Writing.io Jobs

About Tailscale

Tailscale is making safe connection effortless 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.

About the Role

Tailscale is looking for an experienced Manager, Developer Relations Engineering to lead a team of technical builders who help developers discover, understand, adopt, and build with Tailscale. You will be accountable for turning Tailscale’s technology into compelling developer experiences—from integrations and example applications to demos, tutorials, open-source projects, and technical content—that drive meaningful developer and business outcomes.

This is a player-coach engineering leadership role that combines team leadership with hands-on technical execution. You’ll lead Tailscale’s Developer Relations Engineering team while continuing to build yourself: developing integrations, demos, example applications, technical prototypes, workshops, and educational experiences that show developers what is possible with Tailscale. You’ll help the team identify the highest-leverage developer problems to solve and turn successful experiments into repeatable programs.

This role partners closely with Product, Engineering, Growth, Content, Sales, Customer Success, and the broader Marketing team. You’ll maintain a clear technical roadmap for the team, surface developer friction and emerging use cases back into the product organization, and build the systems and measurement practices needed to understand which DevRel investments are driving adoption.

We’re looking for someone with strong engineering and technical credibility, excellent product judgment, and a track record of turning developer insight into technical experiences and projects that make complex products easier to understand and adopt.

Key Responsibilities

• Lead Tailscale’s Developer Relations Engineering team and roadmap, translating company, product, and developer priorities into a focused set of technical projects and programs.
• Manage and develop a high-performing team of Developer Relations Engineers. Set clear expectations, give team members meaningful technical ownership, provide strong coaching and feedback, and help both senior and developing talent increase their impact.
• Lead the team in building high-quality technical experiences including integrations, example applications, open-source projects, demos, workshops, reference architectures, tutorials, and other developer tooling that helps developers quickly understand what they can build with Tailscale.
• Identify and personally contribute to high-leverage technical projects. This is a player-coach role: you should be comfortable opening an IDE, building a prototype, reviewing code, debugging an integration, or creating a working demo alongside the team.
• Serve as a visible technical voice for Tailscale through hands-on work such as videos, presentations, demos, integrations, workshops, and community engagement.
• Ensure DevRel eng work is technically accurate, engaging, relevant to its intended audience, and aligned with current product positioning
• Partner closely with Product, Engineering, Growth, Content, Sales, and Customer Success to coordinate launches, educational initiatives, and developer feedback. Influence product strategy by identifying developer workflows and ecosystem opportunities where Tailscale can create differentiated value, and work with Product and Engineering leaders to validate and prioritize those opportunities. Act as the senior DevRel partner for major launches and strategic bets.
• Define, track, and regularly report on DevRel eng performance, including audience growth, engagement, product activation, integration adoption, and contribution to the self-serve funnel
• Use qualitative developer insight and performance data to prioritize programs, improve execution, and demonstrate the value of DevRel eng investments

What We Are Looking For

• 6+ years of relevant experience in Developer Relations, developer advocacy, engineering, or a related field
• 2+ years of experience managing, coaching, or leading technical contributors and scaling a DevRel or similar function.
• Strong software engineering foundation. You should be comfortable writing and reviewing production-quality code, working with APIs and developer tooling, debugging technical problems, and getting hands-on with unfamiliar technologies.
• Experience building developer-facing technical projects such as integrations, SDK examples, reference applications, open-source tools, demos, workshops, or developer infrastructure—and taking them from idea through launch and iteration.
• Ability to translate product and company priorities into a focused technical roadmap for a small team, and to make thoughtful trade-offs between experimentation, developer education, integrations, and other projects.
• Strong program management skills, including planning, prioritization, delegation, and proactive risk communication
• Strong developer-product instincts and the ability to recognize where developers are getting stuck, what will create an “aha” moment, and whether the right solution is a product change, integration, tool, example, tutorial, or explanation.
• Strong written and verbal communication skills, including the ability to explain complex technical concepts clearly and engagingly
• Experience with and joy for collaborating cross-functionally with Product, Engineering, Marketing, Growth, Sales, or Customer Success teams
• Ability to balance hands-on execution with team leadership and long-term program development
• Experience working in public codebases and developer ecosystems, including comfort with GitHub workflows, pull requests, issue discussions, technical feedback, and collaborating with external developers.
• Experience defining and reporting on DevRel eng metrics, program performance, or contribution to product and business outcomes
• Comfortable operating in an ambiguous, fast-moving environment and creating clarity through direct communication and documented plans
• Low ego, high horsepower with a “yes, and” mindset to collaboration
• You have tried and used Tailscale

