The Startup Playbook for Hiring Your First Engineers and AEs

Today we're going to hear from David

Paffenholse, co-founder and CEO of

Juicebox about how to source great

engineering and sales talent. Juicebox

is an AI sourcing platform backed by

Sequoia and used by Ramp Cursor and

Plexity to recruit the best talent in

the world. First, we'll hear his

presentation and then we'll have a

conversation to dig deeper into some of

his advice for recruiting.

Hey everyone, I'm David, co-founder of

Juicebox. Today we're talking about how

to source and hire your first few

engineers and AEES. Especially as a

startup, you're probably thinking about

a bunch of different things. Getting

your next uh few thousand in MR, hiring

and shipping new product features. It

can be easy to not focus on the specific

people you're bringing on and really

prioritizing speed instead. Speed is

really good, but at the same time,

there's a lot of reasons your first few

hires matter a ton. You're going to be

defining the culture, velocity, and

future of your business. That talent in

the early days is shaping that for

everyone who follows. Your future hires

are going to be looking up to your

founding engineer, your founding AE. And

perhaps even more importantly, you will

be shaping them and they will be shaping

how you run your business, too. Now,

making that even clear, the culture is

defined by the first 10 people in the

company. and perhaps the next 40 people

after that for the first 50 people

total. Today, Juicebox is a team of 20.

We put a lot of thought into who the

first 10 people were we hire and just as

much thought into the next 10 as well.

At the same time, hiring is really hard

and really competitive. We put a

screenshot here uh from an engineer

where you can see the amount of outbound

that they will receive. If you're an

engineer yourself, you might have

received the same LinkedIn DMs, emails,

and more. And so as you're thinking

about you recruiting other talent, keep

in mind that they're receiving a lot of

outbound themselves and we'll need to

make sure that your message and your

outreach stands out. So what really

matters when thinking about where talent

goes? First, we should think about the

options that they have and how they're

probably evaluating joining your company

versus joining another company. We think

of that in three main buckets. The first

one is big tech. Um, fan companies, as

we might imagine, strong compensation

packages and a very stable job. At the

same time, the pace will probably be

slower. And the impact that those people

are having in those roles is less. We

can contrast that with growth stage

companies. And so, a few logos on this

slide are kind of later stage or large

stage growth companies, Stripe, OpenAI,

and Anthropic. But really, most series B

and onwards companies are going to fit

into this category. What matters most

here is that the compensation has pretty

predictable upside. Uh their stock is

likely not going to go to zero and they

can estimate how much they'll be making

in future years as the company continues

to grow and they're probably already

starting at a pretty good base salary as

well. At the same time, their work is

somewhat fast-paced and they still feel

like they're making somewhat of an

impact. At the same time, there's a lot

of structure in place. Um there might be

multi-layer orgs. They're definitely not

working with the founders directly and

they have less ownership about the work

that they actually do. Now, we'll think

about your startup or where you probably

are right now. The reason for an early

hire to join is to be able to shape the

culture, the product, and the

trajectory. They also have the highest

variance in potential outcome on the

economics of your stock. They're going

to receive the largest equity grants in

your company, but they're also the most

likely to go to zero at that point. And

so in some ways the risk that an early

employee is taking on is somewhat

similar to the risk that a founder takes

on. We'll go through different ways to

minimize that risk and sell being at an

early stage company in the best way

possible. So as we think about what

candidates we're bringing on and hiring,

we'll want to make sure that we

understand which of those three groups

are they leaning towards.

Most talent will already have an

inclination one way or another. We might

be able to tell based on the companies

that they recently worked at or

currently work at or even what they tell

us on the interview. When we're speaking

to candidates, the first thing we want

to find out is do they have a leaning in

one of those three directions? If yes,

why? Which of those things matter to

them? And how can we use that to our

advantage to convince them to join our

company? Now, as we continue the process

with them, we want to make sure that

they're staying true to their word. Are

they also interviewing with a big tech

company? If so, that might indicate that

they're not quite sure in which

direction they want to go yet, and we'll

have to circle back to selling on why

should they be joining a startup in the

first place. Now, once we've figured out

that they want to be joining a startup,

we'll have to go to the second question,

which is why should they choose your

startup? We've already established that

they probably want to have high impact.

They're open to pretty high risk and

they want to have the ownership of being

able to work directly on important

features, working with the founder

directly and really being able to

influence that trajectory. Now, those

things can happen at a lot of different

startups. And let's say an early

engineer is speaking with your company,

they're likely also going to be speaking

with other companies, maybe even other

companies in your batch. And so, next,

we should think about why they should

work at your startup.

This is really unique to you. There's a

few guiding points on here that we've

often seen be a main selling point. One

of them is being missiondriven. For

example, if you're working in an

industry that has a specific connection

to certain people. Let's say you're

doing a fintech that addresses

international bank accounts or you're

working on immigration startup. There

might be people that are more driven to

that mission and really want to

contribute. Other candidates might be

more focused on equity and compensation

upside. They view this as a chance to

have a really high variance outcome. And

there we might want to focus more on

what the potential upside is. Um even

provide a stock calculator for where

they might want to go in the future. In

other cases, you might have a really

interesting problem space. This could be

deep tech. Um things that are really

technically big challenges and will

attract a certain pool of people who

want to work on those deep challenges.

