Outliers and outperformers wanted

Outliers and outperformers wanted

Uncork Capital-backed companies are building kick-ass teams in engineering, marketing, sales, operations and more.

Uncork Capital-backed companies are building kick-ass teams in engineering, marketing, sales, operations and more.

Product Advocate



Product, Legal
Canada · United States · Remote
Posted on Saturday, May 20, 2023

About Tailscale

Tailscale builds software that makes it easy to connect and secure devices, no matter where they are. Every day, banks and multinational companies use Tailscale to protect their corporate networks. Hobbyists and start-ups trust Tailscale to collaborate and share access to tooling. We're building a future for the Internet that's easy, small and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, HeavyBit, and Uncork Capital.

Job Description

We are looking for founding members for our new and rapidly growing Product Advocate team. As a Product Advocate, you will:

  • Building credibility with customers by providing best practice recommendations, leading product demonstrations, and taking customers to close
  • Work closely with Tailscale’s Solutions Engineering team to provide exceptional customer experiences and collaborate with Enterprise Sales, Marketing, Product, and Support as needed

This may be a perfect fit for you if you are passionate about networking and security, have experience working with customers in a technical capacity, and want to join a fast-growing startup.


  • Qualify inbound sales inquiries, then quickly close the customer or pass the customer to our Enterprise Sales team
  • Take ownership of meeting and exceeding quarterly goals
  • Provide feedback on campaigns to help move customers from free to paid
  • Provide technical expertise in the form of sales presentations and demonstrations
  • Manage and organize your pipeline and activities in Gong and Salesforce


  • 1+ years of experience in a technical, customer-facing role such as Sales Engineer, Support, or SDR
  • A strong desire to join a high-growth software startup in a fully remote role
  • Excellent communication and presentation skill
  • Ability to manage many activities and opportunities simultaneously at various stages

What We Offer

  • An inclusive, flexible environment where you can be your authentic self. We recognize the impact diverse voices and backgrounds have on the growth of our people, our product, and our company. And that flexibility in how and when you work empowers our team to balance work and life.
  • A competitive total compensation package. This includes base salary and an equity incentive plan.
  • Comprehensive group benefits with no waiting period. Take advantage of coverage for health, vision, dental, and more for you and your family!
  • Remote-first with the opportunity to work from anywhere—enjoy a change of scenery wherever you can get wifi and join our company retreats with fellow Tailscalars!
  • Support for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for professional development, leverage our conference budget to learn from experts in your field, or take advantage of mentorship, coaching, and internal promotion opportunities.
  • Paid time off and a healthy work-life balance. Take advantage of 4 weeks of vacation each year, uncapped sick time when you need it, and support for any situation life throws your way!
  • 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.