Nice to Have

• Experience leading DevRel for a developer-focused infrastructure, networking, security, or open-source product
• Deep familiarity with Tailscale, WireGuard, networking concepts, identity-based access, or Zero Trust architecture
• Experience supporting product-led growth or self-serve adoption
• Experience building technical integrations, example applications, community tools, or open-source projects
• Established experience speaking at conferences, hosting technical videos, or facilitating developer workshops
• Experience developing new public-facing technical voices within a team or company
• Familiarity with measuring developer journeys from content engagement through signup, activation, and paid conversion
• Experience managing agency partners, contractors, program budgets, or external contributors
• Experience working in a fast-paced startup or scale-up environment

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.

CAN Pay Range

$215,740—$269,340 CAD

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.
• Employer-funded retirement contributions. Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.
• 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, the United Kingdom, and Singapore. 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 $500 USD to customize your workstation to make it your own.
• Paid parental leave program. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).

Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.

Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.

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.

About Tailscale

Tailscale is making safe connection effortless 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.

About the Role

Tailscale is looking for an experienced Manager, Developer Relations Engineering to lead a team of technical builders who help developers discover, understand, adopt, and build with Tailscale. You will be accountable for turning Tailscale’s technology into compelling developer experiences—from integrations and example applications to demos, tutorials, open-source projects, and technical content—that drive meaningful developer and business outcomes.

This is a player-coach engineering leadership role that combines team leadership with hands-on technical execution. You’ll lead Tailscale’s Developer Relations Engineering team while continuing to build yourself: developing integrations, demos, example applications, technical prototypes, workshops, and educational experiences that show developers what is possible with Tailscale. You’ll help the team identify the highest-leverage developer problems to solve and turn successful experiments into repeatable programs.

This role partners closely with Product, Engineering, Growth, Content, Sales, Customer Success, and the broader Marketing team. You’ll maintain a clear technical roadmap for the team, surface developer friction and emerging use cases back into the product organization, and build the systems and measurement practices needed to understand which DevRel investments are driving adoption.

We’re looking for someone with strong engineering and technical credibility, excellent product judgment, and a track record of turning developer insight into technical experiences and projects that make complex products easier to understand and adopt.

Key Responsibilities

• Lead Tailscale’s Developer Relations Engineering team and roadmap, translating company, product, and developer priorities into a focused set of technical projects and programs.
• Manage and develop a high-performing team of Developer Relations Engineers. Set clear expectations, give team members meaningful technical ownership, provide strong coaching and feedback, and help both senior and developing talent increase their impact.
• Lead the team in building high-quality technical experiences including integrations, example applications, open-source projects, demos, workshops, reference architectures, tutorials, and other developer tooling that helps developers quickly understand what they can build with Tailscale.
• Identify and personally contribute to high-leverage technical projects. This is a player-coach role: you should be comfortable opening an IDE, building a prototype, reviewing code, debugging an integration, or creating a working demo alongside the team.
• Serve as a visible technical voice for Tailscale through hands-on work such as videos, presentations, demos, integrations, workshops, and community engagement.
• Ensure DevRel eng work is technically accurate, engaging, relevant to its intended audience, and aligned with current product positioning
• Partner closely with Product, Engineering, Growth, Content, Sales, and Customer Success to coordinate launches, educational initiatives, and developer feedback. Influence product strategy by identifying developer workflows and ecosystem opportunities where Tailscale can create differentiated value, and work with Product and Engineering leaders to validate and prioritize those opportunities. Act as the senior DevRel partner for major launches and strategic bets.
• Define, track, and regularly report on DevRel eng performance, including audience growth, engagement, product activation, integration adoption, and contribution to the self-serve funnel
• Use qualitative developer insight and performance data to prioritize programs, improve execution, and demonstrate the value of DevRel eng investments

