Remote Enterprise Account Executive

Tailscale; San Francisco (CA); Remote; USD 250,000 - 300,000; Full time

Benefits offered by this job

Health insurance

Equity

Remote work

Retirement plan

Professional development

Paid time off

Home office stipend

Parental leave

Job summary

Tailscale is hiring an Enterprise Account Executive. You will lead strategic engagements with large customers, owning end-to-end sales cycles and coordinating with SE, CS, Product, Marketing, and Support to drive value and adoption.

You will build executive relationships, navigate complex organizations, and translate technical capabilities into measurable business outcomes, while enabling growth across a remote-first organization.

Qualifications

• 5+ years of closing experience in enterprise sales.
• Experience selling infrastructure, cybersecurity, or developer tools.
• Proven track record meeting or exceeding quota in enterprise sales.
• Experience with complex multi-stakeholder deals and executives.

Responsibilities

• Own and grow a territory of enterprise organizations with net-new and expansion opportunities.
• Self-source pipeline through outbound prospecting and strategic targeting.
• Manage full sales cycle from lead to close.
• Develop strategic account plans identifying stakeholders and priorities.
• Build relationships with Security, Infrastructure, Engineering, Compliance, and Execs.
• Navigate complex cycles with procurement, security reviews, and legal.
• Position Tailscale as a strategic platform for secure connectivity and modern networking.
• Lead cross-functional teams to deliver exceptional customer outcomes.
• Drive adoption beyond initial deployment for long-term growth.

Skills

Enterprise sales

Multi-stakeholder deals

Executive relationships

Forecasting pipeline

Negotiation

Collaboration with SE

Quota attainment

Tools

Gong

Job description

Tailscale is hiring an Enterprise Account Executive. You will lead strategic engagements with large customers, owning end-to-end sales cycles and coordinating with SE, CS, Product, Marketing, and Support to drive value and adoption.

You will build executive relationships, navigate complex organizations, and translate technical capabilities into measurable business outcomes, while enabling growth across a remote-first organization.