From Bureaucracy to Breakthroughs: Changing the Face of Government Technology | The Pair Program Ep31

Sep 5, 2023

From Bureaucracy to Breakthroughs: Changing the Face of Government Technology | The Pair Program Ep31

Interested in a career in govtech?

In this episode, we hear from Alissa Bookwalter and Bryon Kroger – two professionals who have made a huge impact in modernizing the federal space.

They discuss:

  • The traits that they look for in employees who want to join the govtech space
  • What it takes to truly bring modernization into the federal space
  • Common misconceptions about working in the government space
  • How they’ve successfully “hacked bureaucracy”

And much more!

About the guests:

Alissa Bookwalter currently serves as the Chief Talent Officer at the Griffiss Institute (GI), where her work seeks to impact and inspire the federal government’s next generation of technical talent. Prior to the GI, Alissa served as a Chief of Staff at Kessel Run, Deputy Director of Talent Management at the United States Digital Service, and supported military health programs for over 10 years.

Bryon Kroger is Founder and CEO of Rise8. Before that, he spent seven years as a targeteer using terrible software, which led him to cross-train to acquisitions and spend his first year building a transformation at AFLCMC, ultimately becoming one of three co-founders of Kessel Run. Bryon served as Kessel Run COO for two years, leading acquisitions, development, and operations for the enterprise-scale software lab that defined DoD DevSecOps. There he pioneered the first cATO alongside many other DoD “firsts”. Bryon later launched Rise8 in 2019 to help change agents overcome bureaucracy and transform the way they build and deploy software to create outcomes in prod. He has built several cATOs from the ground up on both sides of the aisle and is a leading expert on the topic, as well as defense digital transformation and bureaucracy hacking more generally. 

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Transcript
Tim Winkler:

Welcome to the Pair Program from hatchpad, the podcast that gives you

Tim Winkler:

a front row seat to candid conversations with tech leaders from the startup world.

Tim Winkler:

I'm your host, Tim Winkler, the creator of hatchpad, and I'm your

Mike Gruen:

other host, Mike

Tim Winkler:

Gruen.

Tim Winkler:

Join us each episode as we bring together two guests to dissect topics

Tim Winkler:

at the intersection of technology, startups, and career growth.

Tim Winkler:

Hello everyone, and welcome back for another episode of the pair program.

Tim Winkler:

I'm your host, Tim Winkler, accompanied by my cohost, Mike Gruen.

Tim Winkler:

Um, Mike, I gave you a sneak peek into my, my question for the, uh, guests here.

Tim Winkler:

We always ask Mike, uh, a brain buster here to, to kick things off.

Tim Winkler:

But are they, are you, um, are you a condiments guy?

Tim Winkler:

I mean, yes.

Tim Winkler:

Do you have like a go to, a go to condiment?

Mike Gruen:

I mean, honey mustard is pretty solid.

Mike Gruen:

Uh, I mean, I'm not, I'm not a fan of ranch.

Mike Gruen:

I'm not a fan of blue cheese.

Mike Gruen:

I'm one of those people who doesn't like either of them.

Mike Gruen:

So,

Tim Winkler:

so I just heard about this this morning and, um, maybe folks

Tim Winkler:

have heard it before, but, uh, you know, there's kind of like freestyle

Tim Winkler:

soda fountain machines, like Coca Cola has them in certain restaurants.

Tim Winkler:

Um, so Heinz just created a condiment mixing machine where they'll let

Tim Winkler:

restaurant customers kind of create their own pre mixed custom dipping sauces.

Tim Winkler:

So you start with like a base, like ketchup, ranch, barbecue, like

Tim Winkler:

Heinz 57, and then you can bake in like jalapeno, chipotle, buffalo,

Tim Winkler:

mango, and then spice it up or down.

Tim Winkler:

So I was thinking of like, what kind of, kind of mix would you,

Tim Winkler:

would you go with, uh, if you could.

Tim Winkler:

You know, get a little freestyle condiment going.

Tim Winkler:

Hmm.

Tim Winkler:

That's

Mike Gruen:

interesting because I feel like my, the first thing I would

Mike Gruen:

try to recreate would be like the McDonald's secret sauce, which is

Mike Gruen:

ketchup, mayo, some probably relish.

Mike Gruen:

The Big Mac, the Big Mac sauce.

Mike Gruen:

Yeah, yeah.

Mike Gruen:

Then after that, yeah, I don't know.

Mike Gruen:

I'd have to play with that.

Mike Gruen:

I like spicy.

Mike Gruen:

It depends on what I'm getting, putting it on.

Mike Gruen:

Burger.

Mike Gruen:

It's different than

Tim Winkler:

hot dog.

Tim Winkler:

Hot dogs, mustard.

Tim Winkler:

They can mango, ranch, ketchup.

Tim Winkler:

Oh, interesting.

Tim Winkler:

Mango.

Mike Gruen:

See, I like mango, mango rant, like, I don't know.

Mike Gruen:

I'm

Tim Winkler:

yeah.

Tim Winkler:

Anyway.

Tim Winkler:

Okay.

Tim Winkler:

All right.

Tim Winkler:

Good stuff.

Tim Winkler:

Um, I have to change my pairing.

Tim Winkler:

Good.

Tim Winkler:

Good to know.

Tim Winkler:

Oh, fun fact too on that.

Tim Winkler:

So I was doing like research on this for way too long.

Tim Winkler:

Uh, but, uh, the, the, the guy that invented that Coca Cola

Tim Winkler:

freestyle dispenser Segway.

Tim Winkler:

Oh, not, not the best, not the best track record, but, uh, yeah,

Mike Gruen:

very eclectic inventor.

Mike Gruen:

Yeah.

Tim Winkler:

Um, cool.

Tim Winkler:

All right.

Tim Winkler:

Well, enough sauce, uh, sauce talk.

Tim Winkler:

Let's, let's give our listeners a preview of today's episode.

Tim Winkler:

So.

Tim Winkler:

This is going to be another episode, uh, in line with a recent mini series

Tim Winkler:

that we've been promoting around augmenting innovation from commercial

Tim Winkler:

tech into different areas of the government, like Department of Defense

Tim Winkler:

and different federal civilian agencies.

Tim Winkler:

And so today we want to discuss.

Tim Winkler:

You know, the talent transition from commercial products, uh, into maybe

Tim Winkler:

government services or government contracting or, uh, a consultancy

Tim Winkler:

that's supporting the government.

Tim Winkler:

So we'll explore what commercial technologists should know when they

Tim Winkler:

consider opportunities supporting, you know, like federal software projects.

Tim Winkler:

Uh, and then we'll also kind of like dissect some of the digital landscape

Tim Winkler:

across the federal software ecosystem, highlight what skill sets are trending

Tim Winkler:maybe in:Tim Winkler:

this, this type of innovation.

Tim Winkler:

So, um, to unravel the subject, we've invited two guests with firsthand

Tim Winkler:

experience navigating the world of tech from modern GovTech environments.

Tim Winkler:

Uh, so we're joined by Alyssa Bookwalter, who's.

Tim Winkler:

departments for government agencies like the United States Digital Service,

Tim Winkler:

which is an agency launched almost 10 years ago to modernize government

Tim Winkler:

services and user experience.

Tim Winkler:

Uh, most recently has been helping scale out innovation labs and

Tim Winkler:

accelerators that are impacting, uh, the Department of Defense.

Tim Winkler:

And then alongside Alyssa, we have Brian Kroger.

Tim Winkler:

Brian, uh, I think it was like a, like a visionary in the defense tech

Tim Winkler:

industry, um, served as a captain in the United States Air Force.

Tim Winkler:

Um, Brian, you know, I've, I've read up on your, on your background as well.

Tim Winkler:

And you know, you saw this need for advanced tech in the military created

Tim Winkler:

Kessel Run, uh, as a precursor to your current venture rise eight.

Tim Winkler:

We'll touch on the Kessel Run story in our episode.

Tim Winkler:

I think it's got a lot of relevance to the topic.

Tim Winkler:

But RiseAid is a digital services company that helps customers in high compliance

Tim Winkler:

organizations like the government build and deploy software more efficiently.

Tim Winkler:

Alyssa and Brian, thank you both for joining us today.

Tim Winkler:

Thanks for having us.

Alissa Bookwalter:

Yeah, thank you.

Alissa Bookwalter:

Excited to be here.

Tim Winkler:

Yeah, good stuff.

Tim Winkler:

Well, let's dive into two, um, I'm sorry, before we dive into the discussion.

Tim Winkler:

We can't, uh, skip over one of our favorite segments, which is pair me up.

Tim Winkler:

We'll all go around the room and shout out a complimentary pairing.

Tim Winkler:

Mike, you always start us off.

Tim Winkler:

So what, what do you got for us today?

Tim Winkler:

And I hope it doesn't suck because you already know, but

Mike Gruen:

now I have ketchup and mayo on my mind, but now I'm

Mike Gruen:

going to stick with my guns and I go with a change in optimism.

Mike Gruen:

I think they go pretty well together.

Mike Gruen:

I think there's a lot of people who look at change and get very like wound up

Mike Gruen:

about it and like, sort of see it as.

Mike Gruen:

Bad, um, and especially in engineering.

Mike Gruen:

I've seen that.

Mike Gruen:

So like, sort of just embracing that change happens.