What We Are Looking For

• 6+ years of relevant experience in Developer Relations, developer advocacy, engineering, or a related field
• 2+ years of experience managing, coaching, or leading technical contributors and scaling a DevRel or similar function.
• Strong software engineering foundation. You should be comfortable writing and reviewing production-quality code, working with APIs and developer tooling, debugging technical problems, and getting hands-on with unfamiliar technologies.
• Experience building developer-facing technical projects such as integrations, SDK examples, reference applications, open-source tools, demos, workshops, or developer infrastructure—and taking them from idea through launch and iteration.
• Ability to translate product and company priorities into a focused technical roadmap for a small team, and to make thoughtful trade-offs between experimentation, developer education, integrations, and other projects.
• Strong program management skills, including planning, prioritization, delegation, and proactive risk communication
• Strong developer-product instincts and the ability to recognize where developers are getting stuck, what will create an “aha” moment, and whether the right solution is a product change, integration, tool, example, tutorial, or explanation.
• Strong written and verbal communication skills, including the ability to explain complex technical concepts clearly and engagingly
• Experience with and joy for collaborating cross-functionally with Product, Engineering, Marketing, Growth, Sales, or Customer Success teams
• Ability to balance hands-on execution with team leadership and long-term program development
• Experience working in public codebases and developer ecosystems, including comfort with GitHub workflows, pull requests, issue discussions, technical feedback, and collaborating with external developers.
• Experience defining and reporting on DevRel eng metrics, program performance, or contribution to product and business outcomes
• Comfortable operating in an ambiguous, fast-moving environment and creating clarity through direct communication and documented plans
• Low ego, high horsepower with a “yes, and” mindset to collaboration
• You have tried and used Tailscale

Nice to Have

• Experience leading DevRel for a developer-focused infrastructure, networking, security, or open-source product
• Deep familiarity with Tailscale, WireGuard, networking concepts, identity-based access, or Zero Trust architecture
• Experience supporting product-led growth or self-serve adoption
• Experience building technical integrations, example applications, community tools, or open-source projects
• Established experience speaking at conferences, hosting technical videos, or facilitating developer workshops
• Experience developing new public-facing technical voices within a team or company
• Familiarity with measuring developer journeys from content engagement through signup, activation, and paid conversion
• Experience managing agency partners, contractors, program budgets, or external contributors
• Experience working in a fast-paced startup or scale-up environment

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.

US Pay Range

$161,000—$201,000 USD

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.
• Employer-funded retirement contributions. Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.
• 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, the United Kingdom, and Singapore. 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 $500 USD to customize your workstation to make it your own.
• Paid parental leave program. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).

Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.

Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.

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.

About Tailscale

Tailscale is making safe connection effortless 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.

About the Role

Tailscale is looking for an experienced Manager, Developer Relations Engineering to lead a team of technical builders who help developers discover, understand, adopt, and build with Tailscale. You will be accountable for turning Tailscale’s technology into compelling developer experiences—from integrations and example applications to demos, tutorials, open-source projects, and technical content—that drive meaningful developer and business outcomes.

This is a player-coach engineering leadership role that combines team leadership with hands-on technical execution. You’ll lead Tailscale’s Developer Relations Engineering team while continuing to build yourself: developing integrations, demos, example applications, technical prototypes, workshops, and educational experiences that show developers what is possible with Tailscale. You’ll help the team identify the highest-leverage developer problems to solve and turn successful experiments into repeatable programs.

