How a YC partner uses manual emails to fix B2B outreach

This article summarizes an episode of Y Combinator’s video series featuring Christina Gilbert, visiting partner at Y Combinator.

Christina Gilbert, visiting partner at Y Combinator / Photo credit: Y Combinator

Founders learn more by writing a few careful messages than by sending automated email campaigns that get no replies. Christina Gilbert, a visiting partner at Y Combinator, warns that scaling outreach before understanding what buyers need can lead to failure.

Her approach requires writing at least 100 manual emails to learn from rejections. It also requires clear targeting to test early ideas, along with a six-step checklist to figure out why people are not responding.

Manual outreach compounds proprietary buyer knowledge

Taking this manual approach to email provides a foundation for understanding customers. Holding off on automation early forces teams to evaluate every customer as an individual and understand why they might care about the product.

To build traction, teams must adopt an approach to customer research:

• Custom research: Every personalized email tests which topics grab attention and which employees respond.
• Budget efficiency: Understanding buyer motivations allows startups to focus advertising spend on high-likelihood targets.
• Product alignment: Keeping the process internal ties sales feedback to product development and pricing strategies.

Gilbert stresses that this manual effort creates an asset, noting that “the slog also pays off because your customer knowledge will compound over time.”

Pinpoint targeting trumps clever copywriting

Once this customer knowledge builds, it guides who founders choose to email. Translating that knowledge into outbound success requires treating every contact as a potential learning opportunity and evaluating key criteria before hitting send:

• Analyze previous buyers. Start with the job titles that have purchased the product in the past.
• Isolate maximum risk. Select the individual who has the most to lose if the issue remains unresolved.
• Verify company need. Confirm signs that an organization is ready to buy before reaching out.

Gilbert maintains that targeting drives success, arguing that “outbound prospecting is like looking for a needle in a haystack” where messages fail without the right audience.

A six-step diagnostic framework fixes campaign failures

Even when reaching the right audience, low response rates demand a review process rather than rewrites of the message. To prevent teams from making assumptions about product demand too early, founders must troubleshoot their pipeline in this order:

• Verify the contacted individual is responsible for solving the problem.
• Confirm the targeted company is a fit for the product.
• Test new subject lines and preview text before altering the message body.
• Check that all emails are bypassing spam folders and reaching inboxes.
• Question the product-market fit only after checking all 6 diagnostic areas.

Fixing communication errors helps teams distinguish a lack of demand from a problem with their outreach. By scaling slowly, teams can gather the feedback needed to find product-market fit.