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Inside the AI Marketing OS Running Wispr Flow's Growth Team

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Inside the AI Marketing OS Running Wispr Flow's Growth Team

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1255 segments

0:00

I just dropped the PDF, I don't say

0:01

anything, [music]

0:02

and it's like, oh, this is the insertion

0:04

order. Okay, it's time to start our

0:06

sponsorship scale.

0:07

>> How much is your monthly Claude bill?

0:09

>> Last month, around 4 and 1/2 thousand.

0:11

This month will probably be more. I have

0:13

like between six and 10 sessions [music]

0:15

at any given time on my computer. I'm

0:16

using Logitech MX 4 mouse. One button is

0:19

the hands-free toggle for WhisperFlow.

0:22

So, I just scroll around the sessions,

0:24

give feedback.

0:25

>> Any metrics on business outcomes?

0:27

>> We've had roles that were on the docket

0:30

to be hired, [music] and we've paused

0:32

interviewing and hiring for them because

0:34

of the operating system. It's really

0:36

easy to send the email faster or send

0:38

the Slack faster, [music] but are the

0:40

highest leverage parts of your job also

0:42

AI supported? And the honest answer for

0:45

a lot of people, it's not.

0:46

>> That's Matt Swolinski, head of growth at

0:49

WhisperFlow, and one of the rare

0:51

marketers who dove headfirst into AI so

0:54

he could build [music] the tools his

0:56

team actually needs. In this

0:58

conversation, Matt shares his fully

1:01

automated system for buying newsletter

1:03

ads, how he trains Claude like it's a

1:05

junior employee,

1:06

>> [music]

1:06

>> how his team freed up 20% of their time

1:10

by automating admin tasks,

1:12

>> [music]

1:12

>> and why they've put some hiring on pause

1:15

because their current team has gotten so

1:16

efficient. We're in the age of AI search

1:19

and agents, and a new kind of marketer

1:22

is emerging. We call you the marketing

1:24

engineer, and this show is for you.

1:27

I'm Nick Lafferty from Profound, and

1:28

here's my conversation with Matt. All

1:30

right, Matt, let's start here. How much

1:33

is your monthly Claude bill, and where

1:35

do you rank at the company in AI usage?

1:37

>> Yeah, so last month, I think I clocked

1:39

in around 4 to 4 and 1/2 thousand.

1:43

Uh this month will probably be more. Um

1:46

I'm the number one person outside of the

1:48

engineering team, so definitely

1:50

relatively high up there.

1:51

>> Amazing. Um okay, so can you give a

1:53

quick background of what is WhisperFlow

1:55

and what do you own there?

1:57

>> WhisperFlow is a voice-to-text solution

2:00

that essentially layers in AI to take

2:03

what you say

2:04

and turn it into text anywhere the

2:06

cursor is, which ends up being three to

2:08

four times faster than typing. So, we

2:10

are the all-encompassing layer to

2:12

essentially get everything that's in

2:14

your head out there into the world much

2:16

faster.

2:17

>> Amazing. And then, what do you own at

2:18

Whisper right now?

2:19

>> Yeah, so as head of growth, I own

2:22

every KPI between impression all the way

2:25

to the download event. So, all the

2:27

website, all of experimentation on the

2:29

website, landing pages, all ad channels.

2:31

So, quite a bit of moving pieces given

2:34

the the scale that we're at.

2:36

>> Yeah. Is it mostly self-serve sign-ups

2:39

that is your primary KPI?

2:41

>> Yeah, so we as a business are optimized

2:44

towards B2C,

2:46

but obviously that

2:47

dovetails into team creation and

2:49

enterprise creation. So, we actually

2:52

just last quarter

2:53

hired our first AE ever from the start

2:56

of the business, and a good share of our

2:59

revenue already is teams and enterprise,

3:02

and that's because we've we've focused

3:04

on PLG. That's kind of the the

3:05

philosophy behind all of our growth. So,

3:07

the primary driver of all of our spend

3:10

as well as all of our marketing is to

3:11

make it really easy for an individual to

3:14

kind of gather that magical aha moment

3:16

of what it means to use WhisperFlow and

3:19

never be able to go back. And then,

3:20

those people will convince their teams

3:22

or their orgs to kind of bring it into

3:24

the fold.

3:25

>> Got it. Okay. Yeah, that that makes a

3:26

lot of sense. Okay, so great context on

3:28

Whisper and you and what you do. Before

3:30

we get into tactics around the marketing

3:32

engineer, I kind of want to make the

3:34

case for why this work matters. There's

3:37

a version of this for someone watching

3:39

who

3:40

is someone who just likes to build

3:41

things. And so, what do you think is

3:43

maybe the difference between someone who

3:46

just likes to tinker and build and

3:47

someone like you who has built more

3:50

robust systems at Whisper that is

3:52

actually driving really results for

3:54

y'all.

3:55

>> Yeah, I think the the big difference

3:56

there is a lot of people with the power

3:59

of AI can build cool micro tools that

4:03

are useful to them.

4:05

Uh and the difference becomes when you

4:06

have to turn that little idea into

4:08

something that can actually be

4:10

load-bearing, that it's used in

4:12

practice, used by various people, and as

4:15

scale changes or systems change, that

4:18

doesn't break or it has the mechanisms

4:20

to alert you if it does, right? And I

4:21

think that that's the core difference

4:23

here is

4:24

everyone's become AI native because of

4:26

the existence of the tools. I think very

4:28

few people have tacked on the layer of

4:31

being an engineer, even if you're not an

4:33

engineer, as you're building like an in

4:35

our case around marketing engineering,

4:36

even as head of growth I've filled that

4:38

role here internally at Whisper, where

4:41

I'm trying to take my workflow now,

4:43

apply it into the team, uh and that's

4:45

you know, obviously a a ton of changes

4:47

that are needed, but it's the the

4:48

repeatable loops of actually building

4:50

systems that can, you know, sustain the

4:54

the tide of time, uh and not just be a

4:56

small little item that gets used once in

4:58

a while.

