Director, Strategic Sales
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Job Description
Strategic Sales Director building Tailscale's enterprise sales organization for secure networking software. Personally closing Fortune 1000 opportunities while recruiting and leading Strategic Account Executives.
Responsibilities:
- 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 the world's largest enterprises
- Personally own and close 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 senior decision makers
- Negotiate complex commercial agreements across technical, financial, legal, and executive stakeholders
- Recruit, hire, and develop Strategic Account Executives
- Lead approximately 3–5 Strategic Account Executives initially and expand the organization over time
- Coach account strategy, executive engagement, negotiation, forecasting, and deal execution
- Lead an outbound-first sales motion and personally prospect into strategic accounts
- Partner with SDRs, Marketing, GTM Engineering, Customer Engineering, Customer Success, Product, and Engineering
- Create scalable account-planning and outbound strategies that generate executive engagement and qualified pipeline
- Own account planning, forecasting, pipeline health, and business planning for the Strategic segment
- Inspect deal strategy and qualification throughout sales cycles
- Use data to improve execution, identify trends, and optimize performance
- Provide market feedback to influence product direction
- Build the operating rhythm, metrics, and inspection processes for organizational scale
- Report directly to the Head of Sales
Requirements:
- Founding AE experience at a high-growth startup
- 5+ years as the top sales representative at a high-growth technology company
- Proven success selling to organizations with 10,000+ employees
- Demonstrated ability to close complex six-, seven-, and eight-figure SaaS opportunities
- Consistent track 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 trusted advisors
- Strong business acumen and experience navigating complex buying committees and long enterprise sales cycles
- Comfortable operating in ambiguity and building new processes where none exist
- Passion for building teams, developing people, and creating scalable organizations
Benefits:
- An inclusive, flexible environment where you can be your authentic self
- A competitive total compensation package including base salary, an equity incentive plan, and variable commission for quota-based roles
- Comprehensive group benefits with no waiting period, including health, vision, dental, and more for you and your family
- Remote-first work environment with fully remote work, virtual and in-person social events, and a corporate co-working program
- Employer-funded retirement contributions matching contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of eligible compensation
- Annual company retreat and team off-sites
- $1500 USD annually for professional development, plus mentorship, coaching, and internal promotion opportunities
- Flexible paid time off program
- Company-owned laptop (Mac or PC)
- Monthly home internet reimbursement
- $500 USD home office/workstation customization allowance
- Paid parental leave top-ups: 20 weeks for birthing parents and 16 weeks for non-birthing parents
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