How to Determine if you are Hiring the Right Type of Sales Leader

[0:00] If I left the interview with any kind of part of me feeling unsure, I just thought, gosh, if they can't sell themselves, which is the product they know best, why am I so confident that they can sell my product? Welcome to the Full Funnel Freedom podcast. If you are listening to this, you are likely leading a team responsible for generating revenue. Purpose of Full Funnel Freedom is to support people like yourself and keep your.

[0:32] Music. Welcome to the Full Funnel of Freedom podcast. I'm your host, Hamish Knox. Today, I am delighted to have Karen Gordon as my guest today. Karen is a go-to-market leader who has spent her career building and scaling early and growth stage startups. Most recently, she was the executive vice president and a founding team member at GoodShuffle Pro, a SaaS platform for event companies where she built the company from zero dollars to over five million in annual recurring revenue which led them to their series a funding in january 2024 she is currently working as a consultant and advisor to businesses looking to scale growth that could be found at innofig.com karen welcome to full funnel freedom thank you so much for having me hamish how's it going, It's going pretty well, thanks. I really loved our connection.

[0:32] Funnels consistently, reliably full.

[1:25] Previous guest, Will, connected us, and I really enjoyed our first conversation. I'm delighted that we could get together today and share some of your wonderful ideas and insights with our audience. Before we get there, though, tell us your story. I've given the audience the 30,000-foot view. Tell us about where you started and how you got to where you are today. today? Sure. Well, I, like most people, did not graduate with a sales degree, but found myself in sales right after school.

[1:54] And I, you know, so I've been a revenue generator my whole career, but I left that role. I think at the time I would have told you that I was never going to work in sales again and never going to work in tech again. Turns out both of those were very wrong. But then pretty soon after early in my career, I had the awesome opportunity of being part of a team that really launched and scaled a whole business. It was sort of a business within a business at LivingSocial. And I very quickly got bit by the startup bug and just loved the opportunity to see very high impact work with really smart people. And then continue chasing that and have worked at across several different industries as a revenue leader, scaling across more marketing and sales heavy jobs, as well as working as a kind of GM position and director of product. And then, yeah, the last seven and a half years, I spent growing a SaaS platform, Goodshuffle Pro, and I'm really proud of the team I built there. And now kind of entering a new chapter as I'm consulting and advising for several different different companies, getting to really see, again, opening my eyes back up to multiple industries after having worked in one for almost a decade.

[3:12] Wow, what a cool journey you've been on. And I look forward to unpacking that a little bit more. Specifically, something that you had shared with me in our previous conversation is about the different flavors, for lack of a better term, of sales leaders, of revenue leaders that you can experience in startups. And on one end, you have someone with zero who, you know, kind of got dropped into the role. And then you have the other extreme of someone who's very experienced, but the experience can come in, in different ways. So for the audience, what, what does that look like from your experience of the different styles of sales leaders that you get into a startup? Yeah. So I think there's a few different things to think about when you want some sales leadership in your company. There's one, which is making sure you really know the type of sale you need, Right. There's this there's all different styles and methodologies for sales. And it's really important that people understand that that's going to vary depending on if you're B2B, B2C, if you're selling to SMB or enterprise, that not all sales are created equal. And then I think that also a lot of times folks sort of shortcut and assume it depends on the stage that you're in. And I think that's largely true. I definitely think there's a difference between, you know, a zero to 10 leader and a 10 to 20 and whatnot. not.

[4:24] But I think more important is to think about the why with that, because sometimes it's not as simple as where you are. Meaning, do you know for sure that you have your unique value proposition nailed down? Do you have your buyer personas nailed down?

[4:39] Do you need someone to come in and be wonderful at just managing and growing the sales team? Do you need somebody who's going to to be able to create the sales emails? Do you need someone who's going to, who's worked with marketing and has that sort of full customer journey map in their head? You know, there's just all these different things that a sales leader doesn't necessarily always do. And again, oftentimes it is closely related to how early of a stage, because early stage you're expected to do more. But also sometimes later on, you've pivoted a few times, you may have a certain amount of revenue coming in, but if you're not confident that you have your messaging clear, you're not confident that your pricing strategy is correct, then you wanna make sure that you're considering that in your sales leader, because you may have sales leadership who's coming and is used to taking a baton and just running with it, but if you're not sure if it's the right one, you might want to evaluate that first. That's fair, because ultimately, what I've experienced with founders, especially very technical founders, is they just hope sales happens, and the first person who comes in who goes, I can sell stuff and I can scale a team. They're like, awesome, go do that. And usually that doesn't work out very well.

