Episode 7 Jake Gunn-Sandell

Jake (00:00)

Look at this podcast. Find this YouTube

People that I'd never met before, never communicated with. Random strangers were willing to help and say, that's great that you're starting to think about what could be next for you. Here's what I did.

Kelly Dwyer (00:58)

Today I'm talking with Jake Gunn Gunn-Sandell, the director of strategic affairs at Instructure, the company behind Canvas. That's one of those learning management systems that teachers and students use to do all their work at school.

Everything that used to go in your backpack is now done through tools like Canvas.

So in his role, Jake is helping shape the future of education and technology. He's leading government affairs and he's raising Instructure's voice on the global stage. Before joining Instructure, Jake spent more than seven years in the fast paced world of executive search as a client director at SPMB, where he built what he called the polymath practice. Think of him as a modern day Sherlock Holmes for talent. He led over 120 executive searches, helping place C-suite leaders

across industries from AI and FinTech to healthcare and enterprise software. That's quite a portfolio. Jake's path has been anything but ordinary. He's gone from product manager at Colorado State University to Disney College program recruiter, and he was even a character performer. We'll have to ask you what character. Outside of work, Jake gives back as a board member for the Arapahoe Rescue Patrol, a search and rescue team supporting young leaders in Colorado. And when he's not doing that,

You'll probably find him mountain biking, cheering on the Nuggets or performing at open mic nights around Denver. Welcome, Jake.

Jake (02:22)

Thanks so much, Kelly.

Kelly Dwyer (02:24)

So happy to have you here today. Okay, before we dive into the

that we're gonna talk about, I wanna know what characters were you?

Jake (02:31)

I had a very ⁓ perfect body for a lot of different characters, they said. Like I was just the right height. So normally you only have like three characters, but I was 10 and it was everything from Goofy, Woody, Sully, Beast,

Kelly Dwyer (02:39)

Yeah.

Jake (02:46)

from Beauty and the

Army Man. It was all over the map. And

if there's kids listening to this, we always have to say Jake was friends with Goofy.

not playing goofy. Disney World, yeah, where it was hotter than hell. my gosh, yeah, I sweated quite a bit. I was working out and trying to like gain muscle and I came back to Colorado like weighing less than I did because I just was in a total sauna every single day.

Kelly Dwyer (02:55)

⁓ gotcha. Okay, makes sense, makes sense. And were you at Disney World, Disneyland? Where were you? Okay. I bet, I bet in those costumes.

my God. You're

the, you were the proof of the benefit of saunas from a way less perspective.

Jake (03:22)

That's right. That's right.

Absolutely. Getting paid $8 an hour to be in a sauna. That's right. ⁓

Kelly Dwyer (03:28)

my Lord. Okay.

Well, so happy to

here today.

so life from within is

podcast where we talk about the wisdom and the personal growth that we gained through career challenges. And some of those career challenges could include career pivots. And that's what we're going to talk about today.

lead us in, where do you want to start? What career pivot do you want to tell us about first?

Jake (03:54)

Yeah. I mean, it's funny working in the recruiting world for 10 years. Like I did. I witnessed hundreds of people make pivots or had to try and convince somebody to make a pivot or someone asking me, what do I do next? Where do I go? And I spent three years of my career with a technical recruiting company here in Colorado,

that we actually met

which is just from so long ago, but

I was responsible for building out a program that helps college students find work within

large businesses, but then also partnering with a lot of the different

tech schools out there, like the Galvanizes and the Turings of the world and the coding boot camps. And that's how we met, which was just really fascinating.

Kelly Dwyer (04:39)

Right.

Jake (04:41)

I ended up out of like 200 recruiters at one point I became the number one placing recruiters in the company and

I thought things were going well. was placing solution architects. I was placing senior developers, product managers, all within these pretty much Fortune 500 companies for the most part. And I just thought I was on cloud nine, but I didn't feel challenged enough. I wanted to do something more. And then you actually helped introduce me to my wonderful mentor and boss, Jon Landau at SPMB executive search. And I then realized, I was in the minor league.

I thought I was in the major leagues, but walking into a world where you have different egos, you have different revenue goals, you have different technology, you have different investors,

everything across the board when we were having to place C-level execs within public facing companies that were 500 million and above, all the way down to series A, early stage, seed stage, even startups. I had a total panic. was like, my gosh.

I don't know how to do this. I thought everyone was the same. I thought I just had to ask the same questions and C-level execs

can be intense. And so I remember that pivot being a moment where I was starting to overthink everything and overanalyze everything. And the one thing that brought me

down to earth a little bit was just compartmentalizing that new change in that new world.

called it the three school subjects of what we do every single day with an executive search. And I said it was psychology, it was economics and finance, and it was technology. Like those three, four subjects, if I focused on those subjects every single day, I knew I was going to do well at my job. The psychology piece of understanding someone's personality, understanding how they work with other teammates, understanding how they deal with failure, understanding how they deal with success.

