Actionable strategies and insights for technology leaders, from CTOs to developers to aspiring executives.
At this stage, architecture is about speed and flexibility, not long-term perfection - sometimes you take on technical debt, on purpose, to move faster.
Joseph KaplanDecember 26
Success: engineering scales without CTO bottlenecks, and technical strategy is clear to investors.
Joseph KaplanDecember 26
The CTO role now means balancing technical leadership with business architecture - turning company goals into real technical plans that meet both product needs and investor deadlines.
Joseph KaplanDecember 26
Bottlenecks add up fast - a CTO who blocks 3 decisions a day can stall 15+ work streams a week on a 10-person team.
Joseph KaplanDecember 26
The build vs buy framework at seed is about freeing up engineer time vs. risk factors like vendor lock-in, integration pain, and recurring costs
Joseph KaplanDecember 26
Series A companies using structured evaluation frameworks see 30-40% fewer failed implementations and get to product-market fit faster
Joseph KaplanDecember 26
Biggest Series B mistakes? Underestimating integration pain by 40-60% and treating the decision as just a money thing, not a strategic lever
Joseph KaplanDecember 26
Delegation models are still pretty informal - authority passes mostly through trust, not docs. This gets messy as you approach 20–30 people. Scaling problems often follow.
Joseph KaplanDecember 26
This starts to change only when the first senior technical hire joins (usually around 5–8 people)
Joseph KaplanDecember 26
CTOs lose sole control over infrastructure once tech spend tops $500K/year or security incidents pull in legal or insurance.
Joseph KaplanDecember 26
Empowering employees with decision-making authority is a straight line to agility and faster response at this size
Joseph KaplanDecember 26
Backlog growth rate shows if team capacity matches product ambition - if not, you’ll hit scaling walls and face costly reorgs
Joseph KaplanDecember 26
Technical debt and code coverage (aim for 90%+) are early warnings for future velocity loss - track these before they slow down sprints
Joseph KaplanDecember 26
Metrics are pointless without clear owners, regular reviews, and a real tie to quarterly goals or resource decisions
Joseph KaplanDecember 26Once the seed round hits, the whole model changes - team growth and process start to matter.
Joseph KaplanDecember 26
Success is measured by weeks to launch, number of user feedback cycles, and whether the product proves demand - not by headcount, system architecture, or engineering best practices.
Joseph KaplanDecember 26Failure modes: hiding technical debt, reactive hiring, skipping security basics, and failing to communicate system state to non-technical folks.
Joseph KaplanDecember 26
Usual pitfalls: running too many one-off pilots with no integration plan, unclear lines between CTO and VP Engineering, and trying to keep the “move fast” startup vibe without adding any process.
Joseph KaplanDecember 26
Top failure patterns: trying to stay hands-on, having no M&A playbook, or lacking financial systems for going public.
Joseph KaplanDecember 26
Hiring the first 1–2 engineers is the main non-coding task at this stage.
Joseph KaplanDecember 26Most common fail? Staying heads-down in code too long, then becoming a bottleneck as the team doubles.
Joseph KaplanDecember 26
CTOs here don’t manage teams. They report to the CEO or board, balancing delivery speed with technical debt risk.
Joseph KaplanDecember 26
Remote execution needs documented decision-making frameworks, async communication rules, and clear ownership lines between CTO and senior engineers.
Joseph KaplanDecember 26
CTOs at this stage juggle innovation with stability and have to keep their technical credibility with leadership and investors.
Joseph KaplanDecember 26
Watch out for: hiring too fast before product-market fit, making things too complex too early, or becoming a bottleneck by refusing to hand off decisions.
Joseph KaplanDecember 26
Successful Series A CTOs give investors technical clarity by framing architecture as business risk, not just tech jargon.
Joseph KaplanDecember 26
Winning CTOs? They document processes, keep a close eye on performance, build talent development frameworks, and make sure infrastructure supports growth.
Joseph KaplanDecember 26Fixing bottlenecks works best when you hit the biggest pain first instead of trying to change everything at once
Joseph KaplanDecember 26Authority boundaries help avoid deployment delays while keeping a handle on security, spending, and bigger-picture impacts.
Joseph KaplanDecember 26Metrics must be collected automatically, tracked over time, and have clear owners for improvement
Joseph KaplanDecember 26
Operating model maturity decides if teams can keep delivery speed as headcount grows - structure breaks down before tools do.
