How to Sell by Tyler Bosmeny

Summary

Tyler Bosmeny, CEO of Clever, shares his experiences and insights on sales and the sales process for early-stage startups. He discusses key aspects like prospecting for potential customers, having meaningful conversations to understand their needs, persistence in following up, avoiding common closing traps, and tailoring your sales approach based on your business model. Throughout, he emphasizes the importance of listening, building relationships, and providing genuine value to customers. While sales has mystique, Bosmeny argues founders themselves can excel at it early on through passion, expertise, hustle and learning from experience.

Takeaways

• 😊 Sales is a core responsibility for founders, not just for salespeople
• 👂 Sales is about listening and understanding the customer's needs
• 🚪 Use your network, conferences, and cold emails to find prospects
• 📞 Have quality conversations focused on the customer, not just pitching
• ⏳ Sales requires persistence and systematic follow-up
• 💰 Avoid common closing traps like over-negotiating contracts
• 🎯 Align your sales model to your target customer and pricing
• 😀 Leverage your passion and expertise as advantages in sales
• 🤝 Build genuine relationships and provide value to customers
• 👥 Ultimately you need enough happy customers to sustain business

Q & A

What are some key advantages founders have when it comes to sales?

Founders have two key advantages - passion and industry expertise. Their passion for their product is unmatched, and they understand the problem it solves better than anyone.

What percentage of companies fall into the 'innovator' category according to the technology adoption lifecycle?

Only 2.5% of companies are considered innovators - those willing to take a chance on an unproven startup. This means you need to cast a wide net and reach out to many companies to find potential early adopters.

What makes conferences a powerful way to meet potential users?

At conferences, users are gathered with their peers and focused on learning. Having the attendee list in advance allows you to set up meetings and introduce your product more effectively than cold outreach.

What is the most important skill for sales according to the speaker?

Listening. The best salespeople spend more time listening and asking questions rather than talking about their product. Understanding user needs is crucial.

How can founders avoid getting bogged down during contract negotiations with early customers?

Don't quibble over small details, especially with your first few customers. Getting those initial customer commitments and revenue is vital, so focus on closing quickly.

What are some common closing traps to avoid with potential customers?

Avoid building custom features for a single customer, providing free trials instead of paid commitments, and letting the sales cycle drag on for too long.

How many touchpoints did it take to close one of the speaker's early deals?

The example showed over 15 touchpoints ranging from emails to calls and demos. Persistence and systematic follow-up is key.

How should founders determine the right sales model for their business?

Consider whether you need to land a few large customers vs. many small ones. Then build a sales process sustainable for that number and price level.

When is the right time for a startup to hire sales reps?

Not until the founders have done substantial sales themselves first. Otherwise you won't know what to look for in candidates.

What traits should startups seek out in early sales hires?

Energy, passion, and 'Renaissance' skills - ability to figure things out without much structure or collateral.

Outlines

00:00

🎤 Introduction & context for the startup school talks this week

Adora says they're halfway through startup school. Tyler from Clever will talk about how to sell products. Harsh and Amin from Triplebyte will discuss building engineering organizations. Adora asks everyone to fill out the midpoint feedback form to help improve startup school. She advises carefully choosing metrics that truly measure progress towards success.

05:01

🗣 Tyler introduces himself and the value of mastering sales

Tyler from Clever introduces himself. He explains sales is fundamental but often misunderstood with a mystique around it. He details his accidental path into sales via running ads for his college newspaper. He now recognizes sales as an important craft. He advises founders not to wait to hire salespeople because selling is their responsibility.

10:02

📈 Tyler outlines the sales funnel from leads to revenue

Tyler diagrams the sales funnel: prospecting leads, having conversations to gauge fit, closing deals, and hopefully gaining revenue. He says founders should have a team member fully focused on sales. For prospecting, he recommends leveraging networks, conferences, and thoughtful cold emails to efficiently find the few potential customers.

15:02

🎟 Conferences are an underrated place to meet engaged users

Tyler advocates conferences as the most underrated but amazing places to meet highly engaged potential users. He details how to identify the right conferences, get attendee lists, and efficiently book meetings at them. He calls conferences the most productive days for understanding customers and demand.

20:03

👂 Sales is mostly about listening, not charming persuasive pitches

Tyler stresses the most important sales skill is listening deeply to understand user problems and needs. He observes most founders pitch eagerly without enough listening. The best salespeople listen 70% of the time. This builds relationships and trust to uncover how your solution can uniquely help.

25:03

❌ Sales has many steps and requires tireless follow-up persistence

Tyler shows an example sales process taking months across many communications. Sales requires relentless follow-up persistence, not just a single call. Be embarrassingly persistent to keep doors open, while still carefully listening.

30:04

🤝 Move quickly when negotiating early customer agreements

Tyler advises finalizing agreements with early potential customers as quickly as possible. Their validation is invaluable so don't quibble over minor details, but get the first sales closed expeditiously.

35:07

💡 Tailor your sales approach to target customer lifetime value

Tyler explains sales strategy must fit the number of customers needed and revenue per customer. High-touch sales fits high-value customers but low-value customers need scalable self-service. Align sales approach to target customer lifetime value.

40:08

😊 Concluding thoughts and offer for questions

Tyler wraps up with key lessons learned. He encourages trying sales yourself as the best way to learn. He offers to answer any questions from the audience.

