Over time, we’ve watched benefits stripped away, morale decline, and a culture we once believed in deteriorate beyond recognition. It increasingly feels like leadership is intentionally making things so unbearable that people leave on their own — avoiding severance payouts in the process.
Since CEO John Strosahl took the helm, the cultural shift has been stark and troubling. But he alone isn’t to blame. Many in the C-suite, rather than standing up for what’s right, continue to double down on out-of-touch decisions and tone-deaf commentary that reveal their inability to lead — and their deep disconnect from the people they’re supposed to support.
This isn’t meant to be a vague rant. Below are specific examples of where leadership has failed:
Insurance Cuts: What was once reliable health coverage is now barely recognizable. Even routine bloodwork during annual checkups is no longer fully covered. Deductibles have climbed, and family plans have become prohibitively expensive — hitting lower-income employees the hardest.
BYOD Program Removed: Leadership canceled the BYOD stipend of $70/month, then delayed the removal after backlash — not to reverse it, but to phase it out more quietly by year-end. Employees now must file monthly expense reports, a clear attempt to make reimbursement inconvenient enough that many will simply stop doing it. For those living paycheck to paycheck — especially at a company that pays well below market — that $70 matters. But it’s easy to ignore that reality from behind the cushion of a multimillion-dollar compensation package.
Sales Quotas & Compensation Chaos: Sales reps regularly start quarters without knowing their quotas. When those numbers do arrive, they’re often unattainable and come with no additional resources or support. Access to Sales Engineers is restricted unless arbitrary revenue thresholds are met. Even then, reps must submit a request form for SE support, delaying deals and damaging customer trust.
Incentives have been dangled, promised, and then rescinded. Leadership has openly admitted to “miscalculating” commission structures — resulting in people being underpaid after exceeding expectations. Please note that this decision came AFTER deals had already closed and people were expecting to receive said compensation. Meanwhile, the executives responsible continue collecting bonuses without interruption.
Layoffs & Performance Plans: The first round of layoffs shocked many, handled with more compassion by mid-level managers than by the C-suite. Executives kept repeating they “don’t want to get good at this,” but they’re not even bad at it — they’re careless. Rather than coaching or holding people to the expectations of the job early on, leadership lets people drift until they can be put on a Performance Improvement Plan (PIP) or laid off. It’s easier, and cheaper, but also far less humane.
Quiet Layoffs Are Still Layoffs: When voluntary attrition didn’t meet internal targets, sales executive leadership allegedly instructed managers to push employees out via PIPs — including high performers and Pinnacle Award winners. These aren’t isolated incidents. They’re calculated moves. Let’s call them what they are: quiet layoffs.
Constant Strategic Whiplash: Direction changes every few months. One quarter, we’re told to push a product. The next, we’re told to stop. Later, we’re told it’s fine — but only if a customer buys a certain volume. Onboarding is critical — until it’s not. ARR models are promoted, then reversed when they hurt bottom-line optics. Leadership seems to build strategies without considering consequences, and the sales team pays the price.
Transparency is a Facade: We once brought in the author of Radical Candor to promote transparency — a principle the C-suite clearly didn’t absorb. Direct questions go unanswered. Leadership talks in circles, dodges accountability, and allows sensitive information to “leak” rather than own difficult conversations. Return-to-office mandates, business unit eliminations, additional layoffs — all were first heard through whispers and rumor, not formal communication. Worse yet, when asked what criteria were used in layoff decisions, leadership refused to answer. If employees don’t know what’s expected, how can they avoid being next? You’ve made the decisions, at least give yourself the respect to look people in the eye and own up to what you’ve decided.
Fraternity Culture at the Top: Meritocracy has taken a backseat to favoritism. Strong managers have been passed over for promotions because they challenged senior leadership, while those who toe the line are rewarded. Promotions being handed to individuals before others even have an opportunity to apply for a role - because the role was never even posted. It’s a corporate fraternity — and membership matters more than performance.
Consider this: Dean Hager’s, former CEO and now part of the Board of Directors, son-in-law was granted a newly created role mere days before his colleagues and entire department were laid off during a “restructuring.” Similarly, the CEO’s stepson was brought on as an intern — a blatant conflict of interest that would be unacceptable at most organizations — but unfortunately is just one of the many poor choices made at Jamf.
One Constant Remains: Executive Leadership: Amidst all the chaos — shifting strategies, product changes, reorgs — the one thing that hasn’t changed is the executive leadership team. And while we can assume positive intent, the truth is this team lacks the skillset, empathy, and communication needed to lead. Good intentions don’t excuse poor execution. You can’t lead people if you don’t genuinely care about them.
