How To Get Better At Outbound Sales

The speaker, founder of One Schkeema and YC visiting partner, shares eight evidence-based tips for improving outbound sales effectiveness. Tip one emphasizes doing at least 100 manual outreaches before automating, as this generates learnings about messaging, targeting, subject lines, and deliverability that automated campaigns miss. Tip two argues that targeting the right person beats perfect messaging—the speaker illustrates this with an example of a company sending to wrong job titles (DevOps managers, GTM managers) when they should target senior engineering leaders. Finding the right profiles involves analyzing existing customers to identify who signed contracts and paid, examining job postings for intent signals, and considering company growth stages as indicators of need. Tip three focuses on crafting concise, problem-centric messages that demonstrate understanding of buyer pain points (what keeps them up at night, what gets them fired/promoted) rather than product features. The speaker emphasizes establishing credibility through relevant background or impressive customer names, using specific calls-to-action, and keeping emails to 5-8 sentences maximum. A real example from Aptton founder shows how informal peer-like tone, credibility establishment through previous relevant experience, and clear experimentation-focused CTAs work well. Tip four addresses LinkedIn profile optimization: using profile pictures, turning banners into company ads, rewriting descriptions to focus on value, cutting irrelevant information, and building mutual connections through daily connection activities. Tip five explains how to interpret reply rates diagnostically, suggesting a debugging order of person-targeting, company-targeting, subject lines, messaging, materials (website/profile), and deliverability before concluding it's a product-market fit issue. Tip six covers follow-up strategy using 2-4 follow-ups spaced days apart, with "breakup messages" that reduce pressure and often generate replies. Tip seven addresses the founder accountability problem—blocking specific time on calendars for outbound activity since it's easily deprioritized. Tip eight advocates using actual customer phrasing and feedback about what caught their attention, as customers write better copy than founders. The speaker concludes by noting that founder knowledge compounds over time, making outbound progressively easier and more effective than any agency could achieve.