Director of Strategic Sales

Position:
Director, Strategic Sales

Company:
Tailscale

Compensation:
US Pay Range (OTE) $350,000 - $400,000 USD

Location:
United States

Employment type:
Not specified

Work Arrangement:
Remote

Short Summary:
Tailscale is redefining secure networking, seeking a founding Director of Strategic Sales to build a new organization focused on engaging Fortune 1000 customers and establishing a go-to-market strategy. This role combines selling, coaching, and team building, targeting organizations with over 10,000 employees.

Responsibilities:
- Build Tailscale's Strategic Sales organization from the ground up.
- Design the operating model, territory strategy, and engagement approach.
- Develop repeatable playbooks for winning large enterprises.
- Personally own a portfolio of high-value strategic accounts.
- Lead complex sales cycles and develop executive relationships.
- Recruit and develop exceptional Strategic Account Executives.
- Lead an outbound-first sales motion and create scalable account planning strategies.
- Own account planning, forecasting, and business planning for the Strategic segment.

Requirement:
- 5+ years as the top sales rep at a high-growth technology company.
- Proven success selling into organizations with 10,000+ employees.
- Demonstrated ability to close complex six-, seven-, and eight-figure SaaS opportunities.
- Strong business acumen and executive presence.
- Comfortable operating in ambiguity and building new processes.

Benefits:
- Inclusive, flexible environment.
- Competitive total compensation package including base salary and equity.
- Comprehensive group benefits with no waiting period.
- Remote-first company with opportunities for in-person collaboration.
- Employer-funded retirement contributions.
- Support for personal and professional development with an annual budget.
- Flexible paid time off program.
- Paid parental leave program.