And then the technology piece, understanding what type of tech have you been a part of and how is that transferable to other areas? Like FinTech could be very relatable to

could be MarTech that I was a part of, does have similarities to AdTech. mean, HealthTech has actually similarities to consumer. And so I worked on every type of different tech product you could think of, like you mentioned earlier in the bio, like FinTech, HealthTech, MarTech,

AI, cybersecurity, consumer. It was all over the map.

And

realizing that the psychology piece comes into play, the tech comes into play, but then the economics and finance of like, what type of success did you see or what type of failure did you see within that? How did you help revenue grow? How did you help it flatten? How did you help it get acquired?

And so all of those, those three subjects just really made me realize like, wow, if you pivot into something, you just compartmentalize it and make it a little bit easier to understand it's something as easy as like three school subjects is what I called it. It works out really well.

Kelly Dwyer (07:29)

what I love about the story, the journey you just described is that.

So first of all, you were hired into this role because you had recruiting experience. I would also say that I was very impressed when I first met you. You have a presence, you're very articulate,

you have great energy.

a brightness about you. my guess is Jon saw that and he saw your recruiting experience. And even though you didn't have the executive recruiting experience,

he said, ⁓ this could work out.

so you were

invited into this role that you hadn't done exactly before. And

you found yourself

at a loss of, my God, I don't think I know what I'm doing here. And so what you did was you created, you just described how you kind of created a framework for yourself

of how you were, and you use the word compartmentalized

to break it down into something that felt more understandable and doable and approachable for yourself. Okay, so the psychology, if it's about psychology, what do I need to know?

Jake (08:34)

That's right.

Kelly Dwyer (08:39)

And when you're dealing with executives, you are dealing with some strong egos.

Jake (08:44)

Yeah.

Kelly Dwyer (08:44)

I don't mean like overblown egos. mean, of course, yeah, there are some.

But these

Jake (08:48)

No, just

people, yeah.

Kelly Dwyer (08:50)

don't get into the C-suite if they don't have strong points of

strong personalities,

So there's the psychology, then there was the economics and

finance, and then there was the technology piece.

Okay, so you learned that you came up to speed.

described the polymath practice. How is that different than a normal executive recruiter works?

Jake (09:07)

Yeah.

it was an interesting poll calling it polymath since that just means multiple languages or multiple understandings of a certain study. But Jon and I were working on everything from a CFO to a CEO, to a CTO, to a CRO, to a chief product officer, chief technology officer, a VP of

just covered everything. And a lot of our clients picked up on the fact that

Wow, you did such a good job on just this one type of search as a generalist, which is basically what a polymath practices of what I was trying to establish myself as was if you did such a good job understanding how we could place the CTO, could you help us with our chief product officer? Yes. And then could you help us with our chief executive officer? Yes.

And

were able to shape shift ourselves, but also

more than anything, like pull different,

skill sets out of what somebody is and understanding how a CTO should interact with a Chief Product Officer. Because we've done both CTO and Chief Product Officer searches, we understood how that balance was so important. Same with the CRO, a Chief Revenue Officer and a Chief Marketing Officer, understanding how those personalities work together as well and how those skill sets need to align. But then at the same time, it's understanding, how does a Chief Product Officer, which has to touch pretty much every part of the business, how should they be interacting with a CEO? And we've done CEO searches. So

It felt like we were always pulling different skills or different stories of someone else's background and being able to apply that to the new search that we were targeted or that we were working on.

I came up with the polymath practice just because I wanted to show my clients that. And the example I would give is like, if you want to hire a architect to build your home, that's built the same home over and over again. Great. You have that. Or if you want somebody who's built ranch style homes, condos.

on the sides of cliffs, ⁓ underwater homes. Like we've done that before and that's where I was building my practice to say, we've just seen how different people's personalities and skills and backgrounds might correlate to what it is you actually need or want versus you going after the most obvious source. Like within two weeks of a search, we would understand that what you want.

could work, it's just going to take a lot longer finding that person where it's like, if we think a little bit more creatively, we might bring somebody forward that you didn't even think about that does the job even better for you. And those were the best clients to work with who understood that. so within executive search, lot of, to answer your question, a lot of folks will ultimately either stay with one type of

C level or one type of search, like I only do CEO searches, and then they'll only stay with maybe one type of business where it's like, I only do B2B enterprise, or I only do cybersecurity.

And for us, we did

it was just such a fascinating time. And we called it Polymath because we could shape shift into any type of business.

Kelly Dwyer (11:56)

I

Jake (11:56)

that make sense?

Kelly Dwyer (11:56)

that.

