Christina Gilbert’s Guide to Improving Founder-Led Outreach

YC visiting partner and OneSchema founder Christina Gilbert shares lessons from founder-led sales. Her focus is learning which people have a real problem, then writing a message that earns a response.

Gilbert recommends starting manually instead of sending a thousand automated messages immediately. If a poorly considered campaign gets no replies, it is difficult to tell whether targeting, wording, subject line or deliverability caused the result.

Her starting heuristic is at least 100 individually researched messages before automation. For each person, look at their role and company and ask what problem they actually face; the number is a guideline, not a guarantee.

Targeting can matter more than polishing copy. She recalls a founder selling infrastructure to engineering leaders who was instead contacting people in developer relations, marketing and customer success.

Look at existing deals to find who championed the purchase, signed the contract and paid. If there are no customers yet, reason about who has the most to gain from solving the problem.

Check the company as well as the job title. Prospecting tools can return superficially matching firms that are not the right customer, so review the list rather than trusting a search filter blindly.

Gilbert calls hiring, company growth and similar changes “intent signals.” For compensation software, she gives the example of a company approaching a size where formal job levels may become relevant; the threshold is context-dependent.

For the first customers, she suggests starting with a warm network and asking for introductions. Existing relationships can make an initial conversation easier to secure.

A useful message explains the buyer’s problem and how the sender can help. Gilbert recommends a concise product explanation, a credible reason to trust the sender and a specific request such as a short call.

She suggests five to eight sentences for email and fewer for LinkedIn as rough limits. The purpose is to make the message easy to skim and remove filler, not to follow a magic word count.

In one example, a founder mentions relevant experience, identifies a detail on the prospect’s site and proposes an experiment. Gilbert likes the informal tone and clear request more than a long feature list.

Experiment with subject lines and remember that the first words of the email body appear in many inbox previews. Her examples illustrate a test, not a universal formula for a high open rate.

On LinkedIn, she recommends a clear profile photo, a concise explanation of the company and relevant experience. She also values relevant mutual connections, while recognizing that building them takes time.

A few replies can establish a baseline. For low response rates, Gilbert checks the person and company first, then the subject line, message, supporting materials and deliverability; persistent failure may also prompt a product-market-fit question.

She recommends following up after an initial message and responding promptly when someone replies. Her suggested two to four follow-ups are a personal practice; recipients’ preferences and any applicable rules still matter.

A final low-pressure message can give a prospect an easy way to say no. Gilbert treats a clear refusal as useful feedback for improving future targeting.

Founders should reserve time for outreach, decide how many messages they can thoughtfully send and put the work on a calendar. Consistent follow-through makes the learning process more useful.

Ask customers what caught their attention and what led them to buy. Their own description of the problem can improve future messages more than language invented in isolation.

Gilbert closes by arguing that founder-led outreach compounds customer knowledge. Over time, patterns in replies, job postings and objections can make it easier to identify relevant prospects and communicate clearly.