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Customer Success Engineer Remote Work (United States) ID-8514

About Tailscale:
Tailscale is redefining the Internet with software that makes it easy to securely connect people and their devices, no matter where they are. From hobbyists to multinational corporations, Tailscale empowers teams of all sizes to protect their networks, share internal tools, and more.

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Virtual Assistant, $45/hr, Remote, No Experience, Night Job
Entry-Level Remote Data Entry, $50/hr, Evening Job
Customer Support, No Degree, $40/hr, Remote, Weekend Job
Remote Phone Job, $42/hr, Part-Time, College Student Friendly
Virtual Assistant, $40/hr, Remote, No Degree, Night Job
Part-Time Data Entry, $45/hr, Remote, College Student Friendly
Remote Moderator, No Degree, $50/hr, Evening, Weekend Job
Remote Customer Support, $42/hr, Night Job, No Experience
Live Chat Support, $40/hr, Remote, Entry Level, Part-Time
Virtual Assistant, Remote, $42/hr, Weekend, No Experience
Remote Data Entry, $45/hr, No Degree, Night Shift
Part-Time Customer Support, $40/hr, Remote, College Student
Remote Live Chat, $50/hr, Part-Time, Evening/Night Job
Entry Level Phone Job, $42/hr, Remote, No Degree Required
Weekend Data Entry, $45/hr, Remote, No Experience
Remote Virtual Assistant, $40/hr, Evening, Part-Time Job
Remote Moderator, $42/hr, Part-Time, Weekend, No Degree
Data Entry, $45/hr, Remote, Night Shift, College Student Job
Phone Support, Remote, $50/hr, No Experience, Part-Time
Virtual Assistant, No Experience, $42/hr, Remote, Weekend
Remote Customer Support, $45/hr, Part-Time, College Student
Data Entry, Remote, $40/hr, Night Shift, No Degree
Evening Virtual Assistant, Remote, $45/hr, No Experience
Weekend Customer Support, $42/hr, Remote, College Student
Remote Data Entry, $50/hr, No Experience, Evening/Night Job
Virtual Assistant, $42/hr, Remote, Weekend, Entry Level
Remote Phone Support, $45/hr, Evening, No Experience Required
Data Entry, No Experience, $50/hr, Remote, College Student
Remote Moderator, $40/hr, Weekend, No Degree, Part-Time
Live Chat Support, Remote, $42/hr, Night Shift, College Student
Phone Job, $50/hr, Remote, No Degree, Part-Time, Weekend
Data Entry, $45/hr, Remote, Evening, No Experience Required
Virtual Assistant, No Experience, $42/hr, Remote, Part-Time
Remote Customer Support, $50/hr, Night Shift, No Degree
Remote Data Entry, $40/hr, College Student Friendly, Part-Time
Live Chat Support, $42/hr, Weekend, Remote, No Degree
Virtual Assistant, Remote, $45/hr, Evening, No Experience
Remote Phone Job, $50/hr, College Student, Night Shift
Remote Moderator, $42/hr, Weekend, No Experience Required
Data Entry, No Degree, $45/hr, Part-Time, Remote Job
Customer Support, $50/hr, Remote, Evening/Night Job, No Degree
Virtual Assistant, $42/hr, Remote, Weekend, No Degree
Remote Live Chat, $45/hr, College Student, No Experience
Remote Data Entry, $40/hr, Part-Time, No Degree Required
Phone Support, $50/hr, Weekend, Remote, No Experience
Virtual Assistant, $42/hr, Evening, Remote, No Degree
Remote Customer Support, $45/hr, No Experience, Part-Time
Data Entry, $50/hr, Night Job, No Degree, Remote
Remote Moderator, $40/hr, College Student Friendly, Part-Time
Virtual Assistant, Remote, $42/hr, Weekend, No Experience
Remote Phone Job, $45/hr, Part-Time, No Degree Required
Customer Support, $50/hr, Night Job, Remote, No Experience
Data Entry, Remote, $42/hr, Evening Job, No Degree
Live Chat Support, $45/hr, Weekend, Remote, College Student
Virtual Assistant, Remote, $50/hr, Part-Time, Night Shift
Data Entry, $40/hr, No Experience, Remote, Weekend Job
Remote Phone Job, $45/hr, No Degree, College Student Friendly
Customer Support, $42/hr, Remote, Evening, No Experience
Virtual Assistant, $50/hr, Weekend, No Degree, Remote
Remote Data Entry, $40/hr, Part-Time, College Student Job
Phone Support, Remote, $42/hr, Evening/Night Shift
Virtual Assistant, No Degree, $45/hr, Remote, Part-Time
Live Chat Support, $50/hr, Remote, No Experience Required
Remote Moderator, $42/hr, College Student, Weekend Job
Data Entry, $45/hr, Remote, Night Job, No Degree
Virtual Assistant, $50/hr, Remote, Part-Time, Evening Job
Remote Customer Support, $42/hr, Weekend, No Experience
Phone Job, $45/hr, Remote, Night Shift, No Degree
Remote Live Chat, $50/hr, College Student, No Experience
Data Entry, $40/hr, Part-Time, Remote, Weekend Job
Virtual Assistant, $42/hr, Remote, No Experience, Evening
Remote Phone Support, $45/hr, Night Job, College Student
Remote Moderator, $50/hr, No Degree, Weekend, Part-Time
Virtual Assistant, $40/hr, Remote, Night Shift, No Experience
Customer Support, $42/hr, Remote, Part-Time, No Degree
Remote Data Entry, $45/hr, Weekend Job, College Student
Phone Support, Remote, $50/hr, No Experience, Night Shift
Virtual Assistant, $42/hr, Evening, Remote, College Student
Live Chat Support, $45/hr, Part-Time, Remote, No Degree
Data Entry, $50/hr, Remote, Evening Job, College Student
Virtual Assistant, $40/hr, Weekend, Remote, No Experience
Remote Phone Job, $42/hr, Night Shift, College Student Friendly
Remote Customer Support, $45/hr, No Degree, Evening Job
Virtual Assistant, $50/hr, Part-Time, Remote, Weekend Job
Data Entry, $40/hr, Evening Job, No Experience, Remote
Remote Live Chat, $42/hr, Weekend, No Degree, Part-Time
Virtual Assistant, $45/hr, No Experience, Remote, Night Job
Phone Job, $50/hr, Remote, Part-Time, College Student
Remote Data Entry, $42/hr, Evening/Night Job, No Experience
Remote Moderator, $45/hr, No Degree, Weekend Job, Part-Time
Live Chat Support, $50/hr, Remote, Night Shift, No Degree
Virtual Assistant, $40/hr, Weekend, College Student, Remote
Remote Phone Job, $42/hr, Part-Time, No Experience Required
Remote Data Entry, $45/hr, No Degree, Weekend, Night Job
Virtual Assistant, $50/hr, Evening, Remote, College Student
Customer Support, $42/hr, Weekend Job, Remote, No Degree
Phone Support, $45/hr, Remote, No Experience, Evening Job
Data Entry, $50/hr, Night Shift, No Degree, Remote Job