Mike Gruen:

Change is good and being optimistic about it and trying to figure out

Mike Gruen:

what good can come from this change.

Mike Gruen:

So that's that's my pairing

Tim Winkler:

this time.

Tim Winkler:

Hey, that doesn't suck.

Tim Winkler:

I thought you were I thought you were prepping me for something really.

Tim Winkler:

I mean, I guess

Mike Gruen:

you're right.

Mike Gruen:

Expectations low and then surprise.

Mike Gruen:

That's that's Maybe that'll be, yeah,

Tim Winkler:

I like it, man.

Tim Winkler:

I like that.

Tim Winkler:

Everybody could use a, that type of outlook, uh, in today's world.

Tim Winkler:

So, um, good, good, good call.

Tim Winkler:

Um, all right, I'll, I'll go.

Tim Winkler:

Um, so this past weekend, my wife and I, uh, in our five month old baby now, and

Tim Winkler:

in our dog, we went for a, A Mother's Day getaway and, uh, went out into the

Tim Winkler:

mountains out near Charlottesville, uh, went on, uh, Alice's first hike,

Tim Winkler:

and something that my wife and I would always do when we go on hikes is

Tim Winkler:

touch, touch trees, uh, every so often.

Tim Winkler:

And for us, it was just something that, uh, kind of brings us into the moment.

Tim Winkler:

So something about being present, you know, being, being out there.

Tim Winkler:

Um, and, uh, uh, touching the tree while you're going for a hike.

Tim Winkler:

So mine is going hiking and touching trees.

Tim Winkler:

Uh, and, uh, that's, uh, we actually had, uh, the five month old, we put her

Tim Winkler:

hand on, on the tree and videotaped it.

Tim Winkler:

It was pretty, pretty adorable little moment.

Tim Winkler:

Um, but, um, yeah, big, big, big fan of being outdoors.

Tim Winkler:

So that one was, uh, uh, my pairing for today.

Tim Winkler:

Um, but let's go ahead and pass it along to our guests.

Tim Winkler:

Um, Alyssa, we'll actually start with you if you want to give us a

Tim Winkler:

quick intro and tell us your pairing.

Alissa Bookwalter:

Yeah.

Alissa Bookwalter:

Hi, everyone.

Alissa Bookwalter:

Um, I'm Alyssa.

Alissa Bookwalter:

I spent, oh my gosh, about 10 years, um, first part of my

Alissa Bookwalter:

career supporting military health.

Alissa Bookwalter:

Um, did a lot of stuff with wounded, ill and injured, uh, military

Alissa Bookwalter:

service members, veterans and their families, which is really cool.

Alissa Bookwalter:

Um, and then I made the pivot into kind of civic tech and all things tech.

Alissa Bookwalter:

Um, spend some time working as a federal civilian, like you said, at the digital

Alissa Bookwalter:

service and then actually at Kessel Run.

Alissa Bookwalter:

Um, and now I'm at a small nonprofit.

Alissa Bookwalter:

I'm a chief talent officer, um, called the Griffith Institute.

Alissa Bookwalter:

Um, fun stuff.

Alissa Bookwalter:

I have three cats and two dogs and I live in Washington DC.

Alissa Bookwalter:

Um, and this week my pairing is, um, Doggy Daycare and Usher.

Alissa Bookwalter:

Um, that's a little bit probably off the wall, but, uh, my dog Leo goes to

Alissa Bookwalter:

daycare and he absolutely loves it.

Alissa Bookwalter:

And I get the pleasure of dropping them off most mornings.

Alissa Bookwalter:

Um, One particular, I think it, I don't remember what day it was this week,

Alissa Bookwalter:

but I was just kind of in my head.

Alissa Bookwalter:

There was a lot of, you know, stress going on and I, I drop him

Alissa Bookwalter:

off and I'm walking back to my car.

Alissa Bookwalter:

And all of a sudden I hear, um, one of my favorite usher songs from back in

Alissa Bookwalter:

the day, start blaring on the music.

Alissa Bookwalter:

And I look back and I see my dog just jumping around and having fun.

Alissa Bookwalter:

And I'm like, this is the most bizarre, surreal moment, but I like it.

Alissa Bookwalter:

And it took me back and I'm going to have a damn good day.

Alissa Bookwalter:

Um, so that's my pairing.

Tim Winkler:

Nice.

Tim Winkler:

Oh man, that's great.

Tim Winkler:

Um, that is a throwback as well.

Tim Winkler:

Is, do you have a favorite Usher song?

Alissa Bookwalter:

Um, I just, he's a good artist, but the song that was

Alissa Bookwalter:

playing was, I don't know if you remember, it was, I think it was called Yeah.

Alissa Bookwalter:

Um, it has little John or something, and I don't, I hadn't heard it

Alissa Bookwalter:

in a hot minute, but here we go.

Alissa Bookwalter:

Here we are.

Tim Winkler:

How did our producer know that our producer is sitting in chats

Tim Winkler:

over here saying, yeah, in all caps.

Tim Winkler:

I was like, that's, that's a scary, but he knew it somehow

Tim Winkler:

it is a, it is a popular song.

Tim Winkler:

So, all right, that might be the most random pairing we've ever had on the show.

Tim Winkler:

So that is a good.

Tim Winkler:

Nice.

Tim Winkler:

I like it.

Tim Winkler:

Love it.

Tim Winkler:

Awesome.

Tim Winkler:

Awesome background too.

Tim Winkler:

We're excited to, uh, dive deeper into that.

Tim Winkler:

So, um, cool.

Tim Winkler:

Well, Brian, how about yourself?

Tim Winkler:

Quick intro and, and your parent.

Bryon Kroger:

Yeah.

Bryon Kroger:

So I'm Brian Kroger, CEO and founder of RISE 8.

Bryon Kroger:

Prior to this, I spent 10 years active duty Air Force for seven years.

Bryon Kroger:

I was a targeting intelligence officer on the last three years I

Bryon Kroger:

founded a Kessel Run and served as a chief operations officer before

Bryon Kroger:

getting out and starting RISE 8.

Bryon Kroger:

My pairing, I've been traveling a ton, I've been on the road,

Bryon Kroger:

conferences here in Tampa where I'm located, so it's just been hectic.

Bryon Kroger:

Um, but I live on the water.

Bryon Kroger:

Our office is on the water here.

Bryon Kroger:

Uh, and we have, uh, uh, have a boat club membership.

Bryon Kroger:

So whenever people come to town, I like to take them out on the boat.

Bryon Kroger:

Since it's been so hectic, my pairing lately has been boat lunch.

Bryon Kroger:

So we've been doing a lot of boat lunches.

Bryon Kroger:

I just had some employees that were in town yesterday for some

Bryon Kroger:

recording, took them on boat lunch.

Bryon Kroger:

I think I've done like.

Bryon Kroger:

I don't know, probably like six or seven boat launches this month.

Bryon Kroger:

So, uh, boat launch, I will say though, um, I really liked Mike's, uh, one of

Bryon Kroger:

my favorites, uh, things to pair is optimism and skepticism, skepticism.

Bryon Kroger:

So I always refer to myself as an optimistic skeptic.

Bryon Kroger:

And I feel like, uh, that's like part of the leadership

Bryon Kroger:

OS to be a really good leader.

Bryon Kroger:

You have to have optimism and skepticism.

Bryon Kroger:

So cool.

Bryon Kroger:

Love that one.

Bryon Kroger:

Mike.

Bryon Kroger:

Thank

Mike Gruen:

you.

Mike Gruen:

I like yours as well.

Mike Gruen:

That

Tim Winkler:

was pretty good.

Tim Winkler:

So I've, my buddy's on a, one of these boat subscriptions.

Tim Winkler:

Is it carefree boats?

Tim Winkler:

Is that freedom boat club, freedom boat club.

Tim Winkler:

Cool.

Tim Winkler:

And what kind of boat was a pontoon or you go on party barge for lunch

Tim Winkler:

or what's the, What's the boat of choice that you take these.

Tim Winkler:

Take these folks out on lunch.

Tim Winkler:

Tampa, Tampa's got a good setup.

Bryon Kroger:

There's actually like 16 locations you can rent from and they

Bryon Kroger:

have like, you know, anywhere from like five to 20 boats each location

Bryon Kroger:

here by our office though, has a lot of center consoles, um, deck boats.

Bryon Kroger:

I've taken my kids tubing out here, uh, for this location.

Bryon Kroger:

Um, yeah.

Bryon Kroger:

And they had, they have pontoons too, if we've got a big crowd, but I usually

Bryon Kroger:

grab like a center console with a, like two 50 on the back so we can just

Bryon Kroger:

really all up the river and go get

Tim Winkler:

some lunch.

Tim Winkler:

Wow.

Tim Winkler:

So convenient too.

Tim Winkler:

You don't have to worry about trailer trailing it or anything like that.

Tim Winkler:

Good stuff.

Tim Winkler:

All right.

Tim Winkler:

Good round.

Tim Winkler:

I like that.

Tim Winkler:

Um, well let's, uh, let's, uh, transition and, and get into,

Tim Winkler:

uh, the meat of our discussion.

Tim Winkler:

So, um, again, we're going to be talking about transitioning from, you know,

Tim Winkler:

commercial into, into some of these government environments as a technologist.

