Chris Degnan reflects that financial success made him a worse leader because he lost the desire to do the "hard things" required at scale, like constant global travel and endless internal operations meetings. His passion was for selling and competing, not the operational grind of a multi-billion dollar CRO role.
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According to Snowflake's former CRO, salespeople from Salesforce often make poor hires for growing companies because they don't know how to truly sell. Accustomed to massive inbound demand at a market leader, they function as 'order takers' and lack the skills for proactive, competitive selling.
Brian Halligan reflects that as HubSpot grew, he was coached out of his natural 'founder mode' instincts (e.g., many direct reports, public feedback) and into conventional 'manager mode' (weekly one-on-ones, private criticism). He now regrets this shift, believing his initial, more unconventional approach was more effective.
While the process of acquiring businesses is exciting, managing a large portfolio of acquired companies shifts the CEO's job dramatically. The role becomes less about the 'chase' of deals and growth, and more about managing personnel issues, retaining key talent from acquired firms, and solving interpersonal conflicts—a draining reality of scale.
Promoting top individual contributors into management often backfires. Their competitive nature, which drove individual success, makes it hard to share tips, empathize with struggling team members, or handle interpersonal issues, turning a perceived win-win into a lose-lose situation.
Contrary to the common ambition of top executives, Snowflake's sales and marketing leaders found fulfillment by mastering their specific domains. They had no desire to become CEO, allowing them to shed their egos and focus purely on the craft of their functions, a rare and refreshing mindset in Silicon Valley.
In the run-up to its IPO, Snowflake slowed hiring to optimize for profitability. This caused the sales team to focus on easier upsells from existing accounts (with 177% net retention) instead of new business. As a result, they neglected new logo acquisition for two years, hurting long-term growth.
Despite success, founder Kevin Wagstaff felt like an "imposter" as the company scaled beyond $10M ARR. He recognized his strengths were in the early, scrappy "bias to action" phase, not managing a larger organization. He proactively brought in a seasoned CEO better suited for the next stage of growth.
A founder's role is constantly changing—from individual contributor to manager to culture builder. Success requires being self-aware enough to recognize you're always in a new, unfamiliar role you're not yet good at. Sticking to the old job you mastered is a primary cause of failure to scale.
Chris Degnan got rid of the Customer Success function at Snowflake because he wasn't willing to give the "B team" access to his "A accounts." He made the sales team responsible for the entire customer lifecycle, including upsells and renewals, to ensure top talent handled high-stakes competitive situations.
The transition from 'deal jockey' to operator at a multi-billion dollar company took a visible physical and emotional toll on Snowflake's CRO. He lost his passion for the operational grind, leading to burnout. This highlights the importance of self-awareness for leaders in hyper-growth environments.