---
title: 'Director, APAC Go-to-Market at Tailscale'
canonical: 'https://feeny.ai/job/director-apac-go-to-market-tailscale-singapore-bdt02s8r9m1w'
type: 'job'
last_seen: '2026-09-08'
---

# Director, APAC Go-to-Market at Tailscale

- **Company:** Tailscale
- **Location:** Singapore
- **Work type:** remote
- **Posted:** 2026-08-31
- **Last confirmed live:** 2026-09-08
- **Apply:** https://job-boards.greenhouse.io/tailscale/jobs/4726020005

## Job description

## About Tailscale

Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We're building a future for the Internet that's easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.

## About the Role

Tailscale is looking for a Director, APAC Go-to-Market to build and lead our GTM business in Asia Pacific, starting from Singapore.

APAC represents an important growth opportunity for Tailscale. We have strong conviction in the region and are looking for a leader who can turn that opportunity into a meaningful, durable business: building pipeline and revenue, developing a strong partner ecosystem, winning strategic customers, and building the team we need to scale.

We are looking for someone who has built a region before and wants to do it again from scratch. You will set the APAC go-to-market strategy, determine where and how we invest, recruit and lead our initial regional team, and be directly accountable for commercial results. You will have significant autonomy to determine what Tailscale needs to win in the region.

You will also be a hands-on commercial leader. You’ll spend time with customers and partners, help shape and close our most important opportunities, and develop a deep understanding of how technology companies need to go to market differently across APAC. You’ll bring those insights back to our global Sales, Marketing, Product, and Engineering teams and help Tailscale become a truly global company.

In this role, you will be able to hire the team you need to succeed. We suspect that will include Sales Development, Account Executives, Solutions Engineering, Customer Engineering, and Partner Marketing, but ultimately we will be open to your recommendation based on expertise. These hires will report directly to you with dotted lines to functional departments in North America and EMEA. You’ll lead that team as a region, while working closely with their functional counterparts elsewhere at Tailscale. This role will report to Tailscale’s President, Kevin Kotecki.

## Key Responsibilities

- Own the APAC number. You will be accountable for regional pipeline creation and revenue growth. Establish clear targets, build the plan to reach them, maintain strong forecasting and pipeline discipline, and continuously adjust our approach based on what the data and the market tell us.
- Build and execute Tailscale’s APAC go-to-market strategy. Determine which markets, customer segments, use cases, and routes to market offer the greatest opportunity for Tailscale. Translate global company strategy into a focused regional plan while recognizing that what works in North America or Europe will not always work in APAC.
- Build a high-performing regional GTM organization. Recruit, lead, and develop exceptional sellers and other customer-facing talent in the region. Build a team that operates as one APAC organization while remaining tightly connected to its global functional counterparts. Create the culture, operating rhythms, and accountability required for a small regional team to move quickly and perform at a high level.
- Lead from the front with customers. Personally engage in Tailscale’s most important opportunities in the region. Build relationships with senior technical and business leaders, help the team navigate complex enterprise sales cycles, and serve as executive sponsor for strategic customers. Stay close enough to the market to know why we are winning, why we are losing, and what needs to change.
- Build Tailscale’s presence in the region. Establish Tailscale as a credible and increasingly visible technology company in APAC. Represent Tailscale with customers, partners, at industry events, and within the broader technology ecosystem. Develop the relationships and market intelligence that allow us to identify opportunities earlier than we otherwise would.
- Be the voice of APAC inside Tailscale. Build a strong point of view on regional customers, competitors, partners, buying behavior, and market dynamics. Bring that perspective into company decisions about product, packaging, marketing, partnerships, and future investments.
- Build the region for the long term. We expect the shape of our APAC organization to evolve considerably. Identify what capabilities and investments we need next, make thoughtful resource tradeoffs, and build systems that can scale beyond the first phase of the Singapore office.

