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From IPOs to ICU: Why Maryana Kessel Is Building Different
What happens when the system breaks you and then you decide to fix it?
Maryana Kessel (Box, Flexport, Modern Health) joins Tom Wilkinson on Between Two Hires to unpack what scaling elite teams really takes and why her story led her to Latent.
Maryana shares:
This episode is packed with hard-won lessons, high standards, and high-stakes moments that every hiring leader should hear.
[00:00:09] Maryana Kessel, how are you? It’s good to see you. I’m doing so well. It’s so good to see you too. How are you, Tom? Long time no see I should say. I know. It’s been too long. Yeah, it has been. It has been. I’m doing good. Everything all right on your end? Life good? Yeah, everything’s going great. Yeah. Happy days.
[00:00:30] Happy days. So I want to start with just sort of the background, how you’ve got to where you have today. It seems like you’ve been quite good at picking winners along the way, so speaking to, to some of those journeys along the way would be useful and just want to kind of give any viewers, sort of the, the lowdown on what you’ve done and where you’re at today?
[00:00:56] Yeah. Well, I appreciate that. Yeah. I’ve been really [00:01:00] lucky. So, I grew up in the Bay Area. I got very fortunate that Box was my first job out of school. I started as an SDR. I actually had 13 interviews there. I just kept coming back and someone was like, you would be a good SDR. And so that’s how it all got started.
[00:01:16] Right. So I, yep. Did the SDR role went into the AE role. We went through the IPO, and then after that I joined Flexport as the sixth AE, employee 102. I was a mid-market AE enterprise, and then global key accounts, I became a manager and then a director. Had a sense as a head of sales at a data privacy company.
[00:01:38] Started a consulting company where we met and then I realized that, you know, healthcare is really the only thing that actually matters. So I joined Modern Health to lead their enterprise team. And I was there for three years prior to coming to Latent. Very cool. And shout out to the legend that is Ryan Bash for the- biggest shout out- for the [00:02:00] intro in the first place.
[00:02:00] Yes. And, just reaffirms my stance on great people knowing other great people. Yeah, I would walk through fire for Ryan. So yeah, I think a shout out to him. I think a lot people would say the same thing. Definitely. So then let’s talk about what you’re doing today. And we know each other not from what you’re doing today.
[00:02:20] We’ve known each other for a while now. Yeah. But we do know each other from what you’re doing today because we are partnered. Yes. Yeah. I think we’ve got some exciting news coming up soon, which we hopefully will be able to celebrate there, but yeah. Yes. Maybe just give us a, give us an overview of maybe why you joined what you sort of putting together and anything else you’d talk about with regards to Latent.
[00:02:43] Yeah, so while at Modern Health, I had my daughter and unfortunately during labor I broke my pelvis, which is pretty insane and very uncommon. But ultimately I was in a wheelchair and I had to have a procedure done and a [00:03:00] couple of medications given, and I was, I had a prior authorization delay and then denial.
[00:03:05] And so it was a really impactful time for me. It was actually, truly the lowest point of my life and this uncertainty if I would walk again and what that would be like. And so, you know, I had incredible insurance. I speak English fluently. I’m pretty dang determined. And so if I’m not able to break through the health system process, I felt like this is just an untenable situation.
[00:03:28] And so it sent me on this journey of what is a prior authorization and how is this all working or really not working? And ultimately I found Latent through an executive recruiter. And yeah, I spent two months really digging into the company, understanding exactly how the technology worked.
[00:03:45] And so what we do is we provide healthcare operations, focused in pharmacy. And we solve a number of use cases including prior authorizations.
[00:03:54] We’re very fortunate to work with incredible customers like Yale and Ochsner and Metro Health today, and growing [00:04:00] that very quickly. And so, you know, when I learned about Latent, and shout out to Brandon Herman for that. I was just, you know, the stars had really aligned. This is something that I really, really care about deeply. And you know, I don’t think that we should accept the way that workflows happen today that lead to these kinds of really challenging and very difficult situations for patients.
