Senior Solutions Engineer, Enterprise

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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

We are hiring a Senior Solutions Engineer to partner with Account Executives on enterprise accounts. You will own the technical side of the sales cycle—qualifying use cases, leading discovery and architecture, running demos and proofs-of-concept, and supporting early adoption and expansion. You will act as a trusted advisor to networking, security, platform, and IT stakeholders.

This is a senior individual-contributor role that blends deep networking and security expertise with consultative selling. You will co-own pipeline outcomes, help close and expand enterprise deals, and feed real customer requirements back into product and go-to-market.

This role is a strong fit for a senior SE who wants to stay close to the technology, work enterprise deals from qualification through early adoption, and help customers replace complicated networking—and privileged/AI access—with something simpler and more secure.

Key Responsibilities

• Partner with Account Executives to identify, qualify, and close new enterprise logos and expansion opportunities, confirming technical fit aligned with business goals.
• Lead technical discovery, solution architecture, demos, and proofs-of-concept (POCs) that help customers make confident buying decisions.
• Design Tailscale architectures for hybrid, multi-cloud, and on-premises environments, including identity-based access and secure connectivity patterns.
• Align Tailscale PAM for identity-aware access with session recording, and Aperture as an AI gateway for LLM/API access.
• Translate technical capabilities into clear business value, including security outcomes, operational simplicity, and time-to-value.
• Serve as a trusted advisor across multi-stakeholder deals, guiding implementation and collaborating with Customer Success to drive best-practice adoption.
• Support security reviews and common enterprise diligence (architecture reviews, questionnaires, and compliance discussions).
• Provide structured feedback to Product, Engineering, and GTM teams based on enterprise use cases, blockers, and competitive dynamics.
• Assist in building reusable demo environments, solution blueprints, and enablement assets that raise the quality and consistency of enterprise engagements.
• Stay current on zero-trust networking, privileged access, identity integrations, cloud networking, and AI access/governance so you can position the full Tailscale portfolio accurately and competitively.

What We Are Looking For

• 5–7+ years in a customer-facing Solutions Engineer, Sales Engineer, or Solutions Architect role within networking, security, infrastructure, or related enterprise software.
• Proven experience co-owning pipeline and influencing quota outcomes with Sales on both new business and expansion.
• Deep understanding of zero-trust networking, secure connectivity, and IAM integrations (SSO, SAML, OIDC, SCIM).
• Strong networking fundamentals and troubleshooting skills: TCP/IP, DNS, routing, firewalls, NAT traversal, TLS/HTTPS, and related concepts.
• Hands-on systems administration and troubleshooting across Linux and at least one of macOS or Windows.
• Hands-on architecture experience with AWS, GCP, and/or Azure, including hybrid environments.
• Experience managing cloud and network infrastructure using Infrastructure as Code (Terraform preferred for policy/ACL; Pulumi, Ansible, or CloudFormation also relevant).
• Excellent communication skills, with the ability to explain complex systems clearly and translate technical features into business value for both practitioners and executives.
• Experience running technical evaluations, customized demos, and POCs in enterprise or upper mid-market environments.
• Comfort operating in a high-growth, fully distributed environment with a high degree of ownership and competing priorities.
• Willingness to travel occasionally (approximately 10–20%) for customer meetings, workshops, and internal collaboration.

Nice to Have 

• Experience selling or architecting zero-trust, SASE, ZTNA, VPN, PAM, or secure networking solutions.
• Familiarity with privileged access patterns: JIT access, session recording, least-privilege to SSH/databases/Kubernetes, and replacing shared credentials.
• Familiarity with AI gateways, LLM access governance, MCP/API proxying, or centralized model/provider key management.
• Hands-on scripting or automation experience (Python, Bash, Go, or similar) for demos, POCs, or integrations.
• Knowledge of the competitive landscape in zero-trust, PAM, and AI access control.
• Experience supporting security reviews, architecture diligence, and compliance discussions (SOC 2, HIPAA, PCI) in a pre-sales context.
• Previous exposure to Tailscale, WireGuard, or similar mesh-networking technologies.
• Experience creating reusable architectures, demo environments, or SE playbooks.

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.

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.