Writing.io Jobs

Hallo! Schön, dass du vorbeischaust 👋 Bist du aktiv auf der Suche nach einer neuen Herausforderung? Oder schaust du dich einfach nur auf dem Markt um? Nun… dann bist du...

Hallo! Schön, dass du vorbeischaust 👋 Bist du aktiv auf der Suche nach einer neuen Herausforderung? Oder schaust du dich einfach nur auf dem Markt um? Nun… dann bist du...

Company Description

BlueOptima gives CIOs, CTOs and CFOs objective, code-level visibility into software productivity, AI ROI, and engineering cost. This is a problem that until recently could not be measured at all. With AI-generated code now flowing into enterprise codebases at scale, that measurement gap has become a board-level priority.

10B+ code revisions analysed · 800,000+ developers on platform · 9 of the top 16 universal banks

The business is profitable, bootstrapped, and 20 years deep in enterprise relationships. You are joining a sales organisation that is mid-build. The foundations are in place, the product has genuine enterprise traction, and there is real room to grow fast.

Buyers are CIOs, CTOs, VP Engineering and CFO stakeholders at large software engineering organisations. The conversation is about developer productivity, engineering cost, and AI ROI. These are budget-backed problems that sit at the top of the technology agenda right now. You are not convincing anyone the problem exists.

Job Description

You will lead a team of Account Executives working on enterprise accounts across the UK and EMEA, with deal sizes typically in the £100k to £200k ARR range. You will be cultivating a culture of success and continuous improvement through your coaching. Your leadership will guide the team through complex sales cycles and ambitious growth targets.

You will use sales data and team performance metrics to identify opportunities for improvement. Implement actionable insights to enhance sales tactics and team productivity, leveraging coaching frameworks to work side by side with your team members.

You will work in close partnership with Marketing and SDR leadership to identify new pipeline generation opportunities, and with Customer Success leadership to surface expansion opportunities within the install base.

Qualifications

Required

• Enterprise SaaS sales leadership: At least 3 years managing sales teams closing complex enterprise deals in the £100k to £200k+ ARR range.
• Engineering domain experience: Direct experience selling into software engineering organisations is required. This means you have sold developer tooling, engineering analytics, observability, SDLC platforms, or similar products and can hold a credible technical conversation with VP Engineering and CTO buyers without leaning on a solutions engineer. You do not need to have been a developer, but you do need to understand how software gets built.
• Executive-level selling: Comfortable engaging CIO, CTO, VP Engineering and CFO buyers. You can hold the room with credibility and navigate multi-stakeholder deal structures.
• Hands-on coaching style: Demonstrated ability to develop your team through direct involvement in sales activities, including joint calls and co-selling, to ensure team members reach their potential.
• Data-driven decision making: Highly analytical, you leverage pipeline and performance data to make informed decisions and adapt quickly to capitalise on new opportunities.
• Structured sales methodology: Exposure to value-based selling methodologies and the MEDDPICC discovery framework in multi-stakeholder environments.

Valued

• Experience with AI products, AI governance, or engineering productivity measurement.
• Background in land-and-expand motions within large enterprise accounts.
• Open to using AI to amplify your own skills and strengthen your work, demonstrating curiosity, willingness to learn, and sound judgement in applying AI responsibly to improve efficiency and impact.

Additional Information

Why This Role Makes Sense Right Now

AI governance and engineering ROI measurement have moved from nice-to-have to board priority in the last 18 months. The buyers are funded, the problem is urgent, and BlueOptima is one of the very few companies with a production-grade answer. For a sales leader who wants to work with a team closing real enterprise deals, not chasing SMB volume, the timing is good.

Where This Leads

The natural progression from this role is into second-line leadership. That path is defined and is based on performance and the growth of the company, not tenure.

Benefits we offer

• London HQ, 3 days in office, 2 remote
• 32 days holiday including bank holidays
• 12 weeks paid maternity and paternity leave
• 4 weeks per year flexible remote working from anywhere
• Annual leave purchase up to 10 extra days
• Work from home equipment allowance
• Pet friendly office
• Sponsored learning opportunities
• Cycle to work scheme
• Team socials

Stay connected with us on LinkedIn or keep an eye on our career page for future opportunities!

Who We Are:

SmithRx is a rapidly growing, venture-backed Health-Tech company.  Our mission is to disrupt the expensive and inefficient Pharmacy Benefit Management (PBM) sector by building a next-generation drug acquisition platform driven by cutting edge technology, innovative cost saving tools, and best-in-class customer service.  With hundreds of thousands of members onboarded since 2016, SmithRx has a solution that is resonating with clients all across the country.

