• Define and drive product strategy for experiences that connect planning, source code management, and AI-assisted development. • Help shape spec-driven development workflows that make it easier for teams and AI agents to move from requirements to code. • Work with engineering, design, and other product teams to build product experiences that support human-in-the-loop and autonomous development workflows. • Partner with teams working on demos and prototypes, including near-term work around spec-driven planning and autonomous development modes. • Use customer insights, product usage data, and market context to identify opportunities that can deliver customer value quickly. • Help teams ship fast with quality, balancing near-term execution with longer-term product direction. • Explore how planning can better account for reviewing code, reviewing test cases, and validating that work produced by agents matches the intended outcome. • Collaborate across Plan, Source Code Management, Code Review, and AI product areas to reduce friction across the software development lifecycle.

• Set the vision and roadmap for the Tailscale dataplane. • Define performance and reliability as customer-facing product requirements. • Own connectivity product strategy end to end. • Drive the roadmap for the operational primitives customers use. • Own the application-layer connectivity surface. • Own the operator control surface. • Partner closely with the embedded Network Features design lead. • Own connectivity behavior across the full matrix of NAT types. • Partner with GTM, Customer Success, and Solutions Engineering. • Represent Tailscale's dataplane externally to enterprise customers, cloud partners, and the networking community.

• Set the vision and roadmap for the Tailscale dataplane. This includes WireGuard behavior, DERP relay expansion and capacity, subnet routers, exit nodes, and client-side networking with the goal of making connectivity feel automatic and reliable • Define performance and reliability as customer-facing product requirements • Own connectivity product strategy end to end: regional expansion, capacity planning, relay health observability, enterprise and private DERP/Peer Relay offerings, and sovereign or regulated deployment requirements • Drive the roadmap for the operational primitives customers use such as subnet routers, exit nodes, and Peer Relays including deployment topology, high-availability modes, route management UX, and production operational tooling • Own the application-layer connectivity surface — App Connectors, Services, DNS, and network segmentation — that determines how traffic finds its destination and how AI agents, CI/CD, and Kubernetes workloads reach the SaaS and cloud resources they depend on • Own the operator control surface: how network engineers and IT admins configure, segment, monitor, and troubleshoot their networks at scale, across both the admin console and the CLI • Partner closely with the embedded Network Features design lead to turn abstract networking systems into legible, well-reasoned product surfaces • Own connectivity behavior across the full matrix of NAT types, operating systems, mobile carriers, enterprise firewalls, and the "weird" networks customers actually run, improving both success rates and customer debuggability • Partner with GTM, Customer Success, and Solutions Engineering on production traffic commitments, regulated deployments, and strategic enterprise deals, turning customer learnings into roadmap priorities • Represent Tailscale's dataplane externally to enterprise customers, cloud partners, infrastructure vendors, and the networking community as a credible domain authority

• Own the product strategy and roadmap for core maintenance workflows/ tools/ automations — spanning areas such as work orders, inspections, issues, service entries, preventive maintenance schedules, and parts & inventory. • Drive Fleetio's vision of running maintenance in one connected system, across in-house teams, external vendors, or both. • Collaborate cross-functionally with research, design, engineering, data science, marketing, and customer-facing teams to develop successful strategies and make informed decisions. • Ensure the evolution of Fleetio's maintenance experience is customer-driven, data-informed, and designed to help fleets automate coordination, control costs, and keep vehicles available for work. • Deeply understand the operational realities of both in-house shops and outsourced maintenance, and how they connect. • Balance depth and reliability in high-usage, mission-critical workflows with the pace of shipping new value. • Continuously generate and test hypotheses to iterate and improve the product experience. • Effectively communicate product vision, value proposition, trade-offs, risks, opportunities, learnings, insights, and roadmap updates to stakeholders, executives, and customers. • Work closely with your team to find ways to make our development process more efficient in delivering high-quality features to customers quickly. • Guide features through their entire creative cycle: discovery, ideation, specification, test, delivery, launch / GTM, analysis, and optimization. • Demonstrate initiative and ability to turn business priorities, key themes, and big ideas into a roadmap with minimal guidance. • Identify opportunities for differentiation, zero-to-one innovation, and revenue expansion. • Raise the bar for product quality based on strong evidence.