September 27, 2022

Recruiting and How to Find the Perfect Match with Mimi Gross

by Hacker Valley Studio

Show Notes

Mimi Gross, Founder and Cybersecurity Matchmaker at People By Mimi, connects early stage through Series C cybersecurity startups with sales and marketing talent. As a recruiter and headhunter with over 5 years of experience, Mimi refers to the process of recruiting and hiring as “cybersecurity matchmaking.” Mimi joins Hacker Valley Studio this week to talk about what recruiting and dating have in common (including marriage!), and the ways to deal with rejection during the hiring process. 


Timecoded Guide:

[00:00] Defining the term “cybersecurity matchmaking” as a recruiter

[04:00] Commonalities between recruiting and dating advice 

[07:55] Dealing with job rejection like a bad breakup

[15:17] Balancing hiring manager wants and needs in the recruitment process

[20:11] Emphasizing chemistry between the ideal candidate and their future employer


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Where did the term “cybersecurity matchmaking” come from?

There’s a huge element of matchmaking in recruiting. That’s essentially what you’re doing — you’re matching a potential candidate with a potential new position. Certain recruiters and companies instead treat the act of recruiting candidates and hiring new employees like a sales transaction. This feels impersonal for everyone involved. Referring to recruiting as “matchmaking” reminds everyone involved that there are humans in the process at every stage, from application to references, interviews to onboarding. “Early on, I was disillusioned with recruiting, because I realized that people don't treat it like finding the perfect match. It's like sales for some people. I quickly said, ‘I can't do this thing unless I can call it matchmaking.’ That's where the term came in.” What does dating advice have to do with recruiting?

In both recruiting and dating, you’re trying to find the “right” fit. In dating, both people in a relationship are looking for “the one”; someone to grow with long term and to build a mutually beneficial relationship with. In recruiting, the founder or hiring manager is looking for the right candidate for the role, while the job searcher is looking for the right job for their career. In both dating and recruiting, when you find the right one, it won’t be a huge compromise or a challenging fit; the relationship will feel authentic and natural. “I find that the best matches I make — and I love to call them matches, because they really are — I look back at them, like, ‘You know, that was a good match.’ In those great matches, the chemistry was there right away.”


How do you help candidates deal with rejection?

Rejection is part of the recruiting process, just like how breaking up is part of the dating cycle. There are going to be times when the fit isn’t right and the job you want goes to a different candidate. The trick is to not take it personally. Instead, take a learning approach to the situation. The company might need to go in a different direction, or someone else in the organization may be taking over the position. Unlike dating, the hiring process is unrelated to who you are as a person. Focus on learning and applying your experience elsewhere.

“It’s not just about not taking rejection personally. You have to see that there will be the right fit for you, and that also, the person who is rejecting you now could be a valuable person to know in the future. Never burn bridges.”


What is one of the most important aspects in recruiting?

Chemistry is key in the recruiting process. You may have a company executive or a hiring manager who wants a specific trait from their applicants, like an Ivy League education. As a recruiter, you have to dig beneath the surface to discover the “why” behind a job qualification or educational requirement. Perhaps the employer actually wants someone organized or detail-oriented. Getting to know the “why” means that you can find the actual right fit, while the chemistry between the job seeker and the hiring executive will take care of the rest. “In the beginning, if you find the right match, the dating metaphor here is that nobody's perfect. You have to figure out what kind of imperfect you can handle and you can love, and that's the right match.”



Spend some time with our guest Mimi Gross on LinkedIn

Learn more about cybersecurity matchmaking on the People By Mimi website

Connect with Ron Eddings on LinkedIn and Twitter

Connect with Chris Cochran on LinkedIn and Twitter

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Continue the conversation by joining our Discord

