- The speaker introduces Tyler from Clever who will give a talk on how to sell and Harj and Amin from TripleByte will discuss how to build an engineering organization.
- The speaker mentions that a midpoint feedback form will be sent out and encourages participants to provide feedback to improve startup school.
- The speaker advises against using "bullshit metrics" and emphasizes the importance of setting milestones to measure progress towards success.
- Tyler Bosmany shares his personal journey to sales and highlights the importance of mastering sales as a founder.
- Sales is described as a core responsibility for startup founders and the speaker mentions that founders have unique advantages such as passion and industry expertise that can make them effective at sales.
- The speaker shares that early on in Clever, one founder was dedicated to owning sales.

- The speaker, one of the co-founders, focused on selling the product while the others built it
- Sales is often described as a funnel with different stages: prospecting, conversations, closing, and revenue
- The speaker emphasizes the importance of finding the right prospects and talks about the technology adoption curve
- They discuss different ways to find prospects, including using personal networks, attending conferences, and sending cold emails
- Conferences are seen as an underrated way to meet potential customers, and the speaker shares tips on how to make the most of them
- Cold emails can also be effective if they are short, personalized, and actionable

- The CEO of Clever, Tyler, emphasizes the importance of sending concise and personalized cold emails to get conversations started.
- Sales is about listening and understanding the problems and needs of potential customers.
- It is important to listen and ask questions during sales calls, rather than dominating the conversation.
- Persistence and follow-up are crucial in the sales process, even if it takes multiple attempts to close a deal.
- Getting a "no" can be beneficial as it allows you to focus on other potential customers.
- Closing a contract with a customer can be challenging, and it involves a redlining process and having a proposed agreement ready.
- Y Combinator offers an open-source sales template that can be customized and used as a starting point.

- The speaker advises using a free template from Y Combinator's website as a starting point for sales contracts.
- Startups should not waste time quibbling over small details with early customers, as getting those customers is crucial for success.
- When customers ask for additional features before making a purchase, it is often a sign that they are not truly committed.
- Two ways to handle this situation are to either agree to build the feature if the customer commits to purchasing, or to wait and see if other customers express the same need.
- Offering free trials is not recommended, as it does not provide commitment or revenue.
- Instead, consider offering a 30-day opt-out period in annual agreements to address customer concerns while still ensuring commitment.
- The sales process should align with the price of the product and the sales motion needed to reach the desired number of customers.
- Follow-up emails should be sent within a reasonable timeframe, usually around a week, and should not be excessive.
- It is important to assume the best and not feel like a pest when following up with customers.

- Sending thoughtful and personalized follow-up emails is not annoying, but mail merged templates are disliked
- Product market fit is discovered through yeses, not no's
- Prioritize speed and talk to both big and small companies for reference customers
- Pricing is specific to each company, but guessing and iterating can help determine the right price
- For subscription-based startups with a low price point, focus on marketing rather than high-touch sales efforts
- Case studies and testimonials are not always necessary for customers to buy
- The best way to learn sales is through practice and iteration, but there are helpful books available
- Hiring and managing the sales team is not discussed in the video

- Before hiring salespeople, it is important to have experience in sales yourself
- This is because you need to know what skills are necessary for the job
- After gaining sales experience, you will know the type of people to hire
- Look for Renaissance sales reps who are independent and love figuring things out
- Industry expertise is not necessary for the first salesperson, but hustle and grit are important qualities to look for

- The speaker introduces Tyler from Clever and Harj and Amin from TripleByte who will discuss sales and building an engineering organization.
- Feedback is encouraged to improve startup school.
- "Bullshit metrics" should be avoided and milestones should be set to measure progress.
- Tyler Bosmany shares his journey to sales and emphasizes its importance for founders.
- Sales is described as a core responsibility for founders and the speaker shares Clever's early sales strategy.
- Prospecting, conversations, closing, and revenue are stages in the sales funnel.
- Finding the right prospects is crucial and various methods are discussed.
- Conferences and cold emails can be effective ways to find prospects.
- Sales is about listening and understanding customer needs.
- Persistence and follow-up are important in the sales process.
- Closing contracts involves a redlining process and Y Combinator offers a sales template.
- Startups should focus on getting early customers and not quibble over small details.
- Handling customer requests for additional features is discussed.
- Offering free trials is not recommended, but a 30-day opt-out period can address customer concerns.
- The sales process should align with the product price and desired number of customers.
- Follow-up emails should be timely and not excessive.
- Personalized follow-up emails are appreciated, but mail merged templates are disliked.
- Product market fit is discovered through positive responses.
- Speed and talking to both big and small companies are important for reference customers.
- Pricing is specific to each company and can be determined through guessing and iteration.
- Marketing is important for subscription-based startups with a low price point.
- Case studies and testimonials are not always necessary for customers to buy.
- Sales skills are best learned through practice and iteration.
- Hiring and managing the sales team is not discussed, but experience in sales is important before hiring.
- Renaissance sales reps with hustle and grit are desirable qualities to look for in sales hires.