4:58

>> Yeah, that that makes a lot of sense and

5:00

I do want to get into some of the things

5:02

that you've built. The last time we

5:04

talked, you mentioned building a

5:06

automated waterfall kind of for managing

5:08

newsletter, podcast, and YouTube

5:10

sponsorships, bunch of creator marketing

5:12

work. Can you kind of describe what that

5:14

process looks like and then we can kind

5:16

of like drill into more details?

5:18

>> Yeah, so this was my uh first core use

5:22

case for I'd say a deeper system that I

5:25

built with Cloud Code, and it was just

5:27

like the the biggest thorn in my side

5:30

uh when uh overseeing kind of the whole

5:32

marketing function at Whisper. So I'll

5:34

I'll zoom out a little bit and and and

5:35

note that up until December, so the end

5:38

of last year, I was the single person on

5:41

the entire Whisper Flow team doing

5:43

execution in marketing.

5:45

Which like the the role definition of

5:47

yes, I own the KPIs, but I also own all

5:49

the execution. So, all of meta ads, all

5:52

of Google ads, and everything that

5:53

connects to that,

5:55

um I was running the strategy and

5:57

execution entirely solo. So, I started

5:59

using Cloud Code a bit earlier than most

6:01

uh in in October of of 25. So, this is

6:04

before the the latest models that made

6:06

it truly great, but I already needed the

6:09

the support around some automations.

6:11

And the first thing I needed to automate

6:13

was uh newsletter sponsorships. So,

6:16

newsletter sponsorships, and not a lot

6:17

of people know this, I wish it wasn't

6:19

this way, but they're they're run in a

6:21

really antiquated way. So, you interface

6:23

with a newsletter over email.

6:26

They give you the rates, you negotiate

6:27

the rates, then you get a contract, uh

6:29

then you have deliverables. Every

6:31

newsletter has slightly different

6:32

formats, different copy amounts,

6:34

different image parameters.

6:36

Uh and then you write that copy, you

6:37

send it over email, and then you give

6:39

them a link, you see how it does, and

6:41

then you move on to your next placement.

6:44

So, all of that Now, now multiply that

6:46

times around 100 [snorts] newsletters

6:48

that we run uh placements on any month.

6:51

The audience is different, the framing

6:52

needs to be different, there's a ton of

6:53

copywriting and a ton of data that needs

6:55

to be analyzed, and without AI, it's

6:58

essentially impossible if you're running

6:59

anything else.

7:01

Um so, the first thing that I did is is

7:02

I built a essentially like a master

7:04

skill that invokes other skills along

7:07

the way. And all I need to do if it's a

7:09

new partner, I just drag in a contract,

7:13

and it first looks, you know, does the

7:15

CPM make sense? You know, what what can

7:17

we glean from the the internet as well

7:19

as research around this audience? Are

7:22

they a fit? And that research component

7:24

is the first thing that I would normally

7:25

do. I made that the the beginning part

7:27

of of this master skill, and then it

7:29

gives me some pushback right whether I'm

7:31

negotiating price or trying to

7:32

understand maybe this is a newsletter

7:35

test, and it's not a core ICP, but maybe

7:37

it's worth exploring. I have a thought

7:39

partner in in in AI along that. Uh and

7:42

then also

7:43

um from that moment let's say it goes to

7:45

a signature, I drop in the signed

7:47

insertion order or signed contract,

7:50

and that essentially starts all of the

7:52

copywriting, all of the link creation.

7:55

So we use dub.co for our affiliate and

7:58

link tracking system.

7:59

So with the right UTM parameters, with

8:01

the right promo code, everything

8:03

pre-built into the link, it creates

8:05

everything using a certain voice and

8:07

tone that we know works in newsletters,

8:10

but it's also all fed off of all

8:13

previous data of all newsletters that

8:15

have run. So experimentation newsletters

8:18

is also difficult because

8:19

you commit $10,000 to a single

8:22

placement, and then you kind of like put

8:24

your finger in the air and and hope that

8:25

it works.

8:26

But you want the more that you run, the

8:28

more you've like hopefully learned, and

8:31

you can feed this all into a system that

8:33

removes all of the boring admin, but

8:35

also just makes it way more powerful,

8:37

which I've seen no one that is doing a

8:39

sponsorship

8:40

kind of do this way even if they're an

8:42

individual,

8:43

but I took it all the way to trying to

8:45

fully automate that whole workflow.

8:47

>> Wow, I've so many questions. So when you

8:50

said you you built a master skill, is

8:52

this one are you running this in the

8:54

Claude UI or is this in or the Claude

8:56

app or is this Claude code, too?

8:58

>> Yeah, so I even with co-work or Claude

9:01

code in the desktop app, I like doing

9:03

everything in VS code, and that's just

9:06

because I can spin up many sessions in

9:09

the terminal bottom, and then I see all

9:11

my files plus the the actual MD or

9:14

something that I'm reading right above,

9:16

and it's just like a

9:18

I've gotten used to it. I probably could

9:20

use the Claude desktop app for like a

9:22

similar look and feel, but it it gives

9:25

me a level of advanced control where I

9:27

see where it's pulling context, I see

9:29

all of the thinking, I see the file

9:30

maybe change in real time that like

9:32

removes some back and forth that I still

9:34

have to do with some things in the

9:35

Claude desktop app. But they are making

9:37

it better. Maybe I'll make the switch

9:39

soon, but that's yeah, that's cloud code

9:41

in the terminal is where all of this

9:44

starts. So,

9:45

often I don't even have to do anything.

9:47

I just drop the PDF. I don't say

9:49

anything and it's like, oh, this is an

9:51

insertion order. Okay, it's time to

9:53

start our sponsorship skill.

9:56

First checks if the sponsor exists, so

9:59

it doesn't duplicate any actual work. If

10:01

it doesn't, it creates, you know, a

10:03

folder with context about this partner

10:05

and then all of its research and then

10:07

all copywriting ever created for is in

10:08

one place. So, if someone asked me

10:11

what did you run two months ago for

10:13

TLDR? How much did it cost and how did

10:14

it perform? I could ask the AI. I could

10:17

go to a place in the folder cuz I know

10:18

how it's organized. So, I think the the

10:20

organization and and how you think about

10:22

it is also super important from a

10:23

systems thinking level.

10:25

>> Yeah, okay. Yeah, that's something I've

10:26

been thinking about too is how do you

10:28

organize all these different projects?