Founded in 2019 and backed by Accel, CRV, Insight, Heavybit, and Uncork Capital, we’re a fully distributed team building a safer, more sensible Internet.

Role Overview:
As the Founding Customer Success Engineer (CSE) at Tailscale, you’ll play a pivotal role in bridging technical solutions with customer needs. You’ll help strategic customers onboard, adopt, and succeed with Tailscale’s products. Acting as a trusted advisor, you’ll manage technical support, drive customer engagement, and collaborate internally to ensure an exceptional customer experience.

Key Responsibilities:

  • Lead onboarding processes for strategic customers, ensuring successful adoption.
  • Provide expert technical support, assisting with configuration, troubleshooting, and integrations.
  • Conduct quarterly business reviews (QBRs) to discuss metrics, usage, and future goals.
  • Build and maintain strong relationships with customers, offering tailored best practices and recommendations.
  • Collaborate cross-functionally to relay customer feedback and improve the product experience.
  • Develop technical documentation, FAQs, and guides to empower customers.

What We’re Looking For:

  • Experience: 6+ years in technical roles, with at least 2 years in customer-facing positions (e.g., Solutions Engineer, Sr. Support Engineer).
  • Domain Knowledge: Strong understanding of networking, VPNs, and security principles. Experience with cloud infrastructure (AWS, GCP, Azure), Docker, Kubernetes, and DevOps tools.
  • Communication Skills: Ability to explain complex technical concepts to diverse audiences. Strong verbal and written communication skills are essential.
  • Problem-Solving: Analytical mindset with excellent troubleshooting abilities.
  • Customer Focus: Passion for delivering exceptional customer experiences and fostering long-term relationships.
  • Collaboration: Ability to work cross-functionally with product, engineering, and sales teams.
  • Preferred Skills: Familiarity with Scrum/Agile frameworks, experience supporting US customers, and knowledge of enterprise software solutions.

What We Offer:

  • Compensation: Competitive base salary, equity incentive plan, and performance-based commissions.
  • Comprehensive Benefits: Health, vision, dental coverage, and more from day one.
  • Work Flexibility: Fully remote work with access to coworking spaces and annual company retreats.
  • Professional Growth: $1,500 annually for development, mentorship opportunities, and internal promotions.
  • Generous PTO: Flexible paid time off program (encouraged 4-6 weeks annually).
  • Parental Leave: Up to 26 weeks of top-up parental leave.
  • Home Office Setup: Choose your laptop (Mac or PC), monthly internet reimbursement, and $1,000 to customize your workstation.

Why Join Tailscale?
At Tailscale, we’re building the future of the Internet while fostering an inclusive, flexible work environment. Join our global team of innovators and help shape a safer, smarter Internet for everyone.

How to Apply:
Ready to make an impact? Submit your application today and take the first step toward becoming part of our forward-thinking, collaborative team.

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...

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