The author, an investor with SaaStr Fund, observed approximately ten Chief Revenue Officers (CROs) either departing or being dismissed from startups he works with or has invested in this year. This significant turnover, potentially a record, prompted a deeper look into the underlying causes. While some executive transitions are a natural part of business evolution—such as a company outgrowing a leader or an initial poor fit—the majority of this year's departures were not. Instead, they were "flame-outs": talented executives with impressive backgrounds who, despite their experience, simply couldn't succeed in their roles. This led to an investigation into the recurring patterns behind these unexpected failures.
1. They Never Actively Sold the Product
This was identified as the most prevalent reason for CRO failure. Many Chief Revenue Officers arrive with a strong playbook, having successfully scaled teams, developed compensation plans, conducted Quarterly Business Reviews (QBRs), and implemented sales methodologies. Yet, despite these efforts, sales performance often stagnates or even declines.
The core issue lies in their detachment from the actual sales process. These CROs often fail to engage directly with prospects, run full sales cycles, or truly understand customer objections and deal blockers. The fundamental principle here is: you cannot effectively coach what you cannot do yourself.
In contrast, the most successful CROs actively participate in sales during their initial 30 days. They join calls, conduct demos, and handle follow-up communications—not to meet quotas, but to gain a deep understanding of the product-market fit, differentiate genuine objections from mere noise, and grasp the specific buyer psychology for the current product. Without this hands-on experience, CROs risk offering irrelevant advice, implementing unsuitable processes from previous roles, and hiring sales representatives who, despite past success, struggle in the new environment.
A critical indicator of potential trouble is a CRO who hasn't personally closed at least 5-10 deals within their first 90 days.
2. Insufficient Product Expertise
While related to the first point, this issue is distinct: a lack of profound product knowledge. This goes beyond memorizing a pitch deck or performing a standard demo. It means truly understanding the product "cold." Can the CRO address complex technical inquiries without relying on a Sales Engineer (SE)? Do they comprehend the implementation process well enough to manage expectations accurately? Can they credibly discuss architecture, security, and integrations with technical buyers?
Failing CROs often possess only a surface-level understanding, enough for basic conversations but not enough to build credibility, especially with sophisticated enterprise buyers. An example cited is a CRO who lost a seven-figure deal by failing to answer fundamental questions about data residency during a CISO meeting, leading to the deal's collapse.
Top-performing CROs become product experts, not to replace SEs, but because deep product knowledge fundamentally transforms their sales approach. It dictates what they emphasize, how they manage objections, and which deals they strategically pursue or abandon. Ultimately, a superficial understanding of the product prevents a deep engagement with potential deals.
3. Neglecting the Partner Channel
Partner channels operate distinctly from direct sales, possessing unique dynamics, economics, and political landscapes that require time and relationship-building to master. Many CROs, however, overlook this critical aspect, focusing solely on direct sales and delegating partner-related responsibilities to other teams.
The reality for most B2B SaaS companies exceeding $10M ARR is that partners significantly influence a substantial portion of the sales pipeline, often accounting for 30-40% (as seen with companies like HubSpot and Shopify), and sometimes even more. This can include channel partners, technology partners, consultants, and agencies.
A CRO who fails to grasp the partner ecosystem consistently makes poor strategic decisions. This includes setting direct sales quotas that conflict with partner incentives, hiring sales representatives ill-equipped to collaborate with partners, and designing compensation plans that inadvertently discourage partner-sourced deals. Such CROs often find themselves in pipeline reviews unable to understand or accelerate a large segment of their opportunities. While not requiring expert-level partnership knowledge, a CRO must understand the partner channel sufficiently to integrate it into a cohesive sales strategy, rather than working against it.
4. Lack of In-Person Team Engagement
Despite the rise of remote work and the costs associated with travel, the importance of in-person interaction remains critical for sales leadership. Many CROs who failed this year managed distributed teams primarily through virtual meetings, and the consequences were evident.
Without regular in-person visits, CROs struggle to truly identify top performers, understand diverse local market dynamics, foster team loyalty, detect early signs of cultural issues, or comprehend the specific challenges faced by different offices or teams. An anecdote highlights a CRO who visited a four-city team only once in 18 months and was genuinely surprised when a top Account Executive in Chicago resigned, unaware of their dissatisfaction. This underscores the point that sales is fundamentally a human business.
