In this episode of the B2B Digitized Podcast, you’ll be introduced to Sam Capra, VP of Sales at flexEngage in Orlando. Sam will share his thoughts on B2B sales. 

Sam has worked in the B2B sales space for over twenty years in various sales roles including as a contributor, leader, and trainer. Sam's experience spans various industries from industrial early in his career to SaaS for the past ten years working with organizations from startups to the enterprise-level.

Listen to the full episode of the B2B Digitized Podcast to learn more about:

  • Contacting people on cell phones vs. landline
  • Getting back to basics and mixing things up
  • Hiring your next sales development rep (SDR)
  • Reinvigorating with podcasts
  • Resonating with your target audience
  • Selling to B2B accounts

Watch the Podcast Interview


Watch on YouTube: Sam Capra, VP of Sales at flexEngage (B2B Digitized Podcast)

Listen to the Podcast Interview

Sam has advice on why sales calls should be all about quality rather than quantity:

“You're given a territory, and you're given a set of accounts; there’s a wide variety of different scenarios that can go into this. But I learned, actually pretty late, that it's not about quantity. It's about quality. I remember the days where I used to have 2000 accounts. I never thought that was enough accounts for me to call out like, ‘I don't have enough accounts.’ And now, in today's day and age, it's the opposite. You can have 5 million accounts, but you have to find that ICP or that IAP, whatever you want to call it in today's day and age, or an ABM, that's really in your sweet spot. Who's going to resonate with the message you have, the value proposition you're bringing in, what use cases, other clients you can leverage to that specific industry, sub-industry that's going to resonate?” 

Sam also talked about targeting larger companies vs. smaller companies:

“They (smaller companies) haven't even thought about case studies. There are no case studies to produce. It's adapting and learning and creating on the fly. And that is a big challenge, right? It's a curse and a blessing. It's a curse because you don't have it, but it's a blessing because you don't have it. You can be a little bit more agile and nimble to make some adjustments that, really, to be honest with you, Joshua, you can't do at Salesforce. If I tried to move a little bit to the left, they're going to smack me right back to the right and say, "That's not the way we do it." And in all fairness, they should. They have a well-oiled machine.”

Sam also shared how the sales industry is changing with the pandemic:

“I think COVID shined a light on many things, and it exacerbated certain aspects of our industry from a sales perspective. I never used to get a ton of calls on my cellphone. But since COVID and by being remote to your point, that's the only way of getting ahold of someone. So, I think it shined a light on things: do we do this, do we not do this? I've even seen systems cracking down on that with Verizon and all these robo killers. It's a slippery slope to do that. And I know, just last week alone, I probably received at least 25 calls on my cellphone that were sales-related, not telemarketing, just salespeople in the SaaS market, trying to sell me a SaaS product. And I think you're going to see some changes in that as we start to understand both from a prospect and from a sales perspective what the ramifications might be.” 

All of this and more is discussed in this episode of the B2B Digitized Podcast. To learn more about Sam Capra and contact him with any questions about the topics discussed, you can find him on LinkedIn or at

Lightly Edited Transcript

Joshua Feinberg (00:55): Hi, it's Joshua Feinberg from the B2B Digitized Podcast, and I have a very special guest here with me today: Sam Capra, VP of Sales at flexEngage in Orlando. I’ve known Sam for several years, dating back to us being involved in a marketing-related organization here in Florida. Sam, welcome to the podcast. Thanks so much for joining me.

Sam Capra (01:17): Joshua, thank you for having me. Yeah, we were talking about it offline. It feels like that was two lifetimes ago.

Joshua Feinberg (01:24): Everything in digital marketing seems to. It's like looking at the lifetime of a pet compared to the lifetime of a human.  And then, of course, the last 18 months....

Sam Capra (01:24): Yeah.

Joshua Feinberg (01:24): Earlier generation.

Sam Capra (01:34): Everything is pre-COVID, post-COVID. That's how people are going to start verbalizing them.

Joshua Feinberg (01:40): Yeah, I agree. So, the first place I usually like to start with is for you to give the viewers, listeners, and readers a little bit of context on your background, how you ended up in your current role heading up sales at flexEngage. Did you know that you always wanted to get into sales? Just your calling?

Getting Started in Sales

Sam Capra (02:01): No, not at all, man. I would love to say that I was destined to be in sales. I fell into it. At least most of my colleagues and friends and mentors seem to all have the same story. My dad was in sales. He'd sold anything and everything. And I was always around it. And he used to sell on the phone as well as face-to-face cold-calling. And he’d bring me out on sales calls. When he had no one else to watch the kids, he’d bring me in the car, tell me to sit there, and wait. I’d see him knock on doors, and then he’d come back to the car and debrief with himself. And I picked up on it. I liked it. And then, as I got out of college, I just like the ability to own my destiny. If I wanted to make $100,000, it's all up to what I want to sell from a commission standpoint. I'm not locked into a desk, not locked into a pay structure. I can map my future. And that's really where it all started. And so, I don't have a great story around, "Hey, I always wanted to be a salesperson." It just happens to be what I am. And I am fundamentally passionate about it. That's one thing I am passionate about, is B2B sales and just the craft of sales itself.

