Director, Strategic Sales

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Tailscale

WebsiteLinkedInAll Job Openings

51 - 200 employees

Founded 2020

☁️ SaaS

🔐 Security

📡 Telecommunications

💰 $100M Series B on 2022-05

SaaS • Security • Telecommunications

Tailscale is a company that provides a modern VPN solution founded on WireGuard technology, simplifying networking by creating secure, software-defined networks that connect users, services, and devices with ease. By eliminating the complexities of legacy VPNs, Tailscale offers secure remote access, site-to-site networking, and multi-cloud networking, all while ensuring user-friendly, quick deployment without complex configurations. Recognized for enabling zero-trust environments and seamless workflows, Tailscale supports robust security features such as automated user onboarding, encryption, and access control lists (ACLs). This tool is particularly popular for both enterprise and personal use, praised for its integration capabilities and ease of use, making secure networking accessible anywhere, regardless of infrastructure.

📋 Description

• 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