Operational Turnarounds In B2B SaaS Companies.
Memos for Investors, Boards, and Private Equity.
Operational Turnarounds In B2B SaaS Companies.
This site is a private archive of operating memos written for boards, investors, and senior executives navigating complexity in B2B software companies. The essays focus on decision-making under capital and time pressure, governance breakdowns, execution risk, and the mechanics of turnaround and performance transformation. There are no services offered and no commentary for general audiences, only forwardable analysis meant to be read in boardrooms, investment committees, and leadership teams where real decisions are made.
Latest
The Companies I Won’t Advise: A Public Filter for the Opportunities I Say No To (And Why)
Reading Time: 7 minutesWhy Most Advisors Won’t Tell You This Most advisors don’t publish what they say no to. The incentive structure of advisory work pushes in
How Capital Availability Increases Execution Risk
Reading Time: 4 minutesWhy excess funding often weakens focus, delays learning, and amplifies organizational complexity in Post-PMF B2B SaaS companies Conventional wisdom suggests that capital reduces risk.
Fintech and Healthcare SaaS Are Different Games. If You’re Treating Compliance as an Afterthought, You’ve Already Lost.
Reading Time: 7 minutesTwo Industries That Break Every SaaS Playbook There’s a particular kind of confidence that experienced SaaS operators carry into their first fintech or healthcare
Integration Plans Don’t Fail — Operating Systems Do
Reading Time: 5 minutesWhy most software acquisitions underperform because of organizational design, not integration execution In private equity and strategic M&A circles, post-acquisition underperformance is usually explained
Why I Stopped Hiring ‘Senior’ Engineers and Started Hiring Disciplined Ones: The Difference Cost Us 18 Months
Reading Time: 7 minutesThe Hire That Looked Perfect on Paper A long time ago….., I made what seemed like a brilliant hire. The candidate had twelve years
The First 90 Days After a PE Acquisition Are Usually Misused
Reading Time: 4 minutesWhy the post-close window in private equity-backed B2B SaaS companies fails to create momentum—and how misaligned priorities undermine execution from day one. The first
Talent Is Not the Bottleneck (Structure Is)
Reading Time: 5 minutesWhy execution failure in Post-PMF B2B SaaS companies is rarely a people problem and almost always a system design issue. In moments of underperformance,
Replacing the CEO Rarely Fixes Execution, but why?
Reading Time: 4 minutesThe structural reasons leadership changes fail to resolve execution breakdowns in Post-PMF B2B SaaS companies. Replacing the CEO is one of the most decisive
The False Comfort of Alignment in Board-Led Companies
Reading Time: 5 minutesWhy consensus at the top often hides structural disagreement in Post-PMF B2B SaaS companies. Alignment is widely considered one of the highest virtues in
From -12% to +21% EBITDA in 36 Months: The Single Decision That Made It Possible Wasn’t About Technology
Reading Time: 7 minutesThe Burning Question Every Board Member Asked. When I joined as C-level executive, the board had one question: “Can you fix the unit economics