Joseph KaplanDecember 26Undefined scope causes on-call burnout, slow incident response, and engineers hesitating to touch production due to unclear authority.
Joseph KaplanDecember 26
As the company grows, the job changes fast - from hands-on infrastructure at pre-seed to building self-service platforms and mentoring others by Series B.
Joseph KaplanDecember 26The job bridges development and operations by setting up automated workflows to cut manual work and speed up deployments - while keeping everything stable.
Joseph KaplanDecember 26Demand for DevOps engineers has grown 18% per year since 2020. Entry-level salaries start at $85,000; experienced roles can top $130,000.
Joseph KaplanDecember 26
Tracking cycle time, deployment frequency, and review times shows where managers block progress - often before teams even notice morale or delivery slipping.
Joseph KaplanDecember 26Hitting 10–20 engineers means it's time to split teams, add tech leads, or promote managers - it's not optional anymore.
Joseph KaplanDecember 26Most failures happen when managers either keep too much IC decision power or delegate without clear boundaries.
Joseph KaplanDecember 26Effective authority distribution needs clear approval matrices, rotating code review assignments, and obvious escalation paths for cross-team technical dependencies.
Joseph KaplanDecember 26Common failure modes: over-escalating low-severity issues (alert fatigue), under-documenting escalation paths (coordination delays), and skipping postmortems (missed learning).
Joseph KaplanDecember 26Success = less founder time in standups and 1:1s, steady sprints, and no surprise delivery misses in the first 90 days.
Joseph KaplanDecember 26Waiting too long to hire a manager? You'll end up with deeper problems and rushed decisions that are tough to unwind.
Joseph KaplanDecember 26The best metric programs start with one experiment (scorecard), measure results for 4-6 weeks, and then iterate
Joseph KaplanDecember 26
Biggest risk: scaling management too early, before the team’s big enough for specialized roles
Joseph KaplanDecember 26
The model should clearly define meeting cadence, incident response ownership, hiring approval, and technical RFC processes before the team hits 15 engineers.
Joseph KaplanDecember 26
Good boundaries need team independence, skills fit, single-team ownership, and clear communication contracts
Joseph KaplanDecember 26Success is measured by team output and retention, not your own commits - impact comes from the team, not your code.
Joseph KaplanDecember 26
Success relies on building leverage with systems (hiring, performance, technical standards) instead of personal heroics
Joseph KaplanDecember 26Common pitfalls: trying to keep up as an IC, skipping 1-on-1s during crunch, dodging tough performance chats.
Joseph KaplanDecember 26Teams that don’t restructure engineering leadership at the 30–50 engineer mark see per-engineer output drop 25–50% even as they hire more
Joseph KaplanDecember 26Unlike a VP of Engineering, Heads of Engineering focus on technical leadership and mentoring; VPs handle broad org strategy and exec decisions.
Joseph KaplanDecember 26
Most leaders track 10-15 core metrics to avoid drowning in data
Joseph KaplanDecember 26Success means clear role separation from VP Product and delegation frameworks that push decisions down while keeping architectural guardrails tight.
Joseph KaplanDecember 26
Must communicate well with both technical and non-technical folks, acting as the main bridge between engineering and company direction.
Joseph KaplanDecember 26
Success means managing technical debt, keeping delivery fast with few resources, and building systems that let the team grow 3-5x in 18-24 months (team growth)
Joseph KaplanDecember 26Winning here means making pragmatic platform calls, knowing async workflows, and setting standards without overloading process
Joseph KaplanDecember 26
Solutions mean shifting from “how to build” to “what we need” with policy-driven frameworks, shared responsibility, and AI that translates intent.
Joseph KaplanDecember 26Platform authority stops where app consequences start. Teams with operational accountability must keep decision rights on performance, upgrades, and runtime.
Joseph KaplanDecember 26Cost visibility and experiment velocity highlight whether the platform drives business value and engineering ROI.
Joseph KaplanDecember 26Start with one pilot team close to product engineering, run a 90-day validation, then scale the model using what you learned.
Joseph KaplanDecember 26Big pitfall: platform teams that measure feature velocity instead of developer outcomes see low adoption and shadow IT.
Joseph KaplanDecember 26Boundaries break down when platform teams block progress or app teams rebuild platform features due to unclear service offerings.
Joseph KaplanDecember 26Common failure modes: overbuilding for scale that never comes, forgetting about developer adoption, or becoming the only person who understands how things work.
Joseph KaplanDecember 26The job lands between dev and ops, making life easier for product engineers by hiding away infrastructure headaches.