Joshua Feinberg (03:18): Yeah. No, it's interesting. You bring up the story with your dad. My dad was an accountant, and I remember as a kid going to work with him sometimes on Saturdays, and he was in retail. And I remember there were some cool aspects of it. I think this was pre-PC towards the later stage of his career in the '90s; he eventually got Lotus 123. But I remember the green ledger paper, the adding machine--

Sam Capra (03:39): I do.

Joshua Feinberg (03:40): But what's especially cool is, I remember when we were in elementary school, and my sister was bummed that--Cabbage Patch Kids were the item to have. He was able to pull strings because he worked for a retailer and get a super popular toy in the pre-eBay days when everyone was camping out.

Sam Capra (03:54): Perks of the trade, man. Perks of the trade.

Joshua Feinberg (03:59): It carried me just far enough to have a job in college, I think between my freshman and sophomore year as an accountant, but all I needed to do was spend one summer doing it to realize that--

Sam Capra (04:09): That was not for you.

Joshua Feinberg (04:10): Good knowledge to have. I'll take a few more courses in college. It'll help me with whatever I'm going to end up doing. But yeah.

Sam Capra (04:15): Without a doubt, that's funny.

Joshua Feinberg (04:17): That's always my most interesting advice when college students come to me. ”How do I figure out what I want to do?” I'm like, "Do lots of meaningful part-time jobs and internships and what you think you want to do when you graduate while there's still time to course-correct."

Sam Capra (04:32): Without a doubt, I 100% agree with you. Figure out what you want to do in college, test it, all that fun stuff, try it out. Nine times out of 10, you figure it out pretty quickly that that's not something you want to do, and then you have the ability to adjust and course-correct.

Joshua Feinberg (04:48): And it's changing. There are some schools where you can major in sales and some sales-related organizations, but it's still not nearly as common to major in marketing, finance, or management.

Sam Capra (05:00): No, it's not. I know UCF has a program here in Orlando that's pretty good. I know Purdue has a pretty well-known sales program. I know Samford in Birmingham, Alabama, has a pretty good sales program. And I think Harvard has one now, actually. Those are the only four I'm somewhat familiar with or that I've heard of. So, I don't know if there's... I'm sure there's more. Don't get me wrong. But you're right. It's not like getting a degree in marketing as a fundamental course curriculum.

Joshua Feinberg (05:29): It's important too because, in order for your parents to be excited about telling their friends and family about what you're majoring in, it has to be legit. But yeah, the work that Mark Roberge was doing up in Harvard Business School should dramatically change that over time. But the pace of change is slow.

Sam Capra (05:46): Without a doubt.

Working and Selling into B2B Accounts

Joshua Feinberg (05:47): So, the first big area I wanted to get your insight on is advice you give to someone brand new to selling in a B2B context. Regardless of the size of the accounts, what would you tell them to start with to get their feet wet? What do you think is super important for them to be thinking about in the first couple of years of their career, working and selling into B2B accounts?

Sam Capra (06:09): Yeah. And this may take a lot of different shapes, forms, and fashions because in some organizations, you're given a territory, and you're given a set of accounts; there’s a wide variety of different scenarios that can go into this. But I learned, actually pretty late, that it's not about quantity. It's about quality. I remember the days where I used to have 2000 accounts. I never thought that was enough accounts for me to call out like, "I don't have enough accounts." And now, in today's day and age, it's the opposite. You can have 5 million accounts, but you have to find that ICP or that IAP, whatever you want to call it in today's day and age, or an ABM, that's really in your sweet spot. Who's going to resonate with the message you have, the value proposition you're bringing in, what use cases, other clients you can leverage to that specific industry, sub-industry that's going to resonate? So, I think really getting laser-focused, especially coming into a brand new organization, because you're already going to be overwhelmed from everything else. So, how do you reel it in from a target marketing standpoint or target account standpoint? I wish I would have learned that a lot sooner because I was doing a lot of things but nothing very efficiently or effectively.

Joshua Feinberg (07:31): I find what's super interesting about that also is looking at where the company has been successful in the past like case studies, pattern recognition, and product-market fit. And it's challenging, I guess, if you're brand new to B2B and the company is a startup, and there's no track record or pattern recognition to look for with any of this, especially if you're in any subscription-based recurring revenue type thing. Knowing who's going to be successful with the product is almost as important as knowing who's going to be closable.