And then finally, and I think this is

often missed, is many people join

companies because of the culture and the

team, especially referrals. They already

know people who are working at that

business and they have a reason to be a

part of it. As you pitch your company,

you should make sure that you know which

of those four you're pitching, probably

pitching one or two of them. And they

might also vary depending on the

candidate that you're speaking to. Now

that we have some of the initial things

in place, let's think about the sources

that we have for finding those

candidates.

There's three main ones that we're going

to cover at a high level and then we're

really going to dive into the sourcing

part because that's what's most under

your control. First, you want to

maximize your referrals. People that you

know, people that you've worked with in

the past, people that your existing team

members know as well. You can get very

specific on this. In fact, we've seen

companies where on the first day of a

new hire, they sit down with that hire

and look through every single one of

their connections to see who else could

be a good fit and who else they might

want to reach out to. You might also

want to include a referral incentive or

referral bonus. That can be anywhere

from 10 to 20K, sometimes even more for

successful hires. Compared to the fees

that you'd pay with, say, a recruiting

agency, that referral bonus is often

still a pretty good deal. Next, you'll

want to distribute your job. If you're

YC startup, you'll definitely want to

post on work at a startup. In fact,

Juicebox made its first hire from work

at a startup as well, LinkedIn, as well

as any other job boards. Now, apart from

work at a startup, most online job

boards are likely going to give you a

lot of noise and might not give you the

best hit rate on candidates. At the same

time, you want to look at that channel

and make sure that you're reviewing

those applicants as well. The main thing

you can do there that's under your

control is making the JD very easy to

read. Um, I think the easiest test is if

you were reading that job description as

an applicant, is that something you'd

want to apply to? And finally, sourcing.

This is where we're going to be going

most in depth. proactively identifying

and reaching out to the right candidates

for you. We'll cover a bunch of

different steps on how to make that

good, but first let's talk what is

sourcing and why does it matter in the

first place. Sourcing means proactively

finding candidates rather than waiting

for applicants who come to you. The best

candidates aren't applying. They're

probably already working somewhere else.

You can think of this as very similar to

outbound sales. You're building a top

offunnel pipeline. In this case,

prospecting is like sourcing candidates.

You're doing cold outreach in the form

of candidate emails or DMs, and then

you're tracking your pipeline and

conversion funnel from there. Often

times, we're focused exclusively on the

sales part in the early days of the

company and driving that initial

revenue. At the same time, when we

switch over to hiring and that becomes a

big focus, we want to put the same

attention and care into the hiring

process as we might have when crafting

our initial outbound process, too. So,

how do we win at sourcing? There's a few

different steps to it. The first is

actually finding candidates. That's the

search component. Uh that's where you go

to platforms like LinkedIn Recruiter or

Juicebox to help find top candidates for

your role. You'll then put together

outreach messaging for them. Uh

typically a multi-step campaign. Think

email, LinkedIn messaging, um maybe a

few different founders reaching out to

the same person. Your goal is to convert

them into an interview and then finally

close the candidate from there. So let's

talk how we actually do sourcing

specifically to two roles sales and

engineering. A lot of your early roles

are probably going to be account

executives and software engineers. The

sourcing process for those two roles

will differ. The screenshot we saw

earlier on with all those LinkedIn DMs

was from an engineering role and

traditionally software engineering roles

in particular have been the most

competitive for your outbound sourcing.

Now, while that's a little bit less so

the case on the sales side, if you're

hiring in a competitive market like San

Francisco or New York, your sales roles

are also going to be very competitive,

and you'll want to put the same amount

of attention and detail into those roles

as well. As you'll scale, you'll become

more specialized, focusing on more niche

roles or creating different strategies

altogether. We're going to stay focused

on sales and engineering for the next

few slides as well. So, how do we

actually find people and what specific

criteria we can use to find them? Let's

start with AEES. The first strategy you

want to take a look at is other

companies in your industry. If they've

sold into the same buyer persona, if

they've sold a similar deal size, it'll

make it particularly easy for them to

adapt to your company as well and

hopefully have a faster starting point.

We can look for that based on targeting

specific companies or looking for quota

attainment signals. Many account

executives will publicly list their

quota attainment. You'll see that in the

form of things like 100% attainment in

Q3 or 140% attainment for a full year.

It can be different for every single AE

or different based on how the company

operates. Some of them don't have

calendar years as their annual cycles.

Uh and so some of the metrics may look a

little bit different. Things that are

consistent are President's Club or being

ranked in comparison to other AES.

Another factor that can be useful signal

in AEES is candidates who have quickly

gone through promotion cycles from SDR

to AE, AE to senior AE and more.