Yeah, it makes total sense.

you know, as a coach, I work with executive teams and

one of the things I do. And it's interesting to see the personalities play out

the context of the team. And I imagine

that's part of the psychology piece that you were

for, evaluating for.

hiring a chief product officer and we've got a CEO and this CEO is pretty interested in product

then the CPO has to have a certain kind of personality that's going to be able to handle the CEO being in their business. Right? Right? Versus having a CEO who's pretty sales driven,

Jake (12:33)

Yep, right, that's right. Yeah.

Kelly Dwyer (12:39)

the mix of the team

at least understanding the personalities you're trying to match, I would imagine was a consideration for you.

Jake (12:46)

Absolutely. And I've always told people that it felt like over seven and a half

in executive search, felt like every year I received some type of new MBA because I learned from every single person that I spoke with. And I talked with thousands of execs

it was a 30 minute call with them, an hour call, or spending three weeks with them, trying to help them land the dream job that they wanted to be a part of.

I learned every single time I communicated with them, every single time

had to share their presentation of what they were going to do in the interview or what they wanted to talk about. And so I learned a lot of like what it takes to be a good executive. And I learned also what it takes to be a bad executive from meeting

many different types of people.

it was just, it was a very interesting world of.

Being able to see through a mirror of like how this person got to where they're at

how somebody else got to where they were at. was just very fascinating.

Kelly Dwyer (13:34)

Yeah.

You had talked

you were feeling the overwhelm being in this new role, recognizing that,

isn't what I was doing before. This is different and I need to show up differently.

that?

moment of realization like what were you feeling before the moment? What were you doing to help yourself manage

that stress?

And then how did you hit upon,

⁓ okay, I just need to compartmentalize

Jake (14:04)

I do remember

I was working on a search.

I believe it was a chief revenue officer role and learning right away that chief revenue officers move at a million miles an hour. They care about data. They care about you actually knowing the product and establishing trust and establishing credibility.

They move fast so that you got to talk fast, but you also have to be sharp. And I just remember being like,

When I was working for a Fortune 500 company, it's pretty easy to like say, this is the company I'm working for and I want to place you Mr. or Mrs. Developer,

it's like everyone can think for themselves here. This is a role where I learned I have to work on behalf of our

Like I need to sell their product just as well as their sales leaders are selling their own product to customers. And I have to sell it to these executives. And at the same time, I have to know it inside and out. I have to know the financials of the company inside and out.

as as I can share, I have to know the vision of what the CEO wants to see within the company and where they've missed marks. And all of this just started to hit of like, I didn't know enough. Like I thought,

maybe a short Harvard Business Journal review would be enough. And it's like, no, I need to have a book on each company, each client that I'm working with. And so I do remember having that moment of like, you need to take more time, you need to slow

you don't have to move as fast like within.

recruiting, you're picking up the phone, you're wheeling the deal and you're calling, you're saying the name of the company, people either like it or they don't and they move on. But when you're working for a seed stage company or you're working for a series B company that no one knows about, no one knows anything about the investors, the product, the tech, the customers, the sales, the customer success, anything about it, you need to know all of that. And that was me realizing that I just needed to pause and slow down. But I think the key moment for me that I realized that I need to get better at this and the only way I will get better at this is a

letting my ego know that, hey you were in the minor leagues. You thought you were a big shot and you're not. And two, showing a lot of

many questions to these execs, to our clients, to my boss,

other

exec recruiters.

I had to basically let my guard down and say, I don't know everything and that's okay. And so many of the executives that I talked to when they would say something, I would say, can you go a little bit deeper on that? don't really understand

what type of success that looked like or.

what type of tech it was or what type of customer,

pausing and making everybody realize in the room where it's like, yeah, of course, I'm only going to talk about what I know best. And I expect you to understand that. But

gained a lot of trust with so many of my clients and with the candidates that I

because I was just intellectually curious. I just wanted to know more. And I think that was a big moment for me realizing that I can move past this. If I just ask questions and I show the vulnerability and that worked out really well.

Kelly Dwyer (16:44)

ask questions, show the vulnerability.

basically built a new habit

of

giving yourself permission to be intellectually curious and acting on that.

How long did it take from you to go,

feeling vulnerable about it, like, ⁓ I'm not sure about asking this question. Are they gonna think I'm dumb? Do they think I'm not gonna know what I'm doing? To the place of,

Jake (17:03)

Yeah.

Kelly Dwyer (17:06)

this is the right thing to do. I'm gonna ask this question because I need this information. It's gonna make me better at my

Without any of the mental chatter around what this other person might

about you asking this

Jake (17:16)

think it was about the six month mark where I realized the framework that I established of the three school subjects was really working for me by focusing on the psychology, focused on the tech and focused on the economics and finance of someone's background.

I saw that, wow, this is working

replacing people or our client is excited about it. People were bringing forward on top of that though,

It's the research that is really important as a recruiter and your team that you work with that's doing the

that's probably where I realized

the polymath thing started to stick out more was when I saw myself saying, our clients are only looking for this one type of person, but what if we found somebody from this different type of tech that actually matches this type of tech and matches the types of goals that they've seen, even

we're working with a venture capital client.