Tim Winkler:

And just to clarify here, because a lot of our audience, you know,

Tim Winkler:

they don't have any understanding of a lot of, you know, government

Tim Winkler:

or defense or a lot of that lingo.

Tim Winkler:

Um, so I wanted to kind of, you know, start with by saying that there's

Tim Winkler:

differences between pursuing a role directly with a government agency and

Tim Winkler:

pursuing an opportunity with a company that supports the government, like a

Tim Winkler:

systems integrator or a tech consulting company or a pure product company.

Tim Winkler:

Um, and oftentimes these companies, if they're providing technical services to

Tim Winkler:

the government, then they, they might be referred to as a government contracting

Tim Winkler:

company, just some of the lingo.

Tim Winkler:

Um, and if we're spitting around acronyms throughout this, just kind of like spell

Tim Winkler:

it out, uh, cause I think that's always helpful and the government loves acronyms.

Tim Winkler:

Uh, so that, that will be helpful for the guests, but, um, let's start with, with

Tim Winkler:

you, Alyssa, um, you know, you've, you know, you've kind of run these talent,

Tim Winkler:

uh, teams and multiple environments.

Tim Winkler:

But you know, let's maybe start when you're recruiting talent at like the U.

Tim Winkler:

S.

Tim Winkler:

Digital service.

Tim Winkler:

Um, you know, what were some of the characteristics or traits

Tim Winkler:

that you were looking for?

Tim Winkler:

Um, when technologists, you know, we're joining and then we can

Tim Winkler:

jump to you, Brian and look at this from some other environments

Tim Winkler:

like a castle and rise eight such.

Tim Winkler:

But let's, let's kick that, kick it off with that.

Alissa Bookwalter:

Yeah, so I think, I think the foremost thing that, that

Alissa Bookwalter:

I look for it, it, it's a personal thing, but it was also really based at

Alissa Bookwalter:

the organizations that I worked for.

Alissa Bookwalter:

Um, and whether that was on the government side or whether it was like

Alissa Bookwalter:

a duty contracting side, um, you really want folks who are mission driven.

Alissa Bookwalter:

Um, so you really want folks who are not in it for, you know, a paycheck

Alissa Bookwalter:

or aren't necessarily in it to do the, the latest and greatest because.

Alissa Bookwalter:

As we'll probably get into technology, the state of technology in the government

Alissa Bookwalter:

is a lot different than in the private sector and moves a lot slower, right?

Alissa Bookwalter:

Um, and so you have to have people that have grit, that have tenacity, that are

Alissa Bookwalter:

willing to take on a challenge, um, and that, again, when days get hard, because

Alissa Bookwalter:

they'll get really, really, really hard, you know, they're willing to kind of

Alissa Bookwalter:

keep moving the needle, and maybe they thought the needle move was two miles,

Alissa Bookwalter:

but it's a quarter of an inch, but that quarter of an inch will impact millions

Alissa Bookwalter:

of people, or that quarter of an inch will like, you know, do something to save

Alissa Bookwalter:

the warfighter, um, and that's pretty, You can't get that in the private sector.

Alissa Bookwalter:

Um, and so I, I'd really start with that and that's, that's hard to find.

Alissa Bookwalter:

That's, that's pretty hard to find.

Tim Winkler:

Yeah.

Tim Winkler:

Having somebody, especially, you know, if you're trying to recruit

Tim Winkler:

someone from the commercial space, um, and talk about compensations and

Tim Winkler:

today's market have just been crazy inflated in the last couple of years.

Tim Winkler:

And so when you, when you ask someone to trade off comp for the, for the

Tim Winkler:

mission, um, you really got to have a passion for that mission, uh, because

Tim Winkler:

you get used to a certain quality of life, you know, with a certain,

Tim Winkler:

you know, paycheck, um, and, uh, it might not always be that competitive

Tim Winkler:

in those types of environments.

Tim Winkler:

So, um, I think that's a great, a great, um, call out is, you know, really making

Tim Winkler:

sure that you're prioritizing the mission, um, if you're pursuing that opportunity.

Tim Winkler:

Brian, uh, let's jump, let's jump over to you real quick.

Tim Winkler:

And, uh, I'd love to hear angle on, on this side of it.

Tim Winkler:

Um, maybe from like rise eight, um, and, and Kessel run.

Tim Winkler:

But if you're open to it too, you know, um, I'd love for you to

Tim Winkler:

share your story with our audience on how Kessel run came to be.

Tim Winkler:

I think it's a, I think it's a powerful message, uh, on why there's.

Tim Winkler:

Such a need to push innovation forward in parts of the government

Tim Winkler:

specifically in defense.

Tim Winkler:

Um, so yeah, I'll pass it to you.

Tim Winkler:

Yeah, I love that, uh,

Bryon Kroger:

Alyssa hit on two really important things to me and my story.

Bryon Kroger:

And I think the Kessel Run story, which are, um, you know, mission

Bryon Kroger:

or I'll call it impact and then grit, um, grit's a really good word.

Bryon Kroger:

And actually fun fact, uh, rise eight comes from the Japanese proverb, all

Bryon Kroger:

seven times stand up eight or rise eight.

Bryon Kroger:

Um, which is, uh, a quote that I stole from, uh, Angela

Bryon Kroger:

Duckworth's book, uh, called Grit.

Bryon Kroger:

So she said in there that if she were ever to get a tattoo, she would get

Bryon Kroger:

a tattoo that said Fall 7, Rise 8.

Bryon Kroger:

Uh, in honor of that Japanese proverb, which is, uh, a story

Bryon Kroger:

of transformation, right?

Bryon Kroger:

So if you fall seven times, you would stand up seven times.

Bryon Kroger:

So fall seven, rise eight is about standing up greater than when you fell.

Bryon Kroger:

So, um, grit is what it takes to do that.

Bryon Kroger:

And especially in the government space.

Bryon Kroger:

Um, that's, uh, you know, going to, to my story, I said, I started as

Bryon Kroger:

an intelligence officer seven years doing primarily targeting operations.

Bryon Kroger:

And, um, I, I didn't know much about the air force, especially

Bryon Kroger:

intelligence when I joined.

Bryon Kroger:

So, you know, when you hear you're going to be an intelligence officer,

Bryon Kroger:

you're coming out of college.

Bryon Kroger:

Like I didn't do ROTC or anything, so I had no insight.

Bryon Kroger:

I just applied and I got selected to be an intelligence officer.

Bryon Kroger:

And I thought I was going to go do some Bourne stuff, right?

Bryon Kroger:

Like, oh, Jason Bourne.

Bryon Kroger:

I didn't actually think that, but you like have these expectations

Bryon Kroger:

that like, Hey man, you're going to have this great technology.

Bryon Kroger:

There's going to be like.

Bryon Kroger:

You know, you minority report, whatever, pick your favorite movie of

Bryon Kroger:

like holograms and cool technology.

Bryon Kroger:

And I show up and it like takes me two hours to log into my email.

Bryon Kroger:

Right.

Bryon Kroger:

And so, um, I spent seven years using really bad software to conduct the

Bryon Kroger:

most critical missions on the planet.

Bryon Kroger:

Um, and, uh, you know, the, the, whether you're talking about the battlefield

Bryon Kroger:

or, you know, providing veterans care at a VA hospital or all the crazy,

Bryon Kroger:

awesome missions that you can do inside of the federal government.

Bryon Kroger:

Um, the world around us is operating at digital speed, right?

Bryon Kroger:

Machine speed and in the D.

Bryon Kroger:

O.

Bryon Kroger:

D.

Bryon Kroger:

We have the most advanced hardware on the planet.

Bryon Kroger:

Uh, but oftentimes we're conducting those missions with software that

Bryon Kroger:

doesn't work or is forcing us to operate at human speed when we need

Bryon Kroger:

to be operating at machine speed.

Bryon Kroger:

So I just saw really terrible things happen.

Bryon Kroger:

Um, you know, everything from.

Bryon Kroger:

You know, whether it's civilian casualties, troops in contact that

Bryon Kroger:

we can't support soldiers, you know, getting hurt or bad guys getting away.

Bryon Kroger:

Like, I've seen it all and, uh, like, software is a big differentiator

Bryon Kroger:

there from my point of view.

Bryon Kroger:

And, um, after seeing a particularly bad incident, I actually requested

Bryon Kroger:

to transfer from targeting to acquisitions, which nobody does.

Bryon Kroger:

I'd like the coolest job.

Bryon Kroger:

And then went to like, sorry to say it, people might take issue, but like didn't

Bryon Kroger:

want to go be a procurement person.

Bryon Kroger:

Let's just put it that way.

Bryon Kroger:

The day that I showed up, uh, I called D.

Bryon Kroger:

I.

Bryon Kroger:

U.

Bryon Kroger:

defense innovation unit.

Bryon Kroger:

It was actually X at that time.

Bryon Kroger:

Experimental, um, got put in touch with Colonel Enrique and we started,

Bryon Kroger:

uh, what would then become Kessel run?

Bryon Kroger:

Um, and, uh, later joined by our 3rd co founder, uh, Lieutenant Colonel

Bryon Kroger:

Jeremiah Sanders or Colonel Sanders.

Bryon Kroger:

Uh, yeah.

Bryon Kroger:

And, um, and then, yeah, Kessel Run became, I would say, inarguably the,

Bryon Kroger:

the largest and most successful digital transformation in federal government.

