Tailscale

Account Executive

• Expand and renew current customer accounts
• Find additional customer use cases
• Educate customers on new feature releases
• Ensure successful adoption of Tailscale across existing customer accounts
• Partner with Solutions Engineering and collaborate with Customer Success, Support, Marketing, and Product teams
• Become an expert in how Tailscale helps customers
• Build a credible quarterly pipeline through upsells and renewals
• Own upsell and renewal targets across assigned accounts
• Educate customers on Tailscale's value throughout evaluation and adoption
• Generate short-term results while maintaining annual pipeline coverage
• Provide accurate weekly forecasting and revenue delivery
• Create mutual action and success plans for prospective and existing customers
• Participate in video-recorded customer meetings for training, collaboration, and quality improvement

Senior Customer Account Executive

• Win new business by identifying prospective customers, educating them about Tailscale's services, and helping them succeed with the product
• Analyze market landscapes and customer trends to inform sales campaigns
• Travel to or organize local events and attend large industry events to evangelize Tailscale to prospective customers
• Support customers across all time zones
• Manage and organize activities, pipeline, and forecast in Gong and Salesforce
• Own the sales cycle from prospecting through purchase
• Receive assigned inbound leads and source one third of the role's own pipeline
• Build the playbook for startup sales and earn customer trust throughout the sales process

Business Account Executive

• Become an expert in how Tailscale helps customers
• Build a credible quarterly pipeline through client engagement on upsells and renewals
• Own upsell and renewal targets across assigned accounts
• Educate customers on Tailscale's value throughout evaluation and adoption
• Generate short-term results while maintaining annual pipeline coverage
• Provide accurate weekly forecasting and revenue delivery
• Create mutual action and success plans with prospective and existing customers
• Participate in video-recorded customer meetings for training, collaboration, and quality improvement
• Expand and renew current customer accounts, identify additional use cases, and educate clients on new feature releases
• Partner with Solutions Engineering and collaborate with Customer Success, Support, Marketing, and Product teams

Customer Account Executive

Solutions Engineer

• Act as the pioneering technical voice for Tailscale in APAC, cultivating market presence, initiating customer engagement frameworks, and defining regional technical execution strategies.
• Partner closely with AEs to identify, qualify, design, and close new commercial opportunities, managing the regional pipeline effectively to hit and exceed quota outcomes.
• Lead discovery workshops, deliver tailor-made product demonstrations, and manage technical POCs that resolve technical objections and shorten sales cycles.
• Engage in direct R&D activities such as writing code, developing custom tool integrations, and contributing fixes or features directly back to Tailscale's core product to solve deep technical barriers for strategic regional customers.
• Document and synthesize critical field insights, architectural trends, and regional product requirements to provide structured feedback that informs product, engineering, and GTM strategies.
• Build reusable demo environments, solution blueprints, technical whitepapers, and objection-handling documentation to uplevel the global Solutions Engineering organization.
• Collaborate with adjacent customer-facing technical teams simultaneously building out in Singapore to ensure tight feedback loops, consistent service delivery; partnering together to actively establish and anchor Tailscale’s company culture in the region.
• You will focus on building partner relationships that drive measurable results

Founding Solutions Engineer

Implementation Specialist

• Serve as the founding regional hire for the Singapore customer engineering team, leading the local expansion and recruitment efforts.
• Build and establish Tailscale’s company culture and operational standards within the new Singapore region.
• Manage day-to-day support operations for a pod of 1-3 Tier 1 and Tier 2 Support Engineers.
• Lead the hiring, onboarding, technical mentoring, and career coaching for all direct reports in the region.
• Coordinate in-office time to foster team collaboration, establish the local office environment, and support new hires.
• Oversee the regional support queue to ensure SLA/SLO adherence, focusing on APAC specific tickets and partnering on global queue health.
• Act as an internal escalation point for both complex technical issues and difficult customer situations.
• Partner with the VP of Customer Engineering to align regional team outcomes with the broader global strategy.
• Analyze regional support data and customer feedback (CSAT) to surface trends and insights to leadership.
• Refine support workflows and internal tooling in collaboration with Support and CX Operations.
• Conduct regular quality assurance reviews on tickets to maintain high technical accuracy and a consistent brand voice.