And they were like, we want somebody who came from a VC world. It's like, well, what if we pulled somebody from private equity that was a part of a

scale private equity type firm that acted almost like VC. And it was just that moment of realization of like, wow, with my creative mindset and thinking outside of the box and piecing things together that our client isn't even thinking about, because you just, it's really like, I want a red Ferrari. I want to get that red Ferrari. it's like, did you know like a yellow Porsche could get you there too? And think a little bit outside. And so.

That was the funnest part I realized was the research of being able to bring people forward. Where even Jon or a client would say, why are we talking to this person? it's like, hold the phone, but here's why they have this, this and that. And the client would say, I don't know. it's like, believe me, you'll want to talk to them. And then they'd come back and be like, thank you so much. That was so insightful. Maybe the person wasn't best for them, but it made the client realize I can think

all led from the three subjects that I came up with originally of

doing what I need to ask, but then asking myself, well, if we're running out of room or running out of people, where else can we find someone different and think a little bit outside of the box? And from all of the gathering of those three subjects, we could piece together

somebody else might look like from a similar subject

Kelly Dwyer (19:17)

Yeah,

that's really

know, these are high stakes matches that you're making, right? These are expensive hires. These folks that you're talking to are seasoned

Jake (19:21)

Yeah. Yeah.

Kelly Dwyer (19:27)

their careers. They're not just going to say yes to any conversation. So you're selling them on the opportunity, which is why you need to know enough about the company to be able to sell it to the potential

Jake (19:35)

Great.

Kelly Dwyer (19:42)

higher. And then what you're describing is you're also selling,

the client on this potential candidate. If the candidate doesn't look like the purple cow that the client had described, right? Yeah.

Jake (19:53)

That's right. Yeah.

And I had

close colleague and friend of mine say,

there's three things you need to also do here to be successful. It's established credibility. It's, sell the dream and it's slow down.

if you do those three things, you establish yourself as like someone that you can trust and you sell the dream of what you believe in and whether the company is going to go and what it's doing. And you also just slow down and listen.

you'll go far. And it was just all about once again, the compartmentalizing of like, don't overthink this,

it's okay. There's just follow these few steps and it'll bring you to a whole practice you never even thought about, Jake, of thinking, wow, I have enough courage and enough vulnerability to tell a client, hey, I know what you're looking for is X, but I think there's a Y out there that you haven't even thought about yet. And let's play with that. And the best clients would say, okay, you've got my attention. And it was fun.

Kelly Dwyer (20:39)

Yeah.

I love that, establish credibility, sell the dream and slow down. Okay, with that, let's move on to your next

Jake (20:48)

Slow down.

really quick, I guess just we'll call it a quick pivot

the search and rescue team that I'm a part of the rapid rescue patrol, it's the only youth led search and rescue team in the country.

that's run entirely by high school students. And it's been around for nearly 70 years at this point. I was a part of it when I was in high school, I was a captain of

I

part of four years. I led the search rescue team for two years

we are

fairly the largest search and rescue team because we're all high school students. And

search and rescue teams in Colorado

all volunteer

and that's mostly

so if you're working full time, it's hard to go out on a mission to go save somebody. But when you're high school, you're doing well in your grades, you can escape for a few days and go hike in the mountains and drink a Mountain Dew and keep moving forward.

Anyways, I was a part of it and I ended up joining the board

on our fundraising group a couple of years ago now.

And I came back into it and I was so excited and I was so invigorated, but the world has changed from when I was a part of it years ago to where it's at now where we really need funds. Like we're responsible for all of our trucks, all of our maintenance, all of our

we have to get funds for all of that. And it's donations that make that happen or grants. And I had to soon realize I thought it was going to be fairly easy. was like, I can ask around who wouldn't want to support this, but fundraising is just.

millions of nonprofits.

that was just, I guess, a quick

realizing, wow, this is a lot harder than I expected. This is not the world.

never been in fundraising before. And it was a pivot of realizing, I need help. We need more team members on our board that can support us. And so now we have a committee, we have a fundraising group, we have somebody on our board.

came from a fundraising background. And so she's been leading the charge and establishing steps. I don't have to be the person saying, this is where we should go next, this is what we should do. And it just came back to the same thing that I talked about before. It's vulnerability, it's asking

letting your guard down saying, I am not responsible for having to bring in hundreds of thousands of dollars. It takes a collective

Kelly Dwyer (22:46)

yes and

we'll put the link to the search and rescue in the show notes. So if people want to donate, they can and learn more about it.

Jake (22:49)

yeah.

Yeah.

Kelly Dwyer (22:54)

what I heard you talk about there was trusting your vision. So you stepped into this role, you realized fundraising was

that

the organization needed more than just you focused on

Jake (23:07)

Mm-hmm.