It's particularly helpful if they've

done that while being at the same

company and they've been promoted while

working for either the same manager or

within the same team rather than having

hopped between companies to get those

promotions. And finally, you'll probably

want to look for someone who has been in

a fast-paced startup environment. Now,

it's unlikely that you'll find someone

who's been at a preede or seed company

previously, though those candidates

exist as well. You're more likely to

find people who have been at kind of the

greater number of series A to C

companies where go to market teams

typically scale. Now, let's think

through the software engineering side

and how we can find them. The first

thing I'll highlight for software

engineering is you'll really want to

focus on what advantages you have. And

so if there's something that you as a

founder or with your co-founders know

makes you unique that might appeal to

certain people, you'll want to focus on

that in your search strategy as well.

For example, I'm from Germany, so some

of the initial outreach we did was for

other Germans who now live in the Bay

Area. You can also look at specific

technologies they may have used or open

source projects they have contributed

to. Get as creative as you can, a little

bit like you might do for sales. things

we've seen work particularly well for

early stage engineering candidates is

having shown some experience of building

their own projects or doing something

that's more akin to starting a startup.

Maybe they've even been a startup

founder in the past or they've built

projects that look a lot like a startup.

And finally, you'll want to scale your

outreach by going into specific

communities. Um, think Slack groups,

even through open- source projects or

Discord forums. All of those are great

places to recruit. Next, we'll see what

that looks like in practice. So, here's

a couple criteria in this case on juice

box that we can use to assess different

profiles. In the lower section of the

screenshot, you'll see some of those

criteria uh including in this case for

the AE role, president's club, 100 plus%

attainment, and more. That'll easily

rank those profiles for you and

highlight ones that you might want to

focus on. Same thing for software

engineers. And we'll see some of those

criteria that you can use to assess. So,

moving on to the next step, engaging.

You can think of this as the outreach

step or the email sequencing step of

getting in touch.

There's some similarities for AEES and

squeeze here. We'll want to personalize

the outreach. Um, multi-step campaigns

will work in every case and you'll want

to distribute that outreach across

multiple channels. So, think emails plus

LinkedIn steps. Plus, if you have a

different way of getting in touch like a

Twitter DM can make a big impact as

well. Some things that are more unique

to each of the roles on the AE side, you

can focus on pitching the trajectory.

Um, many times AEES have a very rigid

promotion cycle, especially in large

orgs. Being at a smaller company will

give them a faster path to advancing, be

that through promotions to focusing on

enterprise sales or at some point even

managing a sales team. It also presents

an opportunity for them to get into a

leadership role in the long term. And

so, for example, for candidates who

really want to become a VP sales down

the road, they might have an advantage

by betting on a startup and accelerating

their career path that way too. At the

same time, AEES who join companies that

work out well oftentimes end up having

very strong comp packages because the

sales are going well. They're driving

that they own the majority of the

pipeline and they have a consistent

percentage quote. That's a really good

thing for your company. It might feel

like you're overpaying, especially if

things are going well, but it's a great

signal to attract even more good AES.

They should be making a lot of money if

your company is succeeding. Now on the

engineering side, we want to highlight

the ownership and challenges that they

might be tackling in your role. Often

times great engineers are excited by

that. They want to work on really hard

problems and they're able to do that at

a startup where they can almost choose

the problems that they will be working

on. They'll also be in a very autonomous

and small culture or small team which

drives that culture. It really matters

that the founder, ideally the technical

founder is going to be reaching out for

those sweet hires. For example, at

Juicebox, Ishan, our CTO, does all of

our software engineering outreach. Now,

what does that actually look like for an

email? In the slide, we'll see a few

example points of what makes an email

compelling. Uh, some basic things like

adding variables for the first name,

maybe their current company. You want to

establish legitimacy for your company.

This is a little bit like selling. Why

is your company a great place to work?

Um, what customers do you have? Do you

have momentum in the business? Has it

been growing fast? If you have a funding

announcement that you've recently had or

any other news article that talks about

the company, that's a great place to

include this.

Despite those different points, you want

to keep it somewhat short. Most

candidates are going to read this on

their phone. Uh they're quickly going to

skim through it, and there should be a

few things that catch their attention,

at least enough to be able to give a

quick response or book a call with you

if you include your Calendarly link.

Now, in the follow-up email, we'll want

to add some additional value. And so, in

this case, that's in the third

paragraph. It's another reason why this

role is special, why they'll be able to

have an impact in that role, and why

they should apply. We'll also notice

some previous things like relinking the

job description, making it really easy

for them to book, uh, in this case, also

including a call to action, and giving

them a way out of saying, "Hey, it's not

the right time for me." Now, we'll flip

over to reaching out using a different

channel. Often times, LinkedIn messaging

or LinkedIn connection requests are

going to be your best bet. In this case,

it's intentionally the third step

because the first two steps are

automated. Emailing and follow-up

emails, while LinkedIn steps won't be

automated. You'll have to be doing those

manually to comply with LinkedIn's

terms. Um, often times that means a

quick connection request. U maybe

following up on the previous messages

you sent and again including a booking

link or a call to action. And we can see

what that looks like on Juicebox. Um,

Juicebox will give you a reminder to

send that outreach request so that you

keep your email sequence on track, but

you also do the manual steps uh that you

or your co-founder will complete. Now,

after you've done those two emails and

the LinkedIn message, you want to circle

back with at least one final email. We

have some customers who do like eight

email sequence steps. So, it's really up

to you how many you want to do. They can

relink back to the JD. They might even

mention to the fact that you reached out

to them on LinkedIn. Um, or you can do

things like saying, "My co-founder came

across your profile again," or, um, "I

just thought of another reason that this

role could be a good fit for you," or

noticed something in your background.

