The following points stem from frustration over the untapped potential at Twilio and what "could be" a great company:
* Supporting clients at Segment is extremely challenging and demotivating. The issue isn't the nature of the work but the clients' complete lack of interest in the product and its optimization, combined with lackluster CS middle management and leadership. Those purchasing Segment aren't the ones using it, and those that do use it lack the understanding to use it effectively. Although Segment is defined as a self-service product, it is far from that. It is simply a data routing tool that struggles to accept its own limitations.
* The internal post-sales systems are severely flawed and underdeveloped, with information scattered across various poorly managed apps and systems. Communication between Account Executives, Renewal Account Executives, and Solutions Architects is highly fragmented. Post-sales AE to CSM handoff is near non-existent with many deals being improperly scoped or poorly discovered. Astonishingly, many conversations occur between sales roles and managed accounts without involving the CSM at all. Sales and CS are completely misaligned. Sales teams, though partially responsible for renewing account contracts, often know very little or nothing about the accounts.
* Post-sales technical support is grossly inadequate. If an account doesn't pay for Professional Services, obtaining Solutions Architect support is nearly impossible. Just one 45-minute slot per week is available across hundreds of managed accounts. Even when Professional Services hours are available for the client, they are quickly exhausted, rendering them practically useless. Once these hours are depleted, re-engaging the Architect is a cumbersome process. Customer Success Engineers and Value Engineers exist, but their roles are unclear.
* Supporting materials for Quarterly Business Reviews, "technical business reviews," and other interventions are laughable. Most clients lack concrete KPIs for Segment, yet we are expected to drive strategic conversations. Joint Success Plans are pushed but seldom utilized by clients. Internal Account Plans are outdated, long documents that are impossible to maintain due to frequent account transitions and client disengagement. Customer Health Assessments (CHA) are supposedly used by leadership, but when and for what is a mystery. CS Ops archived numerous CHA fields deemed useless, yet CSMs were tasked with updating these fields for years—a complete waste of time.
* Middle management in CS is overall inexperienced, having been quickly promoted internally within Segment. They are essentially task routers who lack direction and a cohesive team strategy. We are so siloed by region that you hardly ever interface or learn from members in your same role. There's been significant turnover, with 75% of US managers leaving on the same day recently.
* Higher leadership can't seem to stay for a significant amount of time. The previous CS VP left without any parting words, bailing just before a company offsite without explanation.
I won't even speak to the product—it's a total mess.
It pains me to write this, but this is the reality. Post-sales at Segment is in serious trouble.