Joseph KaplanDecember 26Series C hiring switches to specialized platform roles, not just generalist DevOps
Joseph KaplanDecember 26Execution boundaries depend on whether the principal is a broad IC or manages architects and engineers
Joseph KaplanDecember 26Bottlenecks come from process and org structure - not from any individual’s skill or work ethic.
Joseph KaplanDecember 26Success is measured by shared wins, quality of decision processes, and how often teams come back for input - not by how many launches they “own”
Joseph KaplanDecember 26Engineering decisions require professional responsibility, but principal engineers influence through credibility, not by supervising others.
Joseph KaplanDecember 26Most companies struggle here - they use individual contributor metrics for a role built to multiply team results.
Joseph KaplanDecember 26Set clear role expectations (owner/stakeholder/supporter/friend) with each team up front to allocate time properly
Joseph KaplanDecember 26
Principal engineers must teach other technical leaders to use involve-document-communicate principles, so scaling doesn't depend on just one person.
Joseph KaplanDecember 26Compensation reflects both technical and leadership scope; median is about $150,000/year.
Joseph KaplanDecember 26
Moving from Senior to Principal means shifting from solving assigned tasks to spotting and defining the org's most critical technical challenges
Joseph KaplanDecember 26They bridge technical teams and execs, turning engineering strategies into real business results.
Joseph KaplanDecember 26Good principal engineers stay hands-on, checking strategy with real technical work, not just oversight.
Joseph KaplanDecember 26
Fixes: Split strategy from tactics, build decision-making communities, and measure leadership bandwidth as a real constraint.
Joseph KaplanDecember 26As teams grow, senior engineers need to focus less on making every call and more on building decision-making muscle throughout the org.
Joseph KaplanDecember 26Authority grows through influence: helping with cross-team decisions, keeping architecture consistent, and building trust by making sound technical calls.
Joseph KaplanDecember 26Good metrics track contribution, technical influence, and team collaboration - without creating weird incentives
Joseph KaplanDecember 26What sets staff apart: calm under pressure, putting company goals first, and finding ways forward when things get murky
Joseph KaplanDecember 26Senior success = your output quality; Staff success = how the system runs without you.
Joseph KaplanDecember 26You must define formal ownership boundaries before hitting 20 engineers, or roles get messy as you scale
Joseph KaplanDecember 26Senior scope grows to cover on-call rotation, design reviews, and those tricky build-vs-buy calls that juniors and mids can’t really make.
Joseph KaplanDecember 26Unlike at bigger companies, this role is shaped by limited resources, fluid tasks, and direct exposure to whether the business sinks or swims.
Joseph KaplanDecember 26The role is about 60-70% coding, the rest is technical leadership, and there’s way less process overhead than at bigger companies.
Joseph KaplanDecember 26Equity value depends on company growth, dilution from future rounds, and liquidation preferences that affect payouts at acquisition or IPO.
Joseph KaplanDecember 26Pitfalls: drifting into management, losing technical depth, or becoming bottlenecks by centralizing too much.
Joseph KaplanDecember 26Rotating staff engineers into mentorship roles and splitting strategic from tactical work leads to 15-30% faster deployments within six months.
Joseph KaplanDecember 26Effectiveness depends on building influence currency: consistent technical judgment, relationship-building, and helping teams make better decisions.
Joseph KaplanDecember 26Good decision-making needs clear frameworks for reversible vs. one-way calls, documented reasoning, and alignment between tech choices and business goals.
Joseph KaplanDecember 26Managing boundaries well means being clear about your influence type (advisory, collaborative, or decision-making) for each project and keeping management aligned on scope
Joseph KaplanDecember 26Success means balancing deep technical work with organizational leverage: documentation, sharing knowledge, and improving processes.
Joseph KaplanDecember 26Effective models need explicit role definitions, documented decision authority, and regular checks to see if the staff engineer is actually improving delivery speed or system quality.
Joseph KaplanDecember 26The role fails if engineers just keep acting as senior ICs, or if decision rights between Staff, Managers, and tech leadership aren’t clear.
Joseph KaplanDecember 26The role doesn’t work if hired too early (before PMF) or if expected to act as a lead without eng manager support.