This role partners closely with Product, Engineering, Growth, Content, Sales, Customer Success, and the broader Marketing team. You’ll maintain a clear technical roadmap for the team, surface developer friction and emerging use cases back into the product organization, and build the systems and measurement practices needed to understand which DevRel investments are driving adoption.

We’re looking for someone with strong engineering and technical credibility, excellent product judgment, and a track record of turning developer insight into technical experiences and projects that make complex products easier to understand and adopt.

Key Responsibilities

• Lead Tailscale’s Developer Relations Engineering team and roadmap, translating company, product, and developer priorities into a focused set of technical projects and programs.
• Manage and develop a high-performing team of Developer Relations Engineers. Set clear expectations, give team members meaningful technical ownership, provide strong coaching and feedback, and help both senior and developing talent increase their impact.
• Lead the team in building high-quality technical experiences including integrations, example applications, open-source projects, demos, workshops, reference architectures, tutorials, and other developer tooling that helps developers quickly understand what they can build with Tailscale.
• Identify and personally contribute to high-leverage technical projects. This is a player-coach role: you should be comfortable opening an IDE, building a prototype, reviewing code, debugging an integration, or creating a working demo alongside the team.
• Serve as a visible technical voice for Tailscale through hands-on work such as videos, presentations, demos, integrations, workshops, and community engagement.
• Ensure DevRel eng work is technically accurate, engaging, relevant to its intended audience, and aligned with current product positioning
• Partner closely with Product, Engineering, Growth, Content, Sales, and Customer Success to coordinate launches, educational initiatives, and developer feedback. Influence product strategy by identifying developer workflows and ecosystem opportunities where Tailscale can create differentiated value, and work with Product and Engineering leaders to validate and prioritize those opportunities. Act as the senior DevRel partner for major launches and strategic bets.
• Define, track, and regularly report on DevRel eng performance, including audience growth, engagement, product activation, integration adoption, and contribution to the self-serve funnel
• Use qualitative developer insight and performance data to prioritize programs, improve execution, and demonstrate the value of DevRel eng investments

What We Are Looking For

• 6+ years of relevant experience in Developer Relations, developer advocacy, engineering, or a related field
• 2+ years of experience managing, coaching, or leading technical contributors and scaling a DevRel or similar function.
• Strong software engineering foundation. You should be comfortable writing and reviewing production-quality code, working with APIs and developer tooling, debugging technical problems, and getting hands-on with unfamiliar technologies.
• Experience building developer-facing technical projects such as integrations, SDK examples, reference applications, open-source tools, demos, workshops, or developer infrastructure—and taking them from idea through launch and iteration.
• Ability to translate product and company priorities into a focused technical roadmap for a small team, and to make thoughtful trade-offs between experimentation, developer education, integrations, and other projects.
• Strong program management skills, including planning, prioritization, delegation, and proactive risk communication
• Strong developer-product instincts and the ability to recognize where developers are getting stuck, what will create an “aha” moment, and whether the right solution is a product change, integration, tool, example, tutorial, or explanation.
• Strong written and verbal communication skills, including the ability to explain complex technical concepts clearly and engagingly
• Experience with and joy for collaborating cross-functionally with Product, Engineering, Marketing, Growth, Sales, or Customer Success teams
• Ability to balance hands-on execution with team leadership and long-term program development
• Experience working in public codebases and developer ecosystems, including comfort with GitHub workflows, pull requests, issue discussions, technical feedback, and collaborating with external developers.
• Experience defining and reporting on DevRel eng metrics, program performance, or contribution to product and business outcomes
• Comfortable operating in an ambiguous, fast-moving environment and creating clarity through direct communication and documented plans
• Low ego, high horsepower with a “yes, and” mindset to collaboration
• You have tried and used Tailscale

Nice to Have

• Experience leading DevRel for a developer-focused infrastructure, networking, security, or open-source product
• Deep familiarity with Tailscale, WireGuard, networking concepts, identity-based access, or Zero Trust architecture
• Experience supporting product-led growth or self-serve adoption
• Experience building technical integrations, example applications, community tools, or open-source projects
• Established experience speaking at conferences, hosting technical videos, or facilitating developer workshops
• Experience developing new public-facing technical voices within a team or company
• Familiarity with measuring developer journeys from content engagement through signup, activation, and paid conversion
• Experience managing agency partners, contractors, program budgets, or external contributors
• Experience working in a fast-paced startup or scale-up environment

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.

