Counterintuitively, the best sales leaders often come from companies with mediocre products. Their ability to hit numbers despite a weak offering demonstrates exceptional sales skills, which are then amplified when they are given a great product to sell.
To eliminate friction, Snowflake's marketing team, led by CMO Denise Pearson, abandoned MQLs. Instead, they focused solely on delivering qualified meetings for the sales team, treating sales as their primary customer whose success was paramount.
Chris Degnan admits Snowflake's engineering team initially dismissed the need for a data science notebook, despite the sales team identifying it as a critical customer need. This product delay allowed competitor Databricks to gain a significant foothold that Snowflake could have otherwise dominated.
As an organization scales, some leaders become skilled at managing up while being poor managers to their teams. Executives must conduct regular skip-level meetings with frontline employees to get direct, unfiltered feedback and catch these bad behaviors that would otherwise be hidden.
Non-sales founders often don't know how to evaluate or support their first sales leader. The advice is to hire a sales-focused board member or advisor whose primary role is to mentor and care for that new sales leader, providing crucial guidance and a dedicated advocate.
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.
To maintain accountability and create a tight feedback loop, Chris Degnan sent a weekly email to the entire company detailing his sales calls, takeaways, and next steps. This transparency built credibility with engineering and motivated them to build features based on real customer feedback.
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.
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.
Founders can assess their Head of Sales using two core metrics: 1) Can they hire reps who consistently close over $250k in new ACV per quarter within six months? 2) How many sales calls are they personally conducting each week? These are the ultimate measuring sticks of effectiveness.
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.