Cold Emails

While some older outbound sales techniques may no longer be effective, Jason argues that outbound sales can still work if done thoughtfully. Targeting prospects with specific, customized messages about how your solution addresses their most important problems can cut through the noise. Taking the time to understand each prospect and tailor your outreach is important. While you may not close the deal every time, this approach can at least start a dialogue and get some prospects to take a meeting. Jason suggests iterating your outbound approach to focus on reaching senior executives at larger companies who have the bandwidth to consider new solutions and where your product's value is the clearest.

John covers: • Startups, challengers, and champions • Outreach sequences • LinkedIn techniques • Email subject lines + bodies

Cold emails to investors can work if they are personalized, compelling, and show early traction or metrics that demonstrate a clear opportunity. Jason discusses two successful cold emails that he received and then funded - one from Mapistry that summarized the opportunity, customers, and growth profile, and one from Talkdesk that highlighted metrics, case studies, and Go To Market strategy when they were at $1M in ARR. While cold emails face long odds, these examples show that a great pitch tailored to the recipient that indicates the potential opportunity can succeed in getting a founder an initial meeting and potential funding.

Brendan discusses the importance of measuring outbound account conversion rate and contact conversion rate. These metrics show how efficiently an outbound sales team is penetrating their target accounts and contacts. He provides examples to demonstrate how to calculate these rates and argues that these overlooked metrics are crucial for benchmarking reps, determining future hiring needs, projecting market penetration, and accurately forecasting revenue. While conversion rates vary between mid-market and enterprise organizations, the article provides some general benchmarks for "good" outbound account and contact conversion rates.

While product-led growth is effective for early-stage companies, most firms introduce outbound sales motions as they grow past $10M ARR to target larger enterprise accounts. Kyle provides two case studies that detail how outbound representatives at ClickUp and Trustpage focus on engaging existing product users and identifying new opportunities within accounts, often without compromising PLG roots. Attribution can be challenging when outbound interactions precede self-served conversions. Companies address this through tailored incentive structures for representatives. ClickUp's outbound team also conducts traditional cold outreach, but with a smaller scope given the long lead times. Trustpage leverages its security product to provide value and drive adoption for prospects through outbound security comparisons. Both companies emphasize the importance of product-centric messaging aligned with the user experience. Proper attribution policies are critical to incentivizing outbound activities without undermining the customer journey.