Strategic Enterprise Account Executive — Remote

Tailscale; Oregon; Hybrid; USD 315,000 - 385,000; Full time

Benefits offered by this job

Inclusive environment

Equity + base salary

Health, vision & dental

Remote-first approach

Retirement contributions match

Company retreats

Professional development $1500 USD

Paid time off

Home office setup

Parental leave top-ups

Job summary

Tailscale is hiring a Strategic Account Executive to lead a focused portfolio of 10,000+ employee organizations worldwide. You will own end-to-end deals, build executive relationships, and align customer priorities with Tailscale's secure networking platform.

This is a remote-first role with high-growth potential and a collaborative leadership team. You will develop outbound strategies, manage complex negotiations, and contribute to scaling our enterprise motion across Fortune 1000 and Global

Qualifications

• 5+ years of top-performing enterprise or strategic selling in high-growth environments.
• Experience selling to organizations with 10,000+ employees and closing complex six- to seven-figure SaaS deals.
• Proven track record of YoY growth and meeting targets.
• Ability to earn executive trust, engage technical stakeholders, and navigate procurement, legal, and finance reviews.
• Strong communication, judgment, and collaborative, accountable approach.
• Comfort with ambiguity and building a structured sales motion.

Responsibilities

• Own account strategy and build plans connecting priorities to opportunities across units.
• Drive personalized outbound prospecting and cross-team campaigns.
• Lead deals through negotiation, complex buying processes, and close.
• Build executive relationships with CIOs, CISOs, CTOs and senior leaders.
• Coordinate with Customer Engineering, Product, Finance, Legal to win and grow accounts.
• Shape the playbook and test approaches; share customer feedback with product teams.
• Maintain qualification, forecasts, and actionable plans.

Skills

Enterprise sales

Executive relationships

CRM discipline

Forecasting

Communication

Strategic deals

Job description

Tailscale is hiring a Strategic Account Executive to lead a focused portfolio of 10,000+ employee organizations worldwide. You will own end-to-end deals, build executive relationships, and align customer priorities with Tailscale's secure networking platform.

This is a remote-first role with high-growth potential and a collaborative leadership team. You will develop outbound strategies, manage complex negotiations, and contribute to scaling our enterprise motion across Fortune 1000 and Global