## What We Are Looking For

- Significant experience in enterprise technology go-to-market, with meaningful experience leading Sales or a broader GTM organization across APAC.
- You have done this before. You have helped build or materially scale an APAC business rather than only operating within an already mature regional organization.
- A proven track record of owning and exceeding meaningful pipeline and revenue targets in a B2B technology business.
- Deep familiarity with the APAC technology market and experience operating successfully across multiple countries and cultures, with particularly strong knowledge of Singapore and Southeast Asia.
- Established relationships within the regional channel and partner ecosystem, along with a track record of turning those relationships into measurable commercial outcomes.
- A strong network of exceptional GTM talent in the region. You know what great sellers and SEs look like and have demonstrated that you can attract them to work with you.
- Experience leading complex enterprise opportunities personally. You are comfortable moving from regional strategy and forecasting into a customer meeting or deal review and materially improving the outcome.
- Experience selling highly technical products to sophisticated buyers. Experience with infrastructure, networking, security, developer tools, cloud, or adjacent enterprise technology is particularly relevant.
- Strong commercial judgment and analytical ability. You understand pipeline mathematics, forecasting, unit economics, market prioritization, and where to invest limited resources to produce the greatest return.
- Strong cross-functional leadership skills. You can lead a regional team while partnering effectively with global Sales, Marketing, Product, Engineering, Customer Success, Finance, and Operations teams that you do not directly manage.
- Excellent written and verbal communication and strong executive presence with customers, partners, candidates, and internal leaders.
- A builder’s mindset. You are comfortable with ambiguity, limited infrastructure, and changing plans, and you know how to introduce enough process and structure to improve execution without slowing the organization down.
- High agency and low ego. You are willing to personally do the work required to establish the region while simultaneously building an organization that will eventually make you less central to every decision.
- A strong perspective on how technology GTM is changing in the age of AI and what those changes mean for winning customers and building partnerships in APAC.

As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale's compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire's base salary. Individual offers may vary based on experience and skill set. Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. We encourage you to help us break that statistic!

## What We Offer

- An inclusive, flexible environment where you can be your authentic self. We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.
- A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).
- Comprehensive group benefits with no waiting period. Take advantage of coverage for health, vision, dental, and more for you and your family!
- Remote first company—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.
- Employer-funded retirement contributions. Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.
- Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.
- Support for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.
- Paid time off and a healthy work-life integration. Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!
- A build-your-own home office setup. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.
- Paid parental leave program. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).

Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.

Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.

Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit https://tailscale.com/scam-awareness.

## About Tailscale

## Company Overview
- **One-liner**: Tailscale provides a zero-trust identity-based connectivity platform that replaces legacy VPNs, SASE, and PAM to securely connect remote teams, multi-cloud environments, CI/CD pipelines, edge/IoT devices, and AI workloads.
- **Entity Type**: Private (Series B)
- **Headquarters**: Toronto, Canada (fully remote, with team members also in the United States and United Kingdom)
- **Founded**: 2019
- **Founders**: Avery Pennarun (CEO), David Carney (Chief Strategy Officer), and Brad Fitzpatrick (creator of LiveJournal, Memcached, and OpenID)

## Core Business
- **Primary industry/industries**: Secure connectivity, zero-trust networking, VPN replacement, infrastructure security
- **Target customers**: B2B – from small businesses and open-source projects to mid-market and enterprise organizations (30,000+ businesses use Tailscale). Also serves developers, IT teams, and DevOps engineers.
- **Mission or purpose statement**: “We want to help everyone create their own secure networks built around people and their connections. By making connectivity easier and more secure, we empower teams to build systems that scale, without scaling overhead.”

## Products & Services
- **Tailscale (Core Platform)** – A zero-trust mesh overlay network that provides identity-based access to any resource (servers, containers, SaaS tools, cloud instances) without public exposure. Replaces legacy VPNs, bastion hosts, and complex firewall rules. Includes features like SSH, Kubernetes access, database connectivity, and Aperture for securing AI workloads.
- **Tailscale Funnel** – Expose local services to the internet securely through Tailscale’s infrastructure.
- **Tailscale Serve** – Allow specific devices on a tailnet to serve content publicly or privately.
- **Tailscale SSH** – Manage SSH access with identity-based, auditable controls.
- **Tailscale Aperture** – Secure access for AI/ML workloads and data pipelines.