45:25

🤔 Answering audience questions about sales

Tyler fields audience questions on appropriate sales follow-up timing, signs of product/market fit, balancing large & small customer references, determining pricing, low-touch sales for low-value products, and when and how to hire salespeople.

Keywords

💡sales

The main theme of the video is sales - the process of selling a product or service. The speaker shares his experiences and tips on sales, prospecting, holding sales conversations, closing deals, etc. He emphasizes that sales is a core responsibility of startup founders.

💡prospecting

The first stage of the sales funnel, prospecting refers to finding potential customers who may be interested in your product. It often involves a lot of outreach to build a pipeline.

💡conferences

The speaker highlights conferences as an underrated but very effective prospecting channel. By getting the attendee list beforehand and setting up meetings, conferences can become highly productive sales days.

💡listening

The most important skill in sales conversations, according to the speaker. Sales is about understanding customer needs deeply through listening, not just pitching your product.

💡follow-up

Persistently following up with prospects via emails or calls, even if they don't respond. As the speaker's example shows, landing a deal can require relentless follow-ups over months.

💡closing

The stage after sales conversations when a prospect commits to buying. It involves finalizing contractual details and avoiding common closing traps like endless negotiations.

💡first customers

The speaker stresses the immense value of your first few customers for an early stage startup, even advising to "do whatever it takes" to win those initial deals and not lose them over minor issues.

💡sales model

The type of sales motion and customers you target long-term, based on factors like deal size. This shapes decisions like who to hire for sales. Examples are high-touch enterprise sales vs. scalable self-serve models.

💡pricing

How to set the pricing for your product. The speaker suggests starting with a guess, being bold in pitching.

Highlights

Sales has a lot of mystique and lore around it, but in reality it's about listening, building relationships and understanding people's problems.

As founders, you have advantages in sales - your passion and expertise. So don't think you can't do sales even if you've never done it before.

Conferences are hugely underrated for sales. Go where your users are - find the big conferences in your industry and use them to set up meetings.

When you finally get a prospect on the phone, remember to shut up and listen. Listening is the number one sales skill.

Sales is a relationship-driven process with lots of steps. Be prepared to follow up relentlessly - it's normal for even interested prospects to fall through the cracks.

Avoid common closing traps like building one-off features, offering free trials instead of paid pilots, or letting legal kill deals over minor issues.

Match your sales model to your business model based on average deal size. Going from 0 to $1M requires a very hands-on approach.

Use your network to find early prospects. Ask friends and friends of friends if they know of good targets.

Cold emails should be short, personalized and actionable - just trying to start a conversation.

Don't spend time building one-off features for individual prospects - make clear it has to be something you were going to build anyway.

First sales hires should be "Renaissance reps" - scrappy generalists who can figure it out, not specialists who need extensive support.

Don't hire any salespeople until you've done significant sales yourself - otherwise you won't know what to look for.

Use data from your calls to improve - if you dominated the conversation, that's bad. Good sales calls have a 70/30 listen/talk ratio.

Treat early customers like gold - make concessions and close deals quickly rather than losing them by being inflexible.

Pricing is a guessing game - throw out a number, see if you can close it, then double it until you find resistance. Don't be afraid to charge more.