The more personalized you make this,

even if that means individually going in

and customizing each of those emails,

will have a big impact, especially at

that final step. With that, we'll see a

quick snapshot of what that looks like

in Juicebox 2 um, as you manage your

email campaigns.

So, let's take a look at some metrics,

what these look like. Um this is a real

screenshot of Juicebox outreach metrics.

We'll see AEES sw and events managers

and a customer success manager role in

here. And the kind of main metric I'd

look at is the the middle column, the

third one where you can see the reply

rate. And so this was before series A

announcement. Uh Juicebox had not had

any funding public at that time. I think

we're around 10 to 15 team members when

we were sending these campaigns. And

with response rates between 10 and 18%

depending on the rule. In this case, the

SW sequence have the lowest response

rate around 11%. Which is roughly what

we'd expect because it's also the most

competitorful. Now, overall, if your

sequences are in that 10 to 20% range,

you're doing good. It could still be

better. We have some customers who get

40 plus% response rates. Often times,

that's because they have a good brand,

but other times it's because they do a

really compelling job of writing

specific email outreach and

personalizing that to the candidates

that they're reaching out to. Now, the

second metric is whether those

candidates are actually interested in

your role. And so, even if you get a 15%

reply rate, um only roughly half of

them, maybe a little bit more, are

likely going to be interested in your

role. And so, your target there should

be that your response rate is roughly

half of your interested rate. If your

response rate overall is going up, but

your interested rate is staying steady,

that's probably a sign that something

that you're doing in the email messaging

is getting people to say something, but

that could also be things like, "Stop

emailing me or please unsubscribe." And

so reply rate alone shouldn't be the

golden standard. Rather it's the

interested rate that you get beyond the

reply rate.

Going back to these example campaigns

for the AES we have a 9% interested

rate. Um SWE 7% and then up to 11% for

the community and events manager role.

So how do you actually make this a

priority? Um oftent times when I chat

with founders and we kind of go through

some different tips of doing your

sourcing and outreach uh everything

makes sense, people are aligned but then

they don't actually do it in the

following weeks. There's a lot of things

that are going on. There's a lot of

things that are going to seem more

important, especially if you're also

working with external agencies where

you'll also be getting candidate

pipeline. What we found to be really

helpful there is just setting a schedule

for yourself and making a commitment.

Let's say we want to schedule a 100

emails every week that will be spread

out throughout the week. You can do that

on a weekend day. I personally do these

on Sunday evenings. Get ready for the

week, know who I'm reaching out to, and

then it kind of flows autonomously for

me from there. You can do even do it

multiple weeks in advance once you're

calibrated on your roles and you know

kind of what type of outreach you'll be

doing. Your goal should be to speak with

at least 10 candidates a week. You can

either do those all in one day or spread

those out a little bit depending on your

preference. Uh if you're not getting to

10 interviews per week, it's probably a

sign that you're not doing enough

outreach and so you can scale that

outreach up. Think 150 emails, 200

emails per week, etc. And then finally,

every founder should be involved in this

process. uh it's tempting to say oh one

founder is going to you know lead the

charge on on hiring. Um it becomes

really difficult because it also means

that not every founder is giving that

same input or calibration into the

hiring process and so especially with

those early hires going back to what we

talked about in the very beginning it

shapes the culture. It should be that

something that every founder is involved

in and cares about to do that initial

outreach. Quick hack there, especially

if you have, say, a founder who's doing

sales or has a particularly booked

calendar, just block some time that's

dedicated for sourcing or coffee chats.

Now, going on to the interview and

closing stages. We'll be a little bit

shorter on these ones um because a lot

of this will be more custom to your

company. Next up, let's talk about

interviewing the right candidates and

what interview schedule works for you.

There's two example interview schedules

here, one for AEES and one for SWES.

Let's start with the sales side. In the

first round, you'll want to focus on

selling. That can be a 30-minute chat.

It can even be shorter, just sharing

what the company does, why you're

passionate about the company, and what

the vision for the company is. Parts of

that might be similar to even an

investor intro chat. Um, you're trying

to get them excited about the company

and make them remember what it is you

do. You also want to try to understand

what their potential selling points

could be. And so, why is the candidate

interested to speaking with you? What

other companies are they speaking to?

you know, are they squarely in that

startup category of I want to join an

early stage startup or are they still

uncertain whether they fall into maybe I

want to go to big tech or growth stage

company. You want to gather as much

information as you can because you'll

use that to sell later on in the

process.

Second round is where you're going to be

doing most of your assessment. Uh

different companies have different ways

of doing this. Um, I've had some debates

on whether it makes sense, for example,

for an AE role to have the AE demo your

product or demo the product that they

are familiar with, and that might be the

company they're currently working at or

a company they previously worked for.