10:30

And so, like on my machine, I have a

10:32

GitHub folder and then within that

10:34

folder is all the, you know, a new

10:36

folder for every project I build. And

10:38

so, is that kind of how you approach

10:39

this too where you have this is one

10:41

folder and then within that that's where

10:43

all of this kind of operates?

10:45

>> Yep. So, the the Whisperflow marketing

10:47

OS,

10:49

very unique name as it's called, is get

10:52

controlled and shared across the whole

10:53

marketing team.

10:55

Inside of there are essentially

10:57

placeholders as well as like a read me

10:59

for anyone that's installing it to

11:01

essentially it creates like a personal

11:04

folder

11:04

as well as a code base folder.

11:07

So, even though the the whole

11:09

like OS folder is get controlled, inside

11:11

of it we also pull for our analytics DBT

11:13

and our code base

11:15

and those are obviously separately get

11:17

controlled,

11:18

but those are also get ignored from the

11:20

the Whisperflow marketing OS. And then

11:23

personal context, so like working files,

11:25

outputs, things that I don't want synced

11:28

live there. And then everything else

11:30

that essentially bleeds into shared

11:32

context. So, all of the copywriting and

11:34

everything that I'm describing here is

11:36

in a folder called growth. And then

11:38

within that, I have different folders

11:41

based on which growth channel it is or

11:43

if it's strategy. So, this would be

11:44

under sponsorships and then within

11:46

sponsorships, we have some JSONs that

11:48

look at like with whatever quarter we're

11:51

in,

11:52

what name of sponsor and day and dollar

11:54

amount to placements and then details on

11:57

each sponsor within their respective

11:58

folders.

11:59

>> Got it. And so, and then over time that

12:01

system grows too as you work with new

12:04

new sponsors, new placements, you run

12:06

all this stuff and then I guess most of

12:08

it you commit back to the GitHub repo

12:10

minus the things you have that are more

12:12

personal that you get ignore. Is that

12:13

right?

12:14

>> Exactly. Right. So, then like if I'm out

12:17

or anyone needs context around

12:19

sponsorships, they have everything that

12:21

I've ever been working on in a shared

12:23

place.

12:24

So, the the note that I always say,

12:27

assume it's shared unless you have to

12:29

think twice. Like, am I negotiating

12:32

about someone's salary or you know, is

12:33

it like sensitive contract details that

12:36

like the team shouldn't see. Then those

12:38

should be kept personal, but everything

12:39

else like even a contract that's signed

12:42

with a vendor,

12:43

someone is going to ask like, you know,

12:44

when we went through like we're going

12:46

through the process of series B right

12:47

now, you know, from both due diligence

12:50

and finance, we're getting, "Please

12:52

anything over 100k, please send the

12:53

contracts and like organize them this

12:56

and this way." Everyone else on the team

12:58

other than my org, this took them like

13:01

one or two weeks. I just dropped a zip

13:03

with everything pre-sorted cuz it was

13:04

already organized that way in in the

13:06

file system.

13:07

>> Wow.

13:08

Okay, so for someone listening to this

13:11

and they see or this amazing system

13:13

you've built, what is your advice for

13:14

someone who wants to start building

13:16

something like this? Maybe a V1 of their

13:19

own kind of influencer waterfall like

13:21

sponsorship engagement.

13:22

>> I would zoom out even more to to say

13:25

Uh, whole thing from zero was built with

13:29

Cloud Code for Cloud Code. Uh, and

13:31

that's just the the philosophy that I

13:33

always take. If you're unsure of

13:35

everything that we're talking about

13:36

here, everything that you read online,

13:38

try and create it yourself with the help

13:40

of AI. And if there are things that are

13:42

set up a certain way and you don't

13:43

understand them, ask. Like, what is it

13:46

getting ignored? Why are we doing that?

13:47

Like, just ask and and work with the the

13:49

LLM because, you know, we live in a time

13:52

that we have the biggest possible

13:54

learning unlock ever before seen. And

13:56

like,

13:57

I'm not a developer. I've, you know,

13:59

never shipped actual code and I'm

14:01

pushing PRs and, uh, you know, building

14:03

an operating system simply because I've

14:05

taken the time to stress test and learn

14:07

this. So, the reason why I wanted to

14:08

zoom out and not just say for for

14:09

sponsorships is the entire operating

14:11

system

14:13

I started with a prompt. Uh, I want to

14:14

build an operating system for me, uh, to

14:17

do my work. We're going to do these

14:19

things together. Uh, these are some

14:20

workflows. Uh, let's get started on

14:22

that. Asked me a bunch of questions.

14:25

It tell me more about your role. What

14:26

are the things that you need to

14:27

automate, etc., etc. And then we built

14:29

the the first skeleton together with

14:31

Cloud Code of the operating system. That

14:33

was my V1. At the end of the day, the

14:35

skills that you build and the way that

14:37

you use it needs to be meaningful. Like,

14:39

you actually have to use it cuz if if

14:41

you build skills and they never get

14:42

used, then move them into an archive

14:44

because evidently there wasn't intention

14:46

behind what you built and it should be

14:49

repurposed maybe later. So, uh, that's

14:51

the main my main frame of reference

14:53

here. Like, use Cloud Code to help you

14:54

build this because it knows best on how

14:56

to organize it. It won't be perfect and

14:59

that I think the the the frame of

15:01

thinking here needs to be

15:02

AI will only give you what context you

15:04

put in. Uh, and you have to say, "No,

15:06

this doesn't look right. Let's rethink

15:08

about this. Let's It's meant to grow and

15:10

evolve over time as you work on it." And

15:13

that's why like from October of '25 till

15:16

now, it's the same operating system that

15:18

has just gotten better and better and

15:20

better and better every single day via

15:23

just me working with it,

15:24

micro-optimizing it, and then, you know,

15:26

essentially over the last 2 months, I've

15:28

turned my personal OS into a team OS,

15:31

and that's been a, you know, separate

15:32

endeavor.

15:33

>> Nice. Yeah, I do want to ask about your

15:34

migration from personal to team.

15:37

Um before that though, they're built

15:39

this now, is there anything you would do

15:41

differently compared to when you

15:42

started?