Bryon Kroger:

Um, we pioneered a lot of different things, like being able to continuously

Bryon Kroger:

deliver your software to a production environment, which I think in

Bryon Kroger:

commercial we take it, uh, for granted.

Bryon Kroger:

But, um, Kessel Run was one of the first organizations to establish that and in

Bryon Kroger:

doing so was able to continuously deploy software to end users out in the field,

Bryon Kroger:

um, iterate based on their user feedback, uh, which, you know, contributed not

Bryon Kroger:

only to really great mission outcomes, but going to what we're here to talk

Bryon Kroger:

about today, the talent at Kessel Run, we're able to attract unbelievable

Bryon Kroger:

talent because not only did we have that mission, but you actually got to see

Bryon Kroger:

the impacts of your work in real time, which is pretty rare in government.

Bryon Kroger:

Thank you.

Tim Winkler:

Yeah, I love the story.

Tim Winkler:

Um, I, I, I love how it kind of comes full circle for you.

Tim Winkler:

And, uh, you know, as an entrepreneur, um, you know, was this kind of like your

Tim Winkler:

Your step into it, you know, um, you know, did, did you have anything prior

Tim Winkler:

to military that you started anything on your own or was, was this kind of

Tim Winkler:

like your foundation for, you know, pursuing your own thing at rise eight?

Tim Winkler:

Yeah.

Tim Winkler:

I mean,

Bryon Kroger:

I think I probably stepped out on my own a lot,

Bryon Kroger:

uh, throughout my career.

Bryon Kroger:

But nothing ever really like entrepreneurial, maybe like an

Bryon Kroger:

entrepreneur inside the military.

Bryon Kroger:

But, um, I think for me, I wanted to continue achieving that, like, same level

Bryon Kroger:

of impact in the military kind of makes it hard from a talent management perspective

Bryon Kroger:

as a uniformed military member.

Bryon Kroger:

Like, I was a captain, so I was fairly junior.

Bryon Kroger:

Kessel room grew very quickly to the point that it was now like the

Bryon Kroger:

size of an organization that would be taken on by a colonel, right?

Bryon Kroger:

Several ranks where I was.

Bryon Kroger:

So, um, for me, getting out seemed like a natural choice of being

Bryon Kroger:

able to continue to achieve the same level of impact and also.

Bryon Kroger:

In technical terms, we talk a lot about scaling horizontally

Bryon Kroger:

versus, uh, vertically.

Bryon Kroger:

Um, I could keep going and doing like, uh, vertical scaling, like go to the

Bryon Kroger:

next program and do something cool and go to the next one, but at rise

Bryon Kroger:

eight, I get to go all across the federal government and help everyone.

Bryon Kroger:

So that's been kind of, that's what drove me, not necessarily

Bryon Kroger:

anything entrepreneurial, but just wanting to continue to grow the

Tim Winkler:

impact.

Tim Winkler:

Got it.

Tim Winkler:

Yeah, that's cool.

Tim Winkler:

And I want to dive deeper into that, um, those skill sets at rise eight and

Tim Winkler:

how you kind of evaluate talent and how to kind of prep that, but before

Tim Winkler:

we do, and I think it's just kind of a little bit of an ironic coincidence,

Tim Winkler:

but, um, Alyssa, you also, you know, had a, uh, a role at Kessel run.

Tim Winkler:

Um, you know, uh, can you maybe explain on what that looked like?

Tim Winkler:

And then, you know, just maybe speaking to from a talent

Tim Winkler:

perspective, you know, piggybacking on what Brian was alluding to.

Alissa Bookwalter:

Yeah, um, so I was a chief of staff at Kessler Run

Alissa Bookwalter:

for the all domain common platform.

Alissa Bookwalter:

Um, it's one of the product lines and, you know, one of a big component of my

Alissa Bookwalter:

job was finding, finding our talent.

Alissa Bookwalter:

Right?

Alissa Bookwalter:

So who is going to sit in the product line?

Alissa Bookwalter:

Where are we going to get the technologists?

Alissa Bookwalter:

Um, you know, and we had a phenomenal, they still do a

Alissa Bookwalter:

phenomenal chief people officer.

Alissa Bookwalter:

Um, but it's really thinking outside of the box because not only do you

Alissa Bookwalter:

have this phenomenal mission driven organization that really is, was, is

Alissa Bookwalter:

the first of its kind in the DoD and has been replicated, I think, like 25

Alissa Bookwalter:

more times now or something, right?

Alissa Bookwalter:

Um, but you have a very competitive market with salaries.

Alissa Bookwalter:

Um, so Kessel Run really led the way on things like remote work, right?

Alissa Bookwalter:

Like, we can have distributed teams and we can make you feel part of our culture.

Alissa Bookwalter:

Um, Kessel Run had a phenomenal, like a two week boot camp to its culture, right?

Alissa Bookwalter:

And you heard from every single part of the organization and, you

Alissa Bookwalter:

know, how you were part of a mission and how you fit and where Kessel

Alissa Bookwalter:

Run fit into the larger scheme and the impact that you were making.

Alissa Bookwalter:

Um, seeing it in live time is...

Alissa Bookwalter:

Is absolutely real.

Alissa Bookwalter:

Um, and then one of the things that I did, um, just because I love

Alissa Bookwalter:

collaboration and I love partnerships.

Alissa Bookwalter:

What?

Alissa Bookwalter:

And I had a phenomenal, um.

Alissa Bookwalter:

Boss that let me, you know, like go for it, run with it is I, I

Alissa Bookwalter:

brought in a lot of partnerships.

Alissa Bookwalter:

Um, so we brought over a detail from the U S digital service and he actually,

Alissa Bookwalter:

um, decided to stay on at Kessel Run, which is really, really cool.

Alissa Bookwalter:

He loved the mission so much.

Alissa Bookwalter:

Um, we worked with the national security innovation network for, um,

Alissa Bookwalter:

specific talent needs that, you know, we could go out and recruit for,

Alissa Bookwalter:

but maybe we're having some trouble.

Alissa Bookwalter:

They had a huge, you know, newsletter and they had a reach.

Alissa Bookwalter:

Um, so we worked with them a little bit.

Alissa Bookwalter:

Kessel Run does engagement days.

Alissa Bookwalter:

I think they actually have one coming up for any listener that's interested.

Alissa Bookwalter:

And it just talks about what they do in the culture.

Alissa Bookwalter:

Um, and again, you have to make an effort with talent, right?

Alissa Bookwalter:

A lot of government organizations and, and DoD contractors to an extent don't.

Alissa Bookwalter:

And you really have to tie the impact and the effort.

Alissa Bookwalter:

And this is what you're going to be doing in real time results.

Alissa Bookwalter:

Um, and it's just, it's a, it's refreshing and it's a breath of fresh air.

Alissa Bookwalter:

And I, I really loved what I did there.

Mike Gruen:

It's cool.

Mike Gruen:

Yeah.

Mike Gruen:

I just want to jump in on the whole mission thing.

Mike Gruen:

Cause I, one of the things that in my background, I've done a lot of things,

Mike Gruen:

government contracting off and on and private, when people ask me like what,

Mike Gruen:

what projects I worked on that like really still stand out to me, the one

Mike Gruen:

that almost always comes top of mind is, uh, I worked on a software product

Mike Gruen:

that was supporting, um, HSTC, which is human smuggling and trafficking.

Mike Gruen:

And like, just working with those guys and seeing their mission and knowing that,

Mike Gruen:

like, what I'm working on is having a real impact in the world and stuff like that.

Mike Gruen:

That's the type of stuff.

Mike Gruen:

And, uh, you know, that was, uh, over 10 years ago that I worked on that and it's

Mike Gruen:

still top of mind in terms of one of the best projects I've worked on and knowing

Mike Gruen:

that I had that impact, even whatever small middle skill part I played in that.

Mike Gruen:

Um, and I do agree with like, everything you guys are saying about like mission

Mike Gruen:

and the trade offs of technology.

Mike Gruen:

But I also think 1 of the things that I'm curious, you know, Alyssa, um, and Brian.

Mike Gruen:

You're solving really hard technical problems.

Mike Gruen:

You might not have the best software or the best whatever, but in the end,

Mike Gruen:

at least I found that some of the most challenging projects I was working on

Mike Gruen:

were actually government, the ones where I was doing government contracting.

Mike Gruen:

Um, some of those, especially in the Intel community and in DoD, where

Mike Gruen:

some of the most challenging sort of intellectual projects, um, and very

Mike Gruen:

rewarding from that perspective as well.

Mike Gruen:

I'm curious if you guys, if that's sort of been your experience as well.

Mike Gruen:

Brian, maybe start with you.

Bryon Kroger:

Yeah, I mean, that's uh, I'm biased.

Bryon Kroger:

It's like all I want on it.

Bryon Kroger:

You're exactly that.

Bryon Kroger:

So, yeah, um, I find it extraordinarily meaningful.

Bryon Kroger:

I mean, where else can you achieve?

Bryon Kroger:

Like these, these levels of impact, I know, um, I'll use the

Bryon Kroger:

first application at Kessel Run.

Bryon Kroger:

And by the way, we actually got to use the coolest latest technology, which isn't

Bryon Kroger:

always going to be the case in government.

