Pros
Flexible PTO. Smart and kind people willing to help.
Cons
The latest round of layoffs highlights what appears to be a broader leadership and organizational execution problem. It starts at the top. The CEO has openly taken pride in being heavily involved in writing code for Novus, Pendo’s new product initiative. While technical involvement from a founder or CEO can be valuable, there is a point where focus becomes misplaced. Building software and leading a company are two very different jobs. If the CEO is spending significant time acting as an engineer, that inevitably raises the question: who is focused on leading the business? It doesn’t appear to be Todd. There is a reason successful organizations divide responsibilities among executives. A restaurant chef does not spend their shift bartending, hosting, and waiting tables. Every leader should play to their strengths and focus on where they create the greatest value. When the CEO is heads-down writing code, critical responsibilities such as organizational strategy, alignment, culture, execution, and accountability risk receiving less attention than they deserve. The concerns extend beyond the CEO. Following the April layoffs, framed internally as a measure to improve cash flow, the company no longer has a Chief Revenue Officer, Chief Operating Officer, or Chief People Officer. Many of those responsibilities have effectively been consolidated under the CFO, despite the fact that finance expertise is not a substitute for operational, revenue, or people leadership. This creates an obvious leadership vacuum. If the CEO is focused on product development and there is no CRO or COO, who is responsible for defining and executing company strategy? Who is ensuring organizational alignment? Who is driving operational excellence across functions? In practice, many of these responsibilities appear to have fallen to Customer Success leadership, particularly during one of the most significant go-to-market transformations the company has undertaken. That transformation, the decision to merge pre-sales and post-sales responsibilities into a single role structure, has been, by far, the most significant failure in both planning and execution. The concept itself is difficult to scale. More importantly, it was introduced without meaningful involvement from many of the leaders most affected by the change. Pre-sales leadership was not meaningfully included in the decision-making process or really included at all. Instead, the change was announced and employees were expected to adapt. Not just adapt, but to do the role of 4 different individuals within a month. The reality is that this initiative effectively combines four distinct functions into a single role. These disciplines require different skills, different mindsets, and years of experience to master. Expecting one individual to perform all of them at a high level is unrealistic. Returning to the restaurant analogy, it is equivalent to asking the chef to simultaneously serve as the host, bartender, server, and cook. While someone may be capable of performing pieces of each job, excellence in all of them simultaneously is unlikely. The challenge is compounded by the lack of a clear operational plan. Employees are expected to learn entirely new responsibilities while continuing to perform their existing work. Weekly enablement sessions have become substitutes for a comprehensive transition strategy. Rather than providing a proven framework for success, employees are often told to “figure it out as we go.” Even worse, the VP overseeing this new role loves to say “we are building the plane as we fly it”. If that is the level of standard the organization sets for its employees, what does that say about the standard customers can expect? Leadership has characterized this period as a “re-founding moment.” However, from the perspective of many employees, it feels less like a deliberate transformation and more like a reaction to earlier strategic and execution failures. A lack of planning, strategic thinking and execution disguised as a re-founding moment The consequences have been significant. Dozens of highly talented and tenured employees have left the organization. The cost is not simply turnover. Every departure represents lost expertise, disrupted customer relationships, and diminished institutional knowledge. In a company where documentation has historically been inconsistent, much of that knowledge existed only in the heads of experienced employees. The customer impact should not be underestimated. Relationships that took years to build have been disrupted, creating uncertainty among customers about the company’s direction and long-term stability. This will inevitably show up in revenue loss — which might be a blessing because that’s all the C-Suite seems to care about above all else so that wake up call might be what they need to realize this change is not scalable. What has made these changes particularly difficult is the messaging from leadership. During a town hall, when questioned about the transformation, the CEO responded that he did not have time to continue explaining the why behind this change and that people either needed to get onboard or needed to pursue other career options. At other points, the VP of Customer Engineering has openly acknowledged that she expects employees to leave because of these changes and has stated that the company will not reconsider its direction. The justification that “other companies are doing this too” is also unconvincing. Many organizations that experimented with similar models have since reversed course. More importantly, Pendo’s business is fundamentally different from many of the companies being used as comparisons. Pendo sells multiple products to multiple stakeholders within the same customer, often requiring entirely different value propositions, buying motions, and business cases. The complexity of the environment makes direct comparisons difficult and, in many cases, inappropriate. Instead of forcing specialists into generalized roles, the company should focus on strengthening the fundamentals. Improve enterprise sales execution. Hold sales teams accountable for pipeline generation and deal progression. Establish realistic quotas. Ensure compensation plans align with the earning potential highlighted during recruitment. The $50K+ commission is simply not achievable so expect that if you are looking at a job offer, only trust that you are getting your base pay. Most importantly, allow people to operate within their areas of expertise. A dedicated pre-sales organization should focus on solution engineering, technical validation, and implementation. A dedicated post-sales organization should focus on customer success, adoption, renewals, expansion, and long-term relationship management. This recommendation is not new. It has been raised repeatedly by employees across multiple levels of the organization and has consistently been dismissed by higher leadership. We are having people who have no idea about the pre-sales motion making decisions about the pre-sales motion. The perception among many employees is that leadership is more focused on proving its strategy right than determining whether it is actually working.