## Market Standing
- **Valuation/Market Cap**: Not publicly disclosed (private company)
- **Key Metric (Funding)**: Total funding of approximately $105M across multiple rounds. Series A ($35M) led by CRV in 2021; Series B ($70M) led by Accel and Insight Partners in 2022.
- **Key Metric (Customers)**: 30,000+ businesses use Tailscale. Headcount estimated at ~290 employees as of 2026.
- **Notable Investors/Partners**: Accel, CRV, Insight Partners, Heavybit, Uncork Capital. Investors include Amit Kumar (Partner at Accel), Reid Christian (Partner at CRV), Joseph Ruscio (Partner at Heavybit), Rebecca Liu-Doyle (Director at Insight Partners), and Andy McLoughlin (Partner at Uncork).
- **Growth Signals**: 25x headcount growth without dedicated IT resources for onboarding; 90% reduction in internal support requests; thousands of hours saved with fewer connectivity issues. Strong adoption in the AI era for securing workloads.

## Competitive Advantages
- **Built on WireGuard**: Tailscale is built on the modern, audited, and high-performance WireGuard protocol (wireguard-go), with upstream contributions to the open-source project.
- **Zero Trust by Design**: Identity-based access, end-to-end encryption, point-to-point connections (no central VPN server to bottleneck or inspect traffic). User privacy is a fundamental design principle.
- **Simplicity & Speed**: “It has to just work” – installation takes minutes, configuration is minimal, and the platform is cross-platform and infrastructure-agnostic.
- **Open Source Core**: The core client and server code are open source, and Tailscale offers a free plan for open-source projects, building trust and community.
- **Small, Excellent Teams**: The company philosophy is “small is beautiful” – they believe small, excellent teams produce coherent, high-quality outcomes that large teams cannot replicate.

## Strategic Focus
- **AI & Multi-Cloud Connectivity**: Tailscale is positioning itself as the secure connectivity platform for the AI era, with specific features (Aperture) for AI workloads.
- **Expanding Enterprise Features**: Adding capabilities like Privileged Access Management (SSH, K8s, databases), granular access controls, and audit logging.
- **Scaling the Business**: With 30,000+ businesses already onboard, the focus is on converting free/open-source users to paid plans and expanding into larger enterprise accounts.
- **Global Hiring**: Actively hiring across engineering (Go, Infrastructure, Security, Mobile), customer success, sales, marketing, and operations in the US, Canada, and UK, with some roles in Singapore.

## Why Work Here
- **Fully Remote & Flexible**: Tailscale is a fully remote company with team members across the US, Canada, and UK. Flexible working hours are core to the culture – employees are trusted to manage their time around their lives (family, appointments, etc.).
- **Competitive Total Rewards**: Competitive salaries, generous equity incentive plans, group health benefits with no waiting periods, flexible sick days, and an employee assistance program.
- **Work-Life Balance**: 26 weeks of paid parental leave, flexible paid vacation, 12 paid company holidays, and a full holiday closure from Dec 24 to Jan 1.
- **Workspace Support**: Company-provided laptop (Mac/PC), monthly internet reimbursement, and a “build your own workstation” bonus.
- **Engineering Culture**: Strong emphasis on open-source contribution, Go programming, and systems-level engineering. Many team members are active in the Go, NixOS, and SQLite communities.
- **Inclusive & Diverse**: The company is committed to diversity and inclusion, with a team not bound by geography, lifestyle, or life stage. They provide accommodations throughout the interview process.
- **Interview Process**: For technical roles: Recruiter Interview → Hiring Manager Interview → 2-3 Team Interviews → Technical Working Session → Offer. For non-technical roles: Recruiter → Hiring Manager → 2-3 Team Interviews → Offer.

## Sources
1. [tailscale.com](https://tailscale.com/) – Official website
2. [tailscale.com/company](https://tailscale.com/company) – About page, team, investors, guiding principles
3. [tailscale.com/careers](https://tailscale.com/careers) – Careers page, perks, benefits, culture
4. [job-boards.greenhouse.io/tailscale](https://job-boards.greenhouse.io/tailscale/jobs/4525230005) – Current job openings
5. [jobsbyculture.com](https://jobsbyculture.com/blog/working-at-tailscale-2026) – Employee culture review (2026, ~290 employees)

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