CAN Pay Range

$215,740—$269,340 CAD

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.
• Employer-funded retirement contributions. Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.
• 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, the United Kingdom, and Singapore. 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 $500 USD to customize your workstation to make it your own.
• Paid parental leave program. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).

Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.

Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.

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.

About Tailscale

Tailscale is making safe connection effortless 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.

About the Role

Tailscale is looking for an experienced Manager, Developer Relations Engineering to lead a team of technical builders who help developers discover, understand, adopt, and build with Tailscale. You will be accountable for turning Tailscale’s technology into compelling developer experiences—from integrations and example applications to demos, tutorials, open-source projects, and technical content—that drive meaningful developer and business outcomes.

This is a player-coach engineering leadership role that combines team leadership with hands-on technical execution. You’ll lead Tailscale’s Developer Relations Engineering team while continuing to build yourself: developing integrations, demos, example applications, technical prototypes, workshops, and educational experiences that show developers what is possible with Tailscale. You’ll help the team identify the highest-leverage developer problems to solve and turn successful experiments into repeatable programs.

This role partners closely with Product, Engineering, Growth, Content, Sales, Customer Success, and the broader Marketing team. You’ll maintain a clear technical roadmap for the team, surface developer friction and emerging use cases back into the product organization, and build the systems and measurement practices needed to understand which DevRel investments are driving adoption.

We’re looking for someone with strong engineering and technical credibility, excellent product judgment, and a track record of turning developer insight into technical experiences and projects that make complex products easier to understand and adopt.

Key Responsibilities

• Lead Tailscale’s Developer Relations Engineering team and roadmap, translating company, product, and developer priorities into a focused set of technical projects and programs.
• Manage and develop a high-performing team of Developer Relations Engineers. Set clear expectations, give team members meaningful technical ownership, provide strong coaching and feedback, and help both senior and developing talent increase their impact.
• Lead the team in building high-quality technical experiences including integrations, example applications, open-source projects, demos, workshops, reference architectures, tutorials, and other developer tooling that helps developers quickly understand what they can build with Tailscale.
• Identify and personally contribute to high-leverage technical projects. This is a player-coach role: you should be comfortable opening an IDE, building a prototype, reviewing code, debugging an integration, or creating a working demo alongside the team.
• Serve as a visible technical voice for Tailscale through hands-on work such as videos, presentations, demos, integrations, workshops, and community engagement.
• Ensure DevRel eng work is technically accurate, engaging, relevant to its intended audience, and aligned with current product positioning
• Partner closely with Product, Engineering, Growth, Content, Sales, and Customer Success to coordinate launches, educational initiatives, and developer feedback. Influence product strategy by identifying developer workflows and ecosystem opportunities where Tailscale can create differentiated value, and work with Product and Engineering leaders to validate and prioritize those opportunities. Act as the senior DevRel partner for major launches and strategic bets.
• Define, track, and regularly report on DevRel eng performance, including audience growth, engagement, product activation, integration adoption, and contribution to the self-serve funnel
• Use qualitative developer insight and performance data to prioritize programs, improve execution, and demonstrate the value of DevRel eng investments

