How To Get Better At Outbound Sales

Name: How To Get Better At Outbound Sales
Uploaded: 2026-09-12T14:00:16.000Z
Duration: 12 min 42 s
Channel: Y Combinator

Y CombinatorSeptember 12, 202612m

Topics9

Introduction to Outbound Sales Improvement0:01 Tip 1: Start Manual Before Automating0:30 Tip 2: Targeting Beats Perfect Messaging1:31 Tip 3: Craft a Message Worth Reading4:30 Tip 4: Improve Your LinkedIn Profile7:30 Tip 5: Know What Your Reply Rates Are Telling You9:02 Tip 6: Follow Up and Reply Fast10:01 Tip 7: Block Out Time for Outbound11:01 Tip 8: Use Messaging from Your Customers11:30

In a Nutshell

Manual outbound beats automation for the first 100+ prospects, because only personalized research on the right job titles and companies reveals what actually converts. Strong messaging focuses on the buyer’s exact pain points in one crisp sentence plus a low-friction CTA, and reply-rate debugging follows a strict order: person → company → subject line → message → assets → deliverability. Blocking daily time, following up 2–4 times with a breakup email, and stealing phrasing from real customers are the habits that compound into rising reply and close rates.

AI-Generated Notes

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If you're just starting outbound and your reply rates are low, maybe even close to zero, this video is for you. As a founder of One Schkeema, personally generated and closed millions of dollars in revenue through founder sales. As a visiting partner at YC, helped hundreds of YC companies improve their outbound. The video covers eight things that you can do to improve sales outreach.

The biggest mistake founders make is coming with an email pipeline that's all automated. They've loaded up a tool, blasted out a thousand emails and 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.

The recommendation is to do at least 100 outreaches by hand before you automate anything. It's honestly probably going to end up being more. When saying by hand, genuinely by hand means spending 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.

Founders often spend 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 hay stack. You need a person that has the exact pain point that you solve or a perfectly crafted message won't even land.

An example is working with a company in the winter batch who was selling an infrastructure product that should have been sold to senior engineering leaders. But when looking at his LinkedIn and the prospects he was selling to, a lot of them were Devril 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.

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.

Finding the Right Job Titles

The first thing typically done 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.

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How To Get Better At Outbound Sales

Introduction to Outbound Sales Improvement00:01

Tip 1: Start Manual Before Automating00:30

Tip 2: Targeting Beats Perfect Messaging01:31

Sign in to read the full notes