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Hacker Valley Studio 0:07
Who says tech can't be human?
Mimi 0:10
If there's chemistry and respect, mutual respect is also very important. A founder has to want to follow a first sales leader, has to want to follow a first marketing leader. They have to listen to what they're saying and be inspired about their own business.
Hacker Valley Studio 0:30
Welcome to the Hacker Valley Studio podcast.
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Chris 1:25
What’s going on, everybody? You are in the Hacker Valley Studio with your host, Ron and Chris.
Ron 1:30
Yes, sir!
Chris 1:34
Welcome back to the show.
Ron 1:37
Glad to be back again. I have a question for everyone. What if I told you that everything you
need to know about startups, you can learn from dating advice? We think this is what we've learned from our guests. Today, our guest is Mimi Gross. Mimi connects early stage through Series C cybersecurity startups with sales and marketing talent. And Mimi, you also founded your company called People by Mimi. Always a pleasure to have you. And I wanted to say, before we even jump into the matter at hand, where did this term or aka “cybersecurity matchmaker” come from?
Mimi 2:17
That is a great question and I've never been asked that question before. So there we go. Yeah,
it seems obvious because I'm a recruiter, so there's some matchmaking element in it. But the
truth is, it really is a part of who I've always been. I've always matched people up. And that's
how I got into recruiting. So early on, I was kind of disillusioned with recruiting, because I
realized that people don't treat it that way. It's like sales for some people. So I quickly said, “I
can't do this thing unless I can call it matchmaking.” That's where the term came in. But
nobody's ever pushed back on it, which is really funny, because it does kind of make sense.
Chris 3:00
It does make sense because I mean, you are making a match between people and startups andbother companies. We were hanging out at RSA, and we were having this deep conversation about the analogy between it being a dating construct when you're looking at bringing on either additional founders or you're bringing additional people to your team. But where did this really start in your mind?
Mimi 3:24
I think what happened was, I would start talking to both founders and candidates on both sides, where I would start to see that the advice that I'm giving is advice that I was given when I got serious about dating. Let's say when I, in my later 20, when I got serious about finding the right one, which thankfully I did, and I used a lot of advice, I wasn't great at it, naturally. I'm pretty loud. I had to learn to listen. But yeah, I found that I really loved reading dating books and getting dating advice from my friends who did it well. And I started to see that it 100% was naturally flowing out in terms of advice that I had for people while they were in the process of either recruiting a really critical first hire like a sales leader or a marketing leader. So that's from the founder's side. And then from the marketer’s side, it was really looking at their life, their career, where they're headed their goals, and trying to figure out what the right match for them would be. Both sides, but you know, you kind of found that and then once they started getting together, still you see the same stuff: miscommunications, maybe somebody picked up on something, maybe somebody didn't send a thank you note or maybe they're bringing past prejudices into the relationship and maybe not seeing things for what they were. I became very, very aware. It's a little bit like a “Back to the Future” thing, like don't mess with the time-space continuum, which I think that sales-oriented recruiting does that. You want to push someone to join this awesome company and for me, I always felt like I kind of watched the dynamic, I watched the chemistry happen, and it kind of does its own thing.
And that was the best advice when I was dating that I ever got was like, it's gonna be easy,
when you meet the right one, it's not going to be brutal, you're not gonna be struggling through it, you're just kind of gonna know. It might not be like fireworks, but you're gonna kind of know that it's right, and it's not gonna be filled with all kinds of weird crap.And I find that the best matches I make — and I love to call them matches, because they really are — I look back at them, like, “You know, that was a good match.” And those great matches, the chemistry was there, right away. So that's number one, like red flags. That's where this started, because I would start encouraging people to listen to red flags. And people don't listen to red flags in recruiting the way that people don't listen to red flags in dating. Right?
Ron 5:59
You know, recruiting is one of those topics in cybersecurity or even business as a whole, where people don't know where it starts and stops. Sometimes when I hear that someone's a recruiter, I'm like, “Oh, great. They'll help me with everything.” And there's like, “No, I only help you with finding resumes or reviewing them, or the first outreach, and then you handle everything else.” But some people like yourself, you know, you really focus on the match. But let's unpack it a bit. How would you define “recruiting,” especially in this world of cybersecurity?
Mimi 6:30
I define it as matchmaking. I know that's now going to be repetitive. But I do, I really do. I view it as, I take it with a lot of gravity. I'm working with founders, working with sales leaders and
marketing leaders, VCs, sometimes. There's a lot of money at stake. There’s a lot kind of
coming into the future of the thing that's about to happen. And a person who's joining that, that's also a huge decision. So I think, you know, a really good recruiter is a conduit and a channel. You know, it's a matchmaker and kind of somebody there to support the process, gently.
Chris 7:09
The first thing I think about when you think about dating, maybe just because of my track record, is rejection, right? You think about rejection, and a lot of times people take it personal and they're like, “Hey, you know, this was fun. But this will never happen again, right?”
