and I fell into a writing minor there. And I ended up teaching writing at school there to graduate students and undergraduate students. And the reason why I bring this up is we had to read a fair amount of academic literature on the value of introspection. and situating oneself within the broader scheme. And so that manifests itself differently with different people. Sometimes that's pure thought. Sometimes people write after that. I did some journaling, a lot of just deep thinking. But after winning or losing every deal, it's not going to sound crazy. I just thought about what was or was not successful there. And that really was helpful in The management, right? Like, it's easy to get on to the next one, but when you're leading the team with no process, I had to also, I had to bring in numbers, but then also try to figure out like, my time's not going to scale. How can you actually do that? So, and of course, I don't know how successful I was, but I was trying to do that at that point.

Well, you did a postmortem after each deal.

Yeah. And you got it. Yeah. And, you know, the other interesting component is like, you know, what I would highly encourage B2B salespeople when they're early on in their career is like, know the business. It's not enough to know how to sell and what your sales process looks like. You need to understand how what you do affects the organization. You'll get better with your targeting, your segmentation, you'll develop more authority because you've seen what success looks like post-sale.

Yeah.

And that really helped me tremendously. I can't underemphasize that enough, you know, like understanding how sales fit into the broader ecosystem is incredibly important. I think it's underemphasized in a lot of at least earlier stage companies. Sales has to be in lockstep with all the other components. Otherwise, you know, you can really sell yourself into negative cash flow. You can sell yourself into a lot of other downstream implications. So that like It was the other big component that helped with the breadth of understanding.

Yeah. And what's it like being a CEO now?

Well, I'll tell you, there's a lot less literature on how to be a successful CEO than there is on how to be a successful salesperson. I think it's because it's so situationally dependent. But CEOs, I mean, somebody told me when I was early on in my career, there's 2 paths to be a CEO and maybe that's broadened a little bit, but you either get up through sales or you get up through finance. And I certainly don't have the finance background, so I better be a solid salesperson. But at the end of the day, like I sell, 90% of my time is spent selling. It's just selling to different stakeholders, you know, whether that is internal shareholders, whether that's outside investors, whether that is new hires. I spend a lot of time hiring and a lot of times we're not paying what a Google is paying. We're not paying what a Meta is paying. They are buying into perceived contribution, culture, whatever else. So that was fairly straightforward for me as a natural evolution. You know, the one thing that I, it sounds ridiculous that I completely missed is how much my personality affects culture. And it is, sounds crazy that I didn't know that, but that was a miss for me early on. And so, you know, being intentional about what you say, how you show up, what your body language is, has been something that I continue to work on because it, you know, you notice other people's habits start to mimic yours and that is either incredibly constructive or incredibly destructive depending on how you're showing up. So that is, that's been a big challenge for me, but something that I'm still working on today.

And how did the sales experience help you in your current role?

So unfortunately, like we, when I had taken over our sales team was in disarray. The leader, our CRO, had left to pursue other avenues. You know, that was voluntary resignation, somebody we certainly would have retained. And about a month before I joined the organization, the old CEO had actually hired a new sales leader. And to say we had different kind of talent expectations would be a bit of an understatement. So it was actually very challenging to come in and understand where we're at. There's a lot of data corruption in our CRM. So looking back at historicals was not that helpful. But at the end of the day, you know, early stage is early stage. We got our hands dirty and we deconstructed the entire process. We looked at what was successful, what was unsuccessful, rebuilt it, rebuilt our BDR team, rebuilt our AE team. And so I think having the knowledge of what success looked like in the past really helped you start from the beginning again. That's probably the most translatable example.

You know, and in your mind or in your experience, what makes a great salesperson in your market?

Caveat to this is I think when you ask about what's a great or a bad salesperson, it has to be contextualized because what makes a good salesperson for a company who's earlier on in the product market fit probably looks different than a late majority company or a cash cow company who's really like established an incumbent client profile. They are market leaders, you know, whatever else. They have phenomenal brand awareness, good marketing behind them. In early stage, which I can speak to more directly, there's table stakes as with any sales job. You've got to be You gotta work hard, clearly. You've gotta be consistent with your behaviors and not be short-term, be a short-term thinker because what you do today might not pay off for 6 months down the road when you've gotta have that belief that if I just keep putting in the reps, it will pay off. So having a little bit of long-term vision will certainly help. The number one variable that we hire for, and actually this spans beyond just sales, is curiosity. So we just want people that are curious, and that manifests itself to me— like, examples of curiosity for me are like, do they read, or do they try to better themselves? I don't care if it's reading or podcasting or audiobooks, but like, what have you done to make yourself a more effective person, professional, spouse, whatever else? Like, how are you bettering yourself? And On the sales side, curiosity makes sure you get to that root cause of need and you really understand what's going on. A lot of salespeople hear what they want to hear, you know, that prospect will say something and you latch onto that and then you can't stop talking and focusing on that, but you've only hit that tip of the iceberg. And so having a discipline to be curious and really let that prospect flesh out the entire idea set is is super important overall.