Joseph KaplanDecember 26Success is measured by team velocity, architectural choices that avoid rewrites, and ability to drive consensus with engineering and product leaders
Joseph KaplanDecember 26Success means shifting from just coding to influencing decisions across teams - think documentation, design reviews, and building consensus
Joseph KaplanDecember 26Good partitioning means you can reuse modules, avoid duplicate work, and let architects focus on their own piece
Joseph KaplanDecember 26Fixes depend on system stage and traffic: vertical scaling for early growth, horizontal scaling/load balancing for stateless services, database replication or sharding for overloaded data layers.
Joseph KaplanDecember 26Organizations need to spell out veto rights, approval steps, and consultation duties to avoid shadow architecture and accountability gaps.
Joseph KaplanDecember 26Without explicit modeling of decision authority, organizations get slow, escalated decisions and architecture that fails to drive real outcomes
Joseph KaplanDecember 26Effective governance draws clear lines between enterprise architects, domain architects, implementation teams, and service management.
Joseph KaplanDecember 26Architectural metrics are different from dev metrics - they zoom out to cover system-wide constraints, dependencies, and failure modes, not just code quality
Joseph KaplanDecember 26Success relies on clear roles for enterprise architects, domain architects, and engineers - aligned with company stage and org chart.
Joseph KaplanDecember 26Effective architect models define four things before scaling: architecture decision records (ADRs), design review cadence, escalation paths for technical debt, and cross-team dependency resolution protocols.
Joseph KaplanDecember 26Unlike architects at big companies, this role is about moving fast to find product-market fit, not squeezing out every drop of performance.
Joseph KaplanDecember 26Success comes from balancing tech options with business needs and leading teams through system changes.
Joseph KaplanDecember 26Typical scope: API standards, data flow, service boundaries, and technical debt priorities across the org.
Joseph KaplanDecember 26Common fail: trying to influence architecture without operational credibility or clear boundaries with architects
Joseph KaplanDecember 26Most bottlenecks show up between 8–15 engineers, when informal coordination breaks but roles aren’t formal yet.
Joseph KaplanDecember 26Unclear or fragmented ownership causes quality drops, knowledge silos, and deployment slowdowns in larger teams.
Joseph KaplanDecember 26Common missteps: making people decisions without manager support, or forcing standards without buy-in
Joseph KaplanDecember 26Clear boundaries between technical ownership (tech lead) and people management (engineering manager) are essential - set them before things get messy
Joseph KaplanDecember 26Metrics without context can backfire - velocity alone might lead to shortcuts, more tech debt, and declining code quality.
Joseph KaplanDecember 26Common pitfalls: drifting into product management, adding too much process too soon, and underestimating how much context-switching slows you down.
Joseph KaplanDecember 26Success means clearly defining what Tech Leads own (technical decisions, team velocity) vs. what stays with the CTO or VP Engineering (roadmap, architecture vision, hiring).
Joseph KaplanDecember 26The need for a tech lead usually pops up when one team splits, or when technical complexity demands dedicated architectural oversight - something senior engineers can’t quite cover while shipping features.
Joseph KaplanDecember 26Success depends on clear coordination with engineering managers - who owns technical vs people decisions must be explicit
Joseph KaplanDecember 26Usually reports to an engineering manager or CTO, acting as the technical decision-maker for a product team or feature area.
Joseph KaplanDecember 26Key: knowing when to refactor or rebuild, setting clear team ownership, mapping tech roadmaps to 12–18 month business goals
Joseph KaplanDecember 26Typically reports to CTO or CEO, manages 4-8 engineering managers or tech leads
Joseph KaplanDecember 26Solving it depends on trust architecture: define what teams fully own, what needs consultation, and what still requires exec sign-off, based on risk and reversibility.
Joseph KaplanDecember 26Building at Series A locks up 2-3 years of technical leadership bandwidth and creates hiring needs that might not fit your current funding reality.
Joseph KaplanDecember 26At Series B, decision authority shifts: VPs own the framework, and board-level signoff is needed for purchases over $100K/year or build projects that eat up 3+ quarters.
Joseph KaplanDecember 26Common trap: VPs hang onto IC-level decisions instead of letting directors and senior engineers own technical calls.
Joseph KaplanDecember 26Effective decision authority needs documented RACI matrices, weekly product syncs, and clear metrics for when to escalate technical decisions to execs or board.
Joseph KaplanDecember 26Most drama pops up when it’s not clear who owns what - especially with the CTO on architecture and with product leadership on what gets built when.
Joseph KaplanDecember 26You can’t just plug in a rigid KPI model; frameworks must match how your org actually ships software, deals with technical constraints, and impacts the business.
