Leadership:
Lack of transparency and misleading strategic vision
Unrealistic expectations regarding sales targets and growth objectives for the secondary product suites with little to no market adoption
Lack of proper support for the other product team divisions (Altitude & Forensiq in particular)
Lack of cohesion between sales leadership and product. Features were pushed as "ready to sell" with no regard from management which led to unfulfilled promises for prospects and clients.
Inexperienced and underqualified employees were favored and even promoted to the mgmt level
Product:
Lack of focus on the product roadmap and instead ad-hoc solutions for one-off use cases were prioritized.
Product was always deep in a new rabbit hole
UI was broken or had a new problem almost every day. Requests to fix were ignored and Jira tickets would sit idle for weeks - i.e. inaccurate statistical tables and reports
Complicated log-ins for employees and clients using secondary product suite
Highly disorganized feedback loop with sales reps for improvements
Misc:
High employee turnover.
No sales playbook.
Lack of defined and preferred sales methodology.
Siloed teamwork. Some teams did great working together, others not so great.