SaaStr founder Jason Lemkin advises SaaS startups to hire two sales representatives simultaneously when building their first sales team. Lemkin argues that hiring only one rep fails to save money or time and prevents running A/B tests to determine what sales approaches work best. This guidance was shared in a March 2025 post on SaaStr.com, which has since become a common recommendation for SaaS founders.
According to Lemkin, the timing for hiring sales reps varies depending on the startup's capital and sales model. Some startups may hire sales teams on Day 1 if targeting large enterprises with sufficient funding. Others may wait months until closing deals with a high enough annual contract value to justify the cost. Companies like Dropbox, Slack, Monday, and Canva added sales reps years after launch, often when introducing enterprise editions of their products. Lemkin emphasizes that even successful SaaS companies eventually build sales teams, making the decision to hire two reps a critical early step.
This hiring strategy addresses common pitfalls in early sales team building, especially for bootstrapped startups. By hiring two reps, startups can compare different sales tactics and identify the most effective approaches, improving overall sales performance. The advice reflects broader SaaS industry practices where sales team structure and timing significantly impact growth. Lemkin also notes that once a VP of Sales is in place, they can hire additional reps who may not align as closely with the founders’ buying preferences.
Lemkin’s post on SaaStr.com remains a key reference for SaaS founders navigating early sales hires. The article highlights that the decision to hire two sales reps rather than one can influence a startup’s ability to scale sales efficiently and make data-driven hiring decisions.