What We Are Looking For

• 6+ years of relevant experience in Developer Relations, developer advocacy, engineering, or a related field
• 2+ years of experience managing, coaching, or leading technical contributors and scaling a DevRel or similar function.
• Strong software engineering foundation. You should be comfortable writing and reviewing production-quality code, working with APIs and developer tooling, debugging technical problems, and getting hands-on with unfamiliar technologies.
• Experience building developer-facing technical projects such as integrations, SDK examples, reference applications, open-source tools, demos, workshops, or developer infrastructure—and taking them from idea through launch and iteration.
• Ability to translate product and company priorities into a focused technical roadmap for a small team, and to make thoughtful trade-offs between experimentation, developer education, integrations, and other projects.
• Strong program management skills, including planning, prioritization, delegation, and proactive risk communication
• Strong developer-product instincts and the ability to recognize where developers are getting stuck, what will create an “aha” moment, and whether the right solution is a product change, integration, tool, example, tutorial, or explanation.
• Strong written and verbal communication skills, including the ability to explain complex technical concepts clearly and engagingly
• Experience with and joy for collaborating cross-functionally with Product, Engineering, Marketing, Growth, Sales, or Customer Success teams
• Ability to balance hands-on execution with team leadership and long-term program development
• Experience working in public codebases and developer ecosystems, including comfort with GitHub workflows, pull requests, issue discussions, technical feedback, and collaborating with external developers.
• Experience defining and reporting on DevRel eng metrics, program performance, or contribution to product and business outcomes
• Comfortable operating in an ambiguous, fast-moving environment and creating clarity through direct communication and documented plans
• Low ego, high horsepower with a “yes, and” mindset to collaboration
• You have tried and used Tailscale

Nice to Have

• Experience leading DevRel for a developer-focused infrastructure, networking, security, or open-source product
• Deep familiarity with Tailscale, WireGuard, networking concepts, identity-based access, or Zero Trust architecture
• Experience supporting product-led growth or self-serve adoption
• Experience building technical integrations, example applications, community tools, or open-source projects
• Established experience speaking at conferences, hosting technical videos, or facilitating developer workshops
• Experience developing new public-facing technical voices within a team or company
• Familiarity with measuring developer journeys from content engagement through signup, activation, and paid conversion
• Experience managing agency partners, contractors, program budgets, or external contributors
• Experience working in a fast-paced startup or scale-up environment

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.

US Pay Range

$161,000—$201,000 USD

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.
• Employer-funded retirement contributions. Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.
• 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, the United Kingdom, and Singapore. 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 $500 USD to customize your workstation to make it your own.
• Paid parental leave program. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).

Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.

Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.

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.

We believe in the power and joy of learningAt Cengage, our employees have a direct impact in helping students around the world discover the power and joy of learning.

Head of Sales (Player-Coach) – Fleet Safety Training

If you are a hands-on sales builder who still wants to carry a number, coach rising sellers, and shape the go-to-market engine—not just inherit someone else’s playbook—this is a high-visibility opportunity to lead growth for a long-established, PE-backed safety training and software company. You’ll sell directly into public-sector and commercial fleet environments while building the process, cadence, and team capability needed to scale recurring revenue nationwide.

The Opportunity

This company has served safety-focused organizations for decades and supports more than 3,000 active customers across commercial fleets, state and local government, EMS, fire departments, logistics, warehouses, school bus operators, and other vehicle-intensive environments. Following a recent private-equity acquisition, the business has upgraded its technology and launched a recurring training platform designed for larger fleets.

Now the company is ready to expand new-customer growth, increase share of wallet, and build a more repeatable sales motion. This role is part seller, part coach, and part architect: you’ll own meaningful revenue directly while helping junior sellers improve how they prospect, qualify, navigate stakeholders, and close.

Role Snapshot

• Location: Remote within the United States
• Territory: Nationwide U.S.
• Employment Type: Full-time
• Compensation: $110,000–$120,000 base salary with a 50⁄50 split; target OTE around $220,000, with stretch potential around $240,000
• Travel: As needed for industry events, trade shows, and key customer meetings
• Team Scope: Lead and coach a small sales team, including junior sellers and SDR support
• Individual Quota: Expected around $300,000–$400,000

What You Will Own

Carry and Close Your Own Book

• Build a nationwide pipeline across public-sector and commercial accounts.
• Prospect, qualify, run discovery, navigate stakeholders, and close new business.
• Sell safety training, compliance, and software-enabled training solutions into EMS, fire, fleet, logistics, warehouse, transportation, and related environments.
• Manage deal sizes that commonly range from $5,000–$20,000, with larger opportunities reaching roughly $75,000 and some government deals requiring longer procurement cycles.
• Engage buyers ranging from day-to-day safety and training operators to fleet executives, finance leaders, and other senior stakeholders.
• Develop partnerships with insurance, risk, safety, membership, and industry organizations.
• Represent the company at trade shows and industry events.

