Tailscale
Tailscale is proud to be a fully remote company with team members in the United States, Canada and the United Kingdom. We recognize an inclusive workplace starts with a team that is not bound by geographical location, lifestyle, or life stage. No matter where you choose to work, you’ll be supported and empowered to do your best work.
At Tailscale, we’re building the new Internet. Our mission is to remove the overhead and complexity from the “long tail” of software and operational problems that people face every day. We’re searching for smart, passionate people who see the world differently, who aren’t afraid to challenge the status quo and work as a team to solve challenges together.
Are you ready to be part of the change? Check out our current openings below to apply!
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Senior Customer Account Executive
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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
Join our rapidly growing Sales team where you will play an important role at one of the fastest growing companies in the Developer Security space.
As a Customer Account Executive, you will be responsible for helping expand and renew current customer accounts. You will focus on finding additional use cases, educating the client base on new feature releases, and ensuring the successful adoption of Tailscale across all of your existing customer accounts. You will partner closely with the Solutions Engineering team, as well as collaborate with the Customer Success, Support, Marketing, and Product teams.
We're an energetic company with a wide variety of backgrounds. We coach each other, share feedback, and collaborate to maximize our performance and earning potential, all the while aligning with our customers' needs.
Key Responsibilities
- Become an expert in how Tailscale helps our customers
- Build a credible pipeline every quarter by engaging with clients on upsells and renewals
- Own an upsell and renewal number across your accounts
- Help educate customers on the value of Tailscale throughout the evaluation & adoption cycle
- Generate short-term results while maintaining annual pipeline coverage
- Provide accurate weekly forecasting & revenue delivery
- Create mutual action/success plans with prospective and existing customers where appropriate to help them evaluate and expand their usage of the Tailscale product
What We Are Looking For
- 2+ years of closing experience in an AE or an AM role
- A strong desire to join a high-growth software startup
- Has sold developer and/or technical products, especially in a product-led growth (PLG) motion
- Experience presenting to senior managers and executives
- The ability to manage many opportunities simultaneously at various stages, coupled with a strong track record of meeting and exceeding quota
- Experience using Gong, or similar, to collaborate internally and manage pipeline
- Experience partnering with a Sales Engineering team, support, and customer success team to drive positive outcomes for clients
- Proactive from lead to close - the hiring manager for this role is Spencer Cranson. If this opportunity really excites you, please don’t just apply on the website. Prospect thoughtfully and tell us why you’re the best candidate for this position.
- This role is based in Denver and is hybrid preferred (3 days/week in-office). #LI-Hybrid
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!
- Remote first company—most of our teams work fully remotely. 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). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.
- Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, and the United Kingdom. We support intentional in-person connection through team travel and distributed collaboration.
- 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!
- 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.
Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit https://tailscale.com/scam-awareness.
Ready to apply?
Apply to Tailscale
Manager, Sales Development Representative
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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
We are looking for a thoughtful, hands-on Manager to lead our Sales Development team. In this role, you will coach and develop a group of curious, motivated SDRs who are responsible for building qualified pipeline for the sales organization. You’ll guide their day-to-day execution, help refine our prospecting motions, and partner closely with Sales, Marketing, and Operations to align on strategy, messaging, and highest-value opportunities.
If you are passionate about coaching early-career sellers, optimizing prospecting strategies, and helping teams grow in a fast-paced startup environment, we’d love to talk to you.
Key Responsibilities
- Lead, coach, and mentor a team of Sales Development Representatives with clear goals, actionable feedback, and ongoing skill development.
- Become an expert in how Tailscale solves real customer problems, and train your team to articulate that value with clarity and confidence.
- Build, refine, and operationalize our prospecting playbook across inbound and outbound channels.
- Drive team performance through regular coaching sessions, call reviews, pipeline reviews, and weekly/monthly operational cadences.
- Partner closely with Sales, Marketing, RevOps, and Enablement to align ICP, improve lead quality, run campaigns, and accelerate pipeline creation.
- Own SDR KPIs: track performance, forecast pipeline creation, and use data to identify opportunities for conversion improvements.
- Recruit, onboard, and ramp exceptional SDR talent, helping them grow into future Account Executives or leaders at Tailscale.
- Foster an inclusive, collaborative, high-energy culture rooted in curiosity, accountability, and customer empathy.