Kelly Dwyer (23:08)

And so you had this vision for, and you didn't explicitly talk about how this new woman came onto the board and now you have this committee, but my assumption or what I inferred there was you drove that vision.

Jake (23:20)

wouldn't say I drove it on my

our president realized that

is a lot of

our president of the board. And

she saw that I was struggling a little bit.

like, I don't know where to even

there's an ocean of money out there, but who do we

we have things that we need to do on our

I helped bring in a new technology CRM for us to be tracking all of our

It was a collective group, but it was me kind of

this is way harder. This is way more than I expected or signed up for. I didn't realize like how much this was going to be. so showing that vulnerability of versus me

never admitting fault and saying, I got this. have to be the one that does

I can bring in a million dollar check, no problem. And realizing, no, this is so much more than what I expected.

it was a collective effort of our president realizing we do need more help on the fundraising side and bringing in somebody with more experience.

that pivot of realizing I thought I could do it and

a village to make this happen.

Kelly Dwyer (24:14)

Okay, I love

again, that word vulnerability came

Yeah, well, and you're demonstrating, okay, when I'm willing to sit in that discomfort of feeling a little vulnerable and share my honest truth, then

Jake (24:17)

It's a theme.

Mm-hmm.

Kelly Dwyer (24:28)

sort of creates the field from which you can move forward,

all right. So you went from

Jake (24:32)

Yeah.

Kelly Dwyer (24:34)

SPMB to Instructure. Let's talk about that pivot, okay?

Jake (24:36)

Yes.

That's right.

That was a big pivot. Yes.

I love

it was very hard for me to go.

I love the people, the work we were doing was so much fun. mean, helping folks find roles and helping companies build and scale was really exciting. And I was looking though for myself to maybe take on a little bit more of a leadership role and have a bigger team eventually

I'm still younger and I want to be a part of.

a different

industry maybe, but I wasn't sure because recruiting, you just feel like, well, this is my path. I'll become a partner here at the firm. I'll continue building out a bigger team eventually and more clients. And that's great. I thought that would be the path for me, but

had this itch where I was looking to lead more. was looking to travel more and I was looking to meet more interesting people. And I was looking to give back. Like those were my four things. I wrote those down on a board saying, if I do leave,

I need to make sure I hit all four of these

yeah.

Kelly Dwyer (25:33)

Let's review them.

Lead more, travel more.

Jake (25:36)

and meet more interesting people and give back to the community some way,

Kelly Dwyer (25:38)

meet more interesting people and then the fourth and give back. Okay. Okay.

Jake (25:43)

wasn't sure how I was going to find all of that. And going back to what we've talked about

asking questions is everything, but I had such a diverse network of chief revenue officers that I built relationships with

chief product officers, right? All different types of C-level execs where I was reaching out to them and I was just

simply saying,

else do you think is out there for someone

my skill set?

this is something that I do want to share, at least for the listeners to learn about, but finding a job these days is not as easy as an algorithm doing all the work for you. It takes a tremendous amount of

You have to have a spreadsheet, you have to have your goals identified, you have to figure out who it is you want to speak

I've always told people, if you don't know what you want to do next,

figure out who you want to work for.

start with the company first or start

the leader that you're inspired by first and then work your way into a role.

I was just reaching out to people who I

relationships with that

admired. And I thought they were

that stood out to me of like, wow, they're going places and maybe they could give me some advice.

I started

My job starts just by asking so many

what is it you liked about working with me? What was it, my skill sets, do you think that would apply to even your company or other companies? Just information gathering.

And the chief revenue officer of Instructure, I've known him for a few years. I tried to place him a few

established a relationship here in Colorado

good friends.

the side, I

volunteering for the attorney general here in Colorado and he was running for governor. And this was while I was at SBMB and I was still

gung-ho on like, this is where I'm going to be

for my career. But I was doing some side fundraising work

the future

governor of the attorney general. And

invited James to come to an event that was all of these tech leaders who were supporting the attorney

this was just me doing volunteer work. And

It was a political type position. And he saw that in February and then we continued to stay in touch. And then when I talked with him in May, I believe it was, or June,

and I told him, was like, Hey, I'm thinking about this next. I don't know what it is. I told him my four goals. And after we chatted for an hour, he essentially said, I think I have something for you.

it's not going to align exactly

with what you've done before, but he goes, I think it's close enough. And he introduced me to the vice president of government affairs.

I work for now, who then reports to the chief revenue officer. But

by showing a lot of vulnerability, by asking a lot of questions, I was able to find myself somebody taking a little bit of a chance on me and saying, there's enough here where I know you could be a builder and you can help build out this new government affairs practice,

what we're calling strategic affairs.

that's essentially government affairs, it's enterprise client work, and it's also philanthropy and venture work where...