Joseph KaplanDecember 26Metrics gaming fades in healthy orgs where measurement helps teams, not punishes them. Some metrics should actively encourage good habits, like shipping smaller chunks of work.
Joseph KaplanDecember 26Equity: 0.5–2%. Salary: $180K–$250K, varies by stage and city.
Joseph KaplanDecember 26The role sits between hands-on engineering leadership and pure executive function, needing technical credibility and multi-team coordination skills.
Joseph KaplanDecember 26The VP sits below the CTO/CEO and focuses on making the strategy happen, not setting the long-term tech vision.
Joseph KaplanDecember 26This VP doesn't set company-wide tech strategy or roadmap - that's the CTO/executive team's job. The VP enforces execution against those strategies.
Joseph KaplanDecember 26Failure modes: adding process too soon, fuzzy boundaries with the CTO, ignoring technical architecture while scaling the team.
Joseph KaplanDecember 26Common mistakes: micromanaging technical details, neglecting director development, and muddying decision rights between engineering and product
Joseph KaplanDecember 26Success = code-level fluency, efficient cross-team rituals, and building scalable teams before hiring gets reactive
Joseph KaplanDecember 26Most Series B failures? They come from clinging to old startup engineering habits instead of building the right org models and quality gates for this stage
Joseph KaplanDecember 26Establish robust AI governance frameworks and security protocols. Learn how to implement accountability structures, ensure transparency, and embed ethical principles throughout your AI development lifecycle.
Joseph KaplanDecember 6Understand how AI is transforming engineering team structures and roles. Learn strategies for reorganizing teams, upskilling engineers, and building AI-native organizations.
Joseph KaplanDecember 6Master the build vs buy decision for software. Learn a proven framework to evaluate custom development, COTS, and SaaS solutions based on cost, time, and strategic fit.
Joseph KaplanDecember 6Discover proven strategies to reduce cloud spending by 30-70%. Learn cost optimization techniques for compute, storage, and networking across AWS and Azure.
Joseph KaplanDecember 6Compare AWS, Azure, and GCP for your startup. Evaluate pricing, features, and scalability to make the right cloud provider choice for your growth stage.
Joseph KaplanDecember 6Understand when cloud repatriation makes sense. Learn the cost-benefit analysis, technical considerations, and migration strategies for moving workloads back on-premises.
Joseph KaplanDecember 6Develop decision-making frameworks for engineers. Learn how to evaluate trade-offs, manage uncertainty, and make high-impact technical decisions.
Joseph KaplanDecember 6Measure and improve developer experience. Learn how to track DevEx metrics and create an environment where engineers thrive.
Joseph KaplanDecember 6Implement DORA metrics for engineering excellence. Learn how to measure deployment frequency, lead time, and reliability.
Joseph KaplanDecember 6Create career progression paths for engineers. Learn how to build IC and management tracks that retain top talent.
Joseph KaplanDecember 6![Engineering Hiring Strategy: From Reactive to Strategic Talent Acquisition [Unlock Top Talent in 2025!]](/_next/image?url=%2F_next%2Fstatic%2Fmedia%2Farticle_17.ec1e39fc.jpg&w=1200&q=75&dpl=dpl_FbjY5pCH5wePc5F7TaPnyrfuAokL)
Build a strategic hiring strategy. Learn how to move from reactive hiring to proactive talent acquisition that scales.
Joseph KaplanDecember 6Define engineering KPIs that matter. Learn which metrics drive business outcomes and how to track them without destroying team morale.
Joseph KaplanDecember 6Lead engineering teams with limited budgets. Learn strategies for maximizing impact, prioritizing investments, and delivering value with constraints.
Joseph KaplanDecember 6Master the essential skills and frameworks for engineering leadership. Learn how to balance technical depth with team development, make strategic decisions, and drive business impact.
Joseph KaplanDecember 6Master engineering management fundamentals. Learn best practices for team development, performance management, and building high-performing teams.
Joseph KaplanDecember 6Develop critical engineering manager skills. Learn communication, delegation, and people management techniques for effective leadership.
Joseph KaplanDecember 6Present engineering metrics that resonate with boards. Learn which KPIs demonstrate business impact and how to communicate engineering ROI.
Joseph KaplanDecember 6Set engineering OKRs that drive results. Learn how to move beyond task tracking to outcome-focused goal setting that aligns teams with business objectives.
Joseph KaplanDecember 6Create effective engineering roadmaps. Learn how to balance technical debt, feature development, and strategic initiatives in your planning.