You can experiment with both and see

what works. If your company is PLG or

the product is pretty easy to

understand, it could make sense for them

to demo your product as well. During

that call, you'll be taking on the role

of the customer. And so you're

effectively um kind of role-playing the

customer while the candidate is being

your seller and already getting uh

embedded in that role. One of the

advantages of that too is that they get

to know what your company actually does

and the product. If they like the

product, that'll be an advantage for you

later on as you go towards closing. Next

step is the final round. Typically

on-site if you're in person, uh you'll

want to have as many touch points as you

can with other people on the team. So if

there's already other gotomarket hires,

schedule some coffee chats with them. uh

they're mainly for the AEES to get to

know each other and you'll still be

doing most of the evaluation in the

final round at Juicebox. In the final

round, we do another u mock demo or

pitch uh and we'll go through that in

this case with both co-founders present.

Each company has kind of their own style

of doing that and what works best is up

to you. On the software engineering

side, the first call is going to be very

similar, really focused on selling. Why

is your company great? Why should they

be interested in joining? And then also

getting to know, you know, why is that

candidate interested in taking the call

in the first place and what could you be

using later on to sell them? From there,

we'll also want to go into a case study.

Um, for example, in this case, uh,

building a web app on a 1-hour call. Um,

you want to make sure that your

interview is not one that's easily

subject to cheating on an interview. Uh,

and so that might also change the way

you run that second round interview. And

then with the final round, you'll also

bring them on-site. In our case, we try

to make it like almost like a full day,

roughly 6 hours. that includes a system

design portion, a more of a sandbox

project, and then also more traditional

interview with the co-founders. We try

to include something more casual, say a

lunch or coffee chats with the team, so

that they feel like they're actually a

part of the team as well, rather than

just interviewing all day. So, really to

emphasize the selling piece. That's the

number one thing we see founders do

wrong is in the first call, they're just

interviewing the candidate rather than

selling the company. Uh, you should flip

that order. The first thing you do is

sell the company. Uh and then the second

thing you do is interview the candidate.

So for selling the company, uh some

example lines you could use on the kind

of compensation upside, you might focus

on you having done founder sales

previously. And so if you as a founder

have closed over $400,000 in revenue, um

and perhaps you don't even have a sales

background, an AE might see that as an

opportunity for them to go in and do

even better, bring their sales expertise

and push the company forward. on the

team side and perhaps more on the

engineering hiring side. You would

emphasize the backgrounds of you or your

co-founders um why you're building what

you're building or even the investors

that you're working with. Now, let's

talk about the offer stage and closing

your offer. Your main advantage is speed

throughout the whole process. You can

run this process within 7 days, 10 days,

maybe max 2 weeks. Big tech or even

growth stage companies are going to move

much slower than that. They have to

coordinate across many people. They

probably have more interview stages to

their process and you should use that to

your advantage. That means knowing

exactly when the next step is for the

candidate, communicating that clearly to

the candidate, ideally even getting it

scheduled as soon as you have that

confidence in whether they're a good fit

or not. During the offer, you'll want to

emphasize why they should be joining

your company specific to the selling

points that the candidate cares about.

And so oftent times we see those offers

be pretty generic or pretty much the

same across different companies. At this

point you should have a pretty good

understanding of who the candidate is um

why they want to work at your company

and you should be able to emphasize that

in your conversations with them. Ideally

you can also ask the other founder or an

investor maybe an angel investor to

reach out to that candidate and

emphasize that same reason why they

should be joining you. Closing the

offers is going to be hard, especially

with early stage companies. And so, even

if it doesn't work out in your first

offer, that's all right. You'll make it

work in the next one. That's it from me

today. Um, good luck on making your

offers. Please reach out if we can help

with anything. With that, we'll bring on

Harj for a bit of a discussion on

hiring.

>> Thanks, David. That was a fantastic

talk. Um, I had a few questions um I'd

love to discuss with you. So uh first

one high level what are the three most

common mistakes you see founders make

when they're starting to hire for the

first time?

>> That's a good question. Um I think the

first one is one that we talked a bit

about in the presentation as well which

is around uh not selling the company and

not understanding that hiring is really

all about sales and talking about why

your company is great why they should be

joining especially early stage founders

where you know they've done a lot of

selling to customers to investors uh and

then they also need to do selling for

hiring and sometimes that only clicks a

little bit later on.

>> What do you think it is that they do

instead is that they skip to like

interviewing the candidate?

>> Yes. Yeah. They kind of skip right into

interviewing the candidate. um sometimes

like no proper intro on themselves, on

the company, why it's an exciting place

to be uh and much more kind of directly

into more generic candidate questions. I

think the candidates feel that too. They

know if it's kind of being treated like

a process and they might not be as

excited either.

>> And I always found that um it's another

way that you stand out from the bigger

companies is that uh the recruiters can

never sell the company as effectively as

the founders. So just opening up by

talking about yourself, why you founded

the company, knowing that for a

candidate, knowing that they're on the

call with the founder can be really

effective to close those first few

hires.

>> Yeah. And and I think ideally it even

feels conversational. It's like getting

to know the person and like being

excited to be there and hopefully they

feel the same way too.