[5:55] Occasionally, blind squirrel finds a nut, but often that doesn't work out. So from your experience, because you literally were a starting day zero founder for the last seven and a half years as you've shared with us.

[6:08] What sort of experience did you bring to that founding team that was beneficial to go from zero dollars to five million ARR and now set up for success to scale past your time with the company? Yeah, I mean, it worked out very well for some technical co-founders that I started with because I had worn these different hats. So I had not only been a sales leader, I had also worked very much, you know, very closely with marketing. I had worked on marketing initiatives and built them myself. I had worked as basically a GM of a product, doing everything, you know, owning the whole P&L. So I'd really worn all of these hats on the business side and was able to really carry all of the business teams and be all of the business teams and then slowly build out each of them beneath me. And that's, you know, to find that kind of level of a Swiss Army knife is different than what you're normally looking for in a sales leader.

[7:09] But I've seen it, you know, even now as I'm working with different companies, some of them feel like they're, to your point, really just ready to say, OK, just have someone run and sell. And if you don't know what that means, you need to make sure that you're asking questions about what are you saying and why are you saying it? How are you getting that traction and why are you going that route? Out? Why are you using that channel? Is it because that's just what they've done in the past that they are better at in person sales versus virtual, for example? Or is it because they're better at call scripts than email? Or is it because they deeply understand your actual audience and your product and can give you a really valid reason? I mean, I always think of like Simon Sinek's book, Start With Why, like what is your why? And a company should, of course, ask themselves that, but you should be also asking sales leaders that. Can they tell you why a specific method or a specific, pitch is really going to be what does it. I love that you shared that because I was, as you were sharing, my thought was, okay, so for these technical founders who, are not necessarily people-oriented, right? They're wonderful human beings. They're just not, they want to work on the product. Great.

[8:25] How do they identify like red flags, yellow flags in someone who is positioning

[8:31] themselves to be this wonderful sales leader? So you just gave us one about the why. From your experience, what are two or three other red flags and maybe some yellow flags that a founder would want to look out for when they are bringing on a sales leader candidate to scale their business? Well, first of all, I do feel like I have to make the plug that I happen to work with two technical co-founders who are very people-oriented, so they don't necessarily fit the normal mode. I want to make sure I give them proper, proper shout outs and accolades. Yes, absolutely. I mean, even if you are extremely people oriented, it's always the hardest to hire outside of your expertise for sure. And I think that salespeople, it can be tricky because if they're at all decent at sales, they already have a leg up on selling you. Right. Um, but that is actually one of the simple things that, uh, well, as I listening to or reading recently where it was is just so simply put, but I had been laughing because I had been interviewing someone right before I listened to something where they very simply said, if you're not sold, and that was something I kind of came back to oftentimes when I was hiring, you know, senior leaders or even frontline salespeople is if I left the interview with any kind of part of me feeling unsure.

[9:47] I just thought, gosh, if they can't sell themselves, which is the product they know best, Why am I so confident that they can sell my product?

[9:58] The other thing is, are they selling you your product? The number of times that I have had people come in, again, for senior leadership positions and incorrectly explain, our product.

[10:12] You're not doing the research that is needed that you should be doing before each sale anyway. So it sounds like very simple advice, but you would be shocked how often people forget to stop with those basics. Can they sell themselves? Can they sell your product? That's step one and step two. And then from there, I would really not be shy to ask specifics and tactics. You know, as sales leaders, we're taught to speak about our impact. So it's very, you know, natural for me to go in and say, I took this company from this to this. I did this and this and this. I did this with this impact. Ask people, how? How did you do that? And you'll start hearing, well, our team did that. What did you do? What did you specifically do? And how did you come up with that? And if they say, well, I am constantly reading things and I read something Or I have a big network and one of my founder friends gave me this idea. Like, that's the type of person you want to hire because they are curious. They are constantly learning. They will check their ideas. They will, you know, they're growing. If somebody just, yeah, they may have some cool resume bullet point. But if it's because someone else on their team was smart and they kind of rode that way, that's a problem, right? So I think it's that final, it's making sure they can sell themselves the product and then making sure they can explain how and why. Brilliant. It kind of reminds me the first bit about like it's either hell yeah or no.

[11:42] And if you're not feeling, that's what I was hearing from you is, if you're not saying hell yeah, this is the right sales leader candidate, move on. And then the other part of it is that how, and I know I've coached plenty of founders where they bring in a sales leader who had great success at giant company, et cetera, et cetera, and then you found out it was because they had a team. And as soon as they get in the startup environment, all of a sudden everything falls apart because they're used to having three assistants do everything for them, and they don't even know how to log into the CRM, much less enter anything that is going to be worth something. So listeners, go back and rewind, listen to what Karen said about hiring a sales leader several times over because it was absolutely brilliant.