Bryon Kroger:

So I want to caveat that.

Bryon Kroger:

If you're looking to get into government, you might be in more difficult spaces.

Mike Gruen:

People would be surprised to find out that that's still like,

Mike Gruen:

I think people have this idea that they're not going to be able to do that.

Mike Gruen:

But I was, and I was surprised at how often I got to play with

Mike Gruen:

like some cutting edge stuff.

Mike Gruen:

So I'm sorry,

Bryon Kroger:

I'm like, really cool missions.

Bryon Kroger:

The 1st application that, um, it actually was like the precursor to Kessel Run.

Bryon Kroger:

Uh, we ended up adopting the app.

Bryon Kroger:

It was called jigsaws, a tanker planner application to do air to air refueling.

Bryon Kroger:

So like when we're planning, uh, missions overseas in particular,

Bryon Kroger:

um, we're conducting air operations, we refuel planes in midair.

Bryon Kroger:

And, uh, it's a combinatorial data problem.

Bryon Kroger:

Like it's a huge, massive number of combinatorial options because you've

Bryon Kroger:

got not just American aircraft, but you've got coalition aircraft.

Bryon Kroger:

They have different attachment points, different types of fuel,

Bryon Kroger:

they're flying different caps.

Bryon Kroger:

So like, and there's all sorts of rules like this coalition partner won't

Bryon Kroger:

refuel from this coalition partner.

Bryon Kroger:

They like us, but they don't like each other.

Bryon Kroger:

And so it's a really cool data science, uh, data engineering problem.

Bryon Kroger:

Um, but the initial application, we actually didn't even

Bryon Kroger:

have to do any of that.

Bryon Kroger:

Like it was pretty, you know, like standard linear algebra

Bryon Kroger:

to get to the first MVP where.

Bryon Kroger:

Uh, we, uh, made that tanker planning process so much more efficient.

Bryon Kroger:

They were able to say on save on average 1 tanker per day, which equates to about

Bryon Kroger:

214, 000 dollars a day in fuel savings.

Bryon Kroger:

So, the application paid for itself in a week.

Bryon Kroger:

We had spent like 1 and a half million to get to MVP.

Bryon Kroger:

Um, but if you multiply that out for say five years, um, I have to check my mouth.

Bryon Kroger:

It's been a while since I've quoted this stat, but I think

Bryon Kroger:

it's 391 million in fuel savings.

Bryon Kroger:

Where can you have that level of impact?

Bryon Kroger:

Like this, this was a team of like a product manager, a product designer,

Bryon Kroger:

and four software developers.

Bryon Kroger:

And they built in 120 days and shipped to production and application that

Bryon Kroger:

over the course of 5 years will save the DOD 391 million in fuel savings.

Bryon Kroger:

That's just the initial iteration.

Bryon Kroger:

They went on to actually save 2 tankers per day, started to implement

Bryon Kroger:

algorithms that make the planning process more efficient so that we

Bryon Kroger:

need less planners, so there's troops that don't have to deploy overseas.

Bryon Kroger:

I mean, just like crazy impacts.

Bryon Kroger:

Uh, that you can have, like, where else can you do that?

Bryon Kroger:

I always joke, like you walk down the street in San Francisco and

Bryon Kroger:

there's an ad for a job to go work on a, you know, app that helps you

Bryon Kroger:

optimize your dog walking routes.

Bryon Kroger:

So you can find places for your dog to pee.

Bryon Kroger:

It's like,

Bryon Kroger:

it's

Mike Gruen:

San Francisco.

Mike Gruen:

Uh, it doesn't really

Bryon Kroger:

matter.

Tim Winkler:

But the, the reality here though, is that there is some, some

Tim Winkler:

pretty big misconceptions, I'd say, uh, some common misconceptions about, uh,

Tim Winkler:

a lack of innovation or, you know, just so much red tape and, uh, it's, it's

Tim Winkler:

really tough to, to innovate or, or ship, you know, quickly, um, you know, what,

Tim Winkler:

what are some of the ones that, uh, are there any others that you've heard of,

Tim Winkler:

or, or, you know, what, how would you.

Tim Winkler:

Combat those, some of those misconceptions or, or how would you say that, you

Tim Winkler:

know, that could be true, but, you know, maybe navigating these types

Tim Winkler:

of opportunities or with these types of, on these types of projects.

Alissa Bookwalter:

Yeah, so from my end, I think we like to call it bureaucracy

Alissa Bookwalter:

hacking and I think that's a pretty, a pretty standard term these days.

Alissa Bookwalter:

What I would say one of the misconceptions is what you alluded to it's that there's

Alissa Bookwalter:

so much red tape and there's so much bureaucracy and there's people standing

Alissa Bookwalter:

in the way that aren't willing to change or, you know, clinging on to antiquated

Alissa Bookwalter:

processes or policies or regs and they don't want to move and that's actually

Alissa Bookwalter:

a lot of the times not the case.

Alissa Bookwalter:

Um, it could be education.

Alissa Bookwalter:

It could be misinformation.

Alissa Bookwalter:

It could be someone quoting some regular policy that like they've

Alissa Bookwalter:

been told and guess what regular policy doesn't actually have that or

Alissa Bookwalter:

maybe it actually hasn't had a legal interpretation and you can actually do

Alissa Bookwalter:

something really cool and move fast.

Alissa Bookwalter:

It's building relationships.

Alissa Bookwalter:

I mean, whether you're on the government side or the government

Alissa Bookwalter:

contracting side, right?

Alissa Bookwalter:

Having stakeholders trust you and work with you and valuing.

Alissa Bookwalter:

Their input and their expertise, and they're probably most oftentimes decades

Alissa Bookwalter:

of federal service is really important.

Alissa Bookwalter:

Um, and then potentially pivoting and showing them a better approach, right?

Alissa Bookwalter:

I don't think a lot of us are here to kind of come in and

Alissa Bookwalter:

make a buck and leave, right?

Alissa Bookwalter:

And kind of go out and then IG gets involved and it's millions of dollars

Alissa Bookwalter:

in a system that doesn't work, right?

Alissa Bookwalter:

Um, but it's, it's changing that.

Alissa Bookwalter:

And there's a lot of innovative people and processes in the government.

Alissa Bookwalter:

And it's actually a really exciting time to be either in it or supporting

Alissa Bookwalter:

it, because I think we're on a, like a huge change and it's really cool.

Alissa Bookwalter:

It's been a great thing to be a part of.

Bryon Kroger:

Yeah, I agree with that.

Bryon Kroger:

Uh, finding an organization that's hacked the bureaucracy already is like

Bryon Kroger:

a really powerful thing to look out for.

Bryon Kroger:

Fact, actually.

Bryon Kroger:

bookshelf, hack your bureaucracy by Nick Sinai has great stories of people

Bryon Kroger:

hacking bureaucracy and GovTech.

Bryon Kroger:

Um, uh, Marina, uh, was the other coauthor there.

Bryon Kroger:

Um, but, uh, the other thing is if you're going to come into a space,

Bryon Kroger:

uh, you know, we get a lot of people that come even out of the Silicon

Bryon Kroger:

Valley, like presidential innovation fellows, us digital service, and they

Bryon Kroger:

come in with these like high hopes.

Bryon Kroger:

They're going to bring their technical talents.

Bryon Kroger:

Like your technical talent is irrelevant until you hack the bureaucracy.

Bryon Kroger:

And so like, first and foremost, you have to be a bureaucracy

Bryon Kroger:

hacker and you can't hack systems.

Bryon Kroger:

You don't understand.

Bryon Kroger:

So, like, if you want to take this leap, you know, 1 option is to join

Bryon Kroger:

an organization like Kessel Run or similar that's already hacked the

Bryon Kroger:

bureaucracy, or you can go into a new space that you're passionate about.

Bryon Kroger:

Maybe it's like the VA.

Bryon Kroger:

Actually, they're very innovative too, but.

Bryon Kroger:

Maybe you go in there, you have to now become the bureaucracy actor.

Bryon Kroger:

You've got to go study the policies and the regs and figure

Bryon Kroger:

out how to work around them.

Bryon Kroger:

I can guarantee you that there are ways to do all of this.

Bryon Kroger:

We didn't break any rules to start Kessel Run, believe it or not,

Bryon Kroger:

or to do anything that we did.

Bryon Kroger:

We never had to violate a policy or even ask for an exception to one.

Bryon Kroger:

Um, My, my friend, uh, Dan Ward, uh, he was prior Air Force, but, uh, now

Bryon Kroger:

does a lot of government consulting.

Bryon Kroger:

He says that, uh, ignorance of the FAR, that's the Federal Acquisition

Bryon Kroger:

Regulation, or I'll just say rules.

Bryon Kroger:

Ignorance of the rules is a far greater barrier to innovation

Bryon Kroger:

than the rules themselves.

Bryon Kroger:

And I think that, like, stands to reason that if you're going to come into an

Bryon Kroger:

organization, even if it's not government, a large enterprise that has bureaucracy,

Bryon Kroger:

Like figuring out that bureaucracy and then hacking it is the first step.

Tim Winkler:

Yeah, I think that's well said.

Tim Winkler:

And, you know, somebody who's kind of seen it from a couple of sides, right?