- Represent the SDR team in cross-functional planning and help shape our go-to-market strategy as we scale.
What We Are Looking For
- 2+ years experience leading SDR or BDR teams in a B2B SaaS environment
- A track record of coaching SDRs, improving prospecting performance, and consistently meeting pipeline targets
- Experience in outbound and inbound prospecting motions across multiple segments and personas
- Strong written and verbal communication skills with the ability to break down complex ideas simply
- A data-driven mindset - comfortable using metrics, reporting, and tooling (Salesforce, Outreach, Gong, Sales Navigator, etc.) to guide decisions
- Ability to manage many activities and priorities simultaneously while keeping the team focused on what matters most
- A passion for coaching, developing future sales talent, and helping others succeed
- Willingness to travel 25% for industry events and team gatherings, with week-long quarterly stays in Vancouver during the first 2–3 quarters
- This role is based in Toronto (this role will be building out a new sales hub location of Tailscale) and is hybrid preferred (3 days/week in-office). #LI-Hybrid
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!
- Remote first company—most of our teams work fully remotely. 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). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.
- Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, and the United Kingdom. We support intentional in-person connection through team travel and distributed collaboration.
- 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!
- 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.
Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit https://tailscale.com/scam-awareness.
Ready to apply?
Apply to Tailscale
Manager, Sales Development Representative
Share this job
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
We are looking for a thoughtful, hands-on Manager to lead our Sales Development team. In this role, you will coach and develop a group of curious, motivated SDRs who are responsible for building qualified pipeline for the sales organization. You’ll guide their day-to-day execution, help refine our prospecting motions, and partner closely with Sales, Marketing, and Operations to align on strategy, messaging, and highest-value opportunities.
If you are passionate about coaching early-career sellers, optimizing prospecting strategies, and helping teams grow in a fast-paced startup environment, we’d love to talk to you.
Key Responsibilities
- Lead, coach, and mentor a team of Sales Development Representatives with clear goals, actionable feedback, and ongoing skill development.
- Become an expert in how Tailscale solves real customer problems, and train your team to articulate that value with clarity and confidence.
- Build, refine, and operationalize our prospecting playbook across inbound and outbound channels.
- Drive team performance through regular coaching sessions, call reviews, pipeline reviews, and weekly/monthly operational cadences.
- Partner closely with Sales, Marketing, RevOps, and Enablement to align ICP, improve lead quality, run campaigns, and accelerate pipeline creation.
- Own SDR KPIs: track performance, forecast pipeline creation, and use data to identify opportunities for conversion improvements.
- Recruit, onboard, and ramp exceptional SDR talent, helping them grow into future Account Executives or leaders at Tailscale.
- Foster an inclusive, collaborative, high-energy culture rooted in curiosity, accountability, and customer empathy.
- Represent the SDR team in cross-functional planning and help shape our go-to-market strategy as we scale.
What We Are Looking For
- 2+ years experience leading SDR or BDR teams in a B2B SaaS environment
- A track record of coaching SDRs, improving prospecting performance, and consistently meeting pipeline targets
- Experience in outbound and inbound prospecting motions across multiple segments and personas
- Strong written and verbal communication skills with the ability to break down complex ideas simply
- A data-driven mindset - comfortable using metrics, reporting, and tooling (Salesforce, Outreach, Gong, Sales Navigator, etc.) to guide decisions
- Ability to manage many activities and priorities simultaneously while keeping the team focused on what matters most
- A passion for coaching, developing future sales talent, and helping others succeed
- Willingness to travel 25% of the time for industry events or team gatherings
- This role is based in Vancouver and is hybrid preferred (3 days/week in-office). #LI-Hybrid
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!
- Remote first company—most of our teams work fully remotely. 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). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.
- Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, and the United Kingdom. We support intentional in-person connection through team travel and distributed collaboration.
- 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!
- 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.
Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit https://tailscale.com/scam-awareness.
Ready to apply?
Apply to Tailscale
Customer Account Executive
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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
Join our rapidly growing Sales team where you will play an important role at one of the fastest growing companies in the Developer Security space.
As a Customer Account Executive, you will be responsible for helping expand and renew current customer accounts. You will focus on finding additional use cases, educating the client base on new feature releases, and ensuring the successful adoption of Tailscale across all of your existing customer accounts. You will partner closely with the Solutions Engineering team, as well as collaborate with the Customer Success, Support, Marketing, and Product teams.
