Udara Weerasinghege

Being the hero is one of the fastest ways to break an engineering team Early in my career I thought being a strong engineer meant saving the day Prod is down I will fix it Deadline is tight I will stay up late. Docs are missing I will just figure it out. It felt good People noticed I got credit for being reliable But over time I realized I was doing real damage When you constantly step in as the hero a few things quietly happen First systemic problems stay invisible If you patch things silently leadership never sees the broken process that caused it Second you become the bottleneck If you are the only one who knows how to fix things the system only works when you are around Third you block growth Other engineers never really learn how to handle problems because you already did it for them I saw this pattern over and over on teams I worked with and it is one of the reasons we built Aude Most performance systems reward hero behavior Late nights Emergency fixes Big visible saves They rarely reward the work that prevents fires in the first place The boring improvements The documentation The design decisions that reduce risk Real leadership is not about saving the day It is about building systems that do not need saving Sometimes that even means letting things fail so the real issue becomes visible and can actually get fixed It is uncomfortable But it is how healthy teams scale Curious who else has had to unlearn the hero mindset

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Software engineering isn’t just about shipping code—it’s about shaping teams that scale, systems that adapt, and cultures that endure. One of the biggest lessons I’ve learned in engineering leadership is that technical debt is easy to see, but organizational debt is silent — and far more expensive. We spend hours debating frameworks, performance tradeoffs, and system design. But how often do we apply that same rigor to the design of our team processes, feedback loops, or decision-making velocity? Here’s what I’ve seen work: • High-context environments beat high-control ones. Engineers thrive when they understand why, not just what. • Velocity emerges from clarity. The best teams don’t move fast because they cut corners—they move fast because they don’t waste cycles on ambiguity. • Great engineering managers are multipliers. Not the best engineer in the room, but the person who ensures every engineer is at their best. If you’re scaling a team or facing complexity creep, ask yourself: Are we debugging our systems as actively as we debug our culture? #SoftwareEngineering #Leadership #EngineeringManagement #TechCulture #TeamScaling #OrganizationalDesign ⸻ We are proud of the culture and organization we’ve built in Amazon Vancouver. Come meet us! Want to discuss about these in person? See you next Thursday, May 15th at the Amazon Payment Products event!

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I’ve been hearing several people in senior technical leadership roles (Head of Engineering at Shopify, CEO at Sourcegraph) talking about how they’re happy to have every engineer in their team spend $1000/month or more on tokens using coding agents if it produces results. What this means at first is that budget that is allocated for product development and used for hiring new engineers is now being used by engineers made of silicon. So there are fewer hires. But at some point you will speed up your delivery and can serve more customers, which means that you can spend more, you’ll hire more developers again to babysit the silicon engineers. The landscape is shifting fast. How are you adapting? #engineering #ai #llm #codingagent

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More of YC's hottest 🔥🔥 startups that need early team members. Want in? Fast growing, cracked founders, 3x Canadian salaries + equity. Yarn (YC W24) - Founding Engineer https://lnkd.in/gB94ttd6 Powder - Founding Software Engineer, Agents https://lnkd.in/gEJa_u_8 Haplotype Labs - Founding Member(s) of Technical Staff https://lnkd.in/gqfMe_sU Piramidal (YC W24) - Front End Engineer - User Interface https://lnkd.in/gyjXRyPM Reform - Software Engineer https://lnkd.in/gYCjVJGw TrueClaim - Software Engineer https://lnkd.in/gECufWxy Healia Health - Senior Software Engineer (Full Stack) https://lnkd.in/gE9xQZdH VoxOps AI - Full Stack Engineer (heavy backend focus) https://lnkd.in/gDgs6DB8 Forge (YC W24) - Software Engineer https://lnkd.in/g-BcGrBA InspectMind AI - Software Engineer https://lnkd.in/gTT__EWa 🔖 Save this post so you don't lose these links. 🚀 New startup opportunities dropping every week. Follow me to stay ahead of the curve.

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After a few weeks of interviewing across Toronto and San Francisco, I’ve been exposed to a lot of great engineers and ideas. One thing is clear: the definition of a software engineer is changing fast. A few observations: • When I interview now, I try to build something relevant to the company. A small tool, prototype, or demo that shows how I think and solve problems. It’s a much stronger signal than just talking about it. • The best engineers aren’t applying to jobs. They’re building things and letting the work speak for itself. • Some of the most impactful tech companies run with shockingly small teams. Twitter’s core engineering team was around ~30 engineers at one point. • We’re entering the era of the 1-person startup. AI tools are giving builders incredible leverage. • The best engineers aren’t obsessed with code — they’re obsessed with solving problems. Code is just the tool. • Your GitHub, demos, and side projects are becoming your real resume. • Shipping something imperfect beats waiting for something perfect. Feels like one of the most exciting times ever to be a builder. Go build something. What’s your thoughts on these?