15:43

>> Yeah, I think

15:44

at least from my personal experience, I

15:46

probably layered in like the voice and

15:49

copy guidelines a little late, but also

15:52

that I think the models have gotten

15:54

better.

15:55

I have to be very explicit to like avoid

15:58

slop,

15:59

but I would say with the right MD and

16:02

like guardrails, the models can be very

16:05

good at copy, and they still need that

16:07

human touch. I definitely spent a ton of

16:10

time editing the early copy, and like

16:13

giving it feedback in it. It didn't

16:15

persist in the right way, and I didn't

16:17

fully understand maybe the best way to

16:20

approach what I call the the voice guide

16:22

of the do's and don'ts, and how to log

16:25

when I give feedback. There's a reason

16:27

I'm giving that feedback, and for it to

16:29

log that in a certain layer of context,

16:31

and that's where the voice guide comes

16:33

in. So, when I'm updating copy, I don't

16:36

do it directly into the Docker MD that

16:39

it's generating it.

16:40

I prompt it with Whisper flow, and I

16:42

tell it, you know, this doesn't sound

16:44

right. This is how I would say it. Let's

16:46

try that out, and and then let's see why

16:48

does that read better. I know I work

16:50

with Cloud code to essentially get

16:52

there, and then ask it, you know, from

16:54

from where we started to where we ended

16:55

up, you know, how can we ensure that we

16:57

end up here to begin with? That took me

16:59

a little bit to get there, and that's

17:01

just like building the muscle of

17:03

actually giving context, and like

17:05

working with it like a an employee,

17:07

where you give it feedback instead of

17:08

just like making the edit, and then, you

17:10

know, a lot of people do this. They they

17:12

give someone feedback, and then they

17:13

just make the change themselves, and

17:15

then expect the person to do better next

17:16

time, but they never actually gave the

17:18

feedback. So, it's very similar with

17:20

with Claude code.

17:21

>> That's really interesting and something

17:23

I think this is a bad habit I do of I'll

17:25

just make the change in the file, but

17:27

you're saying actually talk to Claude

17:29

and say no, like I want to make this

17:30

change and here's why and tell it your

17:32

thinking and treat it like a colleague

17:34

basically and then that helps the

17:36

context kind of learn and get better

17:38

over time.

17:38

>> Exactly. Yeah, and and that's like

17:41

literally I have like between six and 10

17:44

sessions doing something at any given

17:46

time on my computer

17:47

and

17:49

I've gotten to the point where I'm using

17:50

like a Logitech MX 4 mouse where one

17:53

button is the hands-free

17:56

toggle for Whisper flow

17:58

and then I press it again to end and

18:00

then it pastes wherever I clicked and

18:02

then the haptic button on the MX 4 is

18:04

enter. So, I just scroll around the

18:06

sessions, give feedback and that's like

18:09

my primarily way of working with Whisper

18:11

flow. The vast majority of my words

18:13

dictated are prompts, but they're not

18:15

the original prompts. Like sure I can

18:17

one-shot things if I do a five or so

18:20

minute dictation and I give it the right

18:21

context, but the majority of the inputs

18:24

into the terminal windows is feedback.

18:27

Is is giving the actual context and

18:29

understanding of why this is different,

18:31

why I'm thinking about it differently

18:33

and then it grabs onto that context and

18:34

I think building a bit of a memory layer

18:37

or understanding like where it should

18:39

pull certain things is also what makes

18:41

this easier and we can touch on the like

18:44

session start and session end a bit

18:45

later as well.

18:46

>> Yeah, no, I'd love to talk about that.

18:47

How do you manage You said you're on six

18:50

to seven or eight different sessions.

18:51

How do you manage all of those? Does

18:53

that get overwhelming at all?

18:55

>> Yeah, it it depends on the the duration

18:57

of of some tasks. So, they're usually

19:00

not related at all and they have a

19:03

they have a certain start and end

19:06

which which is you know, really

19:08

important. Like when I open a a new

19:10

terminal, I know what I want it to

19:11

achieve.

19:12

Uh and there there's low likelihood that

19:15

like I I continue on a session for a

19:18

couple days. And there's like various

19:20

reasons for that that that we can touch

19:21

on later as well, but everything covers

19:24

either a different channel or a slightly

19:26

different headspace of something that I

19:27

need to

19:28

be looking at or like analyzing meta ads

19:31

or coming up with new ideas around

19:32

concepts or using the Google Ads CLI to

19:35

get like a deep dive into yesterday's

19:38

data. And these things, you know, take

19:40

time. Like the the models uh I want to

19:41

give them time to think. Um so I usually

19:44

will push, you know, push forward a

19:45

prompt and it will take 10 15 minutes to

19:48

to do some next layer of a task that I'm

19:51

asking it to do.

19:52

Um so because it, you know, usually

19:54

those things would take between, let's

19:56

say, 5 and 15 minutes, uh I can move on

19:58

to the next thing and like check in and

20:00

give it some feedback. It'll do its

20:01

thing and I kind of cycle around uh the

20:04

sessions. And then, you know, some of

20:06

them will have actual manual action

20:08

items that I need to take. Uh so then,

20:10

you know, sessions will go away and then

20:11

I'll go and finish the thing, then go

20:13

close out the session that I needed to

20:15

do with certain set of manual work. And

20:17

then I'll see what's left. So like

20:19

it sometimes drops down to maybe two or

20:20

three, depending on the day, but like

20:22

usually my day starts with at least that

20:25

many uh of kind of top-of-mind things

20:27

that I want to get going.

20:29

Uh and then it dwindles as the the day

20:30

kind of narrows.

20:31

>> Okay. And then, how do you I guess you

20:35

touched on earlier kind of this concept

20:37

of session start and session end? Can

20:39

you kind of talk about that and what

20:41

that looks like for you and maybe why

20:42

it's important?

20:43

>> Yeah, so it's one of the first

20:45

uh skills that I built uh that like

20:48

endured the test of time. Uh but

20:50

essentially uh I'll start with session

20:52

end because to me it's more important.

20:55

It was built for two reasons. Um so as

20:58

as you know, right, with the latest

20:59

models, there's a 1 million context

21:01

window.