We're an energetic company with a wide variety of backgrounds. We coach each other, share feedback, and collaborate to maximize our performance and earning potential, all the while aligning with our customers' needs.
Key Responsibilities
- Become an expert in how Tailscale helps our customers
- Build a credible pipeline every quarter by engaging with clients on upsells and renewals
- Own an upsell and renewal number across your accounts
- Help educate customers on the value of Tailscale throughout the evaluation & adoption cycle
- Generate short-term results while maintaining annual pipeline coverage
- Provide accurate weekly forecasting & revenue delivery
- Create mutual action/success plans with prospective and existing customers where appropriate to help them evaluate and expand their usage of the Tailscale product
What We Are Looking For
- Up to 1 year of quota-carrying or closing experience, in an AE or an AM role
- A strong desire to join a high-growth software startup in a fully remote role
- Has sold developer and/or technical products, especially in a product-led growth (PLG) motion
- Experience presenting to senior managers and executives
- The ability to manage many opportunities simultaneously at various stages, coupled with a strong track record of meeting and exceeding quota
- Experience using Gong, or similar, to collaborate internally and manage pipeline
- Experience partnering with a Sales Engineering team, support, and customer success team to drive positive outcomes for clients
- Proactive from lead to close - the hiring manager for this role is Spencer Cranson. If this opportunity really excites you, please don’t just apply on the website. Prospect thoughtfully and tell us why you’re the best candidate for this position.
- This role is based in Denver and is hybrid preferred (3 days/week in-office). #LI-Hybrid
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!
- Remote first company—most of our teams work fully remotely. 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). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.
- Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, and the United Kingdom. We support intentional in-person connection through team travel and distributed collaboration.
- 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!
- 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.
Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit https://tailscale.com/scam-awareness.
Ready to apply?
Apply to Tailscale
Solutions Engineer - Commercial (New Business)
Share this job
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 seeking an experienced Commercial Solutions Engineer to partner with Sales in driving new business for Commercial customers. You will co-own a book of business with Account Executives, lead technical discovery and architecture design, and act as a trusted advisor to customers. This role blends deep networking and security expertise with strong sales acumen to win competitive deals, scale enablement, and influence product direction.
Key Responsibilities
- Partner with AEs to identify, qualify, and close new Commercial customer opportunities.
- Lead technical discovery, solution architecture, demos, and POCs to accelerate decision-making.
- Guide complex multi-stakeholder deals, aligning technical and business objectives.
- Provide structured feedback to shape product roadmap and GTM strategy.
- Build scalable enablement resources, demo environments, and solution blueprints for the SE team.
What We Are Looking For
- 4/5+ years in a customer-facing SE/SA role within networking or security software
- Proven experience co-owning pipeline and influencing quota outcomes with Sales
- Strong networking fundamentals (TCP/IP, DNS, routing, firewalls) and troubleshooting skills
- Deep understanding of zero-trust networking, secure connectivity, and IAM integrations (SSO, SAML, OIDC)
- Understanding of AI gateway and governance platforms for centralized LLM access, usage visibility, and audit
- Familiarity with privileged access management (PAM) including session recording, just-in-time access, and protocol-aware controls (e.g., Border0, CyberArk, Teleport)
- Experience with infrastructure as code tools such as Terraform, Pulumi, Ansible, or CloudFormation
- Hands-on architecture experience with AWS, GCP, and/or Azure
- Excellent communication skills, capable of translating technical features into business value
- Experience thriving in high-growth or startup environments
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!
- Remote first company—most of our teams work fully remotely. 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). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.
- Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, and the United Kingdom. We support intentional in-person connection through team travel and distributed collaboration.
- 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!
- 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.
Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit https://tailscale.com/scam-awareness.
Ready to apply?
Apply to Tailscale
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 seeking an experienced Commercial Solutions Engineer to partner with Sales in driving new business for Commercial customers. You will co-own a book of business with Account Executives, lead technical discovery and architecture design, and act as a trusted advisor to customers. This role blends deep networking and security expertise with strong sales acumen to win competitive deals, scale enablement, and influence product direction.
Key Responsibilities
- Partner with AEs to identify, qualify, and close new Commercial customer opportunities.