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Execution is the new capital...and these 10 founder lessons from Waterloo Tech Week might prove it. From hiring fast (and firing faster) to guarding your calendar like equity, some of Waterloo Regions’s top tech leaders dropped the kind of startup truth bombs you can't Google. Thanks to MissionSync for sponsoring and Mike Kirkupfor hosting! And a big thanks to Mila Banerjee, Sheldon McCormick, Steve Currie and Martha van Berkel for sharing their knowledge and insights with the group. Check them out 👉 https://lnkd.in/gwSVZh97

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When I began engineering years ago, contributing to a major open source project was a badge of honour. My manager would have cancelled all my work if I got to put my name on (at the time) Spring Boot ecosystem, Maven, Gradle, or a number of other tools. An ARP cache poisoning detector that I wrote in Go picked up a few stars and my manager was so excited, he wanted me to spend a few hours a week contributing to it. ingress-nginx has been used by K8s shops for as long as I can remember. It is truly ubiquitous. Yet I have never seen (and mea culpa, I haven't either) a company contribute to it. Such a fundamental cornerstone of most clusters that is totally neglected. Even its proposed replacement didn't garner enough support. Both of which have now been closed down. As the economy gets tighter and the focus on the craft of software engineering shifts, so too does our apparently unshakeable faith in the open source philosophy. It is a give and take, it always has been. It's the only way that it survives. As my Dad taught me, when you start taking, they stop giving. Open source software has been the single largest driver of application development in the past 15 years. More than AI, more than agile, more than fancy IDEs, but the ability for any engineer to put together production grade applications without a litany of licenses and costs has been enormous. That ability is now in danger. I work at a SaaS company, and I love the offering we provide, but I LOVE that our customers have a viable alternative to build their own simpler version. It's the signal of a healthy market. It forces us to be better, to differentiate ourselves. It also means that companies can get moving quickly with a simple (mostly free) setup and move to someone like Coralogix when it's time to focus on o11y. I won't go into the monstrous damage that multinational companies have done to open source trust and faith in IP rights in their pursuit for training data, but we all know that these things are all connected. Once again, when you start taking, they stop giving. If you want to destroy one of the most successful, distributed, global movements of software engineering ever, then continue to bleed the value out of open source projects without contributing. If you want to preserve the ability for any team to build and run production grade software, and for all products, simultaneously, to improve, then this is a call to engineering leadership who read this. Petition your CEO or your CTO, petition your engineering VPs. If you're consuming major open source projects at scale, and you find a problem, dedicate some time to fixing it at source.

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Some things never change at Shopify (and I mean that in the BEST way). Back in 2021-2022, we had an unusually high bar for engineering managers. Not just leadership craft, I'm talking Staff level technical depth. And here in 2026, that bar is the same, if not higher! 📈 Every manager goes through the SAME pair programming interviews as our ICs. They're expected to: → Write code (with AI, because it's 2026) → Review PRs meaningfully (not rubber-stamp) → Jump into debugging sessions → Make architecture calls "Engineering-driven" isn't a buzzword here, it's literally how we do shit. So if you're an engineering manager who: ✅ Still gets excited about solving gnarly technical problems ✅ Uses AI tools reflexively (Cursor, Copilot, etc.) ✅ Has led teams through ambiguous, complex builds ✅ Wants to work somewhere the technical bar is HIGH ...then you should look at the role below. 👇 We're not for everyone. But if you're technical AND love developing people, you'll probably love it here. https://lnkd.in/gQs8veBq

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Love this framing from Shopify. - stop debating AI adoption, start measuring outcomes. I’ve seen too many teams focus on getting people to use a tool instead of what it’s meant to solve. At Pebl, we use AI to make work easier — so our teams can focus on solving harder, more meaningful problems.

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I told a founder to STOP hiring senior engineers. He was about to spend his entire $500K pre-seed round on a team of 8 senior developers. Six months later, he's at product-market fit with 50% of his funding still in the bank. Let me explain why this was the right call: Pre-PMF startups face a brutal reality: 9 out of 10 products fail because they run out of money before finding what customers want. The founder planned to use all senior engineers to "build it right the first time." But here's the counterintuitive truth most technical leaders know but rarely say out loud: Before PMF, CODE QUALITY IS THE WRONG METRIC. Speed of learning is all that matters. The best senior engineers understand this deeply. In early-stage startups, your primary skill should not coding; it's knowing when NOT to use my full technical toolkit. Instead of an all-senior team, we recommended: - 1 experienced senior tech lead who understood startup constraints - 2 mid-level developers comfortable with rapid iteration - Clear guardrails on what to optimize for NOW vs. LATER By their Series A, they'll absolutely need more senior engineers to fix for scale. The tech debt is PERFECTLY FINE. Because the alternative was a beautifully architected product that nobody wanted. As Jeff Bezos says: Most decisions should be made with somewhere around 70% of the information you wish you had. If you wait for 90%, you're being slow. Senior engineers are invaluable; at the right stage. The best ones know exactly when their full powers should be deployed and when they should be deliberately constrained. #AAcareerMGT #recruiting #tech