Tyler Bosmeny from YC alumnus Clever shares his expertise on how an early stage company should think about sales and about building an enterprise sales team.

You can find the lecture transcript and slides here: https://www.startupschool.org/videos/43

Learn more at https://www.startupschool.org/

All right, good morning everyone We are Halfway through startup school.

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 afterwards, Harj and Amin from TripleByte are going to talk about how to build an engineering organization.

2 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 midpoint feedback form for you guys to fill out.

We really would appreciate getting as many responses as possible.

This is our form of talking to our customers, y'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 were talking a little bit about updates And I've talked to a bunch of people live and some on the forum about updates and what makes sense for updates.

And just to put it bluntly, think hard about your metrics, the ones you're using.

It's a metric that doesn't really measure the road to success for you.

Any startup that you're building is an enormous, complicated, difficult, crazy task.

And no matter what you're doing, if there's no milestone on the way to that, to achieving that enormous task, then you're kidding yourself.

And it's 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.

Email to startupschool at ycombinator.com.

And with that, I think, Tyler, we are ready to go.

So my good friend, Tyler Bosmany from Clever.

It's an honor to be here speaking with you today.

And I wanted to talk to you about something that I think is 1 of the most fundamental and important things any founder needs to master, which is sales.

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 really appreciate and respect as a craft.

When I was in school, when I was in college, I was a math major.

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.

And 1 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 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 doing this for several years, if you know anything about college newspapers, you know 1 of the things, the biggest determinant of how much money they make every year is how well the economy's doing, because a lot of the ads are for recruiters.

But I just happened to be there during some very good years, And when I was leading the advertising sales team, we set records for The Crimson.

And so I thought, OK, this is interesting.

And then as I was getting ready to graduate school, getting ready to graduate, go off to college, or excuse me, go off to work.

I'm doing math, I'm thinking I'm gonna 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.

This was not what I imagined doing after school.

And I was really good friends with this guy, and I said, why the heck not?

So I ended up going on a very different path and joining his startup, building a sales team.

We were selling to newspapers across the country.

And if you've ever worked with or thought about newspapers before, you can imagine they are very hard customers to sell to.

And so I really cut my teeth and had a lot of fun, frankly, over many years figuring out how to sell into this market.

Then fast forward a little bit, and I come on to start Clever.

And 1 of the co-founders started it through Y Combinator about 6 years ago.

And if you don't know anything about Clever, 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 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 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, we think about salespeople, 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 to win the deal.

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 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, then we'll go and hire the salespeople.

And that looks nothing like the mystique, And it 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 when we were doing sales.

You know here he is on a broken chair in a 3 by 3 call room.

I think he's eating a bagel because he probably didn't have time for breakfast.

Could not be further from the Don Draper imagery that a lot of people think of.

And why 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 1 of 2 things, building your product or 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 they say, well, I'm not good at sales yet.

But 1 thing I've learned is that as founders, you also have some very unique advantages that can make you actually incredibly powerful at sales and very potent.

And the 2 advantages that I've noticed, 1 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 1 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 understand this problem more deeply, hopefully, than anyone.

And so these 2 things, even if you've never done sales before, mean you can be incredibly effective.

Early on with Clever, 1 of the things we did that really worked for us was I had 2 co-founders, so there were 3 of us.

And we just decided that 1 of us had to own sales.

It was so important that we needed 1 person to be thinking about this every day.

My other 2 co-founders were focused on building the product and implementing the product and I, we decided this was important enough that I decided I was going to 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 in 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 is a lot of people talk about it like a funnel.

And there's different variations of this funnel.

I have a really simple 1 that I put up here.

Step 1 of the funnel is finding prospects, prospecting.

Who might even be interested in buying your product?

Who might even be interested in taking a call?

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?

Okay, they actually wanna buy the product.