Sam Capra (08:02): Right. And I think to piggyback off that, Joshua, you're right. In those situations where there is no portfolio of accounts, and you're not quite sure who this will resonate with, I think that's key for a sales leader, a marketing team, a leadership team. You've got to be extremely agile. You got to test the whole lot, right? Because what you think might resonate or who you think might be the audience you should be chasing, that may not be the audience you shouldn't be chasing, right? When I first came into flexEngage, we thought we were going to sell enterprise, like the Walmarts of the world. But after a year of grinding it out, you realize that the sweet spot isn't that. They're the big behemoths, but the path to getting your foot in the door in a reasonable amount of time, where you're not going to get bogged down by legal mumbo jumbo and procurement, it's actually that midmarket, which became our sweet spot. But that came through trial and error, right? That just came through time. And I know that's not the greatest answer because, for sales, it's all about today. What can I do today? But what's the old saying, “Fail fast, fail often,” I think that's what you have to do.

Joshua Feinberg (09:12): Yeah, being able to figure out this sales cycle where you can win most often is such a big deal. Everyone's always obsessed with logos. However, it doesn't necessarily need to be the 800 lb gorilla. It doesn't necessarily need to be Fortune 500 logos. If you're going after a niche, recognizable companies with a couple of hundred employees could be very appealing to other companies in that space that are similarly sized or a little bigger, a little smaller.

Sam Capra (09:36): Without a doubt. I think you hit the nail on the head. I don't think logo... they are important. It's always nice to have big logos under your belt because it gives you some credibility, no doubt about it. But I think there's value in actually having the smaller, mid-market SMB, whatever you want to call them, and having a pretty diverse portfolio because it shows your ability if, in fact, your solution is scalable and can resonate with SMB and enterprise. But many times, you start talking to a mid-market company, and all you have is the behemoth enterprise accounts on your portfolio; they think they're going to be too small of a fish and that they're going to get lost. And so, it can be counterproductive from a sales perspective to only tout the big logos. I try to make it a point, depending on who I'm calling on, to find very similar logos. It may not be the exact industry, but from a size standpoint, they're very similar. Because that lets them know, "Hey, we're not just dealing with the Under Armors of the world, we're dealing with the Shane Co.’s and the smaller organizations that are innovating and trying to grow very similar to how you are. And that seems to resonate with those organizations.

Targeting Large Companies vs. Smaller Companies

Joshua Feinberg (10:52): So, with targeting, the size matters a lot. How did the context change a little bit when you moved from working with a huge company to a smaller one? The last time we were hanging out, you were working with a company that Salesforce had acquired. At that time, six, seven, eight years ago, Salesforce was big enough that “blue chip” was a household name. Everyone knew it. How did that change a little bit when you're working with a smaller company?

Sam Capra (11:19): It changed pretty drastically. I was having this conversation earlier today. You go from defined processes, defined workflows like everything is mapped out: "Oh, I need case studies." "Okay, which case study?" You get 4 million case studies to pick from. What industry do you want? All that is fleshed out. Then you go to the startup world. And to your point earlier, they've got no logos, or they’ve got very few. They haven't even thought about case studies. There are no case studies to produce. It's adapting and learning and creating on the fly. And that is a big challenge, right? It's a curse and a blessing. It's a curse because you don't have it, but it's a blessing because you don't have it. You can be a little bit more agile and nimble to make some adjustments that, really, to be honest with you, Joshua, you can't do at Salesforce. If I tried to move a little bit to the left, they're going to smack me right back to the right and say, "That's not the way we do it." And in all fairness, they should. They have a well-oiled machine, and that's fair. But that's not the innovation that I was looking for, which is why I found a whole lot more on the startup side of things. But it was a challenge, no doubt about it.

Joshua Feinberg (12:37): I remember there was a really interesting question from Mark Roberge, who was a CRO at HubSpot. He used to use it as a conversation starter. You have a brand new startup, and he gave four hypotheticals on who your first sales hire should be. And one was, it was the top performer in an organization of 500 at a company in your same space. And then, it was the VP of sales who had an organization of 500 at the same company in your same space. And I forget what the third choice was, but the fourth one was someone who was an entrepreneur in your space. And what he was trying to get at is the person that was sales hire number 117 at their company didn't have to deal with the uncertainty of building the playbook on the fly and all the iteration where they had to run back and forth to the product manager, who at the time was literally a product manager and not a product management department and say, "Hey, this is the third time this month I'm hearing that I could have closed this deal. Why don't we have this feature?"