- Lead technical discovery, solution architecture, demos, and POCs to accelerate decision-making.
- Guide complex multi-stakeholder deals, aligning technical and business objectives.
- Provide structured feedback to shape product roadmap and GTM strategy.
- Build scalable enablement resources, demo environments, and solution blueprints for the SE team.
What We Are Looking For
- 4/5+ years in a customer-facing SE/SA role within networking or security software
- Proven experience co-owning pipeline and influencing quota outcomes with Sales
- Strong networking fundamentals (TCP/IP, DNS, routing, firewalls) and troubleshooting skills
- Deep understanding of zero-trust networking, secure connectivity, and IAM integrations (SSO, SAML, OIDC)
- Understanding of AI gateway and governance platforms for centralized LLM access, usage visibility, and audit
- Familiarity with privileged access management (PAM) including session recording, just-in-time access, and protocol-aware controls (e.g., Border0, CyberArk, Teleport)
- Experience with infrastructure as code tools such as Terraform, Pulumi, Ansible, or CloudFormation
- Hands-on architecture experience with AWS, GCP, and/or Azure
- Excellent communication skills, capable of translating technical features into business value
- Experience thriving in high-growth or startup environments
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!
- Remote first company—most of our teams work fully remotely. 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). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.
- Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, and the United Kingdom. We support intentional in-person connection through team travel and distributed collaboration.
- 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!
- 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.
Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit https://tailscale.com/scam-awareness.
Ready to apply?
Apply to Tailscale
Solutions Engineer - Commercial (Expansion Sales)
Share this job
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 seeking an experienced Commercial Solutions Engineer to partner with Sales in driving new business for Commercial customers. You will co-own a book of business with Account Executives, lead technical discovery and architecture design, and act as a trusted advisor to customers. This role blends deep networking and security expertise with strong sales acumen to win competitive deals, scale enablement, and influence product direction.
Key Responsibilities
- Partner with AEs to identify, qualify, and close new Commercial customer opportunities.
- Lead technical discovery, solution architecture, demos, and POCs to accelerate decision-making.
- Guide complex multi-stakeholder deals, aligning technical and business objectives.
- Provide structured feedback to shape product roadmap and GTM strategy.
- Build scalable enablement resources, demo environments, and solution blueprints for the SE team.
What We Are Looking For
- 4/5+ years in a customer-facing SE/SA role within networking or security software
- Proven experience co-owning pipeline and influencing quota outcomes with Sales
- Strong networking fundamentals (TCP/IP, DNS, routing, firewalls) and troubleshooting skills
- Deep understanding of zero-trust networking, secure connectivity, and IAM integrations (SSO, SAML, OIDC)
- Understanding of AI gateway and governance platforms for centralized LLM access, usage visibility, and audit
- Familiarity with privileged access management (PAM) including session recording, just-in-time access, and protocol-aware controls (e.g., Border0, CyberArk, Teleport)
- Experience with infrastructure as code tools such as Terraform, Pulumi, Ansible, or CloudFormation
- Hands-on architecture experience with AWS, GCP, and/or Azure
- Excellent communication skills, capable of translating technical features into business value
- Experience thriving in high-growth or startup environments
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!
- Remote first company—most of our teams work fully remotely. 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). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.
- Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, and the United Kingdom. We support intentional in-person connection through team travel and distributed collaboration.
- 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!
- 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.
Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit https://tailscale.com/scam-awareness.
Ready to apply?
Apply to Tailscale
Solutions Engineer - Commercial (Expansion Sales)
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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 seeking an experienced Commercial Solutions Engineer to partner with Sales in driving new business for Commercial customers. You will co-own a book of business with Account Executives, lead technical discovery and architecture design, and act as a trusted advisor to customers. This role blends deep networking and security expertise with strong sales acumen to win competitive deals, scale enablement, and influence product direction.
Key Responsibilities
- Partner with AEs to identify, qualify, and close new Commercial customer opportunities.
- Lead technical discovery, solution architecture, demos, and POCs to accelerate decision-making.
- Guide complex multi-stakeholder deals, aligning technical and business objectives.
- Provide structured feedback to shape product roadmap and GTM strategy.
- Build scalable enablement resources, demo environments, and solution blueprints for the SE team.