[12:27] So thank you for that, Karen. The next thing I'm curious about is your experience as a founder and as a sales leader from day zero. Because I'm in Calgary and we have this giant rodeo every year called the Stampede. I'm going to use a rodeo reference. How do you ride that buck and bronco? because day zero is it's not like everybody's going thank god you showed up here's my money.

[12:51] Tell us about that experience. That does take a lot of grit. If you've ever read the book Grit by Angela Duck, that's another book I'll plug. I love that book. I think that that is, it's tough. It's tough to be, especially when you don't have a name to back yourself up. And I think that comes back to, I think people throw around the word strategy a lot these days. But to me, the strategy is kind of connected to that why component. own it. So for example, I was just working with a client of mine, who they've gotten a lot of early traction from doing events. And they talked about how their audience really likes that personal connection from events and how they're going to keep growing with events. And I said to them, you know, I think that is really working for you now. And it's possible that that will always be part of the fabric of your marketing and your growth strategy. But I would encourage you to recognize why that makes sense now and why that might not make sense in a bit, right? That that's not necessarily the most scalable thing. But events and in person connection is a wonderful opportunity. When you are new, nobody knows your name, because you have to build trust somehow. And what I said to them was, look, I have faith that you are on your way to building a level of brand trust, where you may not always need to do the laborious events that you're doing currently.

[14:20] So I think, you know, strategy, meaning thinking about that why, thinking about what makes sense now. Another thing I say a lot is the hardest part is you have to both be thinking about what makes sense now and what makes sense long term. And people tend to over index to one or the other. So for example, they get really caught in the weeds of now. So like that client I just mentioned, maybe just thinking it's always going to be about this one, you know, traction avenue.

[14:51] Or they get really, really, really obsessed with what scales, and they're not willing to do something that doesn't. And in the beginning, you have to do things like.

[15:02] Call your clients and personally chat with them as if you just, you know, aren't running late to your fifth appointment for the day. And so it's, it's knowing what makes sense for now and then building the tracks for what makes sense for the actual long-term and the actual scaling model. I'm a hundred percent aligned with you on that. And then I also know from experience that we just get stuck, right? We just got, we got stuff to do. How do you actually make time to do the execution now? And then the thinking about the future and, and starting to put those building blocks in place? Because theoretically, all of our listeners are nodding right now. And in practice, they're like, that sounds great. I've got, I got stuff on my calendar.

[15:48] So how do you coach your clients to actually make the time to do both? So they're not over-indexed. It's radical prioritization. And I think that one of the best ways to do that is to ask yourself difficult questions such as, what are the things I like to do the most? And am I over indexing on those? What are the things I hate to do the most? And am I under indexing on those? Because when we ask what's the most important, everything's important. And of course, there's other ways for you to sit and look at what's important. I like questions like, what is the one thing that I could do that would have the impact for the rest of the week or beyond?

[16:30] What is the one thing I could not do that wouldn't impact even the rest of my week? Things like that can help with the level of importance but I often find that where we get stuck is being humans it's quite the curse and asking things like what am I getting a little too married to because I just like it or because I feel like I get it I'm the best at it and particularly small business owners you know they will admit that yeah like they probably got into their business because they're really great at certain things and the things that they don't love, they're kicking the can down the road and then they have to stop and say, are any of those really important? And oftentimes they'll know, but once you shed the light on why they're not doing it, then they can be more honest as to whether or not it needs to get done. Yeah, it's a.

[17:22] It makes me think of like for, again, from my own experience as a business owner, and I'm sure you have similar experience as a founder is until you, while you're in it, you don't recognize you're in it. And sometimes you need that third party to be like, Hey, emperor, you have no clothes. Like just, so just FYI, like, I know you think you look awesome and maybe not so much. So how can we trap ourselves almost? Cause we are human, unfortunately, and fortunately, into actually answering those tough questions. Because I can ask that, what do I not like to do all day long? Or what do I like to do? And I'm going to give myself answers that make me feel good. And then I'm just going to keep going down the same path. How do we make sure that we pull our head up so we don't get stuck on that same path forever? I mean, like the cheeky answer would be hire a consultant or advisor to help you. Outside of that, though, I mean, listening to podcasts would be my second cheeky answer.

