Just over a year ago, the new CRO introduced himself with the mantra "One team. One dream." In that time, he has failed to live up even to those trite expectations. He quickly flooded Prove with his Twilio pals, fractured the sales team in the worst re-org I have ever seen, and severed lines of communication between Sales, CS, and Solutions Engineers. Under his leadership, the managers he has hired have forced half-baked and poorly implemented processes onto a team that formerly enjoyed considerable success and tight camaraderie.
The company seemingly expected "big things" to happen under his leadership. It's difficult to see why they would have thought that considering his inexperience and lack of acumen. An early warning sign was the compensation plan. Prove broke with a long-standing practice of rewarding sellers for big deals in favor of a complicated mess designed to limit payments. The compensation plan for Sales Directors has gotten dramatically worse under this CRO. Even worse, the company does not pay out money when it is owed. Sellers who have closed deals are continually frustrated because revenue ops, sales leadership, and finance conspire to cheat employees out of timely commission and bonus payments. The CRO, revenue ops, and finance are also unable to produce a compensation plan in a timely fashion or modify the existing one to correct known problems.
The company seems to ignore long-time employees who have a track record of success in favor of recruiting outsiders (or, rather, Twilio insiders) as managers who turn out to be all sizzle and no steak. After it becomes apparent that they're nothing more than a flash-in-the-pan, they linger like the stale smell of burnt fat that permeates a room. Apparently, the only way for a manager to get fired is for them to have a debilitating substance use disorder or to just not show up to do their job.
A big reason for these problems is many of the managers on the sales team simply have little understanding of Prove's products or services. And they absolutely do not understand the kind of collaborative culture and go-getter attitude that made this team successful early on. Some actively encourage pushing narratives about the company's solutions that are borderline unethical due to chronic problems in the product team delivering promised updates. Others make unilateral changes or insert themselves into larger discussions without understanding the issue or problems that they are trying to address. Even worse, these same managers often betray their direct reports to score points with the CRO.
Leadership and management also change processes and internal toolsets so frequently that it makes it impossible to establish a good working cadence and flow. They suffer from wishful thinking, believing that the next tool, the next piece of software is going to solve all their problems. Instead, the constant rip-and-replace of tools makes it more difficult for anybody to do their job effectively.
Another reviewer said the CRO thinks we sell widgets and not an enterprise software solution. At first, I didn't see it that way. But it really does explain some of the changes he's made. Twilio is, effectively, a digital widget that does some basic stuff. It's a commodity. Prove is not. Prove should be sold as sophisticated enterprise-level software that is solving big problems for premier financial institutions and other industry leaders. Because the CRO has a widget mindset, it explains why he accepts no dissent and, on a recent call, wanted "no debate" as to the way we should be approaching our sales. He does not view us as consultative experts but rather as factory workers on an assembly line pumping out widgets.
The CRO’s solution to these problems that he has created is, apparently, to shift blame to individual sellers, solutions engineers, and CSMs. He seems to think MORE managers and MORE useless tools are a solution to the team’s discontent and underperformance. It boggles the mind when there isn’t a single team that has met its goals and many managers do not understand the markets their teams are selling into.
Recently, the HR team rolled out a training for the EMPLOYEES to learn how to get more out of 1:1s. The 1:1s aren’t the problem. The terrible management IS. A motivated and effective sales team should not need this much “management.” It simply shows how poorly this company has hired over the last year and how much it has suffered from attrition due to the loss of senior and experienced sellers.
It is no wonder why Prove has lost a significant portion of its top talent to other emerging companies in the space. Anyone who dreams this is "one team" must be fast asleep.
