Pros
Historically, Justworks was an exceptional place to work. Culture was not a buzzword, it was lived daily. Leadership trusted its people, encouraged respectful disagreement, and created an environment where opinions were genuinely heard and considered. Leaders led with empathy and collaboration was the norm. That trust and openness created loyalty, long tenure, and teams that were deeply invested in both the company and their leaders. If you look, there are some very long tenured sales people here, some with almost a decade in seat. This is quickly diminishing, which I will get into in the cons.
Cons
Following a new CRO, the culture shifted significantly. What was once a trust-based, people-first environment has become increasingly fear-driven. Metrics are now often used as tools for pressure rather than coaching, and frequent, reactive changes have created instability rather than clarity.
Added to this shift, there has been a constant cycle of changes, from processes, metrics, and expectations. Many of which appear driven more by a desire for leadership ownership than by clear business need or to fix a problem. These changes are often rolled out quickly, without sufficient input from front-line teams, creating confusion week over week around what "good" actually looks like. In several cases, initiatives/changes have failed within six months or less, and quietly reverted to their prior state. There is little to no accountability or reflection on why those changes did not succeed. The result is a sales organization that struggles to build confidence, consistency, or trust in leadership direction as the ground beneath them is constantly moving.
A major challenge is the erosion of trust between the leadership team and the broader sales floor. Front-line managers and AEs feel unheard, disengaged, and hesitant to speak up. This has led to widespread quiet quitting and accelerating people leaving, including the departure of multiple long-tenured managers and AEs. High performers are leaving, and others are actively avoiding promotion due to increased exposure to this leadership layer.
There is also a noticeable disconnect between senior sales leadership and the realities of the product, industry, and day-to-day sales motion. Despite limited familiarity with the health insurance and PEO space, sweeping changes continue to be implemented, often reinventing processes that previously worked well. This disconnect has resulted in disengagement during our weekly "commit" meeting that is just a soap box for our Senior Sales Leaders. A meeting where they get up and bark at you with elementary sales training and call people out for not running with X change that was announced 2 days ago.
Perhaps most concerning is the lack of visible acknowledgment or intervention from senior leadership. There is top down awareness of these sales leadership issues across HR and executive leadership, supported by exit feedback and culture surveys, yet no meaningful action has been taken or even addressed. The impact on morale, retention, and career progression is apparent on the sales floor, like a dark cloud over the office. Without a course correction that prioritizes accountability on our leaders, these issues risk continuing to compound and negatively impact both employee experience and long-term business performance.