[18:18] And reading books and things, right? You know, if you're in your own head, you're going to have your own bias. And you may know best. And I think a lot of people get into business for themselves because they know best. But of course, it's like anything else if you have, whether it is an outside person, or even just an outside source. I mean, like I said, with something else, I was I was listening to something and it was like a duh moment. Oh, with hiring that like, I kind of knew that in my gut, but hearing someone else say, can they sell you on themselves? Why are you considering them for a sales job? It was something I was naturally doing, but hearing the words somewhere else, whether that's again, podcast, audio book, whatever, sits differently, right? Oftentimes the things we're learning in life, in a class, in anything, it's not that it's such brand new information, but it is someone taking a bunch of information that lives somewhere in your atmosphere and synthesizing it and putting it in front of you, which is what we humans need, right? Totally. Totally. I've had a couple of clients, usually very experienced individuals. And we'd be talking about, I can't remember what it was in both cases. And they're like, man, I do this stuff naturally. And I'm like, awesome.

[19:34] I'd rather you did it intentionally. Because then you actually mean to do it as opposed to it's in your comfort zone. Or you're like, oh, I need to move to pull myself out of a tailspin or whatever it might be. So having that third party and yes, listeners, Karen and I have self-interest. We would like you to hire us, right? That's fair. Like, let's just call it what it is. And you You don't necessarily need to do that. You have podcasts. You have audio books like Karen is referencing right now, right? But also, I would highly recommend you chat with Karen because she's awesome. So, Karen. I do think, yeah, it's just about getting outside of yourself. However you want to do that and whatever fits in your budget as well. But I do think that most people who are doing things naturally, like you said, that is where I most often see people plateauing. That they are doing fine. They are growing their business, but it is not with the margins that they want. They're not hitting any sort of big, that big hockey stick that you want. And then they go, well, do I need to just hire a sales leader? Which, depending on the business, may be what you need. You definitely need to make sure you understand, to your point about intention, what it is you're doing well and what it is you're not doing well. Otherwise, it's throwing spaghetti at a wall. Amen. Amen. Yeah. Let's make this success by design instead of by default. I'm completely aligned with you on that.

[20:51] Now, Karen, the DMV, people have opinions and thoughts about what the DMV looks like. I mean, I do. Like, you know, it's government defense. And, you know, if you're into music at all, it's Fugazi. But there's lots of misconceptions about the DMV. And I learned a lot from you when we first connected

[21:07] about, like, all the tech talents specifically. So would you share with our listeners, like, some of the common misconceptions about the DMV and what it actually looks like to do business, and especially in the tech startup world there? Yeah, well, first of all, in case people don't know, DMV, not just the place you wait for the driver's license, which is Department of Motor Vehicles. We're talking about D.C., Maryland, and Virginia, the metropolitan Washington, D.C. area. Second of all, I feel like Dave Grohl, Foo Fighters, is a little bit more known from the northern Virginia part. Okay, fair.

[21:41] But yeah, definitely there's a misconception that it is all government. One of my favorite stories to tell is in the early days of Good Shuffle Pro, I was sending out marketing emails just kind of blindly to event companies. And somebody wrote back and said, your software looks amazing, but I would never purchase from anything made in DC. And we had this little stamp on the bottom of our emails that said, proudly made in Washington DC. We find a lot of the startup people in the area are really proud trying to make sure that people know that this scene exists. But this person, I guess, just really thought that there was some sort of pull that anything out of DC had a political leaning of some sort. And I wrote back just personally and said, talk about things that don't scale. I just wrote back and said, you know, happy if you're if you're if you're not interested in our software, but just want to clear something up. We have no political affiliation whatsoever. We are a software company designed for businesses exactly like yours, we'd love to talk to you sometime. So it is sort of, bonkers to me how many people just really don't understand that there's a city here and then the surrounding area.

[22:53] There's, you know, parts of Reston, Virginia, where AOL was founded. There's an area where Amazon just set up a new headquarters in kind of Crystal City, Arlington area.

[23:04] So people don't always realize it, but there's a ton of tech talent here.

[23:10] And I think all of that's changing, of course, too, because everything is so remote friendly now. So I don't know how many people then are leaving the area. But I think just as much you can bring people in because they maybe they follow a significant other who has the government job. And then they just happen to be in the area. So there's a lot of really good resources here. And I think we're still coming back from that post COVID phase when it comes to networking. But I'm I'm starting to see that when I've gone to events recently of you've got a whole new wave of talent in here because there's tons of universities in this area. Yes. Yeah, very true. And I go to the Baltimore area specifically, but I've been down to Washington and parts of Northern Virginia. Absolutely beautiful area. area, lots of amazing businesses that like, you know, AOL, which for some of our listeners might just be a funny thing to reference and they don't know it was an actual company that was, you know, dominated the tech scene for a while. So thank you for sharing that insight with us. I love to learn about those areas and also bust some myths, right? Because we all have these, I told you on our first call, I had this perception of what the DC, Maryland, Virginia area was like, and you're like, yeah, I can see that. And, and so thank you for sharing that with our audience today. day. Yeah, we're more than just a bunch of big white buildings.