>> I think the second one is really on the

outreach side. Um so kind of making that

more generic. Um especially if you

benchmark against the emails that you

have received inbound uh and use those

examples. They're often pretty bad

examples because I'd say the average uh

recruiting outreach is not a very

well-crafted email. Uh it's probably not

personalized. It probably doesn't have a

clear call to action. Um it probably

doesn't sell the company a lot. And so

instead really thinking first

principles, what is an email I would

respond to and what is an email that

would get me excited and trying to use

that as the as the bar for the outreach

messaging.

>> I would love to go deeper into that. You

mentioned that some of the companies you

work with are getting 40% plus response

rates and it's not just brand, it's that

they're sending these really wellcrafted

outbound emails. Um, what exactly are

they doing to make these emails and

messages so great? Like, and any

examples that might spring to mind?

>> Yeah, I think the there's two things

that that they do well. The first is

creativity on who they actually send the

outreach to. And so, they'll have pretty

creative sourcing strategies or or ways

of finding talent. Maybe that's people

who went to the same high school as you.

Maybe that's people who um happen to

have worked at a similar company

previously and you have some connection

through that. So really going deep and

thinking about every individual person,

why am I actually reaching out to them?

And then that also gets reflected in the

outreach text. And so um for 40%

response rates, those are definitely

going to be personalized. And that may

mean you spend five minutes on

personalizing each outreach message. It

takes a good amount of time. Um, but

it's also worth it because you're going

to be getting in touch with people that

are definitely not going to be

responding otherwise.

>> Yeah, that's really interesting. I mean,

it's so similar to the advice we give to

the companies during the B like sales,

right? It's like so many founders come

in and they think I just need to send a

thousand emails per day. Um, they don't

need to be personalized. It's just

volume. But the number one thing we

teach them is no, you actually have to

spend time handcrafting every email

making it personalized if you want to

see any response rates.

>> Yes. Yeah. I think almost all of the

best practices or even like from the

from the YC content on how to sell apply

pretty directly to recruiting as well.

>> Yeah, I think that's a really

interesting insight that the um like

actually like the the outreach strategy

like who you're even targeting can tie

into the personalization. If you're

looking for people that have you have

something in common with and you put

that in the outbound email, you should

see a higher response rate on that.

>> Yes. Yeah. And and I think it's also

like kind of not being afraid to break

the rules a little bit of um you know

Twitter DM outreach can be really good.

It works particularly well if you have a

bit of a Twitter presence and you post

some content on there. Um and so I guess

just getting creative with what that

means is um I think a pretty high value.

>> Yeah. I was curious on that front um

something else you mentioned you know

for example like recruiting out of a

Discord forum like um like how do you do

that tactically? Like do you just jump

in there and say hey would you like a

job at my company? Like what what like

how should you play that? Yeah, I I

think the cases where it works best is

where it's like one thematically

relevant. So there's kind of some type

of related reason that everyone is in

this discord. Maybe it's a discord about

an open source project and people are

kind of talking about that and that is

the main theme. Um and then two, it

should feel somewhat authentic to the

founder. Um so if this is your first

time opening Discord and you're kind of

starting to send DMs, might get a little

bit tricky, but if you know Discord is

somewhere where you feel at home and

you're in there anyways, it can be a lot

more natural. One question I have I

think that every founder has on their

mind is that when it comes to sourcing,

isn't effectively everybody sourcing for

like the same people and it's highly

competitive and how have you seen any

strategies for how can you be creative

in your sourcing to find people who

might not be so competitive but are

equally talented?

>> I think being able to find people who

are non-obvious on paper um but then

become obvious throughout your interview

process is a a real advantage. It's also

really hard and so I think there's like

no kind of single path that that makes

it work. Some things we've seen people

do that have worked for them is in some

cases just looking through GitHub and

basically clicking through contributors

to open source projects. In other cases,

the Twitter strategy sometimes goes in

that direction because uh even if it's a

Twitter profile you recognize, it might

not be like a LinkedIn profile that you

would click into. I think there's often

a lot of indexing, especially amongst

founders for colleges and a lot of great

talent may not have gone to a great

college. Um, especially from like your

competitive advantage perspective. If

they went to a good university and

worked at a good company, they're going

to get a lot of outreach anyways. If

they've maybe only done one of those two

things, they might still be really

talented and they might not be getting

as much outreach.

>> When people ask me sort of why Juicebox

has got so much traction, I essentially

reply it's because the product just

works. I don't think I have a better

answer. I've always been curious like

why is it so difficult to make the

product work? What's actually so hard

about when I type in I want a software

engineer with 10 years of experience? Um

um why is it so hard to surface like the

relevant candidates and how have you

been able to do that?

>> A little bit of context on Juicebox. We

do search um contact management outreach

and then sync all of that data with your

ATS. And of those, search is really the

hardest part. And so being able to find

the right person is a hard problem for

two reasons. One, there's a long tale of

different search queries. And so if

people are using the platform correctly,

no one will have exactly the same search

query because there's always something

unique about the rule or unique about

the opportunity. That also means that

there's a long tale of um potential

filters we might need or potential ways

to to think through how we filter a

segment of search. And then that relates

to the depth of a profile. So, if

someone has previous experiences, those

are really important in a search result.

