How To Get Better At Outbound Sales
Y Combinator
Start manual before automating 0:01
If you blast out a thousand automated emails and get zero replies, you learn nothing because you don't know whether the problem was your messaging, targeting, deliverability, or subject line. Do at least one hundred outreaches by hand first, genuinely researching each person's LinkedIn and company so you can figure out what would actually capture their attention.
Targeting matters more than perfect copy 1:31
A perfectly written email fails if it goes to the wrong person, like the infrastructure founder who kept emailing DevRel managers and customer success managers instead of senior engineering leaders. To find the right titles, look at who already bought from you or replied to your outbound, or ask who in an organization has the most to gain, the way a chief security officer cares about device monitoring software far more than an engineering manager would. You also need to check that you're targeting the right companies, since tools like Sales Navigator can return mismatched results, and watch for intent signals such as job postings or company growth, like compensation software becoming relevant once a company crosses around one hundred employees. Early on, your warm network, friends, family, investors, even someone you met at a cafe, converts far better than cold lists.
Write a message worth reading 4:30
Your email should give a one sentence, crisp explanation of the problem you solve, because executives care about hitting their quarterly targets, not features like fast uploads or which database you use. Build credibility by naming impressive customers or relevant background, end with a specific call to action like asking for twenty minutes this week rather than a vague question, and keep emails to five to eight sentences, two to five for LinkedIn. A strong example came from the founder of Aptton, who wrote informally, opened by mentioning his Tesla experience, personalized the email by referencing a detail from the prospect's website, and closed with a clear invitation to experiment together. Subject lines matter too, and testing pays off, since a quirky line like broken agents outperformed the more descriptive better agents for every workflow.
Polish your LinkedIn profile 7:30
A profile picture builds trust, your banner should read like a clear, jargon free ad for your company, and your about section should be short and focused on what buyers care about rather than hobbies. Building mutual connections also helps a lot, since shared contacts are the biggest predictor of whether someone accepts your connection request, so it's worth maxing out your connection allowance daily.
Read your reply rates and follow up 9:02
Even two or three replies out of a hundred emails gives you a baseline to improve, and the debugging order should be person, company, subject line, messaging, materials, then deliverability. If everything checks out and replies are still at zero, that can point to a deeper product market fit problem. Never send just one email, follow up two to four times, and use a low pressure breakup message near the end, since a real no still helps you refine future targeting. Once someone replies, chase the calendar booking immediately, because time kills deals.
Protect time and use customer language 10:30
Outbound is unglamorous, so founders need a concrete daily plan for how many messages to send and when, putting it on the calendar or asking a co-founder to enforce it, since following through separates founders who succeed from those who don't. The best messaging comes directly from customers, so ask on sales calls what got their attention in your message and ask existing customers what made them buy, then reuse their exact phrasing. This customer knowledge compounds over time, and no outside salesperson or agency can learn your customers the way you can.
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