Transcripts

all right good morning everyone we are

halfway through startup school can you

believe it already Wow yeah or more

correctly we will be after this week and

this is going to be a great week of

talks lectures conversations today we

have Tyler from clever who's going to

give a talk on how to sell to begin with

and after words harsh and Amin from

triple bite are going to talk about how

to build an engineering organization to

pretty important things if you want to

build a successful company I will start

off quickly with my usual administrivia

we will shortly be sending out a mid

point feedback form for you guys to fill

out we really will appreciate getting as

many responses as possible this is our

form of talking to our customers you all

and getting feedback we're always trying

to improve startup school we hope to do

it every year and make it better every

year

so please tell us what you think and

what you think we should change adora

and i we're talking a little bit about

updates and I've talked to a bunch of

people alive and some on the forum about

about updates and and what makes sense

for updates and just to put it bluntly

think hard about your metrics the ones

you're using do not use metrics

what is a metric it's a metric

that doesn't really measure the road to

success for you it's something you're

making up any startup that you're

building is an enormous complicated

difficult crazy task and no matter what

you're doing if there is no mile stone

on the way to that to achieving that

enormous task then you're kidding

yourself and you're not really a step on

the way to success those milestones are

more than anything for you for you to

measure that you're making progress

towards your goal so don't make stuff up

because you think that's what we want to

hear or just because you're bored

it won't help you okay

as always problems etc email to start-up

school at Y Combinator calm and with

that I think Tyler we are ready to go so

my good friend Tyler basmati from clever

hey everyone it's an honor to be here I

was speaking with you today thanks for

having me

my name is Tyler basmati I'm the CEO of

a company called clever and I wanted to

talk to you about something that I think

is one of the most fundamental and

important things any founder needs to

master which is sales and before I get

started and share some of the things

I've learned and picked up over the way

I thought it might be helpful to share

my own personal journey to sales as

something that I've come to learn and

just you know really appreciate and

respect as a craft when I was in school

when I was in college I was a math major

my you know my graduate degree was in

statistics I was the last person I ever

thought would ever do sales and so my

own journey to getting here was I was

working on the college newspaper I

joined the college newspaper it seemed

like a fun thing to do had some friends

who are on it and one of the roles they

had open was they needed somebody to run

the advertising for the newspaper and so

I was spending in college hours a day

you know figuring out how to sell ads to

local businesses so we'd have enough

money to print and put out the paper

every day and over the doing this for

several years if you know anything about

college newspapers you know one of the

things the biggest determinant of how

much money they make every year is how

well the economy is doing it's a lot of

the ads are for recruiters but B I just

happened to be there during some very

good years and when I was leaving the

advertising sales team we had we set

records for the Crimson and so we just

you know we sold a lot of ads and so I

thought okay this is interesting you

know it's

it's an interesting craft and then as I

was getting ready to graduate school you

know getting ready to graduate go off to

college or excuse me golf to work you

know I'm doing math I'm thinking to go

off to finance do a hedge fund something

like that a buddy's starting a company

and he says to me Tyler I need you to

come join because you're the only person

I know who knows how to do sales and let

me tell you I was offended like this was

not how I saw myself this was not you

know what I imagine doing after school

but I was also really intrigued and I

was really good friends with this guy

and I said oh you know why the heck not

so ended up on going on a very different

path and joining his startup building a

sales team you know we were selling to

newspapers across the country and if

you've ever worked with or or thought

about newspapers before you can imagine

they are very hard customers to sell to

and so I really cut my teeth and have a

lot of fun frankly over many years

figuring out how to sell into this

market and we sold to a lot of

newspapers then fast-forward a little

bit and I come on to start clever and

one of the co-founders started through Y

Combinator about six years ago

and if you don't know anything about

clever you know we're a single sign-on

platform used in schools and today over

half the schools in America use clever

and so we've really done a lot of

selling and really had to figure this

out once again in a different context

and so I was thinking about you know

what would be most helpful to talk about

what I'd most want to hear in your shoes

or what I most would have appreciated

knowing when I was first starting to cut

my teeth on sales and so that's what I

want to share with you today it's just

things I've picked up along the way

some observations I've had and hopefully

some practical tips that you can take

home and implement you know as you get

your startups off the ground running

sales sales has a lot of mystique and a

lot of lore around it or at least it did

to me when I was thinking about sales

early in my career you know when we

think about sales and we think about

people you know a lot of us picture Don

Draper we picture these people who are

so charming so impossibly funny who they

always have the right line at the right

moment you know to win the deal this you

know they're of course incredible

golfers this is how sales is portrayed

in every movie in every TV show and so a

lot of people go through life thinking

that this is what sales is about and

because we have we build up this

mystique of what sales is and the types

of people who can do sales

I hear founders say very often things

like well right now we're just building

the product and once it's finished you

know then we'll go and hire the

salespeople well guess what hire the

salespeople that's you

and it's that looks nothing like the

mystique and it looks nothing like the

lore in my experience you know this is

my co-founder Dan in the early days of

clever and we were doing sales you know

here he is on a broken chair in a three

by three call room I think he's eating a

bagel because he probably didn't have

time for breakfast that's what sales

looks like you know could not be further

from the Don Draper imagery that a lot

of people think of so sales is you and

you know Y Combinator

Paul Graham I remember when we were

going through the program Paul Graham

got up on this stage and he said you

should be spending every moment of every

day doing one of two things building

your product are talking to users and

talking to users a big part of that can

be selling so this is a core

responsibility of every startup founder

is not just building the product but

also talking to your users understanding

their needs and as you'll learn that is

really a big part of what selling is so

this is a core responsibility for

founders you know a lot of founders

think well I haven't done sales before

and that's true and they say well I'm

not good at sales yet and that could be

true too but one thing I've learned is

that as founders you also have some very

unique advantages that will that can

make you actually

the powerful at sales and very potent

and the two advantages that I've noticed