[24:35] Love it. So Karen, I can certainly nerd out with you all day about startups and scale-ups and how do we make sure that we're getting the right sales leader on board. I have a few questions to wrap up for you today. The first one being, if you could go back and coach your younger self, go back as far as you like and say, hey, younger Karen, in the future, you'll have been a founder,

[24:55] you'll have scaled, you'll have all this amazing experience. You will also have a lot of scar tissue and a bunch of bumps and and bruises, what would you coach a younger Karen to say or do differently to get to the same place, but with a little less scar tissue, maybe some fewer bumps and bruises. So much, right? If we could go back, um, I think something that I did, I did do, but was accidentally to your point about intention, once I started doing it intentionally, it made a big impact was take the opportunities where you will learn the most, worry less about your title.

[25:27] Advocate for yourself on things like comp, but take the jobs, the opportunities where you're going to learn a lot, whether that is because you're going to be given more responsibility, you're going to work with awesome peers or mentors. tours.

[25:40] That has been, I mean, to your earlier question, too, about how to get a startup leader, because I had jobs that expected so much of me early in my career and did so much, I was able to come into positions and say, no, I've actually done all of that already. And that learning opportunity is really what propelled things forward. It wasn't about getting any specific title at a certain age or the things you think are important when you're young. Of course. Great answer. I've never heard that answer from a guest yet is about take the learning opportunities. And I appreciate how you said advocate for yourself and comp because sometimes we hear take the learning opportunities and translate into that into take less money. It's not necessarily true. True. Not necessarily true. And I mean, there's a difference between taking like a slight haircut of, oh, I could go be a cog in the machine over here at this big company and make crazy amounts and then get the golden handcuffs. Or I could take a little bit less over here and I think I'd learn a ton. And that's going to mean a lot more, especially in five years. I think that that doesn't mean that you should sit and make new money. Fair. Very fair. You've already shouted out a couple of books already.

[26:51] Grit being one of them, which I love. What else have you read, watched or listened to that you would encourage the sales leaders listening today to check out for their own personal professional development?

[27:02] Well, I am known as someone who actually someone just told me last week that they said, you have a book for everything. So I will try not to give a totally endless list, but I will rattle off a few just because I am a big nerd about reading and read lots of business books. But I will also try to avoid strictly sales books since I'm sure you get tons of really great suggestions there. One I wanted to mention when we talked about hiring is who the A player method, great book really helped revamp our hiring process. For leadership, I would say multipliers is one of my favorite leadership books. I mentioned start with why I'll read anything by Adam Grant or Brené Brown. Those are just great, you know, both personal and professional development.

[27:49] And then podcasts. I'm obsessed with Lenny's podcast for anyone one in the tech space. Very cool. Thank you for sharing those with us. Listeners, go check out all of those recommendations.

[27:59] Last question I have for you, Karen, you've given us great ideas and insight already today. What do you have as a final bit of wisdom, a closing thought, or something to plug? Floor is yours. People can reach out to me on LinkedIn. They can find my website, which I know you're going to drop in as well. But yeah, I think just people, I've been very much on the path of telling people to really find what lights them up and find what challenges them and excites them. And that kind of comes back to the learning opportunity. And that's really what's been most rewarding for me in my career is I'm really big on.

[28:36] Impact, really enjoy finding opportunities where I can very quickly have an impact and And encourage folks to figure out what it is that they're going for. And again, not focus on what the title is or the company name or if it's recognizable to just say, like, what is it that gets you excited on a day to day and find that opportunity? Amazing. Karen, thank you so much for spending time with us today on the Full Funnel Freedom podcast. I'm excited to continue connecting with you online and offline as well. That's great. Thank you. Thanks for listening to today's episode of the Full Funnel Freedom podcast. You can continue to support us by leaving us a review and a rating, sharing this episode with a couple of sales leaders in your network who you care about. I'd love to connect with you. I'm easy to find Hamish Knox on LinkedIn. Also, if you'd like a free 15 minute call with me, go to www.hamish.sandler.com forward slash how to Sandler. Until we connect on the next episode, go create full funnel freedom.

[29:42] Music.