Coach and Build the Sales Team

• Coach junior AEs and SDR-level talent through call reviews, deal strategy, shadowing, and timely feedback.
• Help sellers improve qualification, objection handling, stakeholder mapping, follow-up, and close strategy.
• Support recovery plans for stalled deals and complex multi-stakeholder opportunities.
• Create a practical sales playbook, operating cadence, scripts, messaging, and repeatable process.
• Keep HubSpot clean, accurate, and useful for forecasting and team visibility.
• Report pipeline, forecast, and revenue progress to executive leadership.
• Help hire and onboard future sellers as the function grows.

What Makes You a Strong Fit

• You have 5+ years of Account Executive or sales leadership experience in public-sector, government-adjacent, commercial SaaS, training, compliance, fleet, transportation, safety, risk, or another transferable B2B environment.
• You have owned complex, multi-stakeholder sales cycles and can show evidence of creating pipeline, advancing deals, and closing business.
• You have directly managed or meaningfully coached BDRs, SDRs, junior AEs, or early-career sales talent.
• You are still energized by selling yourself—not just inspecting someone else’s forecast.
• You know how to operate in a small-team, resource-conscious environment where the playbook is still being built.
• You are comfortable selling to practical operators as well as executive and finance stakeholders.
• You can work effectively in a remote environment with strong discipline around follow-through, CRM hygiene, and communication.
• You have a bachelor’s degree or equivalent college education.

Backgrounds That May Transfer Well

You do not need to come from one exact industry to be credible here. Strong fits may come from environments such as:

• Public sector, local government, or government-adjacent sales
• Fleet, transportation, logistics, delivery, warehouse, or vehicle-intensive operations
• EMS, fire, emergency services, or public safety markets
• Safety, compliance, workforce training, or certification-based solutions
• Vertical SaaS or recurring-revenue products sold into operational teams
• Insurance, risk management, brokers, associations, or member organizations

Why This Role Is Different

This is not a large-company sales management role where every process, enablement asset, and resource already exists. It is a builder role for someone who wants ownership.

You will have the chance to influence the sales motion at a company with an established customer base, a real market need, upgraded technology, and executive attention on growth. For the right person, this can be a step toward broader sales leadership as the team scales.

Compensation

The base salary range is $110,000–$120,000 annually, with a 50⁄50 base-variable structure and target OTE around $220,000.

At Urrly, fairness matters. We use AI to review every application against the same clear requirements for the role. Candidates are evaluated only on job-related factors such as skills, certifications, and experience, not personal attributes.

Apply now and get a response within 24 hours.

Req ID:350032 Position SummaryWe are seeking experienced and historically successful Contact Center BPO Sales Hunter for our Agentic AI Customer Service business.

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Headquarters: Texas, USA, Remote

Our Director, Enterprise Sales will provide strategy, mentorship, and guidance for a team of Enterprise Sales Executives who are responsible for driving new business through the full sales cycle.

At Datadog, we place value in our office culture - the relationships and collaboration it builds and the creativity it brings to the table. We operate as a hybrid workplace to ensure our Datadogs can create a work-life harmony that best fits them.

