Francisco Trindade

In SaaS, “modernization” looks fantastic in a value-creation deck. In practice, it is where a lot of plans quietly go to die. When I work with SaaS companies looking to scale, I see the same traps over and over again: 🔻 Trap 1: Rewrite Fever   “We will just rebuild it the right way this time.” The team underestimates how much the legacy platform really does, overestimates capacity, and discovers mid-flight that critical edge cases were never documented. Feature delivery stalls, customers feel the pain, and nobody is sure when the “new thing” will ever be ready. 🔻 Trap 2: Metrics Theater   “We track DORA metrics and have SLOs on a slide.” But the way work is prioritized has not changed. Product, sales, and customer pressure keep pushing “just one more feature” ahead of foundational work. The dashboards exist, but they do not drive decisions, so teams burn out while the architecture slowly degrades. 🔻 Trap 3: SLT Ping-Pong   Every board or SLT (Senior Leadership Team) conversation results in a new “must-have” initiative. Teams zig-zag between pricing experiments, new modules, and half-finished refactors. There is no protected lane for modernization, and no clear “no-go” list. The result: everyone is busy, but tech risk barely moves. What works instead is boring and disciplined: – A 60–90 day diagnostic tied directly to your growth thesis and business goals   – An explicit, board / SLT–approved modernization lane that coexists with feature delivery   – Clear rules for what the team will STOP doing so the plan is actually achievable  There is no one-size-fits-all. Just because another CEO or CTO did it a certain way does not mean it will work for your company’s reality. If you are a CEO or SLT member with a value-creation plan that depends on “platform modernization,” which of these traps feels closest to home right now? #SaaS #PrivateEquity #CTO #SoftwareEngineering #TechnologyLeadership

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These GTM / RevOps / Quality of Life tools are so good I would (and DO, in a lot of cases) pay for out of pocket: - Wispr Flow: Started dictating a couple months ago, and it's been a huge speed boost. 10x better than native Mac dictation - Claude: Claude desktop sometimes, Claude Code other times. Cannot even list all of the use cases because it keep getting more and more helpful. Currently on the $20/mo plan and strongly considering jumping to the $100/mo with how much I use it. - Clay: Yes, everyone and their mother knows about Clay. Still amazing for data enrichment and building some workflows. Plz stop threatening to charge for HTTP/API use thank you :) - Apollo: Oops... Sorry, but the value ratio is still pretty great. - Obsidian: Using this in tandem with Claude quite a bit. Really helpful to give Claude a knowledge repository without messing up .MD files all the time - FullEnrich: My favorite phone data provider. Are there some quality of life improvements I would LOVE to see? For sure. But currently waiting patiently on the roadmap - n8n: About done migrating everything over from Make. Used them both for a while, but after things become more complicated in a Make workflow, it's just not worth it (even though I truly appreciated the extra pre-built nodes that are missing in n8n sometimes) - LinkedIn: Can't live with 'em, can't live without 'em - am I right?

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One of the biggest mindset shifts for me between Iteratively and Clarify has nothing to do with product or category. It is how I think about risk. At Iteratively, I spent most of my time trying to minimize downside. My internal dialogue was basically “how do I keep this company from dying.” I focused heavily on survival. Cost structure. COGS. Keeping burn low. Keeping the lights on. That kept us alive, but it also limited the way I thought. When survival is the only objective, you rarely take the swings that create outsized outcomes. With Clarify, I deliberately flipped that. I assume the company is already dead and then ask a different question. If this is going to work, how do we make it a multi-billion dollar company? That changes almost every decision. You focus more on building a product people love, at a caliber that can actually win the category. You think more about capturing the market, not just hanging on. You explore strategic M&A even as a Series A company if it accelerates the vision. You still watch costs, but you don’t let COGS optimization dominate the roadmap at the wrong stage. It means recognizing that “avoiding death” and “creating something massive” are different games, and they pull you toward different strategies. The question I keep asking myself now is simple: if this does work, what decisions would we wish we had made at this stage? Then we try to make those decisions today instead of waiting until it feels comfortable.