Sam Capra (13:35): Right. That is dead on. That's a constant thing that we weigh, right? So, we're in the interview process. The common thought process is that we want to hire someone with SaaS experience. Let's chase the Salesforce sales reps, Oracle sales reps, or whoever because they have the SaaS background. But to your point, they've also got the rigid playbook. So, everything is handed-- well, I don’t want to say handed, that's not fair. But SDRs on their team that are pumping them leads, webinar machines, all these things that they have a well-oiled process for, and stepping into a startup, a lot of that's going to be on them. And that is an adjustment, and not everyone is equipped or should be in that environment.

Joshua Feinberg (14:21): When you mentioned SDR, it reminded me of something I saw a couple of times on your LinkedIn feed. In the last couple of weeks, you posed a question: Is it a good idea to cold-call prospects on their cell phone? I was curious. Have you gotten any feedback from that?

Sam Capra (14:38): I've got 564 votes. Three days left; it’s got 16,000 views. It's ungodly. It's crazy. And I only did that because I received a call on my cellphone heading into Publix down here in Central Florida. I know they have been down your way as well. And I got to be honest with you, it was not well-received by me. So, I just wanted to get that out there and say, "Listen, how are we approaching this as a sales organization, as a sales industry?" And it's funny, Josh, as you brought that up that if you look at that, behind the scenes, I can see the breakdown in 60/40, all that. If you look at the majority of yeses, yes, it's okay to do that; it’s predominantly salespeople. If you look at the nos, it's predominantly the people that are being called by the salespeople. So, that's a fundamental disconnect between sales and their clients. That's a breakdown. So, if your clients are saying that's not the way to communicate, you're only going to upset me by doing that; you’re actually doing more harm than good... Now, I'm not saying don't do it. If someone's got their cell phone on their business card or LinkedIn, that is an open door, feel free to. I like to challenge, "Hey, is it the right thing to do? Does it do more harm than good in the greater scheme of things?"

Joshua Feinberg (16:05): It's such a different context to know what we're in because nobody has been sitting in an office for the last year and a half. Because you could always count on that if you didn't have a direct number, a mobile number; you call the main number. And the gatekeeper gets you at least a voicemail. Now, I guess you're still getting the voicemail and no one's answering. So, the question is, with people staying remote or people... is this really the end of the landline?

Sam Capra (16:32): Yeah, it's a good point. I think COVID shined a light on many things, and it exacerbated certain aspects of our industry from a sales perspective. I never used to get a ton of calls on my cellphone. But since COVID and by being remote to your point, that's the only way of getting ahold of someone. So, I think it shined a light on things: do we do this, do we not do this? I've even seen systems cracking down on that with Verizon and all these robo killers. It's a slippery slope to do that. And I know, just last week alone, I probably received at least 25 calls on my cellphone that were sales-related, not telemarketing, just salespeople in the SaaS market, trying to sell me a SaaS product. And I think you're going to see some changes in that as we start to understand both from a prospect and from a sales perspective what the ramifications might be.

Recharging and Getting Back on Track

Joshua Feinberg (17:30): So, we talked about some great advice for someone brand new to B2B. What recommendations would you have for a peer who comes to you that's 10, 20 years into the business and maybe they’ve had a rough year the last year, or maybe their industry was particularly hard hit, they lost a lot of team members and a lot of customer churn, and they're feeling a sense of burnout. What would you suggest to help them recharge the batteries and get back on track?

Sam Capra (17:54): Yeah. I think it's a good question. If you're looking at my career, I'm probably on that side of the fence more than the new side. And I got to be honest with you, as I've come out of this post-COVID, and I've taken a bigger, deeper breath and just really taken stock of where I'm at in my career and with my family personally and professionally, I think it's just imperative for people that are longer in a tenured role to actually take a step back, get back to the fundamentals, get back to what got you to where you are, get back to the passion that you had when you very first started this. And that's what I did. I actually started to pick up a book. I've been reading a book once a week. I've been reading one book a week. So, I've been targeting about 20, 25 pages a night. And that's what my takeaways are. And I'm just trying to learn, what don't I know? There's a lot I don't know in this space. And what can I learn? It can reinvigorate me a little bit to actually share that with my team or to try something new. And I think that's important because I think when you get to that stage in your career, you become static, you become stale, you become stagnant. It's really important to mix it up. But I highly recommend taking a step back, getting back to the basics because that's typically what happens, is that you get so far away from the basics as you get more tenured that you lose your train of thought and your roadmap if you will. A pretty simple philosophy, but that's what I highly recommend.

Joshua Feinberg (19:29): Reading and being exposed to new ideas to help spark new playbooks and new thought processes.

Sam Capra (19:29): You got it.

Joshua Feinberg (19:35): Yeah. 

