As companies scale, they shift from inbound to outbound sales. Reps accustomed to a steady flow of leads often lack the desire or skill to build their own pipeline. The CRO guest estimates fewer than half can successfully make this critical career transition, leading to high turnover.
Related Insights
Even successful PLG companies like Figma eventually burn through their early adopter market. To avoid hitting an asymptotic growth curve, they must proactively build a traditional outbound sales team to tackle the enterprise market before the PLG engine stalls. Don't wait until you need it.
"Mercenaries" are transactional reps who perform well but leave when conditions change. "Patriots" are mission-driven team members who build a winning culture. While startups may need mercenaries for early traction, long-term success requires actively cultivating and hiring for patriot-like qualities.
For a service business with more demand than capacity, flip the sales model. Instead of you doing the work to secure funding or partners to onboard a new client, make it a requirement for the client to secure those resources for you. This leverages their desperation and turns your prospects into your sales team.
Because managers don't trust CRM data, they spend their time chasing reps with active deals to secure the forecast. This focus on closing existing business means ramping reps are neglected, which is a primary driver for ramp times increasing from five to nine months and high attrition.
A one-size-fits-all sales role fails in consumption models. Success requires segmenting the team into specialized roles—new business acquisition, customer onboarding, and account management—each with distinct incentives aligned to their specific function, from initial sign-up to value realization and expansion.
Don't hire more reps until your current team hits its productivity target (e.g., generating 3x their OTE). Scaling headcount before proving the unit economics of your sales motion is a recipe for inefficient growth, missed forecasts, and a bloated cost structure.
A sales organization has truly scaled when leadership stops talking about individual deals and starts managing based on predictable capacity. This means knowing that a certain number of ramped sellers will predictably generate a specific amount of revenue each quarter, turning sales into a machine.
Despite wide acceptance of committee-based buying, an alarming number of sales pipelines remain flawed. In some organizations, over 80% of deals in the CRM have only one contact person attached. This data highlights a critical execution gap between knowing the right strategy and actually implementing it.
Instead of a generic agenda, effective CROs design SKO content to solve the specific, known stages where their sales team consistently gets stuck, such as discovery or reaching the economic buyer. If you don't know these bottlenecks, you're not ready to lead.
Successful sales leaders don't just copy-paste their old playbook. They adapt it using first principles, considering the new company's specific product, user behavior, and GTM motion (like PLG). Rigidity is a common mistake that leads to failure.