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I caught up with a friend who works at a mid-size Swedish tech company. Over the last 4 months, their shipping velocity has almost doubled – not because they hired more engineers, adopted some new agile framework, or worked late nights. It came down to a single change in how they build products: they started using Lovable to prototype features instead of writing traditional spec docs. Before Lovable, it usually went like this: PMs drafted long PRDs, trying to anticipate every detail. Multiple stakeholders reviewed these documents, leaving comments and raising concerns. The document grew with each iteration. Alignment meetings were frequent but often resulting in ambiguity. Engineers often began implementation while details were still debated. Inevitably, confusion emerged about trade-offs, timelines got pushed, and features shipped incomplete or scaled back. Now, PMs build interactive prototypes directly in Lovable. These aren’t wireframes or rough mockups – they’re fully clickable, end-to-end experiences that feel like the real product. Engineers don’t have to guess what the flow should be. Designers don’t have to explain interactions. Everyone sees the same thing, from day one. The end result is fewer meetings, fewer misunderstandings, fewer rewrites. What used to take weeks of coordination now happens in a single day. This is what has provided the most value for enterprises using Lovable so far. Over time, the increase of clarity and velocity saves the companies millions of $ in wasted effort.

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Most teams don’t have a delivery problem. They have a portfolio visibility problem. Your execs ask: “Where are we on the strategic initiatives?” “Why are 12 projects red?” “What did we actually commit to this quarter?” “Why didn’t we see this risk coming?” And suddenly everyone is scrambling through: ❌ 47 Jira boards ❌ 12 spreadsheets ❌ 3 disconnected roadmaps ❌ Slides built at midnight Jira works beautifully at the team level. But when you try to use it for portfolio project management without the right structure? It becomes noise. Initiatives don’t roll up correctly. Roadmaps aren’t trusted. Dependencies are invisible. Capacity is guesswork. Leadership loses confidence in the data. And here’s the hard truth: Most Jira admins and PMs were never actually taught how to design Jira for portfolio-level thinking. They were taught tickets. Not strategy alignment. Not funding models. Not cross-program visibility. Not executive reporting architecture. That’s exactly why I’m hosting a 1-Day Portfolio Project Management Workshop right before Team ’26. This is not: 🚫 “Here’s how to create an Epic” 🚫 “Here’s what a board does” This is: ✔ How to architect hierarchy for strategic initiatives ✔ How to structure Advanced Roadmaps for true portfolio visibility ✔ How to manage cross-team dependencies without chaos ✔ How to track planned vs. unplanned work at scale ✔ How to design executive-ready dashboards people actually trust ✔ How to govern portfolio data so it doesn’t decay in 3 months If you’re: • A Jira Admin being pulled into portfolio conversations • A PM expected to report at the initiative level • A Portfolio Lead struggling with visibility • A Leader tired of “slide engineering” every quarter This workshop will change how you think about Jira. Before Team ’26. One full day. Deep dive. Practical architecture. No fluff. If you want Jira to move from “task tracker” to “strategic system of record”, sign up for our conference -> https://lnkd.in/gK8FGx96 Let’s build systems executives can actually trust.

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Velocity as a term is an interesting choice. Velocity = Displacement/Time. If you start at point A, run in a circle at speed of 6 miles/hour and end up back at point A, your velocity is Zero. Your speed is 6 miles/hour. My guess is what most teams measure is speed and not velocity. Throughput is also a measurement of speed, unless combined with some sort of effectiveness measure or feedback. Velocity should be how quickly we are progressing towards a customer outcome. Your speed(Throughput) is one factor, feedback via customer observation is the other. It is a vector quantity, it does not exist without direction. #Agile #Physics

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Any best guesses on how long until Claude Code can: 1. Fire up the browser (without needing the MCP configuration) to evaluate changes 2. Fully leverage the Chrome Dev Tools 3. Use the Ruby debugger I’m finding Claude Code is creating fixes that would have been too tedious or painful. The gap right now is testing and debugging.

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Developers don’t read your docs the way you think they do. They’re not sitting down with a coffee and reading cover to cover. They’re: → Googling your product + error → Scanning examples → Copy-pasting whatever gets them unblocked fastest And yet so many teams write docs like textbooks. Linear. Dense. Outdated. Here’s the fix: Structure around how developers search. Lead with examples. Surface the top 10 “how do I...” questions and answer them clearly. Your docs should work like a great search result, not a PDF.

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