Senior Sales Enablement Specialist
WorkdayFull Time
Mid-level (3 to 4 years), Senior (5 to 8 years)
Candidates should have 3-6+ years of experience in sales enablement, technical sales, or sales engineering at a high-growth B2B SaaS company. Proven success enabling both individual contributors and managers in go-to-market teams selling to IT or engineering decision-makers is required. A deep understanding of developer tools, infrastructure, networking, or security is also necessary, along with a data-driven mindset and excellent communication skills for distilling complex technical concepts. Familiarity with Tailscale or similar products, experience in a product-led growth environment, and a background in technical presales or sales engineering are considered advantageous.
The Sales Enablement Manager will develop and execute onboarding programs for Account Executives, Sales Engineers, and Customer Success Managers. They will build a repeatable framework for ongoing enablement, focusing on product, process, and persona. This role involves collaborating with Product Marketing and Product to translate technical value into clear messaging and content, and designing enablement programs for both individual contributor skill development and manager coaching capabilities. The manager will partner with frontline managers and sales leadership to identify skill gaps, deliver targeted programs, and create scalable, role-specific enablement paths. Additionally, they will own the development and upkeep of enablement materials such as playbooks, talk tracks, competitive guides, objection handling, and demo resources, and drive the adoption of tools like Gong, Outreach, and Salesforce to reinforce best practices. The effectiveness of enablement programs will be assessed using data, and new initiatives will be prioritized based on performance metrics, pipeline trends, and tooling insights.
Secure VPN for remote resource access
Tailscale offers a secure networking solution that allows users to access remote resources like virtual machines and databases from anywhere using a WireGuard-based Virtual Private Network (VPN). Its service is designed for businesses and individuals needing to manage private resources remotely, with a focus on simplicity and minimal setup. Tailscale's freemium model attracts a wide user base, allowing users to start for free and upgrade for additional features. The company aims to enhance data security while providing an easy-to-use remote access solution.