one is just your passion you are more

passionate about the product that you're

building and selling than anyone in the

world because otherwise you probably

wouldn't have irrationally quit your

jobs and moved in with your parents or

whatever you've done to start this

company so one is your passion that is

so powerful in sales and the second

thing you have is industry expertise you

know this problem better than anyone you

know why it needs to exist you

understand this problem more deeply

hopefully than anyone and so these two

things even if you've never done sales

before I mean you can be incredibly

effective and so don't think otherwise

early on with clever one of the things

we did that really worked for us was I

had two co-founders so there were three

of us and we just decided that one of us

had to own sales it was so important

that we needed one person to be thinking

about this every day and so that ended

up becoming me my other two co-founders

were focused on building the product and

implementing the product and I folk I we

decided this was important enough that I

decided I was gonna peel off and spend

almost a hundred percent of my time

selling this product starting from

before it was even built so from that

point you know from early enough on

think about who and your company is

really owning this and it should

probably be a founder and it should

probably be as much of a full-time job

as you can spare so now I want to talk

about how sales actually works and if

you know anything about sales you know

sales 101 as a lot of people talk about

it like a funnel and there's different

variations of this funnel I have a

really simple one that I put up here

step one of the funnel is finding

prospects prospecting these are leads

who might even be interested in buying

your product who might even be

interested in taking a call from there

you have conversations okay so you

figured out they're interested but you

got to have a lot of conversations to

figure out is this the right product for

them

or not third is closing okay you

actually they actually want to buy the

product how

do not snatch defeat from the jaws of

victory and lose the deal oh yes to go

through a closing process and if you

complete all of those things then

hopefully you are in the promised land

and you have revenue when you have your

first sales and so this is how I think

about the funnel and what I'm gonna do

now is just walk you through each of

these stages and share how I've

approached these in my career and some

tips that have worked for me along the

way so your mission in the first stage

of prospecting it's to figure out who

will even take your call and one of the

things that for me was really helpful to

understand is well you're gonna hear

know a lot you're talking you you start

talking about a new product people and

you're just gonna hear a lot of nose but

one of the things that was really

helpful for me to understand is you have

this technology adoption curve this was

put out by a guy Everett Rogers in the

60s and it starts on the left you have

your innovators then you have your early

adopters of new technology or early

majority your late majority your

laggards these are terms that people in

Silicon Valley throw around that I'd

been hearing for years but what I didn't

know was that the inventor of this

framework this technology adoption

lifecycle Everett Rogers he describes it

as a bell curve and he actually went

through the effort of quantifying the

area under the curve in each of these

different segments and one of the things

and so one of the things you notice is

looking at this the innovators segment

is just 2.5 percent of the population

that means 2.5 percent of companies will

will even consider buying a product from

a startup that is unproven with no

revenue and when you realize that - some

founders that's kind of depressing like

wow that's a very small percent of the

market but when I found this out I

actually found it massively motivating

and massively invigorating because all

of a sudden it makes what you have to do

really clear you have to talk to you a

lot of people because you have to find

that 22.5% it's a numbers game means

you're gonna have to reach out to

Atlee

200 companies to find just two and a

half on average who are even in you know

potential buyers for your product you're

basically playing like a version of

Where's Waldo you know where you're

looking for the you know the very few

companies who might be in this innovator

segment and so expect early on sales is

not reaching out to a you know two four

ten companies reaching out to sale

reaching out and doing sales is a lot of

grinding and it's a lot of effort in

order to get the result you want when it

comes to actually starting these

conversations I found there's three

things that work for me so in terms of

finding those innovators the first thing

that work has worked well for me is

using my network the second which is a

little surprising to people is

conferences and I'm going to talk about

that and the third is cold emails these

are the three ways in which I find

prospects I'm not going to talk about my

networks I think most people understand

that but I can tell you many of the

earliest deals I've done it every

company I've been at have been through

people I've known friends of friends so

do not underestimate your network

especially if you know the industry you

might think it's not very big but you

probably know a few people and those

people might know a few people and so

spend some time thinking about your

network because you might find some

really great sales opportunities that

come through there and those are the

best you don't need a hundred people in

your network to get to sales you can

usually do it with much fewer but let's

talk about conferences because I think

conferences are the most underrated

aspect of sales and them and one of the

least understood aspects of sales

when I say conferences a lot of people

think I'm talking about this like CES or

e3 and going you know it's at some place

where there's 80,000 people and it's

basically more like a rock concert than

you know then it's than anything else

and when I say conferences I'm talking

about something very different

usually they look like this usually it's

a bunch of you know executives or

people in a hotel room cooped up for a

couple days you know oftentimes you know

in places like Milwaukee or Kansas and

let me tell you this is such a powerful

way these conferences are such a

powerful way to meet your users you have

to go where your users are and many

times if you're selling to a business or

to a corporate buyer this is where users

are they go to conferences they're there

with their peers they're learning and

that's where you should be - now let me

say a few words about how I've

approached conferences in the past

because this this really is where so

many of clevers initial partnerships and

customers came from one figure out what

are the big industry conferences for

your product in your startup usually

there's not just one usually there's

like 10 and you have to work to figure

out what they are ask people in the

industry where do you what conferences

do you go to which ones do you you know

are on your radar but there's usually

quote there's usually quite a few in

definitely more than one - pick a few

that you're going to attend buy a ticket

sometimes they're expensive you know

thousands of dollars sometimes you don't

even need a ticket you know depends on

the event but figure out the conference

and decide you're gonna go hopefully

weeks or months in advance three get the

conch get the list this is such an

important part of making conferences

like this worthwhile find a way to know

who's gonna be there write to the

organizers write to sponsors you know

maybe it's on the website but figure out

who's gonna be there in advance don't

just show up at a conference and think

you're gonna like network your way and