And it's also quite different than how

search on like a sales tool might work

where it's all about the current company

or the current role. Um, with

recruiting, it's really about their full

depth of experience. And so, I guess

long-winded way of saying that search is

really important and is usually what

drives those outcomes.

>> And so, I guess to get the most out of a

tool like Juicebox, how detailed should

my search be? Like, it's it's almost

like I'm prompting Juicebox. So like am

I trying to write like a full system

prompt here or like give give us like a

a sense of of what I should be doing?

>> I think the easiest way to learn is kind

of by starting with what feels natural.

That might be a couple sentences about

the role and then Juicebox gives you a

few different ways to filter further.

And so we have a feature called

autopilot which is personally my

favorite feature in the platform. It

lets you define criteria and then you'll

get a check mark for every profile who

matches that criteria. Criteria can be

super specific like has published a

paper in at least two peer-reviewed

journals. something that doesn't exist

as a filter otherwise. And you can write

your own. You'll get check marks for

everyone who matches that and then

continue customizing from there. And so

I'd start with like a fairly broad

initial prompt, maybe a couple

sentences, and then as you fine-tune it

and get more narrow, adding additional

criteria.

>> That makes sense. And then the more

criteria you have, the more like

material you have to personalize the

outreach message to those candidates.

>> Exactly. And you can even create like

different um groups of candidates that

you might do similar personalization

for. So maybe like academic outreach,

open source outreach, etc. um which can

be a good way at like personalizing at

scale.

>> When it comes to sort of like the

channels sort of outreach, we have

different channels. Um should I be

trying to contact the same candidate

through every channel or should I be

focusing on one channel? Um and do

certain channels tend to have better

response rates than others?

>> Ideally, yes, we'd reach out to every

candidate on every channel. Um

practically it becomes difficult and and

quite timeconuming. I'd say the default

should always be email because it's what

you can automate and get real data on.

What are your reply rates, open rates,

and more. If you're just sending a

single message, your best response rate

is probably going to be on, I guess,

apart from like a Twitter, it's probably

going to be on LinkedIn. But the

advantage of email is that you're not

just sending a single message. Instead,

you're orchestrating this multi-step

campaign. And so with those multiple

steps, you're going to get a better

response rate on email than you would

with a single message on a LinkedIn. Um,

and so I think the easiest way to get

started is just email automation. Um,

improving your response rates by adding

in a LinkedIn step. And then if you want

to get creative beyond that is when you

can start layering in the other

channels. Your answer are different for

engineers versus AES.

>> Good sellers are often particularly

active on LinkedIn because they're also

communicating with their prospects

there. Um, and so response rates tend to

be higher there. For engineering, in the

comparisons we've seen customers do,

often times emails get better response

rates instead.

>> For referrals, you mentioned referrals,

great source of early hires. Um, once

I've got my team to identify a list of

potential referral candidates, who

should do the reach out?

>> Ideally, you as the founder. In general,

I think the more senior the person

reaching out, the better the response

rate is going to be. And so, ideally,

all outreach always comes from the

founders. Um, a lot of systems will also

let you set sender emails different from

the person operating it. And so, if for

example, you have a recruiter on your

team who's doing outreach on behalf of

the founder, um, can be a good scalable

high impact strategy, too.

>> Often the first thing the candidates

will see when they look up the company

is like the job description. And, um,

are there any things I can do to make

the job descriptions unique or stand

out? I think the bar for job

descriptions is pretty low. Um the a lot

of job descriptions are very wordy, kind

of sound corporate, you know, maybe chat

GPT written. Um and if your job

description is not that, that's already

a big advantage over others. I'd say the

other part that generally trends one way

is job descriptions are often long.

They're kind of hard to read and most

applicants are probably not going to

read the whole thing. And so if you keep

it short, a few bullets of what really

matters to you and what encompasses the

role can be quite impactful. And the

only other advice I'd have is that

oftentimes kind of goes back to the

selling thing. People forget to sell the

company in the job description. And so

that should be at least 30% maybe more

of the job description is why is this a

great place to work? And um what would

that involve for you?

>> Often companies when they're describing

themselves in their job description or

even on their website, it's almost like

they want to cast as wide of a net as

possible. They want to be attractive to

everyone and as a result it comes across

as very bland. It's like just the same

set of values on every single job

description. Um I wish companies would

actually be more opinionated at times

like say what they will trade off like

hey we value collaboration which means

you might not like we value that more

than just autonomy just as like one

example. Um, what do you think? Is it is

it better to cast a wide net or or

should you try and be opinionated? How

much?

>> Opinionated is great. I think it also

shows the character of the founders and

like the culture of the team. Um, that

can be one of your main selling points

as well is like you're joining the team

for the culture and and for that

opinionated selling point. And so I

don't know if I've seen an example of

something that's too opinionated. Um, so

so probably leaning as far there as

possible.

>> Yeah. Because I think it's it's the

point that you made in your talk too is

about you care about like the interested

rate, not just the raw reply rate.

