How To Get Better At Outbound Sales

The YC presenter begins with a familiar founder problem: an automated pipeline sends a thousand emails and receives no replies. The result does not identify whether the fault lies in the prospect list, message, subject line or deliverability.

The recommendation is at least 100 genuinely manual outreach attempts before automation, and probably more. For each person, examine the company and profile, consider the specific problem they face and decide what could earn their attention.

This is not only a slower version of sending a large campaign. It is a way to develop hypotheses about buyers while the founder can still see how each message was chosen. Without that work, a zero-response result can leave the team with no useful explanation.

Targeting comes before perfect wording. The presenter describes an infrastructure company sending messages to people in developer relations, go-to-market and customer success when senior engineering leaders were the intended buyers. A polished email would not fix that mismatch.

Existing deals can reveal the right roles: who pushed the purchase forward, signed the contract or paid? If there are no customers or replies yet, ask who has the most to gain from solving the problem. The security-monitoring example distinguishes the person accountable for a breach from an employee who may not want additional monitoring.

Company fit needs checking too. A list-building tool's category may include businesses that look related but are not suitable customers. Job postings, priorities and growth stages can provide clues. The compensation-software example concerns companies beginning to introduce levels and pay bands; the relevant headcount is an example of a product-specific signal, not a universal sales threshold.

For the earliest customers, the presenter also recommends working through warm contacts and asking people in the founder's network for introductions.

The email should quickly explain how the sender can help. The presenter suggests thinking about the buyer's pressing worries and incentives, rather than listing technical features the buyer has no reason to value yet.

Keep the product explanation to roughly one sentence, establish credibility through relevant experience or customers, and finish with a specific next step. A request for a short call is easier to act on than a vague question about whether the idea sounds interesting. A few available times or a calendar link can reduce scheduling effort.

The lesson's example uses the sender's relevant experience with SMS conversion, a concrete observation that the prospect collects phone numbers, and an invitation to test reactivating leads. It spends little space explaining product mechanics.

As rough length guides, the presenter gives five to eight sentences for email and two to five for LinkedIn. The subject line and first 20 to 30 body characters deserve attention because they shape the inbox preview. A reported subject-line experiment favored “broken agents” over a more descriptive alternative; that is an example to test from, not a guaranteed winning phrase.

06:20View full image

At 06:20, the original slide shows the complete example email. It is an illustration of message structure, not a promise of conversion.

On LinkedIn, the profile helps a recipient decide whether to accept and respond. The presenter recommends a recognizable photo, a banner explaining the company clearly, and concise headline and about text without jargon.

Relevant experience should be easy for a buyer to find. A long biography can bury the parts that establish why the founder can solve this particular problem.

The lesson also emphasizes building relevant mutual connections over time. That recommendation concerns trust within a target audience; the video does not independently establish a universal prediction rule for every market.

Two or three replies from 100 emails can provide a starting point for iteration, according to the presenter. A low rate is not a reason to abandon all learning from the campaign.

The suggested diagnostic order is specific: check the person, then the company, then the subject line, the message, supporting materials such as the website or profile, and finally deliverability.

If all those areas look reasonable and replies remain at zero, the presenter says there may be a deeper product–market fit problem. It is a possibility to investigate, rather than something one failed campaign proves.

A single email may simply be missed. The presenter usually recommends two to four follow-ups, spaced a few days apart, with a final low-pressure message acknowledging that the problem may not be a priority.

That last note makes it easier to say no. A real refusal is useful information: patterns across replies can improve who the founder targets next.

When someone does respond with interest, follow through quickly and move toward scheduling. The lesson treats delay as a risk to an emerging conversation, without promising that speed alone will close the deal.

Founders have many competing demands, and outbound is easy to avoid. The presenter recommends deciding the daily message count, estimating how long a message takes and choosing the actual time to do it.

Putting that time on the calendar or asking a co-founder to help with accountability makes the commitment concrete. The work depends on following through on the chosen activity, not only having an impressive automation setup.

On an early call, ask what caught the prospect's attention in the message. The answer can identify a useful line and open a conversation about the underlying problem.

Ask existing customers what made them buy and how they describe the product. Their wording can be used in future messages instead of relying only on feedback from friends, advisers or the team.

The final argument is that founder outreach compounds customer knowledge. Over time, a job posting can become a recognizable clue, and the founder learns which problem matters for which kind of company. Automation can follow that understanding; it cannot create the initial understanding simply by increasing volume.

Adapted from Y Combinator's “How To Get Better At Outbound Sales.” Message counts, cadence and diagnostics are the presenter's recommendations, not independently measured conversion guarantees.