21:02

Uh but the way that model token pricing

21:04

works is

21:06

as you work longer with the session,

21:08

context grows and the amount of tokens

21:11

every single message sent also grow. So,

21:13

you you definitely seen right in the

21:15

bottom right

21:16

uh {slash} clear to clear 800,000 and

21:18

three tokens, right? Uh the next message

21:21

that you send and the message after that

21:23

is 805,000,

21:25

810,000. It just grows every single time

21:28

you you message it. And that ends up

21:30

being very expensive. So, you don't

21:32

normally need that much context.

21:35

Normally, like if you work in

21:36

checkpoints, so I let's say I'm doing a

21:40

let's say a pretty complex task and it

21:41

has three distinct pages uh phases. I'll

21:45

start a session, let's say it's, you

21:47

know,

21:47

drafting newsletter copy. Uh and once

21:50

it's done, I run session end. And what

21:52

session end done uh what it does is it

21:55

takes everything that we did in the

21:56

session and it logs what we

21:59

accomplished,

22:00

what things I gave it feedback on and

22:02

changed, uh and it logs it in local

22:05

memory of something that we recently

22:07

completed. But, one of the most

22:08

important things that it does is it also

22:11

logs what is not complete. Uh what

22:13

should be a part like a to-do or piece

22:15

of context that will be relevant for my

22:19

next session, which will start with

22:20

session start. So, session end is like a

22:22

all-encompassing

22:24

please persist everything that we worked

22:26

on and have it be just like a little bit

22:28

easier to find and also for me not to do

22:31

a lot of manual work to say I completed

22:33

this or what was that thing that we did

22:35

yesterday? All that is stored in that

22:37

way.

22:38

So, that's session end. Uh session start

22:41

uh essentially starts a session.

22:43

Uh it's primarily around like tell me

22:45

what you want to work on, uh but it

22:47

primarily also pulls from the previous

22:50

session ends. Here's the stuff that's

22:52

still floating that we didn't complete

22:55

and it bubbles it up to the surface. So,

22:57

the likelihood that I missed something

22:59

that is super high priority because I

23:01

didn't have time to finish in some

23:03

session or if I close the session and

23:05

there's like a million action items

23:07

which like is the case like I'm I'm

23:09

floating between

23:10

100 and 200 rolling open to do's that I

23:13

didn't get in time

23:14

and the only way I can manage that is

23:17

and like a lot of that work happens in

23:18

Cloud Code

23:19

and session start just bubbles up what

23:21

is priority specifically as I start my

23:23

day. So those are like the overarching

23:26

beginning and end steps of every single

23:28

session.

23:29

I have like morning and evening rituals

23:32

that are separate from that but these

23:33

are kind of like session locks.

23:34

>> Okay. And [clears throat] then

23:37

is it possible to anonymize or share any

23:39

of those? I'm so interested in how how

23:41

those work.

23:41

>> Yeah, I know I'm happy to share like the

23:43

the vanilla version. I know it works

23:45

because I've gotten every single person

23:47

on the team to start using it and when a

23:50

skill becomes commonplace you know it's

23:52

doing something right. This is the one

23:54

I've definitely tinkered with the most

23:56

and also gotten other people to like

23:58

fully adopt so I'd love to share that.

24:00

>> Amazing. Okay, so it sounds like this

24:02

has saved you a lot of time and maybe

24:04

your team too if they're adopting all of

24:06

these skills as well. Can you talk

24:09

through any metrics on time or team

24:12

bandwidth or just kind of

24:14

uh business outcomes that kind of

24:16

automating this whole system and

24:17

building like the Whisper marketing OS

24:20

has saved you?

24:20

>> This has been a project that we've I'd

24:22

say kicked off in the last 2 months.

24:25

Uh in the last 2 weeks we've gotten

24:28

about 50 to 60% of the marketing team

24:30

were just shy of 20 in like various

24:34

roles in the marketing team

24:36

and this is this covers like all of

24:38

design all the different lanes around

24:40

like influencers, product marketing,

24:43

country leads. You know, we have country

24:45

leads for the UK and India like the our

24:46

whole India team. Uh that's the reason

24:48

why that that team is is as vast as it

24:50

is and we got like 50% of people using

24:54

it right now and how I can quantify

24:55

value is we've had roles that were on

24:59

the docket to be hired and we've paused

25:03

interviewing and hiring for them because

25:05

we made a couple more people on the team

25:07

higher leverage where they could take up

25:09

an additional part of work.

25:11

Like for example,

25:13

we have someone that oversees like all

25:14

of our creator partnerships

25:16

and his whole scope of work was just

25:19

influencers mainly, you know, YouTube

25:21

and LinkedIn. But we actually have him

25:23

now brought into the system that I built

25:25

around newsletters and because it was

25:28

something that is self-contained and

25:29

pretty easy to pick up once you

25:30

understand all the moving pieces, it is

25:32

an additional thing that he could pick

25:34

up. We were potentially going to hire

25:36

for someone to run that system, but

25:38

because of the time saving he has on

25:40

research and actually working with

25:41

creators using the operating system in

25:44

his own way that fits his workflow, he's

25:46

able to attack on another part because

25:48

of savings he's seeing there. The most

25:51

I'd say pervasive time savings and like

25:53

ROI that we can see on the team that

25:55

probably saves, I'd say between 10 and

25:58

20% of every person's week is just like

26:01

admin. So let's say we we want to launch

26:03

a new landing page on the website. Seems

26:06

like a simple task, but there are many

26:08

stakeholders and people involved.

26:10

Someone needs to come up with the brief

26:11

and copy.

26:13

Someone needs to design it. Someone

26:14

needs to develop it. Someone needs to QA

26:16

it. We need to make sure conversion

26:17

tracking works. We need to then publish

26:19

it and do all those things. For someone

26:21

to do that set of work and that's like

26:23

your project management context

26:26

kind of gathering and then sharing

26:28

takes a lot of time and that's like any

26:31

knowledge worker, anyone that works at a

26:32

startup or company spends between 10 and

26:34

20% of their week just in that world of

26:36

admin. And with Cloud Code you you take

26:39

your idea and because there's a skill

26:41

built around a certain lane of work, it

26:43

asks you questions, fills out a brief,

26:45

it puts it into linear, it writes a

26:47

message in a shared Slack channel, then

26:49

sends messages to individual people with

26:51

all of their contacts

26:53

and that takes 10 minutes instead of an

26:56

hour and a half.