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The data is clear - The University of Waterloo in Canada remains unmatched for post grad career outcomes. With over 90% of Engineering grads securing jobs before graduation and median first-year compensation of $305,920. 71% of graduates landed roles at top US tech companies (data from 2022, 2021, 2020). Also - 88% of students paid for half or more of their tuition through co-op earnings alone. link- https://lnkd.in/g4Pv8ZVf

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The FAANG → startup gap is widening. When I was at Uber, we could still reliably hire great engineers out of FAANG. The velocity difference existed, but it was bridgeable. Now? For a seed or Series A team, the ramp is often too steep: ambiguity everywhere no guardrails shipping is the strategy “ownership” means end-to-end, not a slice Here’s what I think happens next as big tech layoffs continue: If you’re hiring: expect more noise. A larger pool of “available” talent won’t automatically translate to startup-ready talent. Your filter gets harder: slope > pedigree. If you’re a FAANG engineer: if you want risk, speed, and real ownership, jump earlier. After ~3+ years in a highly structured environment, the pivot gets meaningfully harder. Not because you’re not capable, but because the operating system is different. And I’m seeing a pattern: A lot of FAANG engineers want to move faster… But many early-stage startups aren’t prioritizing candidates who’ve spent 5+ years in big tech. Not a knock. Just a market reality. Curious if others are seeing the same thing: What’s your “threshold” where the FAANG → seed jump gets tough? 2 years? 4 years? More?

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Y Combinator (YC) recently said it would stop investing in Canadian startups, then reversed its decision days later after backlash. One of the reasons was that they noticed that Canadian startups that perform well end up reincorporated in the US, where the market is better, and more capital can be raised. Here’s my take: Canadian startups seek US incorporation and funding because US investors are less risk-averse than Canadian investors, making it easier to access capital and get twice the average valuation of those that didn’t. My experience as a co-founder, what I’ve seen in the news, and what I read here reinforce it. I know a founder who flew to California who's from here to try to raise funds. Not to mention, YC isn't the only accelerator you can apply to as a Canadian Startup. There are Techstars, Founder Institute, DMZ, and QueerTech, to name a few. For transparency, Bursity were in YC Startup School, and the Founder Institute too. Those of us who understand the startup ecosystem and landscape shouldn’t be surprised by YC's decision. I know I wasn’t. This is not to say “don’t start a startup in Canada” because you absolutely should; you should know that there are more programs out there to help you, YC isn’t the only player on the field. Of course, message me if you have a startup idea. I love to hear it, share my experience, and help you in any way that I can. Have a wonderful Monday.

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Two things about Shopify’s hiring process really stuck with me. 1️⃣ Even VPs have to code. Every engineering director and VP candidate does a coding interview. Not strategy. Not leadership philosophy. A coding interview. Apparently, many VP candidates are shocked. Shopify CTO Farhan Thawar explains it simply: “We believe they are still deeply in love with technology.” The point isn’t that leaders should code every day. It’s that the best engineering cultures are led by people who are still running toward the craft. When leaders step back into coding interviews, something interesting happens: The muscle memory comes back. And whether it does tells you a lot. 2️⃣ AI tools are allowed in interviews. Candidates can use anything. Cursor. Copilot. Claude. Whatever they’d use on the job. But Farhan isn’t just watching for speed. He’s watching how candidates think when AI fails. He described a candidate who ran into a single-character bug in AI-generated code. Trivial to fix manually. Instead of fixing it, the candidate kept re-prompting the model — hoping it would catch the mistake. Farhan stopped them and asked: “Are you really an engineer?” What Shopify is looking for: Engineers who are 90–95% AI-assisted. Not 100% AI-dependent. That last 5–10% matters. The judgment to: • step in • fix the line • understand what broke Speed is table stakes now. The real signal is whether someone can still think clearly in the moments where AI isn’t enough. 🔗

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YC Stopped Investing in Canadian Startups Because of Compliance? Y Combinator has officially removed Canada from the countries where it will invest. This isn’t about talent. It’s about compliance friction. Three compliance deal-breakers behind YC’s decision: 1) Investment Canada Act (ICA) delays New ICA rules require pre-closing filings for AI, quantum, and cybersecurity. A national-security flag can stall funding 45–135 days - fatal for YC’s batch model. 2) Section 116 exit friction 📉 On exit, US buyers must withhold 25% of the gross sale price until a CRA clearance arrives - often 12+ months later. Delaware avoids tax-escrow limbo entirely. 3) SAFE uncertainty ⚖️ YC runs on standardized SAFEs, but Canadian variants and provincial deadlock rules add legal unpredictability. Delaware offers one playbook that scales to thousands of companies. The founder cost YC still backs Canadian founders - just not Canadian entities. Lose CCPC status → up to $2.1M/year less in SR&ED on a $6M R&D spend Lose the $1.25M (2025) Lifetime Capital Gains Exemption The bigger question: Is Canada becoming structurally un-investable for high-velocity global capital or is this the mandatory "price of admission" to the global stage?

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