Revenue Operations and Enablement Manager

About Tailscale 

Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We're building a future for the Internet that's easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.

Job Description

Tailscale is in need of an experienced Revenue Operations and Enablement Manager to develop the strategy for resources, processes, and training necessary to help our teams effectively support and position the value of Tailscale to our customers and prospects. This role will work across departments to build supporting content and programs to enable the Sales, Marketing, Partner, and Customer Experience teams to have consistent, effective, and engaging conversations with customers at each stage of the customer lifecycle while helping to improve efficiency and effectiveness of our organization. In this role, you will be challenged to develop the skills and experience to, over time, lead an enablement department. 

Key Responsibilities

• You are passionate; you throw your energy and conviction into the work you do
• You are naturally curious; you have an innate desire to understand people and help solve their problems
• You are collaborative; you thrive in environments where people work together to create winning solutions
• You commit to self-development and personal growth; you pursue your personal and professional interests with energy and enthusiasm
• You assume positive intent; you believe your teammates and customers come from a place of good intention
• Build and scale learning and development programs that align with business strategy and needs; optimize the employee experience via a roadmap
• Partner with Marketing, Sales, Channel, and Customer Experience (CX) leadership to identify areas of enablement opportunity against current GAPs in selling motion
• Track metrics to identify trends, anticipate development needs, and proactively execute programs that accelerate the growth of people’s skills and acumen
• Provide expert facilitation and training to ensure organizational and individual performance and revenue team effectiveness
• Partner closely with Product Marketing to create resources/collateral  including playbooks, templates, kill sheets, sales training programs, CX onboarding, and other assets as required
• Develop training programs for Sales, Marketing, Channel, and CX teams for new products, marketing programs, and technology that reinforce processes and methodology, drive adoption, and promote best practices
• Design, execute, and enhance enablement programs including onboarding and ongoing training to support the needs of a dynamic, growing organization
• Monitor skill development and manage individual development plans for Sales, Channel, and CX reps
• Work within Revenue Operations to monitor and maintain reporting on enablement effectiveness across the team

What We Are Looking For

• 4+ years of training and enablement experience in high-growth, startup organizations
• 2+ years of B2B SaaS L&D experience with increasing responsibility and ownership
• Experience implementing sales methodology across GTM teams
• Experience working in tools such as an LMS, CMS, Notion, Gong, Salesforce, etc.
• Strategic thinker who can take broad visions and concepts and develop structured plans, actions, and measures and then execute those plans
• Experience in developing and managing Sales competency models and learning paths
• Ability to operate in ambiguity and take broad, aspirational goals and turn them into scalable, repeatable processes, systems, and learning programs
• You are a clear and polished communicator: You can distill complex topics and ideas into something digestible for a wide array of learners, and you can deliver clear and engaging messaging both verbally and written (with an eye toward the ways to adapt communication approaches for different audiences).
• Proven program management and project management skills
• Demonstrates ability to coach peers to up-level performance of the team
• Enjoy working in a high-growth, dynamic company environment, using the broader team within enablement platforms or learning management systems to convey value to customers
• Flexible and adaptable to meet the needs of the changing market, our customers, and our business
• Demonstrated ability to think strategically, and work in complex situations
• Naturally self-driven, results-oriented and able to work as part of a team

As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale's compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire's base salary. Individual offers may vary based on experience and skill set.

For this position, our pay ranges reflect target OTE (on target earnings), inclusive of base salary and variable compensation tied to the attainment of quarterly sales targets.

Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. We encourage you to help us break that statistic!

What We Offer

• An inclusive, flexible environment where you can be your authentic self. We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.
• A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).
• Comprehensive group benefits with no waiting period. Take advantage of coverage for health, vision, dental, and more for you and your family!
• All-remote with the opportunity to work from anywhere—enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). 
• Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team/department off-sites, or use your individual travel budget to meet up with team members in Canada, the US, or the UK. 
• Support for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities. 
• Paid time off and a healthy work-life integration. Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world! We encourage all Tailscalars to take 4-6 weeks of vacation annually. 
• A build-your-own home office setup. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $1000 USD to customize your workstation to make it your own. 
• Generous parental leave program from your first day. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups for up to 26 weeks.