26:57

So that you know that that I would say

26:59

as an admin level of interacting with

27:01

Slack, interacting with linear and

27:03

giving context immediately to people and

27:05

also making it easier for the person

27:07

that also needs to assign a task to

27:09

someone.

27:10

>> Yeah. Is there a way you log or report

27:12

any of that out to leadership or is all

27:14

this kind of like

27:16

gut feel for lack of a better word?

27:17

>> Yeah, right now and I think a lot of

27:19

companies are going through this where

27:21

like we don't have the mandate to

27:22

essentially quantify ROI.

27:25

I look at this as the the overseer of

27:28

the the marketing OS just to make sure

27:30

like in in my point of view if you're

27:32

using these systems and we're spending

27:34

tokens, there has to be an ROI otherwise

27:37

everyone's just doing a lot more busy

27:38

work or just like it just feels a lot

27:40

more work to work with the AI. And at

27:43

least for me that's never the case and I

27:45

want everyone that's also onboarding

27:46

onto this

27:48

feels like a daunting task to begin with

27:49

for people that are like less technical

27:51

and you know don't know how this works.

27:53

But yeah, so I I'm the main person

27:54

that's kind of understanding from the

27:56

whole organization marketing level

27:58

are people more

28:00

effective, do they have higher leverage,

28:02

are they spending more time on more

28:03

important things?

28:04

And that's kind of like in one-on-ones

28:05

and conversations that I have with the

28:07

team.

28:07

>> Yeah, it sounds like that

28:10

yeah, one of one of the outputs is

28:11

higher leverage. Like you said, maybe

28:14

you pause hiring for a role because you

28:16

know using AI can kind of make everyone

28:18

more effective at their job, they can

28:20

touch more surfaces, increase their

28:22

velocity of output. Is there a way to

28:24

tie that to a business KPI for y'all if

28:28

it's signups or installs or downloads?

28:30

Like have you looked at that too?

28:32

>> Yeah, I mean at the end of the day like

28:35

since I was the one person doing a lot

28:36

of this for a while and the business

28:38

case is very clear where like me plus

28:41

this for a very long time, I could hold

28:43

up essentially the the whole side of the

28:45

team. You know that has changed, We we

28:47

have a lot more volume and a lot more

28:48

growth, and thankfully, there's more

28:51

attention and and kind of more focus in

28:53

the dedicated lanes.

28:55

But, I think I'll reframe maybe the

28:57

point of view I have on this

28:59

from your question to say that

29:01

I think

29:02

everyone can be more like more higher

29:04

leverage with AI, but in order to do

29:06

that, each person needs to be a systems

29:09

thinker or, you know, learn to be a

29:11

systems thinker cuz it's really easy to

29:14

send the email faster or send the Slack

29:16

faster, but that's not high leverage.

29:19

Sure, you save a little bit of time, and

29:21

then you do other things, but like are

29:23

the highest leverage parts of your job

29:25

also AI supported? And the honest answer

29:28

for a lot of people, it's not, right?

29:30

And it's like it's too high effort to

29:33

take and push AI through the beginning

29:36

of a brainstorm or thinking, but once

29:38

people can take a step back and analyze

29:40

in their role and in their job,

29:43

what are the systems that essentially

29:45

make the work happen, and how can we, of

29:48

course, scale and speed that up, but

29:50

does maybe spending more time in

29:51

research and understanding the thinking

29:53

that goes even before we assign out the

29:55

task? AI can also really help with that,

29:58

and it can also help out with all the

29:59

admin, right? And I think from from the

30:01

business case, organizations need to be

30:04

teaching this level of systems thinking

30:07

because it's where I see some of these

30:08

pitfalls in trying to say, "Here's cloud

30:11

code and an OS. Go." A lot of people

30:14

don't know where to start because

30:16

they're not taking a step back and

30:17

analyzing their role from a systems

30:19

level, and that's where I think a lot of

30:21

fallacies, even in AI usage at startups

30:24

or enterprises, and like with with

30:26

rampant token usage increasing,

30:28

I think because there's less of a

30:30

narrative on why are you doing this or

30:33

could you do it with AI and make you a

30:34

little bit more powerful,

30:36

like the token usage is is on, I'd say,

30:39

some menial things where like if they

30:41

took a step back and focused on the more

30:43

important higher level things like we've

30:44

said, it would make a bigger difference

30:45

to the business case.

30:47

>> Okay, and so if you're I guess if you're

30:49

a marketing leader watching this and

30:51

you're like, yes, and nodding your head

30:52

like yes, I need my team to be more

30:54

systems thinkers. Like what's one step

30:58

or how would you like encourage people

30:59

to kind of think that way or is that

31:02

part of a hiring plan as you kind of

31:04

like look to re-composition your team

31:06

right now around that?

31:07

>> I think everyone in hiring should be

31:10

hiring for, you know, what everyone is

31:11

calling AI native.

31:13

Um but like

31:15

anyone you can give anyone a chat window

31:17

and they can they can talk to an AI. But

31:19

the the thinking that goes into creating

31:22

the prompt and giving it feedback and

31:24

the the feedback loop around the system

31:27

is I think the main thing that

31:30

like orgs need to start testing a little

31:32

bit more in the hiring process and also

31:35

just doing this more as a a learning

31:36

exercise in the org

31:38

because like however easy it is now to

31:41

just speak your mind with Whisper flow

31:43

and give a more detailed prompt,

31:45

what you say and how much context is

31:47

actually needed is like it's still

31:49

relatively open-ended. I'd rather test

31:51

for how people think and deconstruct

31:54

problems.

31:55

So like if you know, like newsletter as

31:57

we gave as an as an example, the

31:59

question would be okay, like you have

32:01

this workflow.