Gates Foundations or Zuckerberg Foundations will

money into school districts and say, want to use technology to help the school district grow or philanthropy that wants to help that happen, managing those relationships. so everything that

chief revenue officer saw in me,

being somebody who is a connector, who does think outside of the box of where something can fit somewhere else and grabbing somebody's attention by thinking creatively around.

here's how this could help your state or help your country or help your district grow. Jake could be the one to talk about all of that. And with us having over 20 different products and features within our portfolio and the amount of all the different products that I talked about at SPMB, it just all aligned really well. But I'm now in the world of politics. I'm in the world of government. I'm in the world of

needs.

it's different and it's exciting, but

I am going back to my roots again of like, okay, don't panic. How do we compartmentalize this? How do we make this easy to understand? How do we

make this pivot of doing something totally different, but finding the similarities of what I've done in my past to actually be applied to it. And I think a lot of people forget that. think people see titles, they see different industries that they can't be a part of, because like, well, it's not similar enough. And it's like, no, there are

bridge those gaps and not

overstretch it because some people might, but.

think about how different and similar your background and skill set is.

Kelly Dwyer (29:43)

There are a few things I wanna dig into

the trajectory you took us on. First of all, you talked about identifying the four areas or the

travel, the give back, the

tell us,

how did you?

identify those areas? Did you journal? Did you go through a

through conversations with close friends?

Jake (30:03)

a great question.

had an awesome opportunity with SPMB to work with

career coach. And

was based out in Bali.

was

And he helped me identify who I was and what I was really striving for. And he didn't pull me out of ⁓ SPMB by any means, but he made me realize what are my values.

are my top 10 values? And that was huge for me because I never understood what my values were. My top three I realized was challenge, creativity,

and

being inspired or,

inspiring others. And I realized how much I was doing that within SPMB and I was loving,

that.

But I was realizing for

well, can I do more with

four things that I'm asking for? And I came across those by understanding what my values were, what I was loving about the volunteer work I was doing with the search and rescue group, with the attorney general.

I do like politics and I do like the world of giving back in some way. And then one of my values was.

learning as well. Learning can be from travel and meeting interesting people. And so when I understood my values, I then understood,

are like the main things I'm looking for in the next job, the next career

that's how they formed essentially. was understanding my values was really important for me.

Kelly Dwyer (31:20)

it's highly recommended for everyone. If you're listening and you have not identified your

go through an exercise.

something online that'll guide you through it. Meet with the coach, do it with a buddy, a friend. Highly recommend

so then the second thing I want to dive into a little deeper is

you talked about how you had all these relationships with these senior C-level folks.

so you were doing a lot of information gathering is what you called it, and you began to ask them, hey, where could you see someone like me

I want to have these four things in my next career journey adventure,

do you see that I could fit?

How did you get the

to begin having those types of conversations?

Jake (32:06)

think it does start with

Charlie, who was my coach that I worked with. was a just asking him because he had worked with kind of like

he had worked with tons of execs, like yourself, you have worked with.

okay, let's take the knowledge of what he's seen and been a part of. And how does that apply to me? And I felt more comfortable

gathering that information, but it goes back

originally what started my career with an SVMB of understanding, establishing the credibility.

and slowing down and

sell the dream.

I was doing those three things with everyone that I reached out to where I was just like, you know me, you've worked with me, you understand me from my background and how we've worked together.

So that's the credibility piece. And then it was just slowing down and saying, here are the four things that I'm really looking for and the dream of, can these be met? Have you seen somebody with my background

go other

I got, I got a lot of nos. I got a lot of people saying, I'm not really sure.

It took a lot of me repeating myself over and over again.

one of the coolest things that happened, and this is where I don't think people take enough advantage of on LinkedIn is I did a very creative search

that's just.

me obviously knowing how to do so, but you can easily understand it. But I, did a search for people within

tech and who used to be executive recruiters. And then where are they

I was just finding people who used to be an executive search and finding them in leadership roles. And I was reaching out to them and I was saying, Hey, how did you get to where you're at? I saw you started executive search. I'm thinking about what else could I do in my career to get in a different place if I wanted to. And so many people.

got back to me and said, my gosh, I know exactly what you're going through. Here's where I saw myself. Here's how I got where I was. Read this book.

Look at this podcast. Find this YouTube

that I'd never met before, never communicated with. Random strangers were willing to help and say, that's great that you're starting to think about what could be next for you. Here's what I did.

is showing the vulnerability piece. go back to it, but just asking strangers, hey,

you obviously

made a pivot, what did you do? And people were willing to share.

Kelly Dwyer (34:10)

that is brilliant, by the way, the strategy, genius. And when you say,

a stranger's willing to share, you would just DM them on LinkedIn and say, hey, I see you used to be an executive recruiter and here you're doing this now and I'm trying to make a pivot out of executive recruiting. Would you be willing to talk

Yeah.

Jake (34:25)

Yeah, that's right.