But this also happens in cybersecurity. We go to these interviews, we put our best foot forward, we're like, “Oh, this is the perfect company for us.” And then the company says, “Sorry, we found someone that was more qualified” or “It's just not a good fit right now.” And people take it personally. But I mean, I often tell people like, “Hey, you know, if it's not a good match, it probably wouldn't have worked out in the long run anyways, and maybe that's just not the company for you and there's definitely that match out there for you.” Do you see that as the same way when it comes to rejection?
Mimi 7:55
That is an amazing topic to bring up as well. The rejection piece is a huge part of what I do with people. And I'll explain this and actually self-referencing to Hacker Valley Media. Gianna — I don't think they're gonna be upset at me for mentioning this — Gianna and Maria, they met, because one of them was interviewing with the other through me. And it didn't work out. And it didn't work out. And they became great friends. And they created this beautiful thing together. And I always look at that as why my work is so meaningful. We're working in a small community: I only work in cybersecurity. So when I introduce two people, it's not just about “Are they going to have that job?” I'm introducing two humans, who can now know each other. And I think about that. And I think that is a cool piece to think about. And with rejection, I think if you can take the practice of not taking it personally. And if you think of it as dating, that there's kind of a really nuanced, perfect fit for each thing, you can kind of say, “Okay, it wasn't right, maybe I have certain needs today that they don't have” or whatever it is. And I think the same way that you can develop yourself as a person to not take rejection personally. It's not just not taking it personally, but to actually see that there will be like the right fit for you or that also, the person who's rejecting you could be a valuable person to know — never burn bridges. Very important job seeking skill, to be able to see that’s true. Not everybody has the wherewithal to do it.
Ron 9:35
It sounds a lot like building relationships. It's all about that, at the end of the day, from finding an opportunity to getting matched for that opportunity, and even for excelling in that opportunity. I can only imagine if you join an organization and you don't like someone that works there, what is that going to be like for you, your team, your company? This is going to cause a lot of friction. It's almost like going back to that dating situation like marrying someone that hates your family and your family hates them. That could be pretty wild and crazy. When you're looking at matchmaking and bringing the right people in, do employers really know what they're looking for? That's what I hear on LinkedIn quite a bit, especially speaking with Renee and Chris Phoolan. From the Breaking Through in Cybersecurity podcast, they mention this a lot of having great job descriptions and requirements. But I would be curious if that's actually the problem of staffing, cybersecurity professionals, or if it's something else?
Mimi 10:36
We look at job descriptions, like you have to have job descriptions, it's a must have, if you're
gonna put it on LinkedIn, what else you're gonna put there? We need to create these job
descriptions. But what I can say is working with early stage startups, I'm often not working from job descriptions, because I'm doing the first sales or the first marketing, or the second. And so we're really looking at the pain points that the company has today. We're also looking at the projected, let's say, pain points that they're having a few steps ahead. And then we're formulating a really nuanced mapping of what kind of person is going to work there. And so we do that. But then the other piece is really guiding hiring managers to follow their instincts. And there's a lot of pressures. I would love to dig into this a little bit because it's really interesting how VCs play into this. When a founder is hiring, and they aren't clear, let's say exactly what they need. They know better than anyone else what they need. They may not be able to articulate it, but they will know it when they see it. Unless they're clouded by a lot of other people pressuring them to ignore certain instincts or to maybe even artificially create other prejudices or things that they're looking for. For example, let's talk about the Ivy league. I've had searches like that. And when I dug deep enough, I found out it came from the VC. We need somebody from the Ivy League, I believe it was like a CMO role or something like that. I was just thinking to myself, like a good marketer, “How is that connected?” And I dug deeper because — and I try to do it gently — because I do respect everything I'm being told is necessary. And then sometimes we do have to unpack it. Just like with dating, you get to know yourself better as you kind of engage with more people, as long as you're listening
to instincts and developing and honing instincts as well because obviously, we can have dulled
instincts about these things.
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Chris 13:20
I'm sure one of the things that you do with whether you're talking to a candidate or you're talking to the hiring manager is ask why? Right? Oh, “I want someone from an Ivy League school.” “Why?” “Oh, well, because I know they're educated.” Or, “Oh, I'll know they'll be successful.” “Why do you want someone that's successful?” “Oh, well, because then I know they can do X, Y, and Z or provide this, provide that.” And then you kind of tumble down the rabbit hole and figure out what is the true “why” behind everything that you're looking for in this person? Do you take people through that journey and do you have an example of taking someone through?
Mimi 13:57
In general, that happens all the time, when you're talking about a first hire. There's so much
good insight out there about what makes a good first hire for sales or marketing, you know, and it will evolve. And also all those things start to fall away. When, let's say I meet an amazing
