Pros: - Genuinely differentiated product with real technical value and strong market fit - Talented individual contributors across Sales, Solutions Engineering, and Customer Success - Smart frontline employees who care about the work and the customer

Cons: The primary risk at Tailscale is not the product or the market. It is leadership culture and it is reflected in repeated patterns, not isolated incidents. - Attrition is significant and telling. Multiple experienced ICs and revenue employees have exited in a short period. At least two departed under negotiated releases of claims; at least one left without another role secured. - Performance management is subjective and inconsistently applied. Expectations are not always established in advance but are later cited in reviews. In at least one documented case, a rating was reversed after HR involvement because the referenced expectations had been created after the fact and backdated. - Variable compensation has been restructured at least three times in five fiscal quarters. Each change moved in the same direction — away from IC benefit. Candidates should model compensation conservatively and get structure commitments in writing before accepting. - Raising concerns increases friction. Employees who flag issues face escalating scrutiny rather than engagement. HR has intervened in multiple situations involving management conduct but underlying patterns persist. - Outcomes matter less than optics. Day-to-day management emphasizes perceived positivity and style over revenue impact. Strong performance does not protect employees from negative internal narratives. - Feedback processes lack transparency. Performance discussions happen informally and outside direct coaching channels, creating an environment where employees are cautious rather than effective. An example would be the practice of sending unannounced employee feedback surveys to an employee’s peers.

Pros: Fantastic company, culture, and product. One of the best orgs I've worked for in my career.

Cons: Startup growing pains. A little chaotic at times. Some process is not all there yet.

Pros: The role offers a good compensation package and benefits.

Cons: HR promised unlimited PTO but the truth was different