Tim Winkler:

So when we first started hatch, you know, we, you know, based out of the DC

Tim Winkler:

area, a lot of the work we were doing was, was helping, you know, government

Tim Winkler:

contractors, these smaller kind of.

Tim Winkler:

Eight a, uh, companies that were winning work.

Tim Winkler:

Um, and then we ended up transitioning into, you know, commercial startup land.

Tim Winkler:

And one of the interesting things was, um, you know, we saw this bias from a

Tim Winkler:

lot of the, uh, CTOs or the founders.

Tim Winkler:

That they didn't really want to see technologists coming

Tim Winkler:

from systems integrators.

Tim Winkler:

Um, they wanted to see technologists that came from very specific, you know,

Tim Winkler:

product environments that maybe we're at a certain phase in the product lifecycle

Tim Winkler:

versus maybe somebody who had been building, uh, you know, a larger system

Tim Winkler:

for DHS or something along those lines.

Tim Winkler:

And I think, you know, that has changed, um, you know, uh, in the last few years.

Tim Winkler:

But, um, the other interesting change that we're seeing and part

Tim Winkler:

of the reason the catalyst for, for creating some of this media.

Tim Winkler:

Is because there is more interest in commercial technologists pursuing

Tim Winkler:

opportunities in, in these industries and in the government than there ever has been

Tim Winkler:

before that we're seeing, which is wild.

Tim Winkler:

I think one of it is as a, as a result of the economy and the market, you

Tim Winkler:

know, it's just timing right now with, um, you know, funding being

Tim Winkler:

really challenging to come by for, for commercial startups in early stages.

Tim Winkler:

And there's much more stability, uh, when you think about, you know, going

Tim Winkler:

and working with, um, in the government space on maybe a project that maybe

Tim Winkler:

is a little, a larger transformation, but that also means maybe it's a three

Tim Winkler:

year or four year type of project.

Tim Winkler:

And, you know, you might have a little bit more job stability than you do when

Tim Winkler:

your runway just, you know, kick the can after six months and start up world.

Tim Winkler:

So it's an interesting trans transition point.

Tim Winkler:

And that's why I think it's important to kind of continue to build.

Tim Winkler:

Uh, this this type of information for those folks to to navigate, because I

Tim Winkler:

think you put you brought a really good point, Alyssa, about, um, um, maybe it

Tim Winkler:

was Brian, but the relationships that you're building, um, you know, with

Tim Winkler:

these stakeholders, and there's something really unique, powerful about going and

Tim Winkler:

attending some of these conferences, uh, where folks are, you know, really

Tim Winkler:

engaging and, uh, you make make great connections and good relationships.

Tim Winkler:

And And oftentimes it's just like standard networking, you know, but

Tim Winkler:

that's, that's how you can try to get your foot in the door, um, through,

Tim Winkler:

through some of those types of events.

Tim Winkler:

Brian, I wanted to ask about rise eight in terms of like, you know, some of the

Tim Winkler:

types of folks that you're hiring for.

Tim Winkler:

Um, and you know, what are those skill sets that you're, you know,

Tim Winkler:

that you're going to say is, you know, uh, transformative or, or really

Tim Winkler:

progressive right now that you're, that you're trying to tap into?

Tim Winkler:

Yeah, so, uh,

Bryon Kroger:

we do, first of all, we do elite software development

Bryon Kroger:

for mission critical systems, right?

Bryon Kroger:

Those are, that's our focus area.

Bryon Kroger:

And I say elite, like, we're high end software development shop.

Bryon Kroger:

We do custom software development.

Bryon Kroger:

We don't do proprietary products.

Bryon Kroger:

And I believe that the government should own their products.

Bryon Kroger:

Um, with that, we often find ourselves environments, uh, we use this to

Bryon Kroger:

build Kessel Run, who's pairing, love naming the podcast, but we're an XP

Bryon Kroger:

shop, so we do 100% pair programming.

Bryon Kroger:

We also do pair product management and product design, so sometimes

Bryon Kroger:

the government might hire us to come in and just deliver an application,

Bryon Kroger:

but more often than not, we're coming in and pairing with the

Bryon Kroger:

government to build products and upscale them at the same time.

Bryon Kroger:

I think that that's, uh, a trend that I see growing in the

Bryon Kroger:

federal government right now.

Bryon Kroger:

And so skills that I look for as I'm trying to hire people, um, not

Bryon Kroger:

only like technical excellence.

Bryon Kroger:

Uh, but to be able to pair with somebody for eight hours a day, especially

Bryon Kroger:

somebody who's not like on your team and part of your culture, somebody that

Bryon Kroger:

you're trying to transform or change, um, not only upskill their talents,

Bryon Kroger:

but you're also trying to change their culture and work through their cultural

Bryon Kroger:

inefficiencies and bureaucracies.

Bryon Kroger:

It takes a lot of soft skills, um, which are actually the new hard skills.

Bryon Kroger:

So honestly, like I'm looking for engineers, um, that are excellent

Bryon Kroger:

communicators that have high empathy.

Bryon Kroger:

Um, that are able to pair program effectively, which

Bryon Kroger:

we have a way to assess that.

Bryon Kroger:

Um, so I'm looking less right now, like hot skills, like, oh, yeah, I

Bryon Kroger:

need a, you know, prompt engineer.

Bryon Kroger:

Um, I'm looking more at how do I find those unicorn engineers

Bryon Kroger:

who are also incredible.

Bryon Kroger:

Uh, communicators, empathizers, upskillers, coaches, um, so

Bryon Kroger:

that that's really our focus.

Bryon Kroger:

I would say that's somewhat unique in the space still, but

Bryon Kroger:

I see it as a growing trend.

Bryon Kroger:

And if you want to be in this space, I think, uh, having those

Bryon Kroger:

skills is really important.

Bryon Kroger:

Even if you are going to go direct into government as a technologist.

Bryon Kroger:

You're probably going to have four or five people on your team

Bryon Kroger:

who are nowhere near your level.

Bryon Kroger:

So being able to do something like pair programming or pair design, uh,

Bryon Kroger:

with them is, is I think a really valuable skill set to create change.

Tim Winkler:

That's fascinating.

Tim Winkler:

You can't snuff that out with the coding challenge.

Tim Winkler:

Um, that seems like that's a little bit more of a, you know, human,

Tim Winkler:

human, uh, conversation right there.

Tim Winkler:

Alyssa, what about you?

Tim Winkler:

And, you know, I'm, I'm curious on, you know, the work that you're

Tim Winkler:

doing at the Griffiss Institute.

Tim Winkler:

Um, you know, what, what is it that you think is so mission driven about this

Tim Winkler:

and how is it transforming, you know, how technology is being built in defense?

Tim Winkler:

Yeah, well,

Alissa Bookwalter:

the fun thing about where I'm at right now, specifically

Alissa Bookwalter:

what I get to do with our division is our division supports, um,

Alissa Bookwalter:

Department of Defense, mostly for the Air Force, um, internship programs.

Alissa Bookwalter:

So, we are really taking The next generation of technologists with an

Alissa Bookwalter:

end goal of getting them real world experience, getting them to work with

Alissa Bookwalter:

mentors who are federal employees or defense industrial based employees

Alissa Bookwalter:

and getting them interested in it, um, getting them scholarship money.

Alissa Bookwalter:

Right?

Alissa Bookwalter:

And then at the end, hopefully they'll have an interest in.

Alissa Bookwalter:

Joining federal service or going to the defense industrial base

Alissa Bookwalter:

or becoming an entrepreneur and supporting defense, right?

Alissa Bookwalter:

All of it is a win and those things that I hear Brian talk about that holistic

Alissa Bookwalter:

picture of not only the technical chops, but the all around, you know,

Alissa Bookwalter:

nice person, engage with stakeholders, educate people in a way the people skills.

Alissa Bookwalter:

Um, Are what we're doing with the interns, right?

Alissa Bookwalter:

So they, they come on and they have their projects and their mentors, but

Alissa Bookwalter:

they also have classes on leadership and development and all of this really good

Alissa Bookwalter:

stuff that makes a killer, well rounded employee, whatever they decide to do.

Alissa Bookwalter:

And so it's just really great to see that the pipeline, especially for the

Alissa Bookwalter:

DoD is headed in the right direction.

Alissa Bookwalter:

Right.

Alissa Bookwalter:

Um, because I do, I think that's the future of work, right.

Alissa Bookwalter:

And especially in the technical space, whether you're in the

Alissa Bookwalter:

government side or the government contracting side or wherever.

Alissa Bookwalter:

Yeah.

Tim Winkler:

Yeah.

Tim Winkler:

Well said.

Tim Winkler:

Um, yeah, so we only have a couple more minutes, uh, left,

Tim Winkler:

uh, before we transitioned to the, the last segment here, but.

Tim Winkler:

Um, you know, just generally speaking, uh, other, other, um, like

Tim Winkler:

any agencies, um, or specific, uh, resources that you would direct folks

Tim Winkler:

to, uh, it could be conferences, it could be things of that nature.

Tim Winkler:

That maybe is a good starting point, um, for folks that are looking to, you know,

Tim Winkler:

learn more or, or get a little bit more entrenched and meet, meet some folks

Tim Winkler:

that can be beneficial as a technologist.

Tim Winkler:

Absolutely.

Bryon Kroger:

I think, um, 1 just happened code for America, uh, summit, uh, code

Bryon Kroger:

for America is a great organization.