meet everybody although if you can pull

that off by all means do it it's just

not something that that everyone can do

but when you have the list of who's

gonna be there then you can email people

in advance and say hey you know I'm

gonna be at this event I noticed you

were - I'm working on this thing I'd

love to show it to you can we find some

time to chat and don't just do it with a

few people do it with his men

potential buyers or prospects as you can

my goal when I go to a conference or

when anyone from clever goes to a

conference is that we have our entire

days booked up in 30-minute increments

because we've done so much effort in

advance of the conference's trying to

line everything up getting these

meetings and they end up becoming the

most productive day of the year when we

actually go and we actually get to have

all of these conversations and have all

of these buyers and I get to the end of

a night even the first night at a

conference when yeah just been doing one

day and let me tell you every time I am

exhausted and I am also so energized

because there's nothing that's more fun

than meeting with customers and meeting

with potential buyers and hearing their

reactions to what you're building so I

cannot emphasize enough how important

conferences have been in every aspect of

in every company I've worked in sales at

and I highly recommend you explore this

so that's conferences the other and

frankly the you know more probably more

common approach is called emails people

don't really cold call too much anymore

maybe you could make it work but cold

emails I mean I still do that today and

and a lot of people are don't know how

to write cold emails they don't know how

to you know reach out to someone in a

productive way I know this because I'm

on the receiving end of so many bad cold

emails we probably all are they're

really long they're not personalized or

not actionable they're boring they're

irrelevant so don't do that but if you

don't do that like well then what do you

do how do you have a cold email you know

strategy that's effective in the early

days of clever in the early days of

other startups we would sit and sit down

and we'd send you know 10 30 50 emails

to cold prospects and it would look

something like this and I've actually

found an old email and I put it up here

so you guys can see it you feel free to

copy it but it is the simplest thing in

the world

you'll notice it's short it's to the

point it's personalized it's actionable

hey my name is Tyler and I'm the CEO of

clever this is you know what we do I

thought this might be rel

for you because of XYZ reason that's you

know personal to you

even if you're not in the market I'd

love to chat with you about this which

is true do you have some time this week

later this week I'm free I'm free now or

you know I'm free at this time super

simple super you know this will probably

get read as opposed to some of the

paragraph long you know diatribes about

why my product is the best and why

you're crazy for not using it and before

we've even met

all you're trying to do is get a call

with somebody and actually meet them and

so we'll send out cold emails it's it's

very effective but you know make sure

you do it right make sure you're writing

emails that are interesting to people

that aren't too salesy that are

personalized and that are genuine and

remember all you're trying to do is get

a conversation get it out of that

prospecting phase and into stage two

which is conversations so let's talk

about stage two stage two okay if you've

gone to conferences you've done cold

emails you've worked your network and

now you're talking to prospects this is

exciting people want to talk to you they

might want to buy your product this is

what you've been waiting for when this

happens and you get them on the phone

remember to shut up and listen and when

people ask me you know what's your

number one sales tip what's the number

one when new sales people say what's the

number one thing I should practice or

work on if you take nothing else from

this presentation take this sales is

about listening I've had the opportunity

in my life to shadow some of what I who

I think are some of the best salespeople

in the world

incredibly successful salespeople and

they look nothing like the picture I

showed you on the first slide you know

they were soft-spoken they and what I

remembered specifically was that they

were world-class listeners and the

reason that's so important is because

that's what sales is at its core people

think sales is about just you know you

know like a being a battering ram and

just hitting you're getting your points

across and repeating them over and over

until somebody finally you know breaks

down

by your product and let me tell you that

doesn't work and what does work is is

building relationships with people

understanding their problems

understanding what their needs are and

then seeing if you can help them with

your solution and in order to make that

happen

you have to listen so most founders when

I I've shadowed a lot of sales calls and

I one thing I see very frequently is a

founder they're so excited they finally

got someone on the phone they're hooked

they're definitely gonna be the first

customer and they get them on the phone

and they just talk and it's

understandable right you're excited

you're excited that you know about your

product you're passionate about it you

can't wait to show off every bell and

whistle but you've spent months

thoughtfully building but it will

totally kill your sales your sales deal

what you'll naturally do is talk for

seventy percent of the time on the first

call and you know maybe leave 30 percent

of space for the other person the best

sales people in the world when I've seen

them in action it's the opposite they're

listening 70 percent of the time and

they're asking questions like hey tell

me about the problem you're having how

do you solve it today why did you even

agree to take my call what would your

ideal solution look like if you could

have anything they're asking questions

because they care and they want to

understand and they want to figure out

how to help this person solve their

problem and yes their product might be

part of that solution but it involves

deep listening you know we have one one

trick I can share on this is we at

clever we use a tool called uber

conference and every conference is great

but one of the things I love about it is

at the end of each call it sends you an

email and it tells you how much time you

spent talking versus how much time the

other person spent talking and it's

funny because I can look at these and

it's a running joke I'll look at these

in you know sometimes you'll talk to

someone and say I just got off a call it

was great I nailed it you know where

they're gonna definitely buy and then

I'll look at the Eber conference you

know call email

at the end then if it looks like that

I'll say I don't think that call went as

well as you think I don't know if we're

really you know ready to make that sale

quite yet and so the number one thing

that I hope to impress on you today is

sales is about listening and it's not

just about you know a hacker you know

asking the right questions it's about

genuinely listening and if you can do

that the rest is easy it really is so

you've got them on the you've you've

spent all this time prospecting you've

now even had your phone calls you've

done a good job listening and then one

thing another thing to know about sales

is there's a lot of steps to the process

you know up here I have a lot of

different steps that you might go

through in a sales process calls emails

pricing calls you know sending

references talking with different

executives there are a lot of steps to

sales and up here these aren't these

aren't just steps hypothetical steps

what I've put up here are actually all

of the steps from one of my very first