32:02

What are the bottlenecks and what are

32:05

all the inputs and the outputs and can

32:07

the person actually map this out? Do

32:09

they understand you know, all the moving

32:11

pieces? Cuz if you understand all the

32:13

moving pieces and then you add in a

32:15

little bit of AI to help you, you can

32:17

build a really good system, right? It's

32:19

it's like the ability to step back and

32:21

say here all the cogs in this machine

32:24

and this is what makes it hum. A lot of

32:26

people are fixated on the well, here's

32:28

my piece. That's what I'm focused in on.

32:30

I make that a little bit more AI

32:31

focused, but the the whole machine isn't

32:33

necessarily better, right? And I I

32:35

that's that's the frame of reference

32:36

that I would take here is just step back

32:38

and and understand how the team works

32:40

together and what are the biggest

32:41

blocking points. And if you can have AI

32:43

help with those, then ROI is immediately

32:46

clear. Because if there are clear things

32:48

that are taking too much time for

32:49

people,

32:50

and you solve those, then the actual

32:53

adoption of AI is a lot easier because

32:56

people are actually using it for things

32:58

that they immediately feel the value for

33:00

instead of being told, "Well, now use it

33:02

in your job." Right? It's like it's

33:03

really hard to to teach a person that

33:05

doesn't know how to think in this way to

33:06

actually start that way.

33:08

>> Yeah. It almost sounds like interviewing

33:10

for marketing roles becomes more about

33:13

maybe pulling

33:15

tactics or topics from how you would

33:17

hire an engineer to like really more

33:19

around systems thinking and

33:20

deconstructing problems and then

33:22

layering on, "Okay, how would you use

33:24

AI to to do this or do different parts

33:26

of your job or scale parts of your job

33:28

that were super manual in the past?"

33:30

Like is that something kind of you agree

33:31

with?

33:32

>> 100%, right? Like zooming out two years,

33:35

if I was hiring for people to join my

33:37

team, it would be

33:38

"Are you the best in the world at Meta?

33:40

Are you in the best in the world at

33:41

Google?" Right? Channel expertise.

33:44

I think now, yes, that's still a filter,

33:47

but like I would much rather the person

33:49

be like middle-level intermediate to

33:51

advanced but not the best in the world,

33:53

but be a systems thinker where they can

33:55

understand all the moving pieces of

33:58

their channel or their responsibility

34:00

and be able to layer in AI to 10x

34:03

themself or 100% 100x themselves in

34:06

their role because if you're

34:09

a person that's great now in something

34:12

and you don't adopt AI into that

34:13

workflow, the likelihood that you are

34:15

the best in the world in a month is

34:18

extremely unlikely, right? So, I I 100%

34:20

agree with that.

34:21

>> Okay. And so, I do want to come back to

34:23

one one topic and then we can close out

34:25

of I know when you started, you you were

34:27

the only marketer you kind of built this

34:29

system for you and now you're kind of

34:31

rolling it out to your team. Maybe if

34:33

there's someone listening that is trying

34:35

to go through a similar path of one to

34:37

two or three people on their team and

34:39

take a thing they built and have their

34:40

team use it. What is one or two pieces

34:43

of advice you would give them and is

34:44

there anything you would do differently

34:46

now, too?

34:47

>> Yeah, so I mean

34:49

the whole OS was

34:51

it was mine, right? Like the the shift

34:53

between

34:55

Matt's brain and everything and all the

34:57

context that I did,

34:59

I had to, you know, it was not designed

35:01

for that. There was quite a bit of work

35:03

to essentially go through the thinking

35:06

of how do I want to, you know, prep for

35:08

context, what's personal, what's shared,

35:11

how do PRs work, all of this, like there

35:13

was a ton of back and forth even in the

35:15

the first like one or two people that

35:17

were my guinea pigs on the team. Shout

35:19

out to Eric and Dan that

35:21

uh went through that with me.

35:23

So I mean the the number one tip there

35:24

is just assume that everything that you

35:27

build will be shared at some point.

35:29

Because the the individual work that we

35:31

do is useful to other people and

35:35

adding into a shared pile of context

35:37

just makes the whole organization and

35:39

the whole team that much more powerful.

35:41

So the number one tip and the number one

35:43

piece of advice I would give is design

35:45

the tools and the systems you build

35:46

today to be multiplayer, to to kind of

35:50

work with broader context. Because

35:53

that's where I see, you know, this whole

35:54

industry going

35:56

when you look at a lot of new AI

35:57

startups and a lot of investment, it's

35:59

going into the harness, the the memory

36:02

layer and and everything that is

36:03

actually allowing ever growing amount of

36:06

multiplayer people interacting with this

36:08

thing that if you already do some

36:10

workflows, assume is this useful for

36:13

anyone else? And you know, and this is

36:15

like one of the things that I always

36:17

connect to as maybe a second piece of

36:20

advice. And I made this mistake in the

36:22

beginning,

36:23

is never hard coding uh or facts into

36:27

skills or things that you have live in

36:29

the system

36:30

uh because when you do that and you

36:32

share it, it's stale. It won't update.

36:35

Uh but if you have a centralized place

36:37

where let's say it has our latest ARR

36:40

numbers or the latest composition via

36:43

name and Slack ID for the marketing

36:45

team, that's housed in some file

36:47

somewhere and then the skills are

36:49

pulling from that context. So you only

36:51

have to update one place. So a new

36:53

person joins the team or our ARR

36:56

updates, Cloud Code is not losing itself

36:58

trying to find what is the latest,

37:00

what's stale, what's not. And like this

37:01

is usually where it goes wrong and it

37:03

hallucinates. It's using hardcoded facts

37:06

when it should be It should know that

37:08

something is stale and then should run

37:10

another skill to pull the latest data,

37:12

store it locally so then someone doesn't

37:13

need to do that because it sees, "Ah,

37:15

Matt already ran this. This is, you

37:17

know, most updated information." So like

37:19

I push PRs essentially every day

37:21

as maybe another little tip. So like

37:24

things that you build probably will be

37:25

used by someone

37:26

and that's like the multiplayer making

37:29

sure context is is in one place and not

37:31

hardcoding things into skills and and

37:33

things that you're working on. Yeah.