What We Are Looking For
- 4/5+ years in a customer-facing SE/SA role within networking or security software
- Proven experience co-owning pipeline and influencing quota outcomes with Sales
- Strong networking fundamentals (TCP/IP, DNS, routing, firewalls) and troubleshooting skills
- Deep understanding of zero-trust networking, secure connectivity, and IAM integrations (SSO, SAML, OIDC)
- Understanding of AI gateway and governance platforms for centralized LLM access, usage visibility, and audit
- Familiarity with privileged access management (PAM) including session recording, just-in-time access, and protocol-aware controls (e.g., Border0, CyberArk, Teleport)
- Experience with infrastructure as code tools such as Terraform, Pulumi, Ansible, or CloudFormation
- Hands-on architecture experience with AWS, GCP, and/or Azure
- Excellent communication skills, capable of translating technical features into business value
- Experience thriving in high-growth or startup environments
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!
- Remote first company—most of our teams work fully remotely. 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). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.
- Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, and the United Kingdom. We support intentional in-person connection through team travel and distributed collaboration.
- 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!
- 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.
Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit https://tailscale.com/scam-awareness.
Ready to apply?
Apply to Tailscale
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
We are looking for a high-impact Customer Experience Operations Manager to join our Revenue Operations team. This is a critical, cross-functional role that sits at the intersection of strategy, data, and execution, supporting our global post-sales organization, including Customer Success, Customer Success Engineering, and Support Engineering, to operate at scale and deliver exceptional customer outcomes.
You'll partner closely with CS leadership, Revenue Operations, Finance, and Product to design and run the operational systems, processes, and insights that drive retention, expansion, and customer health across our portfolio. You'll shape how our post-sales teams operate, influence strategic decisions, and directly impact our ability to deliver world-class customer experiences.
If you're energized by building scalable programs, turning messy data into clear insights, and being the operational backbone of a high-growth team, this role is for you.
Key Responsibilities
Run and Scale CS Operations
- Own the operational rhythm of the Customer Experience organization: reporting cadences, QBRs, renewal forecasting, health scoring, capacity modeling, and tooling.
- Design and implement the customer journey alongside Product, Marketing, and other cross-functional partners to ensure proper coverage of customer accounts.
- Define and implement customer health scoring models that incorporate product usage, support signals, and engagement data to surface risk and opportunity proactively.
- Implement automated workflows to process renewals and customer programs at scale.
- Maintain data integrity across post-sales systems (Salesforce, CS Platform, BI tools) to ensure CS, CSE, and Support teams have reliable, actionable data.
Drive Strategy, Planning, and Segmentation
- Partner with post-sales leadership to define customer segmentation, coverage models, and engagement strategies across CS, CSE, and Support Engineering.
- Support annual and quarterly planning, including capacity modeling across all post-sales functions.
- Align post-sales motions with company-level goals including NRR, GRR, product adoption, and support SLAs.
Drive Insights and Program Execution
- Translate data signals into proactive recommendations, surfacing trends in customer health, churn risk, product adoption, and team performance for CS leadership.
- Build and maintain dashboards and reporting across customer health and risk, support performance (SLAs, backlog, resolution time), product adoption and engagement, and retention and expansion metrics.
- Receive feedback from CS, CSE, and Support teams to define and prioritize strategic projects and process improvements.
Own Cross-Functional Programs
- Work cross-functionally with Revenue Operations, Finance, Product, and Marketing to support operational programs aligned to broader organizational strategy.
- Improve handoffs between teams (Sales to CS to Support to Engineering) to ensure a seamless, consistent customer experience.
- Identify tooling and process gaps and own the roadmap to close them, leveraging automation and AI to drive efficiency.
Enable the Post-Sales Team
- Develop and operationalize lifecycle programs and playbooks across CS, CSE, and Support covering onboarding, success plans, risk mitigation, escalations, expansion, and renewals.
- Act as the primary point of contact for post-sales tooling, including CS platform administration, Salesforce integrations, and BI reporting.
What We Are Looking For
Experience
- 5 to 8+ years of experience in Customer Success Operations, Revenue Operations, or a related GTM operations role, preferably in a high-growth B2B SaaS environment.
- Proven experience designing and executing programs that scale, from ideation through implementation and measurement.
