Y Combinator Startup Podcast
00:05:36 · Christina Gilbert
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 wanna 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 Appton, which is a YC company in the s twenty four 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 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 Sameer'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 Sameer 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 class style agent product.
00:07:25 · Christina Gilbert
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 wanna 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 section that talks a lot 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 a 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 a 100 emails, here's typically the order I'll start debugging their outbound. First, I'll make sure that they're contacting the right person.
00:09:16 · Christina Gilbert
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. For 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 no's improve who you target in the future. Once you get a reply, you should be like a heat seeking missile and that nothing is gonna 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.
00:11:06 · Christina Gilbert
You can also have your cofounder hold you accountable if it's hard for you to do yourself. The number one difference between founders who actually succeed with outbound 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 adviser, and not your cofounder. 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 gonna 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.