Sam Capra (19:37): Without a doubt.

Joshua Feinberg (19:38): Webinars.

Sam Capra (19:39): Webinars, podcasts, and I think you bring up a good point on that. That's obviously one of the reasons I like to do podcasts, I like to listen to them. Because they are so digestible, right? Most of them are pretty concise, and to the point; you can get through one while you're running, or you're walking, or you're doing something else. So, it's a great consumable platform that I really like, but I'm a big believer that if you're not getting something from one, there's a ton of them out there. Go find something that's really going to resonate with you. And I know they are out there. I've listened to a few that are just fantastic. And there's been a few that I'm like, "I'm never listening to that again." It just isn't in my wheelhouse. But yes, podcasts are a great platform to reinvigorate.

Joshua Feinberg (20:22): Yeah, I used to even--going back pre-pandemic, going back 10, 15 years before podcasting was really big when people used to tell me they didn't have a lot of time for professional development, I'd ask them like, "Do you commute?" "Yes." “How much time a day are you spending in the car? How much time are you  spending driving between meetings?” It was audiobooks back then or audio CDs. Now, it's podcasts, but anyone who works out, whether it's on the elliptical or running or going for a walk… If I did my peak workout every single day, I'd have 30 or 40 hours a month for consuming that stuff. I think at some point, I'm probably on professional development half or two-thirds of the time. Sometimes, I just need to turn it off and put some music on. But there's a lot of time to be able to keep up with everything you need to do from webinars, professional development, training. An interesting thing too that a lot of people don't think about is that I listen to videos a lot of times when I can't watch them, and I'm still getting 90% of it out of it. It's just the same way with this. We're recording on video. We'll have an audio version. Some people will listen. Some people will watch. Some people read the blog.

Sam Capra (21:27): You hit the nail on the head. There's really no excuse in today's day and age on why you can't professionally develop or develop from a career or professionally or personally or whatever you want to develop from. There's really not. I remember the days. I’m sure you do, Joshua. I think we're probably pretty close from an age standpoint. There was a day where you couldn’t just Google something. You couldn’t just type it into YouTube. You had to go and get a book from the library or do some real work to figure it out. Everything's at your disposal. Everything's at your fingertips on your phones. There's no excuse not to take advantage of it.

Joshua Feinberg (22:07): Yeah. I remember reading Cialdini 30 years ago, reading Stephen Covey 30 years ago. There was no YouTube to go to if somebody wanted to do the five-minute version of it.

Sam Capra (22:16): Right. There are no Cliff Notes. It was like, "You got to get the book." Yeah. Yeah.

Approach to B2B Sales

Joshua Feinberg (22:22): With all of that, how does your approach to B2B sales change depending on whether you're talking to someone where you think they're pretty early on in the process versus the middle of the cycle, late process? How do you figure out where they are? And with that in mind, how does your overall approach tend to change?

Sam Capra (22:41): Yeah, that's a tricky question. It's a tough part for a lot of salespeople to navigate because we talk about qualification in sales. But the fact of the matter is, I'm not a big... I'm a believer in qualifying an opportunity to make sure it's a real opportunity. But believe it or not, there are many solutions out there that are not line item budgeted items. They're not something that is required for the business. They're more nice-to-have than they are need-to-have. So, the old models of BANT, Budget, Authority, Need, Time really go out the window because you're more of an educative sale than you are from a line item sale standpoint. So, I think it's fundamental. What I think is the most imperative to the enterprise sales process is, I like to call it, herding cats. You've got to be great at deal management. You've got to be great at running multiple things not in sequence but in parallel. How do you align different people from your organization to the prospect's organization? Because you don't want to wait for one thing to happen before the next thing can happen because that slows down your sales process. But you also need to get the prospect, the client, what they need. You need to educate them so they can make the best decision for their business. So, I rely on coaches and champions. I try to form a relationship with one, two stakeholders within the organization to help me navigate. And I approach it in that form. I don't put a hard sales press on them. I really probe to understand their business, understand what's important to them, and understand what's important to their role and boss. So, I can say, "Hey, are there any synergies here?" because I don't want to waste anyone's time, and I know that their time is valuable. But if there are, then really having them help me navigate that ecosystem or that org chart, whatever you want to call it, to figure out where do those things sync up from a value prop standpoint? So, early on, it's really like you're almost a Columbo. You're an investigator. You're a detective. You're just really trying to figure out, "Is there anything here?" And if there is, how can you help me? Does this benefit you? How can you help me at least plant the seed and continue down the path of the next steps? And that's what I'm always focused on, the old days of Always Be Closing from Glengarry Glen Ross days, which exposes how old I am. I don't think that's a thing anymore. I say that kind of, yes, it is/ no, it's not. But what I mean by that is, you're not always closing on, "Hey, I want the deal done." But you should be closing on what I call micro-steps. What are the next logical steps in the process, in their process, your process? And how do we get to those? And sometimes, I'll be honest with you. It’s very small. Sometimes, they're so minute. It's like, "Are we even moving forward here?" So, that's the process I undergo with these opportunities, these large retailers that we work within my world to try and figure out what the landscape is and then figure out a path forward.