37:36

>> Okay. Yeah, it's almost like an

37:37

engineering concept, right? Of

37:40

instead of hardcoding things, you have

37:41

variables and then you have a variable

37:43

for oh revenue equals this, you know,

37:45

sign-ups equals this and then maybe you

37:46

have a skill that updates your kind of

37:49

like, you know, primary KPI, you know,

37:51

markdown file or whatever every day with

37:54

revenue, you know, any kind of like

37:55

number like that and then all your other

37:57

skills then reference that kind of

37:59

primary KPI file every day. Is that Is

38:01

that an accurate summary?

38:03

>> Exactly, right? Cuz then uh the skill

38:05

always knows the one source of truth

38:07

where those numbers need to go and then

38:10

various skills can reference multiple

38:13

context files and they are The skills

38:15

are always going to be right because

38:17

let's say we're doing a investor update

38:21

and it needs to have our latest numbers.

38:23

In the beginning, when I first was first

38:24

starting, you know, I I didn't keep

38:26

track of this and I I ran the numbers

38:29

and it created, you know, did 30 minutes

38:32

it worked on this report.

38:34

And every single number in the whole

38:36

thing was wrong is because it realized

38:38

it had some local numbers. It didn't

38:40

start a a hex thread, uh which is our

38:42

RBI tool, and uh I had to redo the whole

38:45

thing. 30 minutes wasted, tons of tokens

38:48

wasted, and just like a ton of

38:49

frustrated, you know, time having to

38:51

like quickly rush in order to get to

38:54

that investor update to make sure that

38:55

specifically that everything needs to be

38:57

right. There's there's no room for

38:58

error.

38:59

Uh and uh yeah, like that's a really

39:01

easy way to avoid that.

39:02

>> Yeah. Okay, so if there's someone

39:04

watching this who is like, "Holy cow,

39:06

Matt is super advanced and he's built

39:08

all these systems." Like, how would

39:10

someone start to stair-step their way to

39:13

get to the like kind of more advanced

39:16

level that you're at? Like, have you

39:17

just been doing a process of trial and

39:20

error prompting, like just getting

39:22

better every day? Is that really like

39:23

the solution here?

39:24

>> Yeah, I would say that the number one

39:26

thing is just just do it. Just uh

39:29

give feedback, learn, and start small.

39:33

Your system is going to have maybe one

39:34

or two workflows and as long as it helps

39:37

you, that's already super valuable. It

39:39

won't be as, you know, vast and and

39:40

complicated as we framed it here. It

39:42

should not feel at so daunting that you

39:45

can't start. Like I said, I built the

39:47

original thing with the thing itself,

39:49

right? I told Cloud Code, "I want to

39:50

build an operating system. Let's get

39:52

started."

39:53

Um so, start there and you'll you'll

39:55

already be an intermediate at the end of

39:58

that session cuz you'll have something

39:59

that is unique to you that works for

40:01

you, that maybe doesn't follow exactly

40:03

these these guidelines, but at the end

40:05

of the day, every person in the role is

40:06

unique. Uh and that's the beauty of the

40:08

system as well, right? Like, it's meant

40:10

to mold and adapt to the individual and

40:13

that's what makes it powerful and great.

40:15

And then uh the second tip I would say

40:17

is um X is amazing specifically if you

40:21

curate your algorithm.

40:23

So, you know, go and find you know

40:25

people that are writing about this

40:27

stuff. There's a ton of amazing

40:28

articles.

40:30

I bookmark a ton of stuff on X through

40:32

like two or three little time slots I

40:34

have in the day and then like before I

40:35

go to bed they're fed into read wise and

40:37

then I just read through these posts and

40:40

I pull out some ideas. I go and test

40:42

them the next day and it's all trial and

40:44

error, right? Like a lot of what's

40:45

written you know everyone that's saying

40:47

that they're using their open cloud to

40:48

become millionaires is lying to you.

40:51

So, take things with a grain of salt but

40:52

then you know, take that and maybe try

40:54

it on your own. And there's some things

40:56

that worked some things that didn't but

40:58

it's

40:59

from the intention that matters and

41:01

that's how like how I fill my day, how I

41:02

experiment with everything

41:04

and how I got to the place that I'm at

41:05

now.

41:06

>> Well, I have learned so much from you in

41:08

just the time that we have spoken now

41:10

and then some of the prior conversations

41:12

that we've had and every time I'm like

41:14

honestly blown away at the things you've

41:16

built and just kind of the systems

41:18

architecture and how you think about

41:20

about everything. So, thank you so much

41:22

for coming on and for sharing some of

41:24

your knowledge with us.

41:25

Any of the skills you can package up and

41:27

send our way, we'll put them in the show

41:29

notes or the description here and truly

41:32

final final question for you of if

41:35

people want to follow you or find

41:36

Whisper like where can they find you?

41:38

>> Yeah, you can find me Matt Sullinski my

41:41

first and last name no space on X,

41:44

LinkedIn and Instagram. Probably most

41:46

active on LinkedIn. X is right now I

41:49

mainly digest will be more active with

41:52

with time but that's the best place to

41:53

find me.

41:54

>> Awesome. All right Matt, thank you so

41:56

much.

41:57

>> Pleasure is all mine. Thanks guys.

41:58

>> That's Matt Sullinski head of growth at

42:01

Whisper Flow. We'll drop his LinkedIn

42:03

page in the episode description. If

42:05

you're listening to this just a heads up

42:07

that we put all of these on the official

42:09

profound YouTube page. And if you're

42:11

watching we're on all the podcast apps,

42:13

too. If you want to go deeper on this,

42:16

we have a ton of resources for you on

42:18

our website, trymarketingengineer.com.

42:21

There's a free Marketing Engineer

42:22

University, case studies, our manifesto

42:25

on why every company on the planet will

42:27

hire a marketing engineer this year, and

42:30

so much more. I'm Nick Lafferty. Keep

42:32

building, and I'll see you right here

42:34

for the next episode of the Marketing

42:36

Engineer.

Interactive Summary

Matt Swolinski, Head of Growth at WhisperFlow, shares how he uses Claude Code to build a highly automated 'marketing operating system' that streamlines tasks like newsletter sponsorships, team management, and project coordination. By treating AI as a junior employee and focusing on systems thinking, he has significantly improved team efficiency, allowed for pausing certain hires, and fostered a culture of leverage within his marketing team.

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