I would reach out to maybe like 20 people and at least half would get back to me with

you should try this or looking at

nothing crazy, but it was just enough to get the wheel spinning.

It was cool. Yeah. ⁓

Kelly Dwyer (34:37)

So good, Jake, so good.

made a recommendation to people who are looking to make a pivot,

leading with company and or leader you wanna work with. Tell us more about that.

Jake (34:47)

Yeah, that's something that

do a lot of mentoring with college students just because that's where I started my career

helping college students find roles. And

I work with high school students who are trying to think about within search and rescue, like, do I go to school? Do I become a first responder? And so I've always had a passion for students

helping them figure out their way. And

I've always asked for feedback when I've talked with them and they've always said like, I love how you just simplified.

If you don't know what you want to do, figure out who you want to work for.

I think so many people go

shotgun selling their resume and just applying everywhere. And

it's actually a little bit more sniper related, but you need to be strategic

always tell people, I'd say. Find 10 companies you want to work for that are over 10,000 employees. Find 10 companies you want to work for that are 5,000 employees. Find 10 companies you want to work for that are.

employees and then find 10 companies below that. And before you know it, you have like 40 to 50 companies to choose from. And

you start realizing, well, what type of company is it that I want to be a part of? What type of leader do I want to be a part of? What type of product do I want to be a part of? You start to just compartmentalize and realize, hey, don't overthink it. Like there's actually a lot out there of different businesses, different industries that you could be a part of. And it doesn't have to be the role that you're chasing because

If somebody sees something in you, and especially if you're a recent college graduate, somebody wants you to do something, just get your foot in the door, but you'll be happy that you're working for that type of company, that type of product, that type of leader,

type of industry, and start

think if you choose that one company, I have to stay with it forever.

Start with just very, very small thinking of if you don't know what you want to do, figure out who you want to work for. That's kind of been my attitude to them. And I think that applies to a lot of people still.

Kelly Dwyer (36:24)

That's great. That's good advice. Yes.

Jake (36:29)

people who are wanting to pivot,

like, well, I've only been in cybersecurity my whole career. And

that's okay. You know, what is relatable? What is similar to cybersecurity? Probably FinTech. Like FinTech's really interesting. It's a lot of compliance. It's a lot of different

and regulations that you could probably find yourself fitting

just start with FinTech and find

500 FinTech companies and then find 10 early stage startup FinTech companies and start there.

if they all fail and they all say we don't want cyber security is not good. Okay, think

well system or decide your security

you might during that process you realize? outside of FinTech

crypto could be a really interesting

Kelly Dwyer (37:05)

Yeah, you know,

you

describing before about

reaching out, doing your information gathering calls with these

executives and with the ⁓ strangers, yeah.

Jake (37:15)

Strangers.

Kelly Dwyer (37:17)

you know, I often tell my clients who are looking to make a transition of some

you don't have to know right away the exact role and the title and all of these things. You start...

where you are, you start with what you know, and you started with the four things. Here's what I know that I want. And here's my background. And I don't exactly know where I'm going to land with it. But this is what I want. Do you have any ideas? Does

spark for you person that I'm talking to about what I could do with that, or directions I could go or other people I could talk to? And so you

kind of called it into

willing to be vulnerable and talk about it. Talk about where you're at now and what you're looking for. So bravo. Okay, one last thing, because I know

Jake (38:05)

Yeah.

Kelly Dwyer (38:07)

coming up on

person who ultimately hired

James and Chris, and one of them, I think it was James,

used the word builder for you. ⁓

belief that they could have about themselves. Was that something you knew prior to hearing him call you that that you were a builder? Or was there a

you went through to try that identity on and then embrace that identity and understand what it means for you?

Jake (38:34)

a really good question because I actually think what we started with originally that I started with was I'm very creative and I think outside of the box and I know how to connect people to different areas that they hadn't thought about before. And then both James and Chris said, you know, that's building something that's building someone's career for them. And we're building a future for the company of that person coming on board.

for their goals and what's

I was not using the word

were the ones who kind of saw that in

by me just establishing myself as like, am creative. I know how to think differently. And they said, well, we need someone

out this business unit.

It sounds like you've built other things before, or at least you've started on them and you've had a plan and a roadmap and an idea. And I said, yes,

that is

long as you're conveying, but I think it takes a lot of work for somebody to like, for me to even say, and believe in myself that I am a creative thinker, I know how to think outside the box. And that started with me understanding my values that started with

out the ideas of the three school subjects from years ago and following with

I think everyone can help somebody else find a different path for them. If you know how to effectively communicate.

who you truly know and what your values are and what you've been a part of. And somebody else will hopefully, a good leader will see that in you and say, you're actually this, you are a builder.

You're trying to build, know, even within your Apple rescue patrol and like fundraising, like I was trying to build things, but I was falling. It was just so much work. And it's like, we need to build more around that. And

though like I didn't say accomplished,

building out like a $20 million business,

I started the plans for it, I started the ideas for it, I started the architecture for it, and people see that.

think it's just starting with one word

Kelly Dwyer (40:20)

does.

