Tailscale

Manager, Sales Enablement

United States

Not SpecifiedCompensation
Senior (5 to 8 years), Expert & Leadership (9+ years)Experience Level
Full TimeJob Type
UnknownVisa
Software, Biotechnology, InternetIndustries

Requirements

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.

Responsibilities

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.

Skills

Sales Enablement
Revenue Operations
Onboarding Programs
Product Marketing
Content Development
Sales Training
Technical Sales
IT Persona
Engineering Persona
Customer Success

Tailscale

Secure VPN for remote resource access

About Tailscale

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.

None, CanadaHeadquarters
2019Year Founded
$111.9MTotal Funding
SERIES_BCompany Stage
Enterprise Software, CybersecurityIndustries
51-200Employees

Benefits

Health Insurance
Dental Insurance
Vision Insurance
Flexible Work Hours
Remote Work Options
Unlimited Paid Time Off
Parental Leave
Professional Development Budget
Home Office Stipend
Phone/Internet Stipend
Company Equity

Risks

A critical vulnerability in Windows client poses remote code execution risk.
Cooling venture funding may impact Tailscale's future investment opportunities.
Scalability challenges may arise with rapid enterprise adoption of zero-trust solutions.

Differentiation

Tailscale uses WireGuard's Noise protocol for trusted encryption standards.
It integrates with existing identity providers like GSuite and Office365 for easy setup.
Tailscale offers over 100 integrations, fitting into almost any tech stack.

Upsides

Tailscale's zero-trust solution meets growing demand for enterprise security.
The $100 million Series B funding boosts product expansion and market reach.
Integration with Mullvad enhances privacy with a global VPN server network.

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