[00:04:21] So, yeah. I love what we do here and, very excited about our growth. So very close to the heart. Yes. Yes. And you are actively hiring, I know that because we’re actively working. Yes. What are you hiring for? Who are you looking to join this? Yeah, we are hiring across the board. So we are hiring for account executives, for SDRs.
[00:04:43] We are hiring for account managers, hiring for engineers, product folks, design, a recruiter, because we just need more help.
[00:04:50] So, yeah. Hiring across the board. Can’t recommend highly enough that anyone who’s good in my network, hopefully most people are good in my network, to [00:05:00] reach out to myself or yourself as soon as possible. Yes. Yes. What you’ve got going on. Well, speaking of hiring, I think that’s why we’re actually here.
[00:05:09] Yeah. And I know you know a hell of a lot on the subject. So I would love to just kick off with the numbers. What have you seen over the years? How many people have you hired? Directly or indirectly.
[00:05:24] If direct and indirect, probably over a hundred. If not more. Directly around 30, I would say.
[00:05:29] And then that gives you a good grounding as maybe to have some hiring surprises, I imagine from time to time. Yeah. Maybe if you could tell us the stories of your best and worst hiring surprises.
[00:05:43] Yeah, those won’t be named because that’s just mean. But I think, you know, folks can, especially in sales hiring, right? Confidence is a lot of it. Being able to share stories and kind of bring someone through a journey of your career and, you know, what have you done with different deals.
[00:05:58] I think earlier on [00:06:00] when I started interviewing and hiring for my team, there’s a pressure that you feel to make the candidate experience really wonderful and, you know, if it seems like they can do it or, you know, they seem really confident, you kind of go with that. And as I’ve gotten more experienced, my bullshit meter has gone significantly up.
[00:06:17] And so I’m far more of like digging in early on of, you know, how exactly did you do that and what really did you do versus other folks in the team or in a team selling environment. And so, yeah. We’ve had a few of those and they’re painful. And you know, I take a lot of accountability and ownership over that.
[00:06:36] So you do a lot of reflecting of, what did we miss and, and what can we do better? Yeah. Good stuff. So then I know your network is extremely strong. Thank you. And alongside a lot of A players over the years. I’m just wondering sort of today what your approach or sort of secret weapon to sourcing top talent is.[00:07:00]
[00:07:01] Yeah. I think good people know good people. So, you know, we all, like if you find top performers, they generally hold themselves to unreasonable standards and they would expect that of their peers. I feel like, you know, there’s very much the idea that I had joining Latent was I wanted to join an Olympic team.
[00:07:17] Yeah. Everyone is an Olympian in a slightly different sport, but everyone is an Olympian and my team definitely holds that mentality. You know, I would say that my secret weapon is I really don’t let people off the hook very easily. So if you know, if you’re explaining something or I always start off in my interviews explaining my background and my story, and I do it in more of a storytelling fashion to kind of give someone a layup of this is what you should do, because take me along the journey of your life. I start with where I was born and how I, you know, what I did at uni and et cetera. And then, if they don’t follow that, you know, I start to kind of dig in of like, okay, well, how do you, you know, share a story or craft a narrative around why someone should, you know, be interested in your product.
[00:07:58] And yeah. I would [00:08:00] say that, you know, as folks kind of share different parts of their backgrounds or their stories, I think my secret weapon is, I will dig in and I’ll like. Like a dog on a bone. Like I’ll hold on until, until you tell me not to. Nothing. It gets to- it gets to the root of things pretty quickly.
[00:08:15] Nothing surface level with Maryana. No, no, no. We get, we get deep quick. Good. Weirdest interview moment. I’m sure you’ve seen some stuff along the way. Oh my god. Yeah. You, you get weird situations. I remember one person was thera gunning during an interview, and I was like, you know that like massager thing?