Joshua Feinberg (25:51): Yeah. If it’s any decent size account, there’s always going to be a committee; there are always multiple people. And the most challenging part is what you see on the surface, looking at their About page, looking them up on Sales Navigator, doesn't tell you the subtle nuances that, like, Bob's got to sign off on this. But Bob is 20 years behind the times on technology. So, we got to go to Bob's direct report, who's earlier on in their career, who's more comfortable with the risk and is more likely to be the champion; that's just the stuff you're not going to get without having an internal champion who can give you the lay of the land.

Sam Capra (26:27): You can't be more accurate on that, Joshua, if you tried. And on top of all that, you're not going to get the organization’s political landscape from a navigator, like who likes who, who's always going to go against another person? You've got to be able to jockey those ebbs and flows, that, to be quite candid, you can't control, but you've got to know how to navigate them. Without an internal stakeholder, a champion, you'll never make that leap within the account. You may, but it may just take you forever in a day to get there. And by that time, you're probably not having a job because you've missed your quarter this past year. So, it's a challenge for any sales rep.

Joshua Feinberg (27:07): Or they've moved on.

Sam Capra (27:08): Or they’ve moved on. Yeah, exactly. That's another great point. As soon as you start building traction, they move on to another company. You're like, "Great. Now, I got to start from scratch again."

Joshua Feinberg (27:17): And maybe you have an internal champion in their new job, and maybe it closes fast, and the other one doesn't, but yeah.

Sam Capra (27:23): Right. In retail, it probably happens a lot. It's pretty prominent, where people go from one retailer to the next. And that's a good thing. But I've had it where someone knows a naysayer in one of my deals, and they went to an account that I actually was making great progress in. And then they came in, and they're like, "No, we've had Converse." Just those things you can't account for. You try to. I'm a big believer when I'm talking to my sales reps, where I'm doing a deep dive on an opportunity. I always ask myself, "What am I not thinking of? What could come up in the 11th hour that we're not prepared for or can derail this deal?" And sometimes, thinking of it pessimistically allows you not to be blinded by the optimism of a big commission check or the big ARR deal that you're chasing. But to really be pragmatic and say, "Man, I've never actually talked to Josh, and he's three people above my contact. I think he's essential to the deal, and I've not been able to pin down 30 minutes. So, behind closed doors, I have no idea what Josh is saying about flexEngage." And that is a big red flag because he, with the stroke of the pen, can say, "No, we're not doing it. I'm putting that budget somewhere else." And your champion’s going to come to you and say, "Hey, I can't do anything." Those are things you've got to be real in addressing when you're talking about your opportunities.

Biggest Mistakes in B2B Sales

Joshua Feinberg (28:49): Yeah, that makes a lot of sense. With that in mind, what do you see as the biggest mistake that you see people making in B2B sales? Is it blowing through the need to validate the other levels and other stakeholders? Is that thinking too optimistically, too much happy ears?

Sam Capra (29:05): I think you hit the nail on the head. It's the optimistic. Because the optimistic, it lulls you into thinking, I can skip, right? So, I'm optimistic. "Josh is my guy. He loves me. He loves what we're doing. He loves everything. I don't need to talk to Sam, Henry, Jessica, and Tabitha. He's going to push it through." And you get lulled into, "Hey, I don't need to get more stakeholders involved. I don't need to confirm the budget. I don't need to do the steps that you know in the back of your head as the salesperson that are going to come up in the 11th hour, and you're going to be caught behind the eight ball." But you get lulled into that because you're overly optimistic. And that is a big challenge. That's a big challenge for me, is really trying to play both sides of that and saying, "Hey, do I have blinders on here? What am I not seeing? Why is this not moving?" And that's a challenge. And I always try to get an outside perspective. "Hey, here's the status of this. Here's what I've done. Here's where I'm at. Here's what the next step should be. What am I missing?" And just hearing feedback. And sometimes, to be honest with you, I like to hear feedback, maybe not even from another salesperson, just from someone else, a layman, maybe within our organization. “Well, have you thought of that?” And sometimes, those types of things jumpstart different ideas. So, to your point, I think optimism is the biggest challenge mistake; over-optimism, I should say, is the biggest fundamental mistake from a B2B standpoint.