- Experience supporting multi-functional post-sales teams (Customer Success, Customer Success Engineering, Support Engineering, Renewals, or Professional Services) is strongly preferred.
- Track record of working cross-functionally and building trust with stakeholders across CS, Sales, Finance, and Product.
- Experience with renewal operations and post-sales GTM motions including expansion and professional services.
Technical Skills
- Strong working knowledge of Salesforce (required) and a CS platform such as Gainsight, Planhat, or Totango.
- Proficiency with BI and analytics tools such as Looker, with the ability to build reports and dashboards independently.
- Familiarity with support tooling such as Jira Service Management.
- Familiarity with SQL or BigQuery is a strong plus; data fluency is essential.
- Familiarity with AI-driven tooling or workflow automation platforms to improve post-sales productivity and scale customer programs.
Mindset and Ways of Working
- Systems thinker who can connect workflows across CS, CSE, Support, and Revenue teams.
- Strong analytical skills with the ability to build and interpret complex data, identify the key insights, and communicate them clearly to any audience.
- Customer-first orientation with a genuine passion for improving the post-sales experience through better process and tooling.
- Proven ability to lead strategic initiatives while executing hands-on in a fast-paced, evolving environment.
- Highly collaborative with strong stakeholder management skills and the ability to influence without authority.
- Comfortable operating in ambiguity and building from scratch as the organization grows.
- Excellent written and verbal communication skills with the ability to manage multiple workstreams simultaneously.
Nice to Have
- Experience in a high-growth startup environment.
- Familiarity with product usage analytics tools such as Amplitude or Pendo.
- Experience with PLG or hybrid sales motions.
- Experience building or maturing a CS Operations function from scratch.
- Background working closely with Engineering or Support organizations.
What Success Looks like
- A unified, seamless experience across CS, Customer Success Engineering, and Support Engineering, with clear ownership and consistent handoffs at every stage.
- Customer segmentation and coverage models that are well-defined, actively maintained, and aligned to company growth goals.
- Scalable systems and processes that measurably improve team efficiency and reduce manual work across post-sales functions.
- Leadership has clear, real-time visibility into customer health, risk, support performance, and expansion opportunity.
- Measurable improvements in Net Revenue Retention (NRR) and Gross Revenue Retention (GRR).
- Improved customer satisfaction as reflected in CSAT and NPS scores.
- Faster time-to-resolution and stronger support SLA performance across Support Engineering.
- Strong cross-functional alignment between post-sales, Product, and Sales that accelerates both retention and expansion.
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!
- Remote first company—most of our teams work fully remotely. 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). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.
- Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, and the United Kingdom. We support intentional in-person connection through team travel and distributed collaboration.
- 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!
- 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.
Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit https://tailscale.com/scam-awareness.
Ready to apply?
Apply to Tailscale
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
We are looking for a high-impact Customer Experience Operations Manager to join our Revenue Operations team. This is a critical, cross-functional role that sits at the intersection of strategy, data, and execution, supporting our global post-sales organization, including Customer Success, Customer Success Engineering, and Support Engineering, to operate at scale and deliver exceptional customer outcomes.
You'll partner closely with CS leadership, Revenue Operations, Finance, and Product to design and run the operational systems, processes, and insights that drive retention, expansion, and customer health across our portfolio. You'll shape how our post-sales teams operate, influence strategic decisions, and directly impact our ability to deliver world-class customer experiences.
If you're energized by building scalable programs, turning messy data into clear insights, and being the operational backbone of a high-growth team, this role is for you.
Key Responsibilities
Run and Scale CS Operations
- Own the operational rhythm of the Customer Experience organization: reporting cadences, QBRs, renewal forecasting, health scoring, capacity modeling, and tooling.
- Design and implement the customer journey alongside Product, Marketing, and other cross-functional partners to ensure proper coverage of customer accounts.
- Define and implement customer health scoring models that incorporate product usage, support signals, and engagement data to surface risk and opportunity proactively.
- Implement automated workflows to process renewals and customer programs at scale.
- Maintain data integrity across post-sales systems (Salesforce, CS Platform, BI tools) to ensure CS, CSE, and Support teams have reliable, actionable data.
Drive Strategy, Planning, and Segmentation
- Partner with post-sales leadership to define customer segmentation, coverage models, and engagement strategies across CS, CSE, and Support Engineering.