Joseph KaplanDecember 6Build a comprehensive engineering strategy. Learn a proven framework for moving from concept to execution that aligns technical capabilities with business goals.
Joseph KaplanDecember 6Improve engineering team communication. Learn best practices for async communication, documentation, and cross-team collaboration.
Joseph KaplanDecember 6Structure engineering teams at scale. Learn how to organize teams from 10 to 100+ engineers while maintaining efficiency.
Joseph KaplanDecember 6Master FinOps practices to align cloud spending with business outcomes. Learn how to implement cost governance, chargeback models, and optimize cloud ROI.
Joseph KaplanDecember 6Integrate generative AI into your product development process. Discover how to leverage GenAI for faster iteration, improved user experience, and competitive advantage.
Joseph KaplanDecember 6Improve your technical leadership skills. Learn how to influence without authority, make better decisions, and drive technical excellence.
Joseph KaplanDecember 6Transition into engineering leadership. Learn the skills, mindset shifts, and strategies needed to become an effective engineering leader.
Joseph KaplanDecember 6Hire senior engineers in competitive markets. Learn strategies for recruiting, evaluating, and retaining top engineering talent.
Joseph KaplanDecember 6Measure engineering productivity responsibly. Learn how to track meaningful metrics without harming team culture and morale.
Joseph KaplanDecember 6Scale engineering teams effectively. Learn strategies for growing teams while maintaining culture, quality, and velocity.
Joseph KaplanDecember 6Optimize total engineering infrastructure costs beyond cloud. Learn strategies for on-premises, hybrid, and multi-cloud environments to maximize ROI.
Joseph KaplanDecember 6Master leadership frameworks for technical leaders. Learn proven models for decision-making, team development, and strategic execution.
Joseph KaplanDecember 6Build leadership skills as an engineer. Learn communication, influence, and strategic thinking for career growth.
Joseph KaplanDecember 6Build scalable MLOps infrastructure for mid-market organizations. Learn best practices for model deployment, monitoring, and governance without enterprise-level complexity.
Joseph KaplanDecember 6Master platform engineering strategy. Learn when to build internal platforms, how to staff them effectively, and how to justify ROI to stakeholders.
Joseph KaplanDecember 6Master prioritization frameworks for engineering work. Learn how to evaluate trade-offs and make data-driven decisions about what to build next.
Joseph KaplanDecember 6Demonstrate engineering ROI to leadership. Learn how to quantify your team's business impact and secure budget and resources.
Joseph KaplanDecember 6Calculate ROI for AI tools in engineering. Learn how to measure productivity gains, cost savings, and business impact from AI adoption.
Joseph KaplanDecember 6Operate remote engineering teams at scale. Learn best practices for distributed teams, communication, and collaboration.
Joseph KaplanDecember 6Lead software engineering teams effectively. Learn strategies for technical excellence, team growth, and business impact.
Joseph KaplanDecember 6Master staff engineer leadership. Learn how to influence at scale, mentor others, and drive technical excellence without direct reports.
Joseph KaplanDecember 6Choose between staff engineer and engineering manager roles. Understand the differences, trade-offs, and career implications of each path.
Joseph KaplanDecember 6Master systems thinking for engineering. Learn how to think holistically about complex systems and make better decisions.
Joseph KaplanDecember 6Implement Team Topologies for mid-market companies. Learn how to structure teams for better communication and delivery.
Joseph KaplanDecember 6Understand tech lead responsibilities. Learn how to balance coding, mentoring, and technical decision-making in a tech lead role.
Joseph KaplanDecember 6Develop mental models for tech leadership. Learn frameworks for thinking about systems, teams, and strategic decisions.
Joseph KaplanDecember 6Master tech leadership fundamentals. Learn how to lead technical teams, make strategic decisions, and drive organizational impact.
Joseph KaplanDecember 6Master technical debt management. Learn how to measure, prioritize, and communicate technical debt to secure executive buy-in for paydown initiatives.
Joseph KaplanDecember 6Create a technology roadmap that drives business value. Learn how to balance innovation, technical debt, and strategic initiatives.
Joseph KaplanDecember 6Navigate the 50-engineer scaling wall. Learn why systems break at scale and how to restructure for continued growth.
Joseph KaplanDecember 6Understand VP of Engineering vs CTO roles. Learn when you need both, how they differ, and how to structure your leadership team.
Joseph KaplanDecember 6Browse articles by category