marketing leader, and their skill set is exactly what's gonna make this company shine and it's not exactly what they were looking for. So let's just talk about that. I'm actually thinking of one now. So you know, they were looking for kind of a junior marketer who could kind of carry out some of the earlier demand gen activities just kind of while they were figuring themselves out. And I found somebody who was like a brand genius, and a little weaker on demand gen, but had worked with some of that stuff. And I was talking to them and it just occurred to me that that could be really amazing for the company, whether it was going to be now or later or whatever it was. And so I just kind of gently said to the founder, I said, “You know, I met this person, it's not whatvyou were talking about, but see what happens. And I want to respect the fact that I know you were looking for this, it's a little more than what you're wanting to pay. But could this work?” They talked, and it was like love at first sight. It really was, it was like there was an ease. And the founder felt a lot of the anxiety about certain things that they had had just fell away talking to this person, because of the way that the person talked about some of these pieces and the way they talked about their work and their practice. And they were able to, you know, work out that this could be a first hire, if they supplemented with, let's say, like a demand gen machine that could work. That's an interesting example. Because I guess it could look like I'm pushing people in different directions. But it is like a really good example of somebody thinking they need this exact thing. And then, you know, being able to meet somebody that because the chemistry was there, because the person had other skills,
they were able to envision it. So I don't know, like at the beginning, there's so many things that if you find the right match, the dating metaphor here is like: nobody's perfect. So you figure out what kind of imperfect you can handle and you can love and that's the one.
Chris 16:21
Right. Can you think of a time — because it's making me think about some of the times that I've put myself forward for a position — many times, I didn't have everything that they were asking for. But I'm like, “You know what, I am so confident in my ability to kind of show my value, that even though I'm missing X, Y, and Z, I'm gonna put my best foot forward and I think I'm a good candidate for the position.” Can you think of some times when you've done that, like, “I don't have this, but I'll tell you what I can do” and honestly get the job?
Ron 16:49
When I was early in my career, I wasn't qualified for anything. Because I didn't have a degree, I
didn't start with a degree, I didn't have certifications. But what I did have was something that you could only experience after speaking to me — I had determination, I had drive, I had this ability to learn, maybe even aptitude, some people may call it. And that was really great. Because that's a match. You don't necessarily always know what you need beforehand, like Mimi was describing, sometimes it takes for that person to be presented to know that this is actually even better than what I thought it could be. And the second piece is, we don't apply for jobs anymore. Once you are far enough along in your career, and you've done great work, then there's this chance that you might not be applying for jobs, you're creating your jobs. So what I do now and what we both do together, as we go to organizations and say, “Hey, this is a gap in technology. This is a gap in cybersecurity or content, let me help you fix it. I think I have this characteristic or ability or skill to help you do something that you probably didn't think you were wanting to do in the first place.”
Chris 18:01
What do you think about that, Mimi?
Mimi 18:02
That's the heart of it, because if you are especially bringing it back to startups, we were talking a little bit about how the recruiting part is the dating part. And joining a startup is the marriage part and kind of where you're really bringing yourself to the table, and it's this team that's growing together through all the hard parts. And I would say when you think of yourself when you know yourself well, and when a startup knows themselves well, you can meet on things like determination and curiosity. I know Nathan, his prime quality is curiosity. And I think with startups, you just, you have to have that. If you're curious, you're going to try to figure out something's not working, you're not going to start blaming somebody, you're gonna start blaming the product, you're gonna start getting curious about how to work this through.
So I think it really comes down to what you're saying is like when people meet people, and they feel “Oh, this is a person who has loyalty, who can get through the hard stuff with grit and grace, and is smart and creative and curious.” It takes off the plate, all these weird things on paper that people think have to be all together. And I've seen amazing people pivot in their career, grow in their career, because of that fit. And because everyone's working on themselves. You get good people together in a startup, you get a great team.
Ron 19:25
You know, what I love about your energy, even communication tactics and how it feels in my
mind, is you have this coaching aura about you where you're not helping provide a service, but
you're helping that person get better at what they want to ultimately succeed at. Recruiting,
finding the right team — that's also a culture piece is bringing that person in and having them
help build the culture and you're just describing how it's a bit synonymous from dating and
marriage. You know, we're talking about the marriage part now. Where do you really find your
excellence in what you do with matchmaking, help marry candidates with companies, and what are also some of the elements that make a good marriage for a match?
Mimi 20:11
I always am afraid to sound like I'm being too simplistic, but I'm not. It's the founders have to