Founding Senior Customer Engineer

Product Manager

• Own the roadmap for the native apps experience: TSNet, tailscale-rs, and the tailscale CLI.
• Define what "Tailscale-native application" means — the reference architectures, golden paths, and embedding patterns.
• Own the developer experience end to end.
• Set the Rust SDK family strategy.
• Treat the CLI as a product in its own right.
• Run the internal dogfood loop.
• Partner with GTM and Customer Success on embedding deals.
• Engage developers where they live.

Product Manager – Tailscale-Native Apps

• Own the roadmap for the native apps experience: TSNet, tailscale-rs, and the tailscale CLI
• Define what "Tailscale-native application" means — the reference architectures, golden paths, and embedding patterns, packaged as docs, examples, and sample apps developers can build from
• Own the developer experience end to end: the on-ramp from blog post to running embedded node, API ergonomics, error messages, docs that work, examples that compile, and upgrade paths that don't burn early adopters
• Set the Rust SDK family strategy: which TSNet capabilities to port, which to skip, in what order, and how to position the library to developers.
• Treat the CLI as a product in its own right: scripting ergonomics, output conventions, automation surfaces, and the experience for platform and SRE teams running tailscale in CI and infrastructure-as-code
• Run the internal dogfood loop. Aperture and Tailscale PAM are built on these primitives; make those teams your most demanding customers and turn their friction into roadmap.
• Partner with GTM and Customer Success on embedding deals — AI platforms, developer tools, and infrastructure software shipping Tailscale inside their products — and let what you learn set priorities
• Engage developers where they live (GitHub issues, Discord, office hours) and build a coherent picture of what embedded developers need

Product Marketing

• Becoming the expert on our users and customers — who they are, what their pain points are, and what drives them to seek out solutions
• Collaborating with sales, product and marketing teams to develop and refine product positioning, messaging, and effective content
• Launching new products or features, managing cross-functional projects associated with that launch, and measuring revenue and pipeline generated
• Creating sales collateral and enablement materials— slide decks, one-pagers, training sessions, customer case studies, webinars, etc.. This includes delegating and working with designers/web developers/content marketers as needed.
• Performing competitive and market analysis to inform messaging and campaigns, and influence product strategy
• Represent PMM at industry events by delivering demos and gathering firsthand customer and prospect insights to shape messaging and campaign strategy
• Helping drive meaningful sales pipeline

Product Marketing Manager

AI Engineer

• Partner with engineering leadership to define Tailscale's internal AI-enablement priorities and roadmap.
• Work with the team that's building Aperture by Tailscale – our AI gateway.
• Build, maintain, and iterate on internal tools, workflows, and shareable practices.
• Evaluate new AI models, agents, and tools.
• Work directly with both engineering and non-engineering teams to find high-leverage opportunities.
• Develop infrastructure, guardrails, review practices, and documentation for safe AI use.
• Act as an internal advocate for effective AI practices.
• Track adoption and measure the impact of AI tooling on engineering velocity.

Software Engineer, AI Enablement

• Partner with engineering leadership to define Tailscale's internal AI-enablement priorities and roadmap.
• Work with the team that’s building Aperture by Tailscale – our AI gateway.
• Build, maintain, and iterate on internal tools and workflows.
• Evaluate new AI models, agents, and tools.
• Work directly with both engineering and non-engineering teams to find opportunities to apply AI.
• Develop infrastructure, guardrails, review practices, and documentation for the safe use of AI-generated code.
• Act as an internal advocate for effective AI practices.
• Track adoption and measure the real impact of AI tooling on engineering velocity and quality.
• Expect the day-to-day to span hands-on building, teaching, and prioritization.

