TailscaleOEM Sales Director
Title: OEM Sales Director Location: Remote (Canada)
About Tailscale
Tailscale is building the new Internet 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.
Job Description
We are looking for an OEM Sales Director to build and scale Tailscale’s OEM and embedded partnerships. In this role, you’ll identify, structure, and close strategic partnerships with software platforms, infrastructure providers, and technology vendors embedding Tailscale into their products.
This is a high-impact, quota-carrying role focused on developing new revenue streams through OEM, embedded, and platform partnerships. You’ll work closely with Sales, Product, Engineering, Legal, and Marketing to bring new distribution models to market and grow partner-driven revenue.
If you enjoy building new business motions from the ground up, negotiating complex strategic deals, and helping developers and platforms securely connect their users and infrastructure, we’d love to talk.
Key Responsibilities
Build and scale the OEM motion:
- Identify and close OEM and embedded partnerships with software platforms, infrastructure providers, and technology vendors.
- Structure commercial agreements including licensing, revenue share, and go-to-market frameworks.
- Drive OEM-sourced and OEM-influenced revenue.
Lead strategic deal execution:
- Own end-to-end opportunity management for OEM partnerships—from discovery through contract and launch.
- Partner with executives and product leaders at target companies to align on product integration and commercial strategy.
- Negotiate complex agreements involving pricing models, embedded licensing, and co-selling.
Develop the OEM ecosystem:
- Create and execute a repeatable OEM go-to-market strategy.
- Identify priority segments (developer platforms, cloud services, enterprise SaaS, infrastructure tools).
- Build pipeline and land strategic lighthouse customers.
Collaborate internally and externally:
- Work closely with Product and Engineering to align OEM opportunities with the product roadmap.
- Work with marketing to launch joint solutions to drive brand awareness
- Align with Customer Experience to support OEM customer adoption and expansion.
- Educate and enable partner teams on how Tailscale solves real networking and connectivity problems.
- Develop best practices for partner onboarding, enablement, and revenue growth.
What We Are Looking For
- 8–12+ years experience in enterprise sales, business development, or strategic partnerships.
- Experience structuring OEM, embedded, platform, or licensing partnerships in SaaS, developer tools, networking, or infrastructure.
- Track record of closing complex multi-stakeholder deals with large technology companies.
- Strong commercial instincts and comfort negotiating revenue share, licensing, and platform agreements.
- Ability to work cross-functionally with product, engineering, and legal teams.
- Exceptional communication and executive relationship-building skills.
- Self-directed and comfortable operating in a fast-moving, distributed environment.
Nice to Have
- Experience with developer platforms, networking, cloud infrastructure, or security products.
- Background in platform ecosystems or developer tooling.
- Experience launching new partner programs or distribution channels.
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.
For this position, our pay ranges reflect target OTE (on target earnings), inclusive of base salary and variable compensation tied to the attainment of quarterly sales targets.
CAN Pay Range (OTE)
$178,220—$222,440 CAD
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.
- 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, and the United Kingdom. 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 $1000 USD to customize your workstation to make it your own.
- Generous parental leave program from your first day. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups for up to 26 weeks.
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.