Great. Hey, this has been a great conversation. Where can people go to follow you and learn more about your company?

Yeah, would love that. So you can find us on LinkedIn, you can find us on our website, enjoywishlist.com. We do rewards and recognition programs for organizations. So would love to chat with anyone if you've got something that's not working well, or if you're trying to develop a program from the ground up, we can certainly provide some advice.

And to become great at sales, the best way is to model somebody who already has become good at sales and to hear other people who have become great at sales and the journey that they're going through, the false beliefs, the misnomers, the mindset issues, all of the stuff that gets in our way between where we are and the income that we want. Let's face it, we're in sales because we're money motivated, we're competitive, we want to be better every day than we were yesterday. And how do we do that? Um, does really, you know, read a book, uh, listen to a podcast— that's good, good start, I like it. But then you have to take action, and then you want both tactical and strategic. Ideas. You want mindset. You want strategy. You want to understand how companies buy. You want really deep content and examples, case studies, so that you can learn from other people's mistakes. That's what I'm here for. I'm here for you to learn from my mistakes. And boy, do I got a lot of them. So go to b2brevenue.com. Sign up for the courses. There's 2 major ones. Start the conversation, get the meeting, fills up your pipeline, gets rid of that problem of, oh, I don't have enough leads. I don't have enough meetings. It gets those conversations started with the people you want to talk to. Now, it's not about a pitch. It's about a conversation. Now, everybody thinks of conversations when you're talking or you're online at the same time, or you're on the phone or Zoom at At the same time. That's not a conversation. A conversation's when the client is talking about what they care about, what they're interested in. And that is what we call qualification, where we can sense where are they and how do we build up that curiosity into interest into urgency to get a deal. And these are skills that we need. They're lifelong skills that we need. And then how do we get a deal closed? Yes, anyone can take an order, but what if they don't know how to get it done? You got a new account where you're trying to get a big change done internally. What are the issues? If you're not planning that through, odds are it's not going to get done no matter how much your champion wants it. So winning the complex sales solves that problem. for you. Why waste all your time on these false positives or these no decisions? Because they don't pay very well. They pay 0.0. What you want to do is pay a lot. So sign up today. Invest in yourself. You're the asset in sales. Quit waiting for somebody else to approve it or train you. See if you can get it expensed. That should be your first sales obstacle. Your first sales challenge is how do you get your company to pay for it? Just go down, tell your manager you want to do this. I put a little example email in the show notes right below here. Just swipe up and take a look at that. And if they won't, you got to ask yourself, why won't you? Why won't you? Why won't you? Oh, it takes time. Well, you work all day. You're working wrong all day. Why not improve that? There's the time right there. Oh, the money, Brian. It's money. Well, you make more money if you become better in sales. And Start the Conversation pays for itself the first week because you're going to get at least 2 meetings Just learning from the very basics of it. Closing the Complex Sale will pay for itself 100 times over. Students in it tell me it's the best money they ever spent because they now have control over their deals. And it doesn't end. Some give up. Some give up after they win their first deal and they think they've got enough. No, come back. Come back. Keep going. You can get even bigger deals, more deals, faster deals. That's what it's all about. Sign up today. Put the excuses away. Yeah, excuses feel good, but they're expensive. Excuse— you know what the excuses are costing you? Tens, 50, maybe a couple hundred thousand dollars a year in lost income.

Really?

Yeah. The difference between where you are today— let's say you're making $150,000. Decent, decent income. But you know, there's other people in your industry making $300K, $400K, $500K. Well, how are you going to do that? You all think it's just about getting a better job, a better territory, a better manager. They can help. Go do that. Then what happens? It's still you there with those leads, trying to close those deals. And Do you have the game? Few people do. Everyone thinks they do. Why not prove it? The market tells you what you're worth. Accept it. Now become better. And the way to become better is to improve every day. Really make a daily routine of learning and developing because it's not At the knowledge level. You have to become unconsciously competent at these skills, which takes time, repetition, and emotion. And I show you how to do it, how I did it, how I've taught hundreds of people to do it. But you have to want to because I can't force you. A lot of people wish I could. So do I, but I can't. So sign up today. We'll see you next time.