What You’ll Do: 

• Manage, hire, train and ramp a team of Enterprise Sales Executives responsible for new and expansion bookings
• Achieve annual Enterprise bookings quota with monthly and quarterly targets
• Develop and manage Enterprise Sales Executives on productivity metrics such as deal size, win rate, and forecast accuracy as well as how to lead a customer through a proactive sales cycle
• Coach Sales Executives through building executive relationships with Named Enterprise accounts in their territories and through complex Enterprise deals and negotiations
• Shape the direction of the go-to market strategy and execution for your region
• Work collaboratively with Marketing, Product and Success to build targeted messaging and collateral, and mapping a customer journey for the specific business needs of your region
• Conduct weekly forecast meetings 
• Support direct reports by participating and leading in client and prospect meetings. Engaging other corporate resources as required

Who You Are:

• Experienced in managing a high performing Enterprise Sales team for a B2B technology company
• A strong relationship builder with 5+ years of overall Enterprise sales experience working with Fortune 1000 companies 
• Confident in managing complex sales processes with multiple stakeholders and negotiations with pricing based on business value, legal and procurement 
• Knowledgeable in selling to C-level executives in the IT space 
• Experienced in setting quotas and managing people against those quotas
• Passionate about coaching others with a successful track record as an individual contributor and can share relevant and complex closing experience with a growing team
• Role requires regular travel to client sites, within your area and other regions, using various modes of transportation (car, train, air), depending on business needs

Datadog values people from all walks of life. We understand not everyone will meet all the above qualifications on day one. That's okay. If you’re passionate about technology and want to grow your skills, we encourage you to apply.

Benefits and Growth: 

• High income earning opportunities based on self performance
• New hire stock equity (RSU) and employee stock purchase plan (ESPP)
• Continuous professional development, product training, and career pathing 
• Sales training in MEDDIC and Command of the Message 
• Intra-departmental mentor and buddy program for in-house networking 
• An inclusive company culture, opportunity to join our Community Guilds
• Generous and competitive medical benefits package
• Retirement savings match
• Pet adoption and insurance program

Benefits and Growth listed above may vary based on the country of your employment and the nature of your employment with Datadog.

#LI-Remote

Datadog offers a competitive salary and equity package, and may include variable compensation. Actual compensation is based on factors such as the candidate's skills, qualifications, and experience. In addition, Datadog offers a wide range of best in class, comprehensive and inclusive employee benefits for this role including healthcare, dental, parental planning, and mental health benefits, a 401(k) plan and match, paid time off, fitness reimbursements, and a discounted employee stock purchase plan.

The reasonably estimated yearly salary for this role at Datadog is:$158,000—$210,000 USD

About Datadog: 

Datadog is the leading observability and security platform for the AI era, providing businesses with unified visibility across the technology stack to manage complexity at scale. It brings applications, infrastructure, data, models, and security into one place, using AI to detect and resolve issues before they impact customers. Trusted globally by Fortune 500 companies and high-growth AI leaders, Datadog enables businesses to move faster with clarity and confidence. Learn more about #DatadogLife on Instagram, LinkedIn, and Datadog Learning Center.

Equal Opportunity at Datadog:

Datadog is proud to offer equal employment opportunity to everyone regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, veteran status, and other characteristics protected by law. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. Here are our Candidate Legal Notices for your reference. 

Datadog endeavors to make our Careers Page accessible to all users. If you would like to contact us regarding the accessibility of our website or need assistance completing the application process, please complete this form. This form is for accommodation requests only and cannot be used to inquire about the status of applications. 

Privacy and AI Guidelines:

Any information you submit to Datadog as part of your application will be processed in accordance with Datadog’s Applicant and Candidate Privacy Notice. For information on our AI policy, please visit Interviewing at Datadog AI Guidelines.

To apply: https://weworkremotely.com/remote-jobs/datadog-director-enterprise-sales

Die Syngenta Seeds GmbH in Bad Salzuflen sucht eine/n: Regionalleiter (w/m/d) Saatgut SüddeutschlandRollenbeschreibung: Als Regionalleiter führen und entwickeln Sie Ihr Team von Verkaufsberatern nach dem Syngenta Way of Working und vertreten Ihre Region in den Seeds-Leitungsgremien.