Bryon Kroger:

Um, the name speaks for itself.

Bryon Kroger:

I think, uh, really great mission, mission oriented folks.

Bryon Kroger:

They don't play as much in the D.

Bryon Kroger:

O.

Bryon Kroger:

D.

Bryon Kroger:

Space.

Bryon Kroger:

Um, it's mostly like federal state, local agencies.

Bryon Kroger:

Um, really great crew amazing networking.

Bryon Kroger:

You hear the craziest stories.

Bryon Kroger:

Um, it's hard to walk away from there and not want to go work for government.

Bryon Kroger:

And then, you know, the illicit part of this group, but like anything that

Bryon Kroger:

stemmed out of the U S digital service kind of, um, title wave that came through.

Bryon Kroger:

So there was defense digital service, there's 18 F and the technology

Bryon Kroger:

transformation services within the general services administration.

Bryon Kroger:

Um, 18 F had some of the most incredible people from Silicon

Bryon Kroger:

Valley that came work for it.

Bryon Kroger:

A lot of people might know Jess Humble.

Bryon Kroger:

He was like one of the people that really inspired me to build

Bryon Kroger:

a continuous ATO based on the work they did at, uh, 18F building cloud.

Bryon Kroger:

gov.

Bryon Kroger:

Um, so there's all sorts of really cool use cases.

Bryon Kroger:

And then the DoD software factories, they're like very vocal and active on

Bryon Kroger:

like LinkedIn and other social media.

Bryon Kroger:

So, um, and lots of like recorded videos and they participate in

Bryon Kroger:

conferences, uh, like, you know, they were just at KubeCon and, uh, you know,

Bryon Kroger:

they're just out there everywhere.

Bryon Kroger:

You can find them.

Bryon Kroger:

Um, so follow them on social media and, and, uh, 18 F in particular

Bryon Kroger:

has a bunch of playbooks.

Bryon Kroger:

So it's a really, in fact, a lot of them are used by commercial organizations.

Bryon Kroger:

They're like taking them back out of government and like, Oh, let's

Bryon Kroger:

use this at our commercial org.

Bryon Kroger:

So, uh, definitely worth checking out their website and some of

Bryon Kroger:

the things they have going on.

Bryon Kroger:

And then plug, just because they're one of our, my favorite, like current customers,

Bryon Kroger:

the VA, uh, just cause I'm a veteran and, uh, I think the mission is so cool.

Bryon Kroger:

Um, but the VA is really forward leaning in.

Bryon Kroger:

Uh, organization.

Bryon Kroger:

I think, you know, hearing what's been on the news over the last several years, I

Bryon Kroger:

mean, they've taken a rough, uh, beating in, in the public space just because of

Bryon Kroger:

some of the inadequacies of veteran care.

Bryon Kroger:

Mm-hmm.

Bryon Kroger:

, a lot of that's like policy and government.

Bryon Kroger:

When you step inside, like V A I t, like those are mission oriented

Bryon Kroger:

people working their butts off.

Bryon Kroger:

They're super innovative, they're doing cool things.

Bryon Kroger:

I'm like very impressed and humbled by what they do.

Tim Winkler:

That's awesome.

Tim Winkler:

Alyssa, anything you'd like to add to that?

Alissa Bookwalter:

You know, I think, I think Brian hit on

Alissa Bookwalter:

a lot of the organizations.

Alissa Bookwalter:

I mean, that, that, that covers the gamut and he's, he's spot on.

Alissa Bookwalter:

Um, the, another conference is the Grace Hopper Conference.

Alissa Bookwalter:

Um, that's a, that's a really great innovative one for especially,

Alissa Bookwalter:

um, diversity in tech or gov civic tech, gov tech, whatever

Alissa Bookwalter:

you, whatever your spiel is.

Alissa Bookwalter:

Um, and I, I want a second rep for the VA.

Alissa Bookwalter:

Um, so we, when I was at USPS, we, you know, we had a digital

Alissa Bookwalter:

service team there and they've built out a whole huge organization.

Alissa Bookwalter:

Um, from that, but really, really transformed care for veterans.

Alissa Bookwalter:

And my husband's a disabled veteran and uses their services.

Alissa Bookwalter:

And it's, it's like night and day from, you know, a couple of years ago.

Alissa Bookwalter:

So I want to, I want to second their efforts.

Alissa Bookwalter:

That's really cool.

Tim Winkler:

That's great.

Tim Winkler:

I like this is, these are different than some of the other ones that we received

Tim Winkler:

from previous episode, like, um, like DARPA and, uh, Johns Hopkins, uh, applied

Tim Winkler:

physics lab and have Ryan shake his head.

Tim Winkler:

Um, well, I think, um, I think this is, uh, this is a

Tim Winkler:

great, uh, educational piece.

Tim Winkler:

Um, I know it's, it's certainly going to be useful.

Tim Winkler:

Um, I want to spend the last 10 minutes here, uh, on a fun segment,

Tim Winkler:

uh, that we'll transition to called the five second scramble.

Tim Winkler:

Um, so this is a, a quick hit kind of Q and a, uh, I'll ask

Tim Winkler:

each of you a series of questions.

Tim Winkler:

Uh, try to give me your response within, within five seconds.

Tim Winkler:

Um, some, some are business, some are, are personal.

Tim Winkler:

Um, I'll go ahead and start with you, Brian.

Tim Winkler:

Um, we'll kick it off here.

Tim Winkler:

So what, what is your, your favorite aspect of working at rise?

Tim Winkler:

Eight?

Tim Winkler:

Uh,

Bryon Kroger:

pairing.

Bryon Kroger:

I love pairing with government, um, rather than just delivering things.

Bryon Kroger:

So I love when we get to pair and help upskill

Tim Winkler:

people.

Tim Winkler:

Oh, you'd love the pair program.

Tim Winkler:

I appreciate that plug.

Tim Winkler:

What, uh, what would you describe as your favorite piece of your culture?

Bryon Kroger:

Uh, Growth mindset.

Bryon Kroger:

I think, um, this idea that everything has to revolve around learning,

Bryon Kroger:

uh, this is a learning journey.

Bryon Kroger:

Think, um, you know, not having the right answer up front, not having to try to plan

Bryon Kroger:

and, you know, coming out of government.

Bryon Kroger:

We try to predict the future, stop trying to predict the future and start trying

Bryon Kroger:

to find the future, uh, through iterative product development, iterative learning.

Tim Winkler:

Nice.

Tim Winkler:

You might've answered this question earlier in the episode, but

Tim Winkler:

what, what kind of technologist thrives at, at rise eight?

Tim Winkler:

Hmm.

Tim Winkler:

Uh, let me

Bryon Kroger:

just, well, having a growth mindset is a big one.

Bryon Kroger:

I think grit is another big one.

Bryon Kroger:

Um, you know, outside of all those soft skills, like you have to have

Bryon Kroger:

great, if you're going to work in the government tech space, uh, grit being

Bryon Kroger:

defined as passion and perseverance.

Tim Winkler:

Nice.

Tim Winkler:in:Bryon Kroger:

More mission impact, uh, we just keep growing and keep

Bryon Kroger:

producing more outcomes in production.

Tim Winkler:

Do you have a favorite book or podcast on leadership?

Tim Winkler:

Uh,

Bryon Kroger:

I read a ton of books and I always rattle off a bunch, so

Bryon Kroger:

I'll just go with my most recent.

Bryon Kroger:

My favorite, like, most recent read, um, was Farther, uh, Faster

Bryon Kroger:

Earth, Far Less Drama by Jason and Janice Frazier, who are actually...

Bryon Kroger:

Two mentors of mine at Pivotal Labs when we started Kessel Run.

Tim Winkler:

What do you love most about yourself?

Tim Winkler:

It's awkward.

Bryon Kroger:

That I'm humble.

Bryon Kroger:

You know, uh, I.

Bryon Kroger:

I guess maybe like most proud of, uh, you know, being a father of

Bryon Kroger:

four and still being able to do this whole entrepreneur thing.

Tim Winkler:

That's awesome.

Tim Winkler:

Yeah.

Tim Winkler:

We need to have you on it for a second episode about

Tim Winkler:

parenting and entrepreneurship.

Tim Winkler:

Uh, it's, it's something that's top of mind for me.

Tim Winkler:

So, um, What, uh, what's the most, um, I'm sorry.

Tim Winkler:

What's the worst fashion trend that you've ever followed?

Tim Winkler:

You

Bryon Kroger:

remember those like t shirts for your feet?

Bryon Kroger:

It was like ugly Nikes.

Bryon Kroger:

I don't remember what they were called.

Tim Winkler:

T shirts for your feet, though.

Tim Winkler:

I got to Google this now.

Tim Winkler:

T shirts for your feet.

Tim Winkler:

Wow.

Tim Winkler:

All right.

Tim Winkler:

We'll accept that.

Tim Winkler:

Um, what, uh, Oh, if you could have dinner with any historical

Tim Winkler:

figure, who would it be?

Tim Winkler:

And why, uh,

Bryon Kroger:

Marcus Aurelius?

Bryon Kroger:

Cause I wish I was more stoic.

Tim Winkler:

Nice.

Tim Winkler:

What is a charity or corporate philanthropy that's near and dear to you?

