Loading…
Topic
11 posts about Engineering Management. Every summary links to the original.
See the idea
Boards of directors turn ownership into a governance control loop: shareholders elect directors, directors set strategy and guardrails, committees verify independently, and management executes inside those limits.
The Good Stuff
Paid picks we use ourselves. Links carry a referral code — a subscription through one earns us a commission at no extra cost to you.
Newest first
Marc Hedlund, a veteran engineering leader and former VP at Stripe and Etsy, discusses his experience shutting down his startup Skyliner and the lessons learned. He explains that Skyliner failed because its value proposition was not compelling to a wide enough market, and because Amazon released a competing product, Code Star, which he advises entrepreneurs not to build solely on AWS. Hedlund contrasts the rational decision to close Skyliner with the emotional difficulty of shutting down his earlier startup Wesabe, where customer impact was deeply felt. He emphasizes that startups should focus on making users happy quickly rather than pursuing long-term hoped-for outcomes, and that founders must be honest about market signals. Hedlund addresses tech diversity through his board work with Code2040, sharing that simple actions like smiling and saying hello to Black and Latinx visitors can significantly impact recruitment.
Large engineering organizations often face siloed knowledge and culture as teams focus on their own domains. Intercom addresses this with engineering tours, where engineers temporarily transfer to another team to work on a specific project, such as building a scalable solution for database performance issues. New engineers go on tour within their first few months, and all engineers are encouraged to tour at least once a year. Tours are designed with a mentor and can be feature-oriented, shipping a new product or tool with a demo at the weekly Show and Tell, or tech-debt oriented, fixing bugs or performance issues. Beyond code, tours build relationships and spread culture across offices in Dublin, London, and San Francisco, and the concept has expanded to other departments like Customer Support and Marketing; engineers bring back learnings to their home teams.
The post draws on Aristotle’s golden mean to argue that great products require a balance between design and engineering, not compromise. Engineers naturally focus on functionality and performance, wanting to ship features and increase speed often without customer requests, while designers aim for optimal user flows and catch subtle interaction details. The OAuth implementation exemplifies this, with engineers building the technical side and designers crafting user flows, each pursuing their own self-interest through daily stand-ups and whiteboard sessions rather than compromising. This self-interest, guided by Adam Smith’s invisible hand, yields superior products than continual compromise, which leads to mediocrity. The post recommends embedding designers in product teams via a hub-and-spoke model, and leaders trusting their teams to find equilibrium rather than imposing rules.
Intercom’s primary product principle “Start with the problem” guides all its teams to focus on understanding real customer issues more deeply before designing any solutions. The company argues that many businesses fail because they quickly jump to solutions without thoroughly exploring the underlying problem, leading to solutions that often miss the mark, do not match real customer needs, and end up unused entirely. Common pitfalls include insufficient problem comprehension, failing to update problem understanding over time, and solving problems that are too niche, not urgent, or not aligned with customer needs. To counter this, Intercom dedicates about a third of a team’s effort to problem definition before any building begins, using problem statements and customer research. This whole-team approach builds shared understanding, ensures accurate solutions, and allows “porpoising” between problem and solution understanding while defining measurable success metrics upfront to validate impact.
Discovery calls with engineering organizations reveal that widespread use of AI agents has not translated into faster team delivery. Individual developers gain speed, but three structural bottlenecks stall team-level progress. Teams lack shared prompts, rules, and configurations, forcing every agent to start cold and re-explain conventions. Code review processes designed for human-paced change become the new constraint, with some teams measuring increased pull request time. Automating routine work like library upgrades creates its own operational burden, as teams struggle to maintain and distribute automation pipelines across projects. Without shared infrastructure, coordination breaks down and the gap between proficient users and the rest widens.
Intercom’s engineering enablement team transformed the company from a patchwork of legacy systems and recurring incidents into a stable infrastructure that empowers fast-moving product teams. The company learned that selecting core technologies is not enough without a clearly defined strategy for understanding, guiding their use, and investing in the teams behind them, as lacking this leads to persistent friction. They defined a dedicated core technology team, learned and standardized their tooling, and implemented approaches to hire and grow engineers who own the infrastructure. These efforts reduced operational friction and incident frequency, allowing the business to move more confidently. As a result, product teams run faster and the infrastructure is now a reliable foundation for growth.
Notion appointed Max Schoening as CTO, reflecting its ethos of merging technology with liberal arts and integrating engineering and design as one job. Schoening, who joined last year, led product and design and shipped significant launches including Custom Agents for everyday knowledge workers and the Developer Platform allowing extensions. His background includes early design at Heroku, Cloud Run at Google, and six and a half years at GitHub working on Issues, Pull Requests, Actions, and cloud development environments used by millions. He advocates open customer-first platforms, and Notion’s open, agent-neutral context aims to benefit customers from small coffee businesses to large global enterprises balancing innovation, token costs, and governance at scale. As a two-time founder, Schoening embodies the multidisciplinary approach Notion values, and the company hires people whose work cuts across traditional discipline boundaries.
Dropbox has learned that deploying AI at scale requires examining workflows end to end, addressing new bottlenecks like too many code reviews or infrastructure strain. The company uses a framework measuring speed, effectiveness, quality, and impact, with proxy metrics including pull request throughput and change failure percentage. Dropbox reports around 70% AI-generated code, comparable to top technology peers, and its pull request throughput ranks in the top 5% of a custom benchmark while change failure percentage is at the 75th percentile. The company connects AI token usage to engineering value through its internal agent service Nova, and it uses ground-up initiatives like boot camps and aligned incentives to drive adoption. Human skills like problem solving, judgment, and leadership become more critical as AI lowers the cost of producing software, and Dropbox aims to extend AI workflows beyond engineering to product, design, and customer experience teams.
When AI Agents resolve most customer conversations, support organizations need to move beyond tiered models centered on queues, handoffs, and volume-based productivity. The proposed AI-first operating model distributes four foundational responsibilities: an AI operations lead monitors and improves performance, a knowledge manager maintains structured content, a conversation designer shapes communication and handoffs, and a support automation specialist builds executable workflows. Existing enablement, QA, workforce management, and leadership roles also evolve, with player-coach leaders managing both AI performance and people. Examples from Dotdigital, Clay, Lightspeed, and Intercom illustrate dedicated roles and an Intercom structure organized around Human Support, AI Support, and Support Operations and Optimization.
The post presents an engineering-leadership perspective on how the author incepted and grew Ramp’s Core Engineering team from zero to 50+ engineers, while noting that the guidance is shaped by a company under Dunbar’s number. It defines an engineering manager’s role as unblocking reports, appreciating their contributions with technical depth, and helping them advance through the leveling deck. The central leadership practice is “pay attention”: build a coherent organizational model, maintain consistent direction, understand motivations, and avoid feedback that misses important tradeoffs. Core Engineering favored hiring individual-contributor engineers and moving some gradually into management after testing their aptitude. The post also presents one-on-ones as a way to build organizational context, and describes slow growth, intern mentorship, and prompt dispute resolution as forms of compounding management quality.
Lawrence Mandel, a Director of Production Engineering at Shopify, describes a career that moved from software development into technical leadership and the lessons behind that transition. He leads Developer Acceleration, a team that builds tools, conventions, and documentation so Shopify’s development organization can scale effectively. His path included web services, XML, open source, release engineering, project and release management, and self-taught Perl and CGI programming during a work term at IBM. Mandel says leadership required accepting that he could not know every technology or always be the most knowledgeable person in the room, while trusting others’ expertise. He also says prioritizing family and health before work improved his relationships and made his work more deliberate and efficient.
The best engineering reads, once a week.
