Dakota McKenzie how are you doing my friend?
Doing great. How are you?
Very good. Very good. I was excited about this one for numerous reasons, but certainly know that your knowledge capital on some of these matters is well, deep and very insightful. So I’m looking forward to getting into it with the mate. Kind of to kick off.
Do you want to just give a brief overview of how you got to where you are today?
Yeah. So I’ve been doing kind of the enterprise software thing for a little over a decade, working for a bunch of different companies, early stage. So started my career at Demandware, eventually got acquired by Salesforce many years later after they went public. Worked at Yesware early stage.
Went to a lot of amazing technical companies like Sumo Logic, Databricks, and Segment. All that experience allowed me to go work at Unusual Ventures, which is kind of how I got into all this fun stuff. And so at Unusual Ventures, a big thing for us was, you know, being in the seat with founders and
taking technical companies or technical founders from zero to one, being an idea and getting to a few design partners to getting to their first couple million dollars in revenue. Participating in everything from building things from the ground up to hiring the reps, managing the reps, participating in board meetings and kind of scaling the go to market efforts so they could round out a leadership team, brought a bunch of different teams to a million in revenue there.
Loved it so much that I decided to go do this on my own. It’s been a little over a year and we’ve worked with a lot of amazing companies. So it’s been a lot of fun. Good.
Sort of in that vein, what advice do you have for founders looking to transition from founder led to making their first sales hire?
Yeah, I think the thing that we really try to focus on and why I think we’ve been so successful, my partner Trey and I, over the last year doing this together is, first thing is to be obsessed over your business. And most advisors and sales consultants will have a hard and fast rule or a playbook of like, you got to be at a million in revenue, or you got to find a repeatable process,
you have to know your ICP. Like you have to know your company and your problems first. I think the consistent challenge that we usually see is, the question you should ask yourself as a founder is, is it bandwidth or is it need? So if you have a bandwidth problem and you haven’t figured out how you sell, it doesn’t matter if you bring an account executive, they’re probably gonna be a failure even if they’re amazing at selling. Because they don’t know the problem in the market and you don’t yet either and it’s your idea in your company, right?
And so the other thing is like on the need side, if you’ve proven that you can close those deals consistently How do you figure out the type of hire and who do you need? Right. And what are you planning for? Is it scale? Is it to get to your first 500 K in revenue, your first million? I think the big mistake that people try to figure out on the hiring type or make the mistake on the hiring type is actually like hiring the capital E enterprise rep, because everyone thinks that they’re ready to go do the big deals.
And I have no problem with that. I love lots of enterprise sellers who sell million dollar deals, multimillion dollar deals, but that profile type is when the company is ready to bring that person in. Usually you don’t need that type of seller at the beginning. So I think the big things that we try to figure out when we partner with founders is what do you need now?
What are you planning for in the next six months? And especially as your product matures and develops and people like know what your product does, who do you actually need in the seat for that? So maybe a little bit of a long winded answer to your question, but I think it’s like a really important set of things to kind of vet out before you go on, you know, the endeavor of hiring a really expensive person that also requires commission payment and all that fun stuff.
Very good. Just on the way, I’m sure you’ve seen some pretty interesting surprises and within that, can you talk to maybe some of the hiring surprises, both good and possibly bad as well?
Yeah, I think on the good side, it’s like when sometimes you’re like, all right, this person’s pretty good. I think they can develop into the role.
And you’re like, okay I can actually coach them into success by giving them some stuff outside of maybe their skill set that they were hired for. And we’ve seen tons of success in that area. And I could, you know, name drop a few clients, of course. But really, really proud of some of the account executives that our clients have hired that have just like exceeded expectations.
And I think like the worst surprise, and I think you and I have probably experienced this in some way, shape or form is like when a rep who’s expected to kill it just to miss hire. And either we’re brought in to figure out like diagnose what’s going on or like, hey, you know, what do we actually need to hire for in the future?
And I think that’s a really tough surprise, whether it is like you’ve made that hire or you inherit someone like that, trying to figure out what to do in those scenarios. So it’s a really tough part of the job because it doesn’t mean that that person’s not successful. It’s just, are they a fit for this role in this company at this time?
And that’s a really tough thing to figure out most of the time.
What are you looking for when you’re sourcing top talent?
Yeah, I think the first thing, and this is like a, I think also said a lot more recently is do they know what great looks like? So what types of companies that they worked at, or do they have great mentors or whatever that looks like.
I think understanding what a great company and a great process is and they internalize it, that stays with them forever, especially if they’re a top performer. Another thing for our particular line of work is like stage fit. Have they done something at this stage? Have they started a company? Have they been a founding AE?
If they’ve joined at an earlier stage, they see what good skill looks like. That’s kind of like a really important thing. Unique or interesting backgrounds I think are kind of interesting or useful of like, do they have a different talent? There is actually, ironically, one of our clients, they’ve talked to several people that are cruise ship performers.