Bryon Kroger:

Uh, the wounded warrior project's a big one, but like all

Bryon Kroger:

things related to veteran, veteran care being veterans, you know, off

Bryon Kroger:

the streets and away from suicide.

Tim Winkler:

What is one skill or hobby that you've always wanted to learn,

Tim Winkler:

but you haven't had the chance to yet?

Bryon Kroger:

I don't know that I have one.

Bryon Kroger:

I do all the things I want.

Tim Winkler:

I love what I do.

Tim Winkler:

You can get back to us on that.

Tim Winkler:

Um, What if you could have a personal theme song that played

Tim Winkler:

every time you entered a room, what song would you choose?

Tim Winkler:

Uh,

Bryon Kroger:

Rise Up from

Tim Winkler:

the Hamilton soundtrack.

Tim Winkler:

Oh, cool.

Tim Winkler:

And then last question, what, who is the greatest superhero of all time?

Tim Winkler:

Uh,

Bryon Kroger:

I'm partial to Superman, the cliche answer, but that's it for me.

Tim Winkler:

All right.

Tim Winkler:

All right.

Tim Winkler:

That's it.

Tim Winkler:

You, uh, you nailed it.

Tim Winkler:

You nailed it.

Tim Winkler:

We still, we're still going to need that answer from, uh, the, the skill or hobby.

Tim Winkler:

We'll, we'll, we'll wait for that, uh, uh, at another time, but, uh, well done,

Tim Winkler:

uh, Alyssa, are you, uh, are you ready?

Tim Winkler:

Hope you weren't taking notes.

Tim Winkler:

Cause none of these questions.

Tim Winkler:

I wasn't

Alissa Bookwalter:

taking notes, but those were intense.

Alissa Bookwalter:

So, all right, let's see what you got.

Tim Winkler:

Okay.

Tim Winkler:

All right, let's go.

Tim Winkler:

Um, explain, uh, Griffis Institute to me as if I were a five year old.

Alissa Bookwalter:

Sure, Talent and Technology Accelerator, if you like

Alissa Bookwalter:

Star Wars, like running around with forks on your shoulders, being able

Alissa Bookwalter:

to use lightsabers, aka pool noodles to demonstrate really, really cool

Alissa Bookwalter:

things with cybersecurity and science, you would love the Griffiss Institute.

Tim Winkler:

That's perfect.

Tim Winkler:

So I'm going to apply tomorrow.

Tim Winkler:

Um, what, what is your, your favorite part, uh, about the

Tim Winkler:

culture at Griffith Institute?

Tim Winkler:

I love

Alissa Bookwalter:

laughing and a sense of humor.

Alissa Bookwalter:

Um, I have, I have a wicked sense of humor, whether People like it or not.

Alissa Bookwalter:

Um, and most of my colleagues share the same.

Alissa Bookwalter:

So I'm, I'm going to go with that.

Tim Winkler:

Nice.

Tim Winkler:

What would you say is a company value that is important to you?

Alissa Bookwalter:

Yeah.

Alissa Bookwalter:

Psychological safety.

Alissa Bookwalter:

Um, it's, it's really important that everybody has psychological

Alissa Bookwalter:

safety to speak their mind, to disagree on things, but commit.

Alissa Bookwalter:

Um, and a safe space to, you know, show up authentically for who you are.

Alissa Bookwalter:

Um, and that's really important for me, wherever I go.

Tim Winkler:

Do you have a favorite book or podcast on technology?

Tim Winkler:

Oh,

Alissa Bookwalter:

um, you know, it's not technology specific, but the last really

Alissa Bookwalter:

amazing book I read, I was a little slow with hack your, hack your bureaucracy.

Alissa Bookwalter:

I mean, we just, we did hack the bureaucracy.

Alissa Bookwalter:

It.

Alissa Bookwalter:

It was spot on and I needed, I needed that inspiration and I hate

Alissa Bookwalter:

to shout it out a second time, but that was, that was so good.

Alissa Bookwalter:

And it's, it's so much more than technology, though.

Alissa Bookwalter:

It has a lot of really good, um, examples for

Tim Winkler:

it in government.

Tim Winkler:

I feel like we're just running a, a promo ad here, , uh, for, for the book, uh,

Tim Winkler:

about seeing influx in, uh, and sales.

Tim Winkler:

Um, what is, um, I'm sorry.

Tim Winkler:

Who is your biggest role model and why do they inspire you?

Tim Winkler:

Oh,

Alissa Bookwalter:

good one.

Alissa Bookwalter:

Um,

Alissa Bookwalter:

I have a lot of, um, amazing people, but it was a, a former

Alissa Bookwalter:

coworker, um, who actually now works as a contractor at Kessel Run.

Alissa Bookwalter:

Um, and she's a retired O5, um, military psych nurse.

Alissa Bookwalter:

And I worked with her when I was supporting, um, wounded, ill and

Alissa Bookwalter:

injured soldiers at Walter Reed.

Alissa Bookwalter:

And she just really, she inspires me.

Alissa Bookwalter:

She lets me be myself.

Alissa Bookwalter:

She, you know, gives me some good life lessons, but she's

Alissa Bookwalter:

also one of my biggest superfans.

Alissa Bookwalter:

Um, so Mary, if you're listening, thank you.

Tim Winkler:

Nice.

Tim Winkler:

What is a charity or a corporate philanthropy that's near and dear to you?

Alissa Bookwalter:

You know, I, I hate to sound redundant,

Alissa Bookwalter:

but anything veteran related.

Alissa Bookwalter:

Um, I, when I was on the government side, I.

Alissa Bookwalter:

Help stand up a new initiative for military spouses and families who worked

Alissa Bookwalter:

or wanted to work in federal service.

Alissa Bookwalter:

Um, and it's, it's life changing with employment just in general,

Alissa Bookwalter:

um, for military families.

Alissa Bookwalter:

Um, and I got to do a lot of cool stuff with that.

Alissa Bookwalter:

I got to talk to a lot of military families firsthand and, uh, it's something

Alissa Bookwalter:

that drives me and I'm always inspired by.

Tim Winkler:

Awesome.

Tim Winkler:

A lighthearted transition here.

Tim Winkler:

What is your favorite cereal?

Tim Winkler:

Um,

Alissa Bookwalter:

Honey Nut

Tim Winkler:

Cheerios.

Tim Winkler:

Classic.

Tim Winkler:

If you could live in a fictional world, from a book or a movie,

Tim Winkler:

which one would you choose?

Alissa Bookwalter:

Uh, Harry Potter.

Alissa Bookwalter:

Hogwarts.

Alissa Bookwalter:

Um, all the way.

Alissa Bookwalter:

All the way.

Alissa Bookwalter:

Huge Harry Potter super fan.

Alissa Bookwalter:

Have Hogwarts legacy.

Tim Winkler:

Nice.

Tim Winkler:

Have you been, uh, to, to the, um, spot in Disney, the Harry

Alissa Bookwalter:

Potter?

Alissa Bookwalter:

It's actually at Universal and yes, I have, um, several times.

Alissa Bookwalter:

It's pretty amazing.

Tim Winkler:

I stand corrected.

Tim Winkler:

I have not been, obviously, so, um.

Tim Winkler:

Now you know how it feels, Tim,

Bryon Kroger:

when,

Tim Winkler:

there.

Tim Winkler:

Do you have a celebrity doppelganger?

Alissa Bookwalter:

You know, I don't think I do.

Alissa Bookwalter:

Um, yeah, I, I don't, unfortunately.

Tim Winkler:

Okay.

Tim Winkler:

I don't think that's unfortunate.

Tim Winkler:

Do you have any phobias or irrational fears?

Alissa Bookwalter:

Um, I, a little bit.

Alissa Bookwalter:

I generally have to like psych myself up and talk myself up off

Alissa Bookwalter:

the ledge mentally when I'm going to do anything with heights, but I

Alissa Bookwalter:

do it because I think life's not a journey and I do what I want to do.

Alissa Bookwalter:

Um, but it's always a little bit of a struggle getting there.

Tim Winkler:

If you could have any superpower, what would it be?

Tim Winkler:

Um,

Alissa Bookwalter:

probably being like 90 places at one time, because

Alissa Bookwalter:

there's a lot of things that I like to do and I can't hit the ball generally.

Tim Winkler:

Nice.

Tim Winkler:

And then we'll close with, uh, your favorite Disney character.

Tim Winkler:

Hmm.

Tim Winkler:

Hmm.

Tim Winkler:

That's hard.

Tim Winkler:

Um, and we're encompassing like modern Disney too.

Tim Winkler:

So everything, um,

Alissa Bookwalter:

Can I just uh, it's not Disney, but I'm just gonna

Alissa Bookwalter:

go with Harry Potter and Hermione Because I think she's pretty cool.

Alissa Bookwalter:

Sorry, it's not Disney specific, but we'll keep the Harry Potter theme

Tim Winkler:

We'll accept it.

Tim Winkler:

Cool.

Tim Winkler:

That's a wrap This has been a lot of fun.

Tim Winkler:

Thank you both for joining us and tackling a topic that is important

Tim Winkler:

It's very Uh, in our industry anyways, it's, it's very front and center.

Tim Winkler:

Uh, so I appreciate you all sharing some knowledge on it and, uh,

Tim Winkler:

joining us on, on the Pair Program.

Tim Winkler:

Thank you.

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