Joshua Feinberg (30:39): To what extent do you see systems, processes, CRM, and deal stages helping to prevent some of that? Or is it a matter of, do you know enough about what the steps should be to get it into a methodology that can be followed or tracked like that?

Sam Capra (30:58): Yeah, I think they're all good. I think you have to have a process, right? That's the only way you can replicate anything. The only way you can scale is to have a replicable process. So, I think a process is fundamental. I think the technology to help you manage it and drive efficiency and effectiveness is fantastic. But from a tech stack standpoint, it's only as good as what you put into it. And it's not going to take the human element and, “Have you done your due diligence to move that deal forward?” So, from a technology standpoint and a process standpoint, it's only as good as the human that's driving it. If you're not following the process, you're skipping steps because you're overly optimistic, or, "Hey, I just can't get to the decision-makers, so I'm going to set up shop here, or I'm just going to be stagnant here." It just comes down to the individual and how they manage deals. I talked about it a little bit earlier. I think right outside optimism, I’ve got to be honest with you, is deal management. That is not a core function of a lot of salespeople, selling ultra-complex deals where you have 8, 9, 10, 15 people that have to put their stamp on it at the minimum, but eight, nine of them have to work with you alongside you every step of the way. And they’ve got to give you buy-in at every step. That's a lot because you're managing availability. You're managing their schedule. You're managing what they like, what they don't like, and sometimes they contradict one another. And what they like is what the other person doesn't like. Those nuances that's what makes it a challenge from that standpoint.

The Future of B2B Sales Success

Joshua Feinberg (32:37): Coming down the home stretch and looking at the big picture, what do you see going on right now that's going to fundamentally change what it means to be successful in B2B sales? What do you think we're going to look back on now, 18, 24 months out, 24 months ahead of where we are right now, and see that, "Oh, yeah, that was just a major inflection point."

Sam Capra (32:59): Yeah. I think it dovetails into the technology piece. I think we went through this way where these cool technologies--we use Outreach over here. There's SalesLoft, and there’s HubSpot. There's a lot of these automation tools that put it into a sequence and a cadence and all that fun stuff, which is fantastic from an efficiency standpoint. But if it's not managed the correct way, it becomes very vanilla, very saturated, because everyone's sending out the same message. And it gets harder and harder to separate yourself from the noise. I was talking to someone the other day, and they were saying, "On average, a decision-maker at any potential retail or organization is getting 60/70 sales-related emails a day." They're getting on average 20 phone calls, pre-COVID. But maybe now on a cellphone, we don't know. There's so much noise. I think what you're going to look back on in three, four, or five years, the differentiator between the great salespeople versus the mediocre is how they separate from that noise. What do they do differently? How do they continue to personalize, how do they understand the buying behavior? And what I mean by that, I'll give you a real example. Someone, after I put that poll up, I don't hide my profile. It's visible to anyone. I must’ve got 30 different requests. "Hey, can we meet? Can we meet? Can we meet?" There's only one person that said, "Hey, I saw your poll, and I understand that there's a challenge that we're facing: ‘Hey, should we reach out on a cellphone?’ So, I want to be respectful before I reach out. Is it okay to call you on your cellphone? And here's what I'm doing in the space.” If they tried to connect the dots between something I posted to make it more personable versus just batching and blasting and sending something out. And I think that's always been kryptonite for sales. It's a challenge to do personalization at scale. And you know this from a marketing standpoint; it’s such a challenge. And I think it's really impacting sales. Let's go back to our original conversation. You don't need 2000 accounts because you can't personalize at that level. You need to get down to 50. And within those 50, find your top three or four personas that you can reach out to, and then systematically approach those in a very personalized manner. Scour their LinkedIn. What is the company talking about in their activity? Are they active on LinkedIn? Are they involved in any charitable organizations? Are you reading that they're big avid golfers? They like cigars. They're big whiskey drinkers—all that stuff, which on its own may not mean a lot. But when you start to connect those dots, you can start to separate yourself from the pack. And I think that is what we're going to look back on, and we're going to say, "How did you get those deals?" And you're going to find that, "Hey, this is how I got it. And this is the level I took to get those opportunities on the docket."

Joshua Feinberg (36:01): So, the reality is just as important for the company as the employer to build the brand; the sales professional intensely needs a brand to be able to differentiate, which argues for like putting deep roots down in a particular vertical to the business.

