The Trick to Hiring Top Sales Talent with Jessica Schultz

INTRODUCTION: Welcome to The Daily Bolster. Each day we welcome transformational executives to share their real world experiences and practical advice about scaling yourself, your team, and your business.

Matt Blumberg: Welcome to The Daily Bolster. I'm Matt Blumberg, the co- founder and CEO of Bolster, and I'm here today with Jessica Schultz. Jessica is the founder and CEO of Amplify Group, which is a strategic consulting firm that specializes in go- to- market strategy and execution, and rev ops for B2B startups. Jessica, welcome to The Daily Bolster.

Jessica Schultz: Thank you. Glad to be here.

Matt Blumberg: So you live in the world of helping B2B companies on go- to- market. One of the things we see at Bolster all the time is early and mid- stage companies coming to us looking for help with sales leadership, and I would say one of the things that we observe with that is sometimes what they actually need are some really good sellers as opposed to needing a Chief Revenue officer when they're a company. So my question for you today that I think will work really well for our audience is what are your top three tips for hiring top sales talent, not necessarily top sales leadership, but top sales talent?

Jessica Schultz: Yeah, and I love this topic. It's actually what you just said is the reason why I started the company, was because I kept observing startups getting this part wrong, especially at the seed and series A stage. So it's one I'm very passionate about, but the top things I would say, I have lots to say, but if I had to sum it down or sum it up into a few key points, number one, get really clear on the role that you actually need. So I think a lot of founders maybe aren't familiar with all the different types of sales roles. So if you don't know, reach out to me or talk to some folks or maybe your investors about the different types. But for example, there's a major difference between an SDR, so sales development rep and an account executive and a head of partnerships. There's all different types of sales roles. And so, first you want to get really clear on what you really need, AKA, do you need just top of funnel lead generation? And so then you're looking more for an SDR, and maybe you as the founder can handle closing the deal. And I usually say, if you're less than a million in revenue, you as the founder are the best person to close the deal, and you should be the one front and center. And so maybe you do just need some top of funnel acceleration, or are you really ready to hire someone that's going to be the quarterback of the deal from beginning to end, et cetera, et cetera. So there's a lot to just get clear on there.

Matt Blumberg: For sure. Yeah.

Jessica Schultz: And then the second thing I would recommend is build an ideal candidate profile. So this is akin to an ICP for sales, and-

Matt Blumberg: How is that different from the first tip?

Jessica Schultz: So first you just need to hire or first you need to figure out, " Do I need an SDR? Do I need an AE? Do I need a head of partnerships, et cetera." Then once you figure out, " Okay, I'm hiring an AE, I've decided that's what I need." Then you want to build an ideal candidate profile, which is much more specific. And I'll go into details, and this is different from the job description, although you need one of those too. An ideal candidate profile, just like you wouldn't put your ICP for whatever product or service you sell on your website, right? That's more like an internal document that you socialize with your team and you educate your team on this is who our best customer is. The same is true for, it's actually funny how much sales and recruiting to me are so much the same. So the same thing, you'd want your job description, which is your public facing artifact that you're using to attract candidates, but you also want to have an internal ideal candidate profile. And this is going to include things like, for example, I'm working with a client right now that sells professional services, and as I'm sure you know, selling services and selling software are wildly different sales.

Matt Blumberg: Very good. Yeah.

Jessica Schultz: So people are way less predictable than software, actually. And so it takes an entirely different approach to closing a services business sale, in addition to the fact that usually services are sold with an MSA and an SOW. And so there's like a heavier lift on drafting that SOW and all of the complexities that go into that, and understanding and scoping the work properly. So for example, with this one client I've been talking to, I'm like, " Look, we need to get super clear that our ideal candidate is someone who has sold professional services before." We don't even want to look at people that just have experience selling software, because it's just so, so different. So that's an example of a thing. Or another example is do we want someone that's sold to SMB or enterprise? Those are also drastically different things. Also, what was the prior ACV of the product or service they sold? Because again, someone that might be really comfortable selling a$ 50,000 product might not be the same person that's equipped to sell a$ 2 million product. So all those kinds of things are what you want to really flesh out internally. And Sorry, you were going to say something?

Matt Blumberg: No, no. I was just going to say, all right, so you know what role you're hiring for. Now you have the profile of what you're looking for, what's number three?

Jessica Schultz: Number three is pay attention to the questions they ask you. And I'm focusing on this because I-

Matt Blumberg: I like that. I like that.

Jessica Schultz: Because I hope everyone else already knows that you want to be thoughtful about the questions you're asking them and all that other stuff. So I thought, let me think about something that's maybe more unique. So I think pay attention to the questions they're asking you. For example, if they're an SDR or they're an entry- level salesperson, I'd go a little easy on them. They might not know what to ask yet, but if you're hiring an account executive or anyone that has, let's call it three or more years of sales experience, especially if you're hiring a revenue leader, they should be asking you about what your average deal size is? How long your deal cycle is? What are your average close ratios? How do you compare to your competitors? What are the major objections that you're facing? Who are your existing clients? How are you getting your existing clients? Is that coming from inbound leads, coming from outbound? If they're not asking you questions like that, to me, they are not the right person, because any really good sales rep is going to be asking you those questions to determine if they are going to be able to be successful in the role. And all really good salespeople are money motivated, and so they're trying to determine, can I have success with this product in this market, et cetera, et cetera, and am I actually going to be able to hit the OTE that they communicated to me? What's the reality of that outcome?

Matt Blumberg: Yeah. Well, and the thing I would build on with that last one before we wrap is most contemporary selling methodologies, whether you're training someone on spin selling, solution selling the challenger sale, are all about discovery, identification of needs, and the sales rep asking questions as opposed to just doing feature benefit.

Jessica Schultz: You got it.

Matt Blumberg: So you kind of want them to do that about themselves. They're selling themselves as the product, so it's almost a good audition as well.

Jessica Schultz: Totally.

Matt Blumberg: Yeah. Jessica Schultz from Amplify Group. Thank you so much for being here today. These are great, great tips.

Jessica Schultz: Yes. Thank you for having me.