deals at clever this is one deal and

frankly some of the stuff is kind of

embarrassing right like met the person

they were interested I emailed no

response I emailed him again no response

I emailed him again they responded I

scheduled a call email no response I

mean this is straight-up embarrassing

and this is from someone who wanted to

buy our product isn't that crazy

so one of the things I hope to impress

on you is it is a lot of work to do

sales well and it takes a lot of

follow-up and you kind of have to have

this inhumane like willingness to just

keep going and push through this this

whole lifecycle probably took about two

months it ended up we ended up closing a

hundred thousand dollar-a-year customer

but this is what it took and I I talked

to a lot of founders who maybe they have

a good meeting they do a follow-up email

and

they don't get a response and they're

like oh well maybe they weren't

interested after all maybe it's not a

good fit and they disqualify themselves

well just remember this is what a

success case looks like at least if

you're doing enterprise sales and you

know it's not over till it's over and

it's not over till they say no but

sometimes you do have to kind of remind

them you know hey I'm still here hey are

you still interested because probably

your buyers have a lot on their mind

that's not you or your startup and

probably they have a lot of other things

going on in their life and so being

persistent isn't rude being persistent

can be helpful if you do it in the right

way and you're respectful now I will say

one thing here follow-up is really good

and really important but what's also

really good sometimes you get to know

and getting those noes can also be

really good and really helpful because

when you're a small startup with this

you know founder small founding team

you've got to figure out where to spend

your time and energy and you can't have

a pipeline of hundreds and hundreds of

deals going at one time you just can't

you you won't be able to do it and so

there's actually a lot of value my

friend Steve Garrity taught me this

there's a lot of value to driving

conversations to a yes or no quickly

because knows you can move on and get

and start filling the pipeline with

other people that could become yeses so

I would encourage you to have relentless

follow-up you know be determined go you

know don't let don't let things drop but

at the same time if you get a know you

know see it as a as a as a blessing in

disguise because you can move on to the

next deal that could be a yes okay so

you've prospected you've had these great

conversations with customers you've you

know made it through the rigmarole

you've gone through all these steps now

let's talk about closing this is an area

that it just it's weird it's foreign so

you have to figure out how to close a

contract with a customer who's told you

they want to buy it's harder than it

sounds a lot of deals get messed up in

here so let me just walk you through a

few things I've learned one assuming

you're doing a you know an enterprise

contract

you'll need an agreement and then you'll

send it over to the company and they'll

want to change the agreement though it's

a process called redlining and then

their lawyers will send it back to you

and you might look at it or your lawyers

might look at it you might have more

changes and you go back and forth in

this redlining process so the first step

is you need to have an agreement to

propose and by the way they're gonna

expect it from you they're gonna say

okay you know when they're interested

they're gonna say send me an agreement

and make sure that you have something or

you've been working on something so that

you know it's not like oh I'll get back

to you in a month if you don't have

something I've good news which is if

you're not aware YC has an open-source

sales template posted on their website

and I worked on this with James Reilly

it could when Proctor and some other

folks including the Y Combinator legal

team and wisely decided to open source

this so any of you can use it obviously

you'll probably need to customize it for

your needs and at some point you want to

get counseled but as this basic starting

point there's a free template that you

can use for sales and Y Combinator's

website and then once you have your

going into this back and forth I'll

never forget it I have seen some

founders let this process drag out for

months fighting over the dumbest things

when you are at an early stage startup

when you are trying to get your first

customers early customers are like manna

from heaven

they if you get and if you don't get

them you're not gonna go very far you're

done and yet I have seen startups in the

early phase because they think that what

they're supposed to do or someone gave

them bad advice quibble over the dumbest

things so my advice for you is when you

get to this step especially for your

first early customers they're gonna want

to put weird things in the contract with

indemnity clauses and warranty clauses

and don't say you know get it reviewed

by a lawyer don't sound anything dumb

but your goal is to finish and move on

and just keep that in mind and if you're

going through four or five six revision

processes you're doing something wrong

so figure out how to move this quickly

and don't quibble over small things

get get the first customers because

that's what you need to you know keep

going

okay another closing trap you got the

customer interested they want to buy

things look great and they come to you

and they say hey actually I want to buy

but only only if you had this one other

feature would I buy it sounds so

promising you're so close they just want

one more thing sure you can build that

thing it wouldn't be that hard

unfortunately once you start hearing

this in my experience unfortunately it

is more often a pass than anything else

and the thing to remember is

unfortunately building that one thing

when someone says oh I would buy it

except it's just missing that one thing

if you built it there might be there'd

probably be another thing after that and

another thing after that and you don't

want to be in a world where you're

building lots of one-off things for

customers now your first customer second

customer do what it takes folks but but

very quickly you get in a world where

you keep where you start hearing this

and you realize it's not a good thing

and so two ways I've seen of solving

this one is well if you really want the

sale and you really want to hold them to

their word and have that commitment say

okay well I'll build it if you if you

agree to you know figure aided by the

product which means I can't demo up for

you today I can't you know show you

reference customers on this thing you

want but I will build it for you if you

if you sign up and if you've spent the

time listening and building the

relationship and they trust you that can

work the other thing is you say look

we're gonna build what you know what

customers need and we're gonna wait till

we hear from four more customers and you

know oftentimes I find even in that case

if they still want the product they'll

buy it even without that one feature and

hopefully end up building what they need

anyways but but at least then you're not

building something for just one customer

third closing trap free trials you get

so close to someone they're so

interested there that your perfect first

customer and then they say yeah we just

like to try it for for 60 days folks

when you are starting your company and

when you are out there trying to

make your startup work you need things

like commitment you need validation you

need revenue and guess what a free trial

doesn't get you any of those things and

so I at every company I've been at I've

never worked at a company where they did

free trials we just said we can't do it

we're spending a lot of time out here

trying to find the right customers for

