My experiences at Cloudbeds started out positively within the sales organization. My direct managers were clear-headed, organized and helped me grow within my role. This was a couple of years ago. The company had built up a lot of goodwill with me, especially throughout Covid in 2020 with the company-wide decision not to downsize any employees.
Throughout my time at Cloudbeds I had known of leadership issues at the top within Sales, however I had mostly been shielded from it by direct managers who bore the brunt of the small-mindedness & chaos.
Things changed in the summer of 2021. Up until this time, I had felt that the sales leadership and the Market Managers (Account Executives) were aligned in their goals and that sales leaders had our best interests at heart (as far as a company's leadership can be). Other departments seemed to be this way and the company as a whole seemed to have weathered the storm that was the initial stages of the pandemic and things looked bright.
Then the sales leadership decided to restructure the entire sales organization by creating additional sales roles. Not only did it seem illogical, it seemed redundant and overcomplicating at first. After the announcement, everyone was left confused and bewildered, especially regarding the varying commission structures. It definitely seemed like the sales leadership was intentionally designing sales roles and commission structures with the express goal of reducing payroll costs within the sales organization. This couldn’t be? An intentional pay cut? It seemed unlikely given the Market Managers had been working hard through 2021 and were having great success achieving our individual and company wide sales goals.
We asked for clarity surrounding the changes and the impacts on the account executives. Initially we were ignored and no clarification was given. Then sales meetings began to dry up and concern grew. Sales leadership finally held a Q&A with one team of Market Managers. This meeting will live in infamy. It started with the sales leadership asking us to send him our questions prior to the meeting and then dictated a hard 30 minute stop on the meeting length.
Once the meeting began, everyone in the room knew something was wrong. He proceeded to talk and run out the clock without answering any questions. 20 minutes passed before people were able to interject and ask the questions they had come to the meeting to be answered. After continued dissembling, the meeting ended and our hearts sank. Sales leadership was lying (I do no use that word lightly) and attempting to give us a pay cut through changing our role and its commission structure.
For me personally, all goodwill I had with Cloudbeds was lost. Not long after, salespeople began to leave around me, moving on to much higher paying roles at more exciting companies.
What caught me by surprise was how much of an inflection point this became for the sales organization as a whole. Not only did experienced account executives and middle managers leave, but newly promoted and hired employees began leaving as soon as they began, and then SDR’s began leaving as they saw no career growth opportunities.
I can understand a leader making a mistake like this. However, to rebuild trust a good leader would; acknowledge an error in judgment, apologize, and take some remedial action to reassure those he is responsible for leading. Sales leadership was given multiple opportunities to resolve the breakdown in trust and chose not to. This was a failure of leadership.