Jake (40:22)

who you are and somebody else hopefully gravitating towards that and seeing something in you. But you have to be able to demonstrate that and talk effectively about it.

Kelly Dwyer (40:31)

Yes, and be willing to talk about it. Right, right. Be willing to talk about

Jake (40:33)

Yeah, that's right.

Kelly Dwyer (40:35)

what haven't you said yet in our conversation that you want to make sure that the listener hears?

Jake (40:42)

think we've talked about it a

you don't have to have everything figured out, ask a lot of questions, show the vulnerability.

I will say to a lot of the execs that are listening to this,

ask for feedback all the time,

the recruiter that you're working with, from the boss you're interviewing

show the vulnerability of like, I don't know everything. What else did I miss on?

because I've seen tons of execs fail because they use the word I versus we.

see them not being able to understand that to be an exec, you have to have a two for one. Like if you're in sales, you need to be a numbers person and you need to be spreadsheet driven, not just motivating people. have to also have your products. You need to be a sales product person. You need to get sales pumped up on what you're doing, but you also need to get technology pumped up to build. And if you're a technologist and you're a CTO, like you need to understand, well, what's customer success talking about? What is the CS team? Like you need to have a two for one for everything you're a part of. so.

think, I think a lot of executives out there think that they have everything figured out where a recruiter can be a gateway to them saying, well, I talked to thousands, thousands of different people of different backgrounds and I can help you grow differently and you should use those recruiters in your life to,

grow

and before you know it, that's you establishing the vulnerability of saying, I don't have it all figured out. You probably talked to a lot more people. What else am I not saying or what else should I be

Kelly Dwyer (41:59)

the two for

can't end without me diving into that a little deeper.

Jake (42:03)

Ha ha ha!

Kelly Dwyer (42:04)

everyone should have a two for one. So tell me as a coach, like what would be my two for

Jake (42:08)

what's coming to mind immediately

active listening, but it's also active applying, right? It's like, okay, well, if I'm hearing what you're saying, I'm applying

these skills of what other people have said to me prior. And I think that

for

it's almost being like

I'm a psychologist and psychiatrist in a

listening to everything, but I'm going to then the psychiatrist

I'm going to give you a dose of something and that's you applying to what their needs are.

and if I had to put it in executive terms,

so many. It's being product, it's being marketing, and it's being,

say it's maybe those two combined, those two functions where

I'm understanding the person themselves as the product of who they are, but then we have to market you for where you need to go next.

think that's the two for one

a coach should bring is understanding the person, the product, them, and then understanding the marketing of, how do we get people to be attracted to who you are? And how do you get people to be attracted to who you are? And understanding all the different products that you have.

Kelly Dwyer (42:59)

Yes. Yes.

Yes, I love

that is for anyone who's making a career privet for sure. And as a coach, anyone who's trying to make any kind of transformation. And so the way I interpret what you just said was

it's the listening and the reflecting back and understanding who the person is in front of me that I'm hearing and interacting with. And then it's taking that and

Jake (43:21)

Mm-hmm.

Kelly Dwyer (43:25)

offering

ideas, suggestions, perspectives based on all the years of coaching conversations, based on all

background that I have, right? So I'm

what I know, offering it, right? And then they can choose to take it or leave

Jake (43:43)

Yeah, that's right. But if you were to talk to a CEO who wanted to hire you as like, say, their CEO, and they were to say, Well, what can you bring?

you just compartmentalize it again, and you just say, Well, I've done product, which is people and understanding their products, who they are, and their skills, and what they have to offer, but I've had to market them as well. I'm your product and your marketing leader.

That's what I know. And it's thinking

so simple and so creatively in that way. And there might be a little bit of sugar coating on top of that. But

That just gets the wheels spinning, right? It just gets you thinking a little bit differently about yourself and not taking everything so

wow, I do run those two functions within my business of coaching or whatever it is you're a part

just simplify it a little bit, but make it fun.

Kelly Dwyer (44:24)

Okay, simplify and make things fun. So Jake, if anyone wants to follow up with you after they listen or watch this conversation, where do you want them to go to find

Jake (44:27)

Yes.

LinkedIn is like my best friend. I know it well. So find me on LinkedIn.

I'll always get back to somebody on LinkedIn.

Kelly Dwyer (44:42)

Thank you so much for your time today, Jake. This has been a wonderful conversation. ⁓

Jake (44:44)

Thank you. This has been great, Kelly.

Thanks for all the questions and thanks for doing what you do with inspiring people and helping people realize what their potential is.

we need more people like you.

Kelly Dwyer (44:54)

Thank you. Well, I love my

Jake (44:57)

You too.

Kelly Dwyer (44:55)

Have a wonderful day.