How do you not snatch defeat from the jaws of victory and lose the deal?

You have to go through a closing process.

And if you complete all of those things, then hopefully you're in the promised land and you have revenue and 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 is to figure out who will even take your call.

And 1 of the things that for me was really helpful to understand is, well, you're going to hear no a lot.

You start talking about a new product, people, and you're just going to hear a lot of nos.

But 1 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.

You have your innovators, then you have your early adopters of new technology, your 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 1 of the things, and so 1 of the things you notice is looking at this, the innovators segment is just 2.5% of the population.

That means 2.5% of companies will even consider buying a product from a startup that is unproven with no revenue.

And when you realize that, to 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 a lot of people Because you have to find that 2.5%.

Means you're going to have to reach out to at least 100 companies to find just 2 and 1 half, on average, who are even potential buyers for your product.

You're basically playing a version of Where's Waldo, where you're looking for the very few companies who might be in this innovator segment.

And so expect early on sales is not reaching out to 2, 4, 10 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 3 things that work for me.

So in terms of finding those innovators, the first thing that has worked well for me is using my network.

The second, which is a little surprising to people, is conferences, and I'm gonna talk about that.

These are the 3 ways in which I find prospects.

I'm not gonna talk about my network because I think most people understand that, but I can tell you many of the earliest deals I've done at 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 100 people in your network to get 2 sales.

But let's talk about conferences because I think conferences are the most underrated aspect of sales and 1 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 to some place where there's 80,000 people and it's basically more like a rock concert than anything else.

And when I say conferences, I'm talking about something very different.

Usually it's a bunch of executives or people in a hotel room cooped up for a couple days, oftentimes 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.

And many times if you're selling to a business or to a corporate buyer, This is where users are.

Now let me say a few words about how I've approached conferences in the past because this really is where so many of Clever's initial partnerships and customers came from.

1, figure out what are the big industry conferences for your product and your startup.

Usually there's not just 1, usually there's like 10.

And you have to work to figure out what they are.

Ask people in the industry, what conferences do you go to?

But there's usually quite a few and definitely more than 1.

2, pick a few that you're going to attend.

Sometimes they're expensive, thousands of dollars.

Sometimes you don't even need a ticket, it depends on the event.

But figure out the conference and decide you're going to go hopefully weeks or months in advance.

This is such an important part of making conferences like this worthwhile.

Find a way to know who's going to be there.

But figure out who's going to be there in advance.

Don't just show up at a conference and think you're going to network your way and meet everybody.

Although if you can pull that off, by all means do it.

It's just not something that everyone can do.

But when you have the list of who's going to be there, then you can email people in advance and say, hey, I'm going to be at this event.

Do it with as many 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 conferences, 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 I've just been doing 1 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.

The other and frankly the you know more probably more common approach is cold emails.

People don't really cold call too much anymore maybe you can make it work but cold emails I mean I still do that today and And a lot of people don't know how to write cold emails.

They don't know how to reach out to someone in a productive way.

I know this because I'm on the receiving end of so many bad cold emails.

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 down and we'd send 10, 30, 50 emails to cold prospects.

And I 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.

I thought this might be relevant for you because of XYZ reason that's personal to you.

Even if you're not in the market, I'd love to chat with you about this, which is true.

This will probably get read, as opposed to some of the paragraph-long 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.

It's very effective, but 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 out of that prospecting phase and into stage 2, which is conversations.

Stage 2, okay, 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 wanna talk to you, they might wanna buy your product.

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 1 sales tip, what's the number 1, when new sales people say, what's the number 1 thing I should practice or work on?

If you take nothing else from this presentation, take this.

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.

And they look nothing like the picture I showed you on the first slide.

You know, they were soft-spoken, and what I remember 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, like being a battering ram and just hitting your, getting your points across and repeating them over and over until somebody finally, you know, breaks down and buys your product.

And what does work 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, I've shadowed a lot of sales calls, and 1 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.

You're excited that you know about your product.

You can't wait to show off every bell and whistle that you've spent months thoughtfully building, but it will totally kill your sales deal.

What you'll naturally do is talk for 70% of the time on the first call and maybe leave 30% of space for the other person.

The best salespeople in the world, when I've seen them in action, it's the opposite.

And they're asking questions like, hey, tell me about the problem you're having.

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 1 trick I can share on this is, at clever, we use a tool called Uber Conference.

And Uber Conference is great, but 1 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.

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How to Sell by Tyler Bosmeny