[00:08:38] I was like, yeah, that’s so weird. People have said wild things to me. I like there was, uh, there was a person who, yeah, it’s like definitely not safe to say on a podcast. But like truly, I mean it’s hard to say things that I will be shocked by, but like, it was shocking of like, you know, when I did this and f [00:09:00] this and blood this, and I was like, yo, like we are in a different type of environment right now.
[00:09:04] So, yeah. Had someone’s dog throw up during an interview like you, I like saw it happen. It was like, you know what I mean? Like, there’s like- and that one I think is actually one of the better ones because it’s like so human. Yeah. Like, how do you respond and how do you, you know, work with someone through that.
[00:09:23] So yeah, I would say that was the positive. That interaction went well. Talk about icebreaker. Just have your dog throw up. Yeah, exactly. Uh, amazing. Okay, so moving on. Now, not to give away too much in terms of your tricks of the trade, but do you have an unconventional or sort of secret interview question or tactic? Yeah.
[00:09:48] I would say that starting off with my story is helpful because it kind of sets the stage to be, you know, more transparent. So that’s definitely a secret that, that I would recommend. It’s worked really well to really get [00:10:00] at the heart of who someone is. The other piece that I would say is I will ask, like, talk to me about a deal that you really wanted and didn’t land it, and what would you have done differently then, and what would you do differently now?
[00:10:12] Which I feel like is a fairly common question, but I want to feel pain. Mm-hmm. What I want is that person to experience that moment, because that is what drives those top performers. Like I can talk all day long about wonderful deals that I’ve done that have been meaningful to me for various reasons, but I will never forget the ones that I didn’t get.
[00:10:33] And so that’s, that’s definitely something that I want to see. Yeah, I like it. Wisdom you wish you’d know earlier specifically on recruitment? Yeah. Sharing wisdom. Is there things that you now know that you wish you’d known earlier? Yeah. Recruiting is a constant thing. It is always. It’s like discovery. You know, I talk to my team a lot. Like we are [00:11:00] always discovering, it’s not like a part of the sales cycle. It’s always, and recruiting is always that too.
[00:11:05] I’ve been so fortunate that at Latent, I have a number of folks here that have worked with me in the past that have decided to come here. And that wasn’t because I was recruiting them, it was because we had worked together and, you know, consistently keeping up those relationships of wonderful people.
[00:11:20] And you never know what someone is going through in their life. And in fact, a lot of folks here have had personal experiences within the healthcare system that have made them so passionate about what it is that we’re doing. And so I think bringing on top talent is the most important thing you can do as a leader.
[00:11:36] And to do that well, you have to always be recruiting, always be, you know, speaking about what it is that your company is doing, what culture that you’re developing and making it a place where, you know, actively building a place where people want to be to do their best work. So, I think that the piece that I would tell myself is that just because you hired an amazing person does not mean you’re done.
[00:11:58] Just because you don’t have headcount open right [00:12:00] now does not mean you’re done. You gotta keep going. You gotta keep doing the work every day. It’s never ending. Never ending. And so, red flag. That’s beautiful though, right? Yeah, it’s like, I think it’s a beautiful thing. A red flag as well for any sales leader that is unable to bring folks from their past across with them should they, you know, want or not, it is very telling of them.
[00:12:23] I’ll be really transparent. You know, the first time I was the head of sales, I really struggled with that and I think it should have shown me that I just wasn’t ready at that point. And that’s okay, right? That was five years ago. And you know, I had a moment where I was like, it’s my time and it certainly wasn’t my time.
[00:12:38] And, you know, go back to the drawing board and build again. And this time it is my time. And so I think with that comes experience and that’s okay. It was very painful, I’m not going to lie. But I think now having that, having gone through that, I’m able to build the team in a very intentional way here and you know, create the energy and the culture of [00:13:00] excellence that I think that Latent deserves. Yeah.
[00:13:02] Right place, right time. Right sales leader. Maryana, thank you so much. I’m going to be seeing you soon no doubt because again, yes, we’ve got work to do. But thanks for- we’ve got work to do some great nuggets here. Thanks for taking part in this. It was a pleasure, Tom. Thank you so much.
[00:13:21]