our product you're spending a lot of

time building the right product you know

we're not gonna we're not gonna give it

away for free on the hopes that maybe

you'll decide you want it but we flipped

it around and said but we want to be

reasonable and we know you're taking a

chance on us and you know there's risk

so we only do annual agreements here

that's our that's how we operate but if

for any reason you're not satisfied in

the first 30 days you can opt out of the

agreement and there won't be any penalty

and cancel and flip it and having it

that way where the default is they're a

customer but if something goes wrong

they're still protected actually meets

both part it's kind of both parties

meeting in the middle and it and it

solves for their concern that they're

taking a risk on someone new well not

while solving for your concern which is

that unique commitment and validation to

keep going and way better to be in a

case where the default is that they're a

customer then the default is well you

need to renegotiate something in 60 days

from now and you're right back where you

started so to the extent you can avoid

the free trial trap so that's closing so

now you know how I've approached

prospecting how I've approached the

conversations how I've approached

closing happy to answer questions on

these when we when we when we break but

just step end on some final parting

thoughts what I've described here is the

enterprise sales process I've used going

from 0 to 1 million first million in

revenue this is this is the exact

process we've used multiple times and

it's worked but not every company well

every company is different and one of

the things that I love to encourage

founders to think about early is what

kind of company and specifically what

kind of sales motion are you going to

have in the long term

Kristof chance who's a VC has this

really incredible blog post I just love

how memorable it is but he says there's

five ways to build a hundred million

dollar business from a sales perspective

if your average customer pays you a

hundred thousand dollars well then you

just need to find a thousand customers

and you're done or if your average

customer pays you ten thousand dollars

then you need to find ten thousand

customers and you're done or on the far

end so those are your elephants and your

deer on your far end he has these flies

and they only pay you ten dollars but

you need 10 million of them and so it

helps to think about as you're starting

to think about your sales motion well

how much are my customers paying and

therefore how many of them I gonna need

to have and what sort of sales motion is

going to be sustainable for my business

because if you're it's the way you're

selling your product today is you're

flying to people you're meeting them at

conferences you're doing everything I

touch you know I described this very

kind of high touch high energy sales

process but your customers are only

paying you $10 a year or $100 a year or

$1,000 a year and you're gonna have to

repeat that 10 million times it's

impossible it's it's impossible and it's

you know way too expensive

for you to build your business that way

on the other hand if you're successful

in building a low touch sales model

where you're able to do things you know

scalably maybe you're selling to small

businesses you know of which there's

millions maybe you have some way that

people doing self-service and sign up

well then you can be over on the right

side of this graph and you can have and

you can have a lower price product but

the price of your product and and your

sales motion are inextricably connected

and that's something that you know took

me a little while to understand but I

thought this graph really helped make

clear is depending on how much you're

able to charge for your product and

depending on how much people are willing

to pay for your product that'll change

how you approach sales as you're

building your company and building your

sales team so those are some lessons

I've learned along the way doing sales I

want it to end and just say good luck

out there

you know you guys are figuring in this

out it's it's the most fun time of your

company you get to have these really

energizing conversations with with tons

of users and figure out if they're

potential buyers and good luck because

you'll always look back on this is one

of the most fun parts of your journey so

thanks for having me

and I think we have some time for Q&A

yeah why don't we start here thank you

very much for the talk quick question

you mention about follow-ups and so

forth what would be the appropriate time

between emails and you know just so you

don't feel this you don't seem

overbearing and how I I'd say on average

maybe a little under a week so if you

email someone and they don't get back to

you I think it's you know polite and not

overeager to nudge you know five six

seven days later yeah

oh here hi my name is raisin I was

happiest on sales day at what point

throughout your process did you feel

like you were pestering the customers

you kept you put in a nice way you know

like oh you got to keep on going you got

to keep on asking you got to keep on

sending them along the process did you

ever feel like you were pestering your

customers or not yeah so the question

was do you ever feel like you're

pestering your customers when you send

them follow-up emails I like to think

that if they haven't told you know then

you you know you're within your rights

to follow up you know a reasonable

number of times if you're talking about

emailing someone eight times and they

haven't gotten back to you I mean take a

hint great but you know I think if they

haven't told you know and especially if

you had a earlier conversation where

they were interested you know assume the

best assume they're busy assume that

they've got other things going on you

might not be their top priority but

there's nothing wrong especially if

you're doing it on a you know weekly

cadence or something like that and your

emails are thoughtful and personalized I

have never once in my life been annoyed

by somebody sending respectful

follow-ups as long as they seem

thoughtful and personalized don't forget

that part if it's just like I'm getting

mail merged every week with another

template I mean you know nobody likes

that person but yeah over here

yeah I would say you don't learn about

product market fits from oh sorry the

question was when you're getting these

nose or in early sales conversations how

do you know it when they're just not an

early adopter or an and how do you know

when they're just you should be reading

signs of product market fit or lack

thereof and my answer to that is I don't

think you discover a product market fit

from the nose I think you only discover

it from the yeses

so I think when you get nose there's a

lot of reasons people could give me

giving you nose and I wouldn't even

necessarily believe you know the reasons

that people you know give nose because

in the same way that you can't trust

when VCS give you know you know the

reasons is there's just people struggle

to be upfront and honest and you know

everybody wants to be polite well you

get to product market fit and you know

you have something as when you start

hearing yeses and so you just have to

try and if you can't get any yeses

well there's your signal that you don't

have a product market fit and if you can

get yeses there's your signal that you

do have product market fit and I think

that's all that matters what is the

importance of reference customers in

terms of would you prefer going out to

big brands big names even if they

require far more work than going full

that's know but yeah that's a great

question it is how should you prioritize

big companies which would be amazing

names and logos if you had them as

reference customers or small companies

which might be faster

you know I I think about the advice YC

