Product Manager identifying and validating new products, markets, partnerships, and business models for OpenSesame’s AI - powered learning marketplace. Driving customer experiments, roadmaps, pilots, and growth recommendations.
About the role
- Principal Product Manager leading Tailscale's secure networking dataplane. Setting strategy for connectivity infrastructure serving millions of devices and critical enterprise workloads.
Responsibilities
- Set the vision and roadmap for Tailscale's dataplane, including WireGuard behavior, DERP relay expansion and capacity, subnet routers, exit nodes, and client-side networking
- Define performance and reliability as customer-facing product requirements
- Own connectivity product strategy end to end, including regional expansion, capacity planning, relay health observability, enterprise and private DERP/Peer Relay offerings, and sovereign or regulated deployments
- Drive the roadmap for subnet routers, exit nodes, and Peer Relays, including deployment topology, high-availability modes, route management UX, and operational tooling
- Own the application-layer connectivity surface covering App Connectors, Services, DNS, and network segmentation
- Own the operator control surface across the admin console and CLI for configuring, segmenting, monitoring, and troubleshooting networks at scale
- Partner with the embedded Network Features design lead on networking product surfaces
- Own connectivity behavior across NAT types, operating systems, mobile carriers, enterprise firewalls, and unusual customer networks
- Partner with GTM, Customer Success, and Solutions Engineering on production traffic commitments, regulated deployments, and strategic enterprise deals
- Represent Tailscale's dataplane to enterprise customers, cloud partners, infrastructure vendors, and the networking community
- Report directly to Tailscale's VP Product
Requirements
- 10+ years in product management owning networking, transport, edge, or infrastructure products at scale
- Deep networking fluency across routing, NAT traversal, MTU/MSS, congestion, latency, packet loss, overlay routing, proxies, connectors, DNS, and network segmentation
- Ability to engage engineers across networking teams as a peer
- Demonstrated ability to define performance commitments and customer-facing SLOs
- Experience operating under real production expectations and handling missed commitments
- Familiarity with VPN/tunneling protocols such as WireGuard, IPsec, or OpenVPN is nice to have
- Familiarity with low-level networking stacks such as kernel, eBPF, or userspace is nice to have
- Experience operating globally distributed infrastructure POPs, relays, and edge nodes is nice to have
- Familiarity with subnet routing, BGP, MPLS, cloud VPC peering, or data residency constraints is nice to have
- Experience with service mesh, API gateways, DNS, proxies/connectors, or network segmentation and policy is nice to have
- Track record building admin console and CLI operator control surfaces is nice to have
- Background in regulated industries is nice to have
- Public technical writing, conference talks, or open-source networking contributions are nice to have
- Hands-on experience with Tailscale at work or home is nice to have
Benefits
- Equity incentive plan
- Variable commission for quota-based roles
- Comprehensive group benefits with no waiting period, including health, vision, and dental coverage for employees and families
- Flexible remote-first work environment
- Virtual and in-person social events
- Corporate co-working program
- Employer-funded retirement contributions matching contributions dollar-for-dollar, up to 0.75% of eligible compensation annually
- Annual company retreat and team off-sites
- Team travel and distributed collaboration
- $1500 USD annually for professional development
- Mentorship, coaching, and internal promotion opportunities
- Flexible paid time off program
- Company-owned laptop, with choice of Mac or PC
- Monthly home internet reimbursement
- $500 USD home office workstation customization allowance
- Paid parental leave top-ups: 20 weeks for birthing parents and 16 weeks for non-birthing parents
- Accessible and inclusive hiring process with accommodations available
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