Sam Capra (36:18): Without a doubt. I think it's our job as salespeople. It's not all on the company to do employer branding, and employee, all that stuff. I think you've got to develop your own personal brand. I'm always shocked when I go to a salesperson's LinkedIn page. And obviously, their profile picture, it's missing. It's just like, "Come on, man." And then, there's no activity. I don't even care if you're re-sharing someone else's articles on the RSS feed. At least do that. That's at least something. But to not take that and leverage that from a thought leadership standpoint, you're only doing yourself a disservice and then trying to reiterate to get better and get more of a thought leadership role. Doing podcasts like you and I are doing. I reached out to you, Josh. "Hey, looking for guests?" And that's how this came about. There's no harm in reaching out. And that's what we do on a day-to-day basis in sales. We're constantly reaching out. Reach out to build your own personal brand, do a podcast. Those things are fantastic.

Joshua Feinberg (37:20): Always looked at as well if you're prospecting someone and they have a very weak or almost nonexistent LinkedIn presence, and you're selling technology, they’re probably not going to be your digital transformation champion. Along the same lines, if you have to twist their arm to get them to turn the webcam on Zoom, it's the same thing. So, it's interesting. It's on both sides. It's not just on the prospect side. It's on the sales professional side. I can't imagine a scenario where someone in B2B sales, especially mid-market or enterprise, survives the next five or ten years if they're allergic to being on webcam and being in videos and don't have basic competency with LinkedIn.

Sam Capra (37:59): Yeah. I think you're right. I think it is an indicator. Is this going to be my champion? Is this the one that's going to push this innovative technology to the organization? Probably not. But to your point, yeah. I think back to my dad and my mom and their challenge of adopting technology. And that’s always been top of mind for me as I've gotten older. I'm no spring chicken. But I've always tried to stay as much ahead of the curve as I could. There's a Beta List and Product Hunt, seeing what's the next thing out there, so I can at least be aware of it. So, if it impacts me in any way, I at least have a knowledge of it that I can start adapting. And I think far too many people just say, "Hey, this is what I've always known. And I'm not going to adopt Zoom. I'm going to go face-to-face." If that's what you lived by, you died on the vine when COVID hit because there's no face-to-face in that environment. So, you're right. You probably are phasing your way out of the job.

Joshua Feinberg (39:04): Or if the unit economics simply don't support--I've had those conversations with startup CEOs many, many times over the years. And early on, they'll spend a couple of $1,000 to visit a client for a $199 sale, but after a while, that either has to go totally low touch or even 10x that, it's not going to be face-to-face. It's got to be inside.

Sam Capra (39:24): Well, I think that's a good study or good exercise for people, even including myself, to do an assessment of the closed deals over the past four years and see how many of those deals where face-to-face was involved versus Zoom or a video or only web share. And to see how much it impacted the deal from a sales cycle standpoint and actually getting it over the goal line. I think you're right. I think you're going to find out, especially post-COVID, that face-to-face is not as important as it used to be. I think there's a lot of value in meeting someone face-to-face and shaking their hand. Don't get me wrong. There's an intrinsic value there. But I don't think it's mission-critical. I don't think it's a deal-breaker if you can't do that. And five years ago, six years ago, 10, somewhere that neck of the woods, man, a deal just couldn't get done on an enterprise-level without meeting someone face-to-face.

Joshua Feinberg (40:25): I think a lot of what's changed in the last 12 or 18 months was the bar just went up. If before the bar was a $10,000 deal, for example, maybe it's a $50,000 or, even in some cases, $100,000 deal, that can get done without flying a whole team off to a client. So, it sounds like it'll still be there to a certain degree, but the methods--and a lot of it too depends on the digital assets that are deployed on the website and the whole structure of the deal and being able to start small and phase in the commitment and everything. But, Sam, this has been super helpful. I appreciate you taking the time to join me on the podcast today. If someone wants to learn more about what you're up to or connect with you, you're active on LinkedIn, right? Is that the best place for someone to reach you or?

Sam Capra (41:06): Yeah. By all means, if you want to connect with me, I'm on LinkedIn. I'm one of those open connectors. I love to connect on LinkedIn. I'm happy to help in any way I possibly can. As you mentioned earlier, we will be launching a podcast here in the next couple of months. We got all of our interviews and content very similar to what we're doing here lined up. So, you'll be able to find more about that on my LinkedIn profile. And then, obviously, heading up the sales team at flexEngage here in beautiful Orlando, Florida, if we can be a resource in any way. By all means, I'm happy to have all those conversations via LinkedIn.

Joshua Feinberg (41:41): That's just

Sam Capra (41:41): Yep,

Joshua Feinberg (41:46): Awesome. Thanks so much. I've been speaking with Sam Capra, who's the VP of sales from flexEngage. Sam, thanks for all your help and sharing so generously today. Really appreciate it. Stay safe, and I look forward to being able to see you face-to-face again.

Sam Capra (42:01): Definitely, thanks again, Josh. Have a fantastic night.

Joshua Feinberg (42:04): You too.

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