Y Combinator Startup Podcast - 8 Ways To Improve Your Outbound Sales

Episode Date: September 13, 2026

The best outbound starts before you automate anything. Founders need to learn who actually has the problem, what gets their attention, and what makes them reply. YC Visiting Partner Christina Gilbert recommends doing at least your first 100 outreaches by hand so you can learn those things yourself.Drawing from her experience generating and closing millions of dollars through founder-led sales at OneSchema, Christina shares eight ways founders can improve their outbound, from targeting the right people and writing emails worth reading to following up, debugging low reply rates, and using customer language to sharpen your message.

If you're just starting outbound and your reply rates are low, maybe even close to zero, this video is for you. As the founder of my company, One Schema, I personally generated and closed millions of dollars in revenue through founder-led sales. As a visiting partner at YC, I've helped hundreds of YC companies improve their outbound. So in this video, we're going to cover eight things that you can do to improve your sales outreach. Tip number one.

You want to start manual before you automate. The biggest mistake I often see founders make, they'll come to me during office hours, and they'll show me their email pipeline. and it will all be automated. They've loaded up a tool, they blasted out a thousand emails, and they ended up getting zero replies. The biggest issue with this is if you get zero replies from a campaign that you didn't give any thought to in the first place,

then at the end, when you have zero replies, you've learned nothing. The problem could be your messaging or your company targeting, your prospect selection, your deliverability, or your subject line. So my recommendation is to do at least 100 outreaches by hand for you automate anything. It's honestly probably going to end up being. more. And when I say by hand, I mean genuinely by hand. Spend time thinking about one individual person. What is her problem specifically? What would actually capture her attention? Visit her LinkedIn page

and read about her company. Doing this homework personally is how you'll come up with your highest converting outbound ideas. Tip number two. Targeting beats perfect messaging. I often see founders spending hours tweaking their email copy, but they barely even think about who they're emailing. Outbound prospecting is kind of like looking for a needle in a haystack. You need a person that the exact pain point that you solve or a perfectly crafted message won't even land. So here's an example. I worked with a company in the winter batch who is selling an infrastructure product that should have been sold to senior engineering leaders. But when I opened up his LinkedIn and looked at the prospects that he was selling to, a lot of them were devrail managers,

Gtm managers, there was even a customer success manager. He was sending hundreds of these messages and was wondering why he wasn't getting any replies. So if you spend a little bit more time thinking about whether or not the person you're sending the email to actually has the pain point, you'll often end up seeing a huge increase in your reply rates. Those wrong job titles were never going to buy, no matter how good your email was. So how do you find the right job titles? The first thing that I typically like to do is look at the customers that you already have. Then look at the sales process.

Who is the person who is pushing the last deal to close? Who actually signed the contract? Who is the person who paid? Look at all of their job titles and then reach out to people who have similar profiles. You should also look at who has already replied to your outbound. So if you're at the very earliest stages of your journey and you don't have any customers or any replies yet, ask yourself who in the organization has the most to gain from buying your software. Here's an example. Imagine you're selling software that monitors employee devices for security purposes.

A chief security officer might get fired if there's a data breach, so they would really be interested in something like this. But an engineering manager would probably rather not be monitored at all, so they're not a great person to target. It's also really important to make sure that you're reaching out to the right companies. One mistake I'll often see companies make is they'll do a search in a tool like Sales Navigator, and it will return a bunch of profiles that maybe sort of match what they were looking for, but were actually the wrong type of company. For example, if you search for tech companies in LinkedIn Sales Navigator, you're often going to get a bunch of IT implementation consultancies.

So you want to be really thoughtful about how you're using list building tools. Verify individually that each company is a good fit for your customer or your message is going to fall on deaf ears. As you do more outbound, you'll start to discover clues about a company that indicate that they need your product. These are called intent signals. A great place to look is often at job postings, as they'll tell you a lot about a company's priorities. Company growth is another very common intent signal. Imagine you're building compensation planning software.