- Support annual and quarterly planning, including capacity modeling across all post-sales functions.
- Align post-sales motions with company-level goals including NRR, GRR, product adoption, and support SLAs.
Drive Insights and Program Execution
- Translate data signals into proactive recommendations, surfacing trends in customer health, churn risk, product adoption, and team performance for CS leadership.
- Build and maintain dashboards and reporting across customer health and risk, support performance (SLAs, backlog, resolution time), product adoption and engagement, and retention and expansion metrics.
- Receive feedback from CS, CSE, and Support teams to define and prioritize strategic projects and process improvements.
Own Cross-Functional Programs
- Work cross-functionally with Revenue Operations, Finance, Product, and Marketing to support operational programs aligned to broader organizational strategy.
- Improve handoffs between teams (Sales to CS to Support to Engineering) to ensure a seamless, consistent customer experience.
- Identify tooling and process gaps and own the roadmap to close them, leveraging automation and AI to drive efficiency.
Enable the Post-Sales Team
- Develop and operationalize lifecycle programs and playbooks across CS, CSE, and Support covering onboarding, success plans, risk mitigation, escalations, expansion, and renewals.
- Act as the primary point of contact for post-sales tooling, including CS platform administration, Salesforce integrations, and BI reporting.
What We Are Looking For
Experience
- 5 to 8+ years of experience in Customer Success Operations, Revenue Operations, or a related GTM operations role, preferably in a high-growth B2B SaaS environment.
- Proven experience designing and executing programs that scale, from ideation through implementation and measurement.
- Experience supporting multi-functional post-sales teams (Customer Success, Customer Success Engineering, Support Engineering, Renewals, or Professional Services) is strongly preferred.
- Track record of working cross-functionally and building trust with stakeholders across CS, Sales, Finance, and Product.
- Experience with renewal operations and post-sales GTM motions including expansion and professional services.
Technical Skills
- Strong working knowledge of Salesforce (required) and a CS platform such as Gainsight, Planhat, or Totango.
- Proficiency with BI and analytics tools such as Looker, with the ability to build reports and dashboards independently.
- Familiarity with support tooling such as Jira Service Management.
- Familiarity with SQL or BigQuery is a strong plus; data fluency is essential.
- Familiarity with AI-driven tooling or workflow automation platforms to improve post-sales productivity and scale customer programs.
Mindset and Ways of Working
- Systems thinker who can connect workflows across CS, CSE, Support, and Revenue teams.
- Strong analytical skills with the ability to build and interpret complex data, identify the key insights, and communicate them clearly to any audience.
- Customer-first orientation with a genuine passion for improving the post-sales experience through better process and tooling.
- Proven ability to lead strategic initiatives while executing hands-on in a fast-paced, evolving environment.
- Highly collaborative with strong stakeholder management skills and the ability to influence without authority.
- Comfortable operating in ambiguity and building from scratch as the organization grows.
- Excellent written and verbal communication skills with the ability to manage multiple workstreams simultaneously.
Nice to Have
- Experience in a high-growth startup environment.
- Familiarity with product usage analytics tools such as Amplitude or Pendo.
- Experience with PLG or hybrid sales motions.
- Experience building or maturing a CS Operations function from scratch.
- Background working closely with Engineering or Support organizations.
What Success Looks like
- A unified, seamless experience across CS, Customer Success Engineering, and Support Engineering, with clear ownership and consistent handoffs at every stage.
- Customer segmentation and coverage models that are well-defined, actively maintained, and aligned to company growth goals.
- Scalable systems and processes that measurably improve team efficiency and reduce manual work across post-sales functions.
- Leadership has clear, real-time visibility into customer health, risk, support performance, and expansion opportunity.
- Measurable improvements in Net Revenue Retention (NRR) and Gross Revenue Retention (GRR).
- Improved customer satisfaction as reflected in CSAT and NPS scores.
- Faster time-to-resolution and stronger support SLA performance across Support Engineering.
- Strong cross-functional alignment between post-sales, Product, and Sales that accelerates both retention and expansion.
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!
- Remote first company—most of our teams work fully remotely. 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). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.
- Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, and the United Kingdom. We support intentional in-person connection through team travel and distributed collaboration.
- 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!
- 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.
Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit https://tailscale.com/scam-awareness.
Ready to apply?
Apply to Tailscale