It's better to have a smaller number of

applications from highly

convert

the kind of value per interested

response you'll you'll see depending on

the role it can be like maybe 20

interested responses gets you to higher

maybe five interested responses gets you

to higher and so even that like relative

value can can change quite a lot

>> as it gets towards more of the you've

identified someone you want you've

interviewed them you know you want to

hire them you mentioned a lot about sort

of convincing them to join you over a

bigger company. How hard should you try

actually to convince someone? Um, and

when do you know if maybe you're trying

too hard?

>> It's again a little bit like enterprise

sales like knowing what does the

candidate or in the sales comparison the

prospect actually want? What are they

really looking for? And you might get

signals early on that they really want

to be in big tech and that can be really

hard to convince them otherwise

especially if it's like say comp package

related or stability of jobreated. it's

probably not worth fighting that battle

because they are likely going to end up

going that direction. I think in the

later stages if they have indicated they

want to be at a startup and you've kind

of you know checked in on that a few

times and you're pretty convinced they

want to be at a startup then you should

fight really hard because then it's you

against a different company and um you

should try to win that. Yeah, this is

one of the things I think it's really

hard in like the heat of the moment to

stick to it because you're behind on

hiring. You feel desperate. You get the

superstar engineer and you know it's

really tempting to tell them like when

they say things like I like a bigger

company maybe I'll have like more

stability and it's like you can't

convince you shouldn't try and convince

them that oh like your startup's going

to have as much stability or like

working hours I think are often like a

thing that come up. Um it's like having

the discipline to be like you know what

maybe actually this candidate isn't

going to be a good fit and I should just

move on.

>> The related part to that as well is

hiring is a repeated game. Like the same

you even if you don't hire the candidate

now you might be hiring them a year from

now. We had a candidate who we made an

offer to at the time they were concerned

about like the stability of a company

and whether it makes sense to join and

then they ended up joining six months

later. And so um I think kind of

choosing when to fight that battle and

and when you're in the best position to

do so as well can make a big impact.

>> Yeah that's a good point there. I think

some of the elite founders um that I've

worked with um throughout the YC career,

they are essentially in a sense always

recruiting, but they're always looking

to meet people who they think are really

smart and interesting whether they're

available or not. And it's so common to

hear stories from them of, hey, actually

I hired this person after like catching

up with them and doing coffees and

lunches for 2 years. Um, and I think you

assume, it's easy to assume that's just

for these like executive level hires

once you're a big company. But I

actually think the elite founders just

do that from day one, even for like

individual engineers that they really

want to hire.

>> And and I think that instinct is often

really good, too. Like if if it's if you

know it's an IC who will make a big

impact, like trusting that gut instinct

and following that, it can make a big

impact.

>> Final question from me here is of course

founders should do all the recruiting

themselves at first. um especially for

those first few hires. But let's talk

about when should they think about

hiring a recruiter and maybe you could

start by just giving us a quick primer

on what uh are the differences between a

contract recruiter, a contingency

recruiter and an in-house recruiter.

First thing I'd think about is roughly

how many hires are you certain you're

going to make in the next 6 to 12

months. And then that's going to

influence which of the three options you

go with um because they kind of

correspond with your commitment level as

well. And so we'll start with the

highest commitment which is hiring a

full-time recruiter. They join your team

and that is their job function and their

goal is to bring on new talent into your

team. And

>> this is in-house recruiting.

>> In-house recruiter. Exactly. And they're

usually not compensated on commission or

hiring fees. Um they typically have

mainly a base salary and then some

equity upside in the company as well.

The second slight slightly lower

commitment option is for a contract

recruiter or an embedded recruiter. And

they'll be working with you for a

certain number of hours every week. And

there might be a predefined contract

length, say 3 months or six months. Um,

but it could also be a month-to-month or

even a week-to-eek arrangement. Um,

advantage there is that your costs are

somewhat in control. It's predictable

and you can also adjust if you need to.

For example, if your hiring doesn't end

up being as much as you thought it would

be. And then the final option is the

most flexible, which is a contingency

recruiter. On a contingency recruiter,

you pay a percentage of the placement

fee. Oftentimes, that's somewhere

between 20 25% maybe even a bit higher

than that. for more senior roles. It's

quite expensive because you're, you

know, potentially paying $50,000 plus

for every hire that you make, but it's

also most flexible and you could be

working with multiple contingent

recruiters at any point in time. And so,

it can also be the most scalable option

if you quickly need to make a lot of

hires and you have the budget to be able

to pay the contingency fees as well.

>> When should founders think about getting

this help? I think as soon as you're

making multiple hires, um I like to

think I can work on one hire really well

at one point in time and my co-founder

can do the same. And so if we're working

on two hires, that's roughly where we're

at capacity. And so if you're hiring

more than that, it can start making

sense to think about those um recruiting

options.

>> Two hires per month, per quarter,

>> as long as it takes you to fill them. Um

ideally it's a month, but uh in our

case, I think especially for the early

hires, it took us more than a month to

fill them. We were always just working

on two at a time. We tried doing more,

but it didn't really work. And then we

kind of narrowed it back down to each of

us focusing on one role at a time.

>> Thanks so much, David. That was really

informative.

>> Thanks for having me.