really connect with these, especially these two first roles. And it is chemistry. If there's chemistry and respect, mutual respect is also very important. A founder has to want to follow a first sales leader, has to want to follow a first marketing leader. They have to listen to what they're saying and be inspired about their own business. Like a marriage, when you speak to somebody who you're going to spend the rest of your life with, you want to feel inspired about life with that person. You don't want it to be something that ahead of you looks really complicated and rough. And I would say the most beautiful times when I see those things happening, are when founders are self aware enough, and people are self aware enough, and they come together and obviously, there's certain things that have to be on paper. Nobody can ever say about me that I don't have, you know, there's a checklist of things that need to be there. But once the chemistry is there, you can do so much. And the respect, that is what I've seen to be where that goes really beautifully.
Chris 21:27
One thing that I think about as you're talking about matching people up is sometimes the person that you want, isn't the person that you need, in a lot of sense, like whether you're talking about dating, and you're talking getting to marriage, or you're talking about someone that's in a startup, because then you think about things like diversity. Diversity of thought, diversity of culture, it's easy to have that chemistry when everyone thinks the same, and everyone's slapping high fives. But sometimes the person that you need is very different, thinks very differently about problem sets, thinks very differently about maybe it's finances, or selling or maybe it's just a different way of looking at the product. How do you balance making sure that you're covering your bases from a diversity standpoint, but also having that chemistry because I think there's a balance there. And how do you coach people through having that balance?
Mimi 22:18
There's a chapter in my book, and it's called the Manic Pixie Dream Girl. Zooey Deschanel, like
all the characters she plays, it's like this extremely sprite, otherworldly girl, and there's some guy who, she's their dream girl. But like, she has no personality, they have nothing actually in
common. And it's like her whole existence is just somehow in the movie, to create some
meaning for him. It's this kind of really off dynamic that was a theme, like in the 2000s. I think startups often have that, where either they're having their eye on a competitor, and it's a little too intense. They're like, “We need to be like that, we need to be like that. And that and that, and that.” And then they're not focusing on that kind of deep sense of self-knowledge, you know, and they're like, “Okay, we're a little too serious, let's find a really fun CMO, or like a really out there sales leader who's gonna be like, make us laugh every day,” whatever it is. But if that's not the vibe of the company, it's gonna get old really fast. My personal approach — I am a recruiter, and I see a lot on the diversity side — I'm gonna report from my end, that diversity is in really good shape, from my side. I only see people excited to diversify things, diversify their teams. I know that that's not necessarily politically correct but I'm just reporting what I see. I have never had any kind of — and I would say it because it's popular to say, and I would say it — but I don't see any pushback when it comes to diversity. When I'm talking about chemistry, I don't see, let's say, two people who are similar culturally, necessarily having that chemistry only. It really is a deeper thing. And I think that's right back to marriage: love is blind. I do see beautiful matches, and the most beautiful matches I've made have nothing to do with cultural similarities. In fact, the opposite because I work with a lot of international companies. So I am dealing with actually guiding people with different cultures to connect with each other and find ways that they can meet and actually find the chemistry. That's what I would say, I think when companies and founders know themselves and they're confident in their instincts, and candidates know themselves and they're comfortable in their instincts. I do think these things go off the table.
Ron 24:52
What I love about all of this and what I also love about you, Mimi, is that you are a hacker. I'm
not sure if you knew that did, you know that?
Mimi 25:00
That's the best compliment I've probably gotten a long time. So I'll take it.
Ron 25:06
Yeah, what hackers do best is they take all of these disparate pieces of information and use it to make a story. And you've taken so many parallels between dating and building successful
cultures and also many other things. What I wanted to ask was for anyone out there, like if
you're a startup, or you're an individual, how do you hack this game of recruiting and
Mimi 25:34
That is all about knowing yourself. I think you guys will appreciate that. I know you are always
into developing oneself as a way of being a better professional. And I tell that to job searchers,
you know, it's a time there are layoffs right now. I tell it to hiring managers, I tell it to anyone
that's coming to me and wants to prepare for this experience of matching up, meeting up to
create a beautiful startup — you have to be at your best. If you're looking for a job, make sure you have accomplishments that you can point to every day in your life, whether it's work-related or not work-related. But the deeper you know yourself, you're always going to be better off in this market. You'll look at the right things, you won't be chasing the Manic Pixie Dream Girls of the world, and you'll be looking for your match and your spot and your place and your people. And when you can do that from a really deep place, you will always make the right choices.
Chris 26:41
I love that. That is beautiful advice for anyone to listen to: understand yourself, and then look for what you need. Whether we're talking about dating or cybersecurity. Mimi, it has been an honor to hop on the mics with you and chop it up. If anyone's looking for more about Mimi, be sure to drop into the show notes below wherever you're listening to this and get more from her. And with that we will see everyone next time.
Hacker Valley Studio 28:01
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