Companies below 100 employees probably aren't introducing levels for their employees, so they won't need your software. Companies above 500 probably already have compensation bans set. So when they're crossing somewhere in that 100 employee range, that's a great intent signal that they need your product. Every product has signals like this. Your job is to discover yours. One more thing on targeting. For closing your very first customers, it's also far easier to start with your warm network.

You really want to shake the tree to make sure you hit everyone you know because the conversion rates will be much, much higher. Start with your personal warm network and then ask for interest from friends, families, investors, your college roommate, a guy you met a cafe. truly whoever you can think of. Tip number three, craft a message worth reading. The single most important thing you can do in your email is to give a crisp explanation of how you can help the person that you're emailing. Think about the top three things that keep your buyer up at night. What would get them fired? What would get them promoted?

Why should they believe that you can actually help them? When you write an email and the buyer thinks, that's exactly the problem that I have, they really get it. They're likely to take the call, even without fully understanding or trusting your solution. your solution. The truth is that executives don't care about your product futures. They don't care that you have blazing fast uploads. They don't care that your database is built in rust. They're worried about how they're going to hit their quarterly target. For the product explanation,

I would try to make it just one sentence. You don't want to spend paragraphs and paragraphs of details here. That's typically what the first call is for. You want to make sure that you establish credibility that you're the right person to help. Two common ways to do this are first to list the names of other impressive companies that you're helping. Or if you don't have that yet, talk about your very relevant background for solving this problem. At the end of your email, you want to include a very specific call to action. It should be something like, got 20 minutes to hop on a call this week, not, does this sound interesting to you? You want to make it really easy for them to follow up with you.

Last, you can include a calendar link or a few time slots that work for you, again, to make it really, really easy for them to schedule. You want to make sure to keep your emails really short. People are extremely busy and they're going to skim your emails. Every filler word that you use dilutes the ones that matter. As a rough guide, five to eight sentences is good for email, no more than two to five for LinkedIn. Longer than that, you should probably cut something. Here's an example of an email that I think is really good. It's from the founder of Aptain, which is a YC company in the S24 batch. Here are some things I really like about this email. First, notice that it's written in a really informal tone that makes him sound like a peer.

He's not using any jargon, he's not trying to sound super impressive. This is an email that could have come from his friend. The next thing I like about this is that he's he establishes credibility by showing that he solved the same problem at a previous reputable company. This is that first line. I used to be a software engineer at Tesla. We got crazy good at using SMS to convert the people who visited our website into car buyers. The next thing I like about this email is that it has a very clear call to action. At the end, he says, would you be open to an experiment to see if we could improve your conversion rate by using AI to reactivate leads?

As the buyer, I'm thinking, okay, is this something that I would want to experiment with? and it makes it really easy for me to directly follow up with him. The email also feels personalized to Sumer's company by mentioning that he noticed on their website that they collect phone numbers in the sign-up process. And notice, he barely spends any time in the email at all explaining how this product works. He focuses exclusively on how he's going to help Sumer solve his problems.

After you read a great message, focus on your subject line. You should also pay attention to the first 20 to 30 characters of the body of your email, because that's what shows up in the Gmail preview. Experimentation is the best way to come up with great subject lines. I find that creative and kind of weird ones can end up being the winners. For example, I worked with a company selling an open-cloth-style agent product. The subject line, broken agents, performed a lot better than the more descriptive but less interesting, better agents for every workflow. Tip number four, improve your LinkedIn profile.

If email has subject lines, LinkedIn has your profile. It's how people decide whether or not to accept your connections and to reply. Here are a few quick tips for making sure that your profile is great. The first one is you want to make sure that you have a profile picture. It will really increase your trust level and show your prospect that you're actually a real person. The second is you should turn that banner on the top of your LinkedIn page into an ad for your company. Typically, it should have a really clear and concise explanation of what your company does. Make sure that you avoid jargon here as well.

