Shifting from a self-serve, inbound-led model to a proactive, outbound enterprise sales motion is a massive cultural and skills-based change. Livestorm found their existing sales team, accustomed to handling warm leads from a CRM, could not make the transition. They had to reset and hire a new team with traditional outbound and complex deal experience.
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Moving from transactional to value-led sales is an HR challenge before it's a sales one. It demands hiring new profiles who can translate tech into business language. For existing teams, it's not just about training; it requires a deep assessment of whether current employees have the right skills and are in the right roles for the future.
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.
Leaders often misapply successful playbooks from past roles. Instead of force-fitting, they should deconstruct the sales motion from first principles: who is the user, what's already working, and how do they *really* buy in this specific context? This ensures the playbook fits the new company's unique dynamics, especially in a PLG environment.
Snowflake's initial high-velocity sales model hit a wall with large enterprises. New CEO Frank Slootman mandated a change, forcing CRO Chris Degnan to "rip the bandaid off" and restructure the entire GTM organization in the middle of a fiscal year to create a dedicated enterprise sales motion.
Don't "stuff the channel" by forcing your existing sales team to sell an acquired product with a different model. At Cisco, a usage-based product was kept separate from the enterprise sales team, who were incentivized by large deals and wouldn't have prioritized it.
The "PLG Trap" occurs when founders assume moving upmarket is just a pricing change. In reality, shifting from PLG to enterprise sales requires a difficult, company-wide transition across product (e.g., SOC 2 compliance), organization (e.g., sales engineers), and culture.
Ethic's unique, consultative sales process didn't fit traditional molds. They couldn't hire typical SaaS salespeople or financial wholesalers. This created a talent challenge, forcing them to invent a new playbook and hire for a hybrid role combining technology setup and deep client discovery.
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.
Traditional, one-off training events are obsolete because the sales environment now demands constant agility and speed. Many experienced salespeople are struggling because their established playbooks and skills were developed for a market that has fundamentally changed, making continuous learning essential for survival.
Never give expensive, company-generated inbound leads to the same team doing cold outbound. Outbound should be the training ground. Only the top outbound performers graduate to the inbound team, ensuring your best closers are on your most valuable leads.