• Partner with engineering leadership to define AI-enablement priorities.
• Work with the team building Aperture by Tailscale.
• Build, maintain, and iterate on internal tools and workflows.
• Evaluate new AI models and make recommendations.
• Collaborate with teams to find opportunities to apply AI.
• Develop infrastructure and practices for safe use of AI-generated code.
• Advocate for effective AI practices through documentation and coaching.
• Track adoption and measure the impact of AI tooling.
• Expect varied tasks including building, teaching, and prioritization.

Events

• Planning and running the company-wide offsite - venue, logistics, budget, agenda, and the on-site execution itself.
• Planning team-level events and offsites with team leads, balancing what each team wants against overall budget and timeline.
• Running a regular cadence of virtual events that actually keep a distributed team feeling like one team.
• Managing relationships with coworking providers and physical space vendors, including renewals, capacity planning, and day-to-day issues as they come up.
• Acting as the point person for in-office or coworking space needs - desk capacity, meeting room access, badge/access logistics - so teams can just show up and work.
• Evaluating and recommending new coworking locations as the team grows or shifts geographically.
• Owning rewards and recognition end to end, from the platform itself to nominations and the moments that make people feel seen.
• Improving the remote and hybrid experience generally - swag, onboarding touches, the small rituals that matter when you rarely see the office.
• Sourcing, negotiating with, and managing vendors: venues, caterers, travel, AV, swag, event platforms.
• Owning event budgets from the forecast through reconciliation, and flagging variances before they become a problem.
• Handling the full logistics chain - invites, RSVPs, travel, run-of-show docs, day-of execution, wrap-up - so nothing falls through the cracks.
• Collecting feedback after every event and actually using it to make the next one better.
• Traveling as needed to support offsites and in-person events (roughly 10–25% of the time).

Events Manager

Support Engineer

• Own high-severity, post-sales technical escalations from intake through resolution or engineering handoff. This includes deep-dive investigations and reproduction of difficult-to-isolate bugs.
• Get on calls with customers, pull logs, and communicate with the customer about leading theories.
• Build engineering handoff packages that require minimal follow-up questions: reproducible case, log evidence (timestamps, node IDs), version matrix, impact scope, what's already been ruled out, and a proposed engineering team to own the fix.
• File and track issues for confirmed bugs, keeping the ticket/issue link intact so engineering retains full customer context.
• Monitor for patterns across escalations to catch recurring or systemic issues early; translate what you learn into product improvements, tooling, and runbooks that raise the technical bar for the whole Support org.
• Partner with Support, CSE, and Product/Eng, while staying within this team's scope.

Senior Customer Support Engineer, Customer Escalations

• Become an expert in how Tailscale helps our customers
• Build a credible pipeline every quarter by engaging with clients on upsells and renewals
• Own an upsell and renewal number across your accounts
• Help educate customers on the value of Tailscale throughout the evaluation & adoption cycle
• Generate short-term results while maintaining annual pipeline coverage
• Provide accurate weekly forecasting & revenue delivery
• Create mutual action/success plans with prospective and existing customers where appropriate to help them evaluate and expand their usage of the Tailscale product
• Participation in video-recorded customer meetings is a core part of this role. Recordings are used for training, collaboration, and quality improvement

• Serve as the primary escalation point for technically complex tickets raised by paying customers, taking full ownership through to resolution.
• Diagnose and troubleshoot advanced Tailscale-specific issues like ACL misconfigurations, subnet routing/exit node configurations, and integration with identity providers (e.g. Okta, Azure AD).
• Manage a ticket queue with a consistent focus on SLA adherence, ensuring timely first responses and resolutions.
• Drive positive user outcomes and maintain high CSAT scores by providing clear, helpful, and accurate technical guidance.
• Balance a high volume of daily ticket replies while maintaining the technical depth required to troubleshoot complex networking issues.
• Partner cross-functionally to identify recurring friction points and advocate for improvements to the user experience.
• Own escalations of technically complex tickets from Tier 1, including those originating from free-tier users, ensuring issues beyond Tier 1's scope are resolved efficiently and thoroughly.
• Mentor and support Tier 1 colleagues through ticket reviews, escalation guidance, and documentation contributions.