The third is you should rewrite your one line description and your about section for your company into short, concise descriptions of what your company does, similar to what you put in your banner. And fourth, elevate anything in your profile that a buyer would care about, like, relevant, impressive experience by cutting everything else that's irrelevant. If you have this really long about about your hobbies and other interests and things that aren't relevant, your buyers are less likely to see the ways that you can help them. Another area to invest for LinkedIn is building up your number of mutual connections. The number of shared contacts is the single biggest predictor of whether or not somebody is going to accept your connection request in the first place. So you should focus on building relevant mutual connections with your target audience. because often people within the same customer profile are connected to each other. This takes time, so you should make it a daily habit to max out your connection allowance.

Tip number five, know what your reply rates are telling you. At first, your reply rates might be very, very low. But that's okay. As long as you're getting a few replies, you have a baseline to improve on. Even just two to three replies on 100 emails is a great place to start iterating. If I'm working with a founder that has on the order of two to three replies on 100 emails, here's typically the order I'll start debugging their outbound. they're outbound. First, I'll make sure that they're contacting the right person. Second,

I'll make sure that they're contacting the right companies. Third, I'll make sure that their subject lines are good. And then, only then, will I actually start looking at their messaging? After that, I'll look at their materials. So, for example, make sure their website looks good and their LinkedIn profile looks good. And then finally, I'll look at deliverability. If you go through all six of these areas and they all seem to be reasonable and you're still getting zero replies, this often might be indicative of a deeper product market fit issue. Tip number six, follow up and when they reply reply fast. You never want to just send one email because it's very, very possible that the person

simply just missed it. I typically like to follow up two to four times spaced out by a couple of days. But the last email that I send a prospect, I often send what's called a breakup message. This is something usually to the effect of since I haven't heard back, it seems like sales tax automation isn't a priority for you right now. Just let me know and I can spare your inbox. You'll often get a reply to that one. Reply rates I find are much higher on these breakup emails because it makes them really low pressure for them to say no.

A real no is actually very useful to you. In aggregate, the many knows improve who you target in the future. Once you get a reply, you should be like a heat-seeking missile and that nothing is going to get between you and getting onto their calendar. Every founder will at least once experience the very painful lesson that time kills deals. So hopefully maybe watching this video, I'll save you from that lesson. Tip number seven, block out time for outbound. This is actually one of the biggest mistakes that I see founders make. When you're a founder, there are going to be so many things competing for your attention. And Outbound is typically one of the least fun things to do for most founders, so you'll find excuses to do literally anything else demanding your attention.

So you should come up with a concrete plan. Decide how many messages am I going to send per day? How long does it take for me to send a typical message? When exactly am I going to send these messages? It might sound like micromanaging yourself, but I actually like to put it on my calendar to hold myself. accountable. You can also have your co-founder hold you accountable if it's hard for you to do yourself. The number one difference between founders who actually succeed without bound and founders who don't is actually following through on the activity that they commit to. Tip number eight, use the messaging

from your customers. The best feedback on your messaging always comes from your customer, not a friend, not an advisor, and not your co-founder. Here are a couple ways that you can get great messaging from your customers. First, on the sales call, one of the first questions I like to ask is what got your attention about my message. They'll typically tell you the particular lines in your message that they thought were most interesting, and you should make sure to include those in future messages. It also gets them open-endedly talking about their problems, which is exactly what you want in a first call anyway. The second thing I like to do for this is ask your existing customers how they think about your product. Ask them the single thing they got them to buy and then use their

phrasing in future messages. Your customers are always going to write better copy than you do. I know that outbound can be a slog. I have personally sent thousands of outbound emails in my life. But before you go, though, one reminder, you're the founder, and that's your superpower here. The slog also pays off because your customer knowledge will compound over time. You'll spot a job posting and instantly know that that company has pain. You'll learn why it's better to talk about pain point A instead of pain point B with smaller companies. No salesperson or agency will ever be able to learn about your customers the way that you can. Your outbound will only get easier over time.

Thanks so much for watching. Go close some deals.