gives for investors which is to do a

breath for breadth-first search meaning

optimized for speed and optimize for you

know I would say talk to all those

companies talk to the big company talk

to the small company but then you'll

know which ones can can move quickly and

not and optimized for speed a customer

is better than than no customer and the

big companies are never the are never

these great they're great references you

imagine necessarily I would go for who

needs your product the most and who will

move quickly and the reference stuff and

you know the logo stuff you know I don't

think you have to worry about that in

the early days you're just looking for

validation and customers yeah over here

hi area elevate this club I'd like to

hear about your pricing journey and we

have asked of interested customers that

were beginning to now get nervous about

the pricing so one of you about your

journey PS I did had sales at the UCLA

baby bro oh nice oh good to meet you

so your question was about the pricing

journey yeah and how to set pricing that

is a hard question because it's so

specific to every company I'll tell you

what we did at clever we guessed you

know we guess and you get feedback it's

actually kind of neat you get feedback

from the market you know pretty quickly

and you can in the early days you can

iterate you know there's a there's a

Patrick McKenzie likes to talk about how

most startup founders need to charge

more and we'll usually guess too low so

maybe one strategy for guessing would be

to guess a number that seems reasonable

to you and if you can close that sale

you know try doubling it the next time

and if you can close that sale try

doubling it again you it's really hard

to know what customers will pay but I'll

tell you that that you know that

original deal I mentioned for $100,000

that we closed very early on

why was it $100,000 and not you know

half of that or double that it was just

you know us doing a little bit of this

and guessing but we got feedback and you

know iterated from there on the on the

pricing model so I think you just got to

try things be bold

whatever you say you got to believe it

this is the right price for our product

there's no other price would that would

be fair for this you know this thing and

but then quickly you know be willing to

iterate as you get that feedback yeah no

problem in the back there yeah I'm not

sure I understand the question yeah so

yeah so the question is how do you if

you're talking about a $50 price point

for a product how do you and you know

early on in a company's journey how do

you bootstrap a sales effort around that

I mean if you're talking about a $50

product even $50 per month you are

basically basically you probably

shouldn't do any of these things and you

should instead invest in a marketing

function because you are gonna need so

many customers and you know you can't do

it in a high-touch way so you know I

look at things like you know demand

generation and email campaigns and

self-service signup flows and referral

codes and things that you know companies

that that small price point kind of have

to do to be scalable or raise the price

of your product to support you know a

true sales either way but that's

probably how I'd approach it

[Music]

why isn't there anything on your website

yeah there's no product other than the

product that's something I don't talk

okay it sounds like sometimes founders

do this I said what what if there's not

enough case studies on our website for

people to come by

I thought of founders think they're the

net it's never enough whatever they have

is never enough to get people to buy if

they were one had one more reference

account if they had a few more case

studies that's what people you know

that's what it would take for people to

buy guess what if you go on the Wayback

Machine for clever calm from 2012 we

didn't have any case studies you know we

didn't have any customer testimonials

all we had was a page that described the

product and and you know and that was

enough to get you know for people who

had the need they didn't care about any

of that they were like oh finally

someone's built a solution to my problem

great I will run through walls to get it

and we didn't you know we maybe we have

some of that stuff five six years in but

we certainly didn't have it at the

beginning so uh yeah over here sorry one

more time

oh what resources yes the question is

what resources have I learned from you

know in doing sales there is well first

there's no excuse there's no there's no

substitute for doing it I've read a

number of books on sales I've you know

watch things online ninety five percent

of what I've learned has just come from

trying it over and over again and

actually it really appeals to the math

and statistics side of me because you

kind of get to a be test everything yeah

you try something new in a conversation

oh that didn't really work okay gonna

you know try something again

you just get to eater

over and over and over again and so that

is that is the number one way to learn

sales there are some books there's this

one that I love it's called how I picked

myself up from failure to success in

selling it's from like the 1950s and

it's written in this kind of hokey corny

way but it so beautifully encapsulate

the journey of learning sales and you

know some of the hustle and things that

I was describing as part of it earlier

so that's one resource I've recommended

to founders but really you just got to

try it

okay last question yes you look I give a

question hiring salespeople first of all

you have no business hiring salespeople

until you've done a lot of sales on your

own could be good and the reason is not

just you know because of what I was

saying earlier about how you know good

you are it's because you won't even know

what kind of people to hire until you've

done a lot of sales on your own you

won't know what the core skills are is

it is it traveling a lot is it a lot of

phone calls is it a lot of like you know

really good emails you just won't know

once you have done sales for a while the

good news is you'll know exactly the

kind of people that you should hire and

typically that's how I've done it so

I've done sales you know by myself for

three six nine twelve months done made

it repeatable to a to a degree and then

there's you know there's there's

literature out there about what you want

your first sales reps to look like and

oftentimes the term that's used

Renaissance sales rep I and that's kind

of differentiating from the

coin-operated sales rep maybe you know

coin-operated meaning like they they

need everything they need every piece of

collateral every play book every script

but then they can go out and execute on

it just relentlessly on the other side

of that spectrum you have the

Renaissance reps what you needed to

start up and these are folks who don't

need a lot of direction don't need a lot

of playbook and they just

figuring things out and probably your

earliest reps you know even a clever

today I you know we're Renaissance but

you know bigger companies will have much

more on the other end of the spectrum

and so you want to look for those

Renaissance players who can are really

love to learn oftentimes they'll have

some industry expertise but maybe not

too much you know you probably don't

need the person is your first

salesperson who has you know just you

you probably don't want someone you know

don't be too blown away by fifty years

of experience not that that's bad but

it's also you can probably get away you

know if you have the hustle and the grit

that's what's most important at this age

more than experience and so yeah those

are the things I look for is so a lot of

energy a lot of passion kind of that

Renaissance sales rep mentality and then

pattern matching to what I've been doing

in the sales process if they have those

skills great thank you

thanks guys

you