Director, Strategic Sales

Responsibilities

Build a New Business

• Build Tailscale's Strategic Sales organization from the ground up.
• Design the operating model, territory strategy, account segmentation, and engagement approach.
• Develop repeatable playbooks for winning large enterprises.
• Shape the long-term vision for Strategic Sales as the business scales.
• Partner with executive leadership to influence go-to-market strategy for major customers.

Lead From the Front

• Own a portfolio of high-value strategic accounts.
• Lead complex, multi-stakeholder sales cycles from initial engagement through expansion.
• Develop executive relationships with CIOs, CISOs, CTOs, Chief Architects, infrastructure leaders, and other senior decision-makers.
• Serve as the executive quarterback on major strategic pursuits.
• Negotiate complex commercial agreements across technical, financial, legal, and executive stakeholders.

Build an Elite Team

• Recruit, hire, and develop Strategic Account Executives.
• Initially lead approximately 3–5 Strategic Account Executives.
• Coach account strategy, executive engagement, negotiation, forecasting, and deal execution.
• Foster a high-performance culture built on accountability, collaboration, curiosity, and continuous learning.

Create Pipeline

• Lead an outbound-first sales motion.
• Prospect into strategic accounts and build executive relationships.
• Partner with SDRs, Marketing, GTM Engineering, Customer Engineering, and Customer Success on account plans.
• Create scalable account-planning and outbound strategies that generate qualified pipeline.
• Establish best practices for strategic prospecting, account planning, and executive alignment.

Drive Operational Excellence

• Own account planning, forecasting, pipeline health, and business planning for the Strategic segment.
• Inspect deal strategy and qualification throughout the sales cycle.
• Use data to improve execution, identify trends, and optimize performance.
• Partner with Product and Engineering to provide market feedback that influences product direction.
• Build the operating rhythm, metrics, and inspection processes needed to scale.

Requirements

• 5+ years as the top sales representative at a high-growth technology company.
• Proven success selling to organizations with more than 10,000 employees.
• Demonstrated ability to close complex six-, seven-, and eight-figure SaaS opportunities.
• Consistent record of building outbound pipeline and winning net-new enterprise customers.
• Executive presence and ability to engage CIOs, CISOs, CTOs, and senior business executives as a trusted advisor.
• Strong business acumen and experience navigating complex buying committees and long enterprise sales cycles.
• Comfort operating in ambiguity and building new processes.
• Passion for building teams, developing people, and creating scalable organizations.

Compensation & Benefits

• Target OTE: $350,000–$400,000 USD.
• Compensation includes base salary, equity, and comprehensive benefits.
• Flexible, inclusive work environment.
• Equity incentive plan.