Pros
Much better work/life balance compared to other sales organizations I've been a part of. Leadership is largely receptive if you're proactive with asking for help. Many great people and relationships on the Sales team.
Cons
Leadership lacks basic alignment. The three founders don't communicate with each other, giving mixed messages and different signals to the entire company as they're each pursuing individual agendas. Internal numbers are manipulated in a desperate plea to keep the board comfortable, and it shows. Our investors were sold an inflated picture of the company's value, over-invested based on it, and are understandably frustrated now that performance isn't matching expectations.
That gap between promise and reality gets pushed straight down to the sales team in the form of quotas that have always been unattainable. In practice, only the single best performer on the team has come close to hitting OTE. In Q2, only one person hit above 70% to quota, with 90% of team below 50% attainment.
Promotions into management go to people without the experience to lead, with no training provided to close the gap. The few managers who are genuinely qualified are stretched across so much ground that they can't meaningfully support a sales org that's already struggling.
Cost-cutting shows up in strange, morale-killing places: no spouses or plus-ones at company events, minimal employee perks, and subpar health insurance. Meanwhile, after three consecutive quarters of YoY decline, the response hasn't been to bring in experienced sales leadership , but a rotating cast of outside consultants. The cheapest option gets chosen over the effective one, every time.
The commission structure (and lack of raises) is also a major problem. Reps don't see commission until roughly a year after closing a deal, because the company's infrastructure isn't built to support the size of deals being sold. On top of that, the sales team has been forced to sell products that weren't market-ready (gas detection and cooling controls), and both times the products failed publicly, leaving the sales team holding the reputational damage.
Guidance from leadership on sales strategy is consistently out of touch with what actually drives deals to close.
I could go on.