They just happen to like draw this type of talent. And those people are the top performers at those companies. And then I would say like best in class background, former Olympians, division one athletes, they’ve done something really exceptional. I think that’s like also- if they’ve done it in some previous capacity that they’ve dedicated their time and effort to, I’m pretty sure they can learn sales if they want to, right?
It’s just more of a professional choice. Another thing that’s kind of like an interesting angle that we try to look for is not everybody can pick the best company. Maybe they’ve had a good run at one company and they worked at a not as great one the second time around or whatever that path looks like, but they’ve sold a number two.
So selling a number two product that isn’t as good, and they know how to win deals. And you’re like okay, customer doesn’t really like our solution as much or maybe they do, but I’ve got to fight my way into like selling value on this deal. Knowing how to do that and being a top performer, those are usually the best salespeople you’ll ever hire.
They’re very hard to find because there’s a reason why, you know, sometimes the number two company has number two people, but occasionally you have that like diamond in the rough, amazing hire or candidate that has sold a number two and they’re top performer and they just need like a good shot at a great company.
So those are kind of the main things
that we typically look for. I love those. I’ve heard similar from some of the best out there as well. So I think it’s a great point. So let’s say we found our awesome
pipeline, what are we doing interview process wise? How are we constructing a successful process?
Yeah, I mean, I could go on for days and list out my entire process. But for brevity, I think the main thing that you always want to test for is how much they understand what they understand about sales. So bad interview is,
how did you perform in your last company? I did 250 percent of my number. Okay, great. Sounds like you’re a top performer. Right? Well, you actually want to say it’s like, cool. You did 250%. How did you do in comparison to your peers? Oh, well, I was number one. Well, what made you number one in comparison to these other people, right?
Or if you weren’t the best performer, tell me what could have made you better. Because they might actually have a good answer. If they’re blaming their territory, like they’re not going to be a great fit. If they’re like actually, you know, ” I’m under two of the best salespeople I’ve ever met and I consider them mentors and I want to be like them someday”
great. So figuring out like how much they actually are self aware and understand their process is really important. Another thing that we always do with our clients and, you know, I’ve done this my entire career is really digging into like the 30, 60, 90 process and like a scenario that shows sales acumen.
And it’s not, okay, well, I’m going to learn, and then I’m going to be a sponge. And then I’m going to learn. And then I’m going to like send emails. It’s like, I want to know your approach on like how you’re going to hold yourself accountable. How you do that today? What do best in class tools look like?
What do you need for me to be successful? And how do I make sure, or how do you make sure that you’re going to hit your number in the first quarter? And the better that you can explain that, even if it’s overaggressive and we can figure out the right way for you to be successful, that’s what I’m looking for.
How much do you actually understand in that process? That’s something that we really take seriously.
Do you have a secret or unconventional interview question tactic?
Yeah. There are certain parts in the process that we make intentionally vague. And what I want to know is like, are you confident in asking questions or clarifying questions?
And also like, how do you handle ambiguity? In an early stage role, not everything’s going to be played out. There is no playbook and you get weird requests. Some things are off. Like you kind of want to see how that person will react. The other thing is like, how do they collaborate with you?
If they’re going to be working with you as the founder, right, the founder is effectively the CEO, but also the sales manager. How does this person like work with you on day one? And how do they react to those things? However they handle this interview process is likely how they’re going to operate day to day. Right?
When you’re in an interview and you’re going through that process, you’re in a little bit of glow up mode, right? Like you’re dressing really well, you’re trying to impress the person. So that’s like your highest bar. So anything kind of below that, you’re like, nah, I got some questions. So that to us is like a really important thing that we focus on, which is like, how do you handle that ambiguity?
And what do you do to show like your sales acumen and your approach to handling that process?
Very good. What’s your wisdom that you wish you’d known on hiring earlier?
I think one thing that I try to take really seriously is usually when you have a top candidate, you’re usually selling them more than they’re selling themselves.
And so what you really have to do early on in the process and throughout the entire candidate experience, like understand what they value, show that you care, and show that you’re just as excited about them joining as, you know, you want them to be excited about the opportunity. But the best people, like they’re making a ton of money.
They have a great gig. Them taking a gamble on your company, like they have to know that this is awesome and a great experience when things are hard. I think that just is a common and normal thing to approach just as hiring salespeople. It’s especially important in early stage company because it’s a huge gamble.
These people are making half a million dollars plus, and then they have to like decide if they can go get a meaningful amount of commission and that their equity is going to be worth something in the future. And so I think going into selling mode is really important, but knowing why you’re going into selling mode for the right candidates, I think is important.
Good.
Some nuggets here, Dakota. Last just to finish up, are you accepting new clients at the moment?
Yes, always. So feel free to reach out to me over LinkedIn, go to McKenzie. You can look at more about us at dm.studio. Always working with a lot of amazing different technical founders and companies ranging from seed to series B and series C.
And so excited to hear from you.
Yeah, I’ve seen the impact of your work. Reach out to Dakota Dakota, thanks very much mate. Appreciate the nuggets. Thank you.