We pride ourselves for our mission-driven and collaborative culture that inspires our employees to do their best work. We believe that the U.S healthcare system is in need of transformation, and we come to work each day dedicated to making that change a reality. At our core, we are guided by our company values:

• Integrity: Our purpose guides our actions and gives us confidence in the path ahead. With unwavering honesty and dependability, we embrace the pressure of challenging the old and exemplify ethical leadership to create the new.
• Courage: We face continuous challenges with grit and resilience. We embrace the discomfort of the unknown by balancing autonomy with empathy, and ownership with vulnerability. We boldly challenge the status quo to keep moving forward—always.
• Together: The success of SmithRx reflects the strength of our partnerships and the commitment of our team. Our shared values bind us together and make us one. When one falls, we all fall; when one rises, we all rise.

Job Summary:

The Senior Director of Account Management is a strategic people leader responsible for leading, developing, and scaling a high-performing Account Management organization. This role is accountable for building a strong leadership culture, developing talent, establishing clear performance expectations, and ensuring the team has the structure, capabilities, and resources needed to deliver exceptional client outcomes.

The Senior Director will lead a team of Account Executives and/or Account Management leaders, serving as a coach and strategic partner while creating consistency in how the organization manages client relationships, escalations, performance, and growth opportunities.

This leader will partner closely with executive leadership and cross-functional teams to ensure the Account Management organization is aligned to company priorities and positioned to support continued business growth.

What you will do:

People Leadership & Talent Development

• Lead, coach, and develop Account Executives and Account Management leaders to achieve individual and organizational goals.
• Establish a high-performance culture grounded in accountability, collaboration, client advocacy, and continuous improvement.
• Conduct regular talent assessments and identify high-potential employees, succession opportunities, and performance gaps.
• Create and execute individualized development plans to strengthen leadership, strategic thinking, client management, and business acumen.
• Provide clear, timely, and actionable performance feedback.
• Build a strong leadership bench and succession plan for critical roles.
• Ensure appropriate staffing, capacity, spans and layers, and role clarity as the organization scales.
• Partner with Talent/HR on recruiting, onboarding, performance management, promotions, and employee engagement.

Account Management Leadership

• Establish clear expectations, operating rhythms, and performance standards across the Account Management organization.
• Ensure AccountExecutives are operating proactively and strategically rather than primarily responding to client issues.
• Coach teams to develop strong executive relationships and become trusted strategic advisors to clients.
• Drive consistency in account planning, QBRs, client communications, escalation management, and business reviews.
• Monitor team performance against key client and business metrics, including retention, satisfaction, engagement, and financial performance.
• Ensure appropriate escalation and executive engagement for high-risk or strategically important clients.

Organizational Effectiveness

• Evaluate team structure, workloads, account assignments, and capacity to ensure sustainable performance.
• Identify opportunities to improve processes, tools, training, and operating models.
• Develop scalable frameworks and playbooks that enable consistent Account Management practices.
• Establish meaningful OKRs and reporting to measure team effectiveness and identify opportunities for improvement.
• Partner with leadership to evolve the Account Management model as the business grows.

Cross-Functional & Executive Partnership

• Partner with Operations, Product, Sales, Finance, Clinical, Legal, Member Services, and other functions to deliver an integrated client experience.
• Represent Account Management in leadership discussions and strategic initiatives.
• Escalate organizational and client risks with clear recommendations and action plans.
• Translate company direction into clear priorities and expectations for the Account Management team.
• Serve as a visible and trusted leader across the organization.

What you will bring to SmithRx:

Leadership Expectations

The successful candidate will:

• Lead through others rather than becoming the primary problem solver.
• Develop talent and consistently raise the capability of the team.
• Create accountability while maintaining a supportive, collaborative culture.
• Think strategically and connect day-to-day client management to broader business objectives.
• Make decisions and provide clear direction when the team encounters ambiguity.
• Anticipate challenges rather than operating reactively.
• Build strong leaders, not dependency on the Senior Director.
• Champion change and help the organization adapt as the company scales.

What you will bring to SmithRx:

• 10+ years of experience in Account Management, Client Success, Customer Success, or a related client-facing function..
• 5+ years of people leadership experience, including managing managers and/or senior-level professionals.
• Experience working with various clients ranging in size from small to enterprise level employers, Health Plans, TPAs, brokers, and consultants.
• Demonstrated success building and developing high-performing teams.
• Experience managing organizational growth, capacity planning, or evolving operating models.
• Strong executive presence and communication skills.
• Demonstrated ability to coach leaders and address performance issues effectively.
• Strong strategic thinking, business acumen, and decision-making skills.
• Experience working cross-functionally in a complex, fast-paced organization.
• Bachelors Degree required
• Healthcare, benefits, pharmacy, PBM, or related industry experience strongly preferred.

What SmithRx Offers You:

• Highly competitive wellness benefits including Medical, Pharmacy, Dental, Vision, and Life Insurance and AD&D Insurance
• Flexible Spending Benefits
• 401(k) Retirement Savings Program
• Short-term and long-term disability
• Discretionary Paid Time Off
• Paid Company Holidays
• Wellness Benefits
• Commuter Benefits
• Paid Parental Leave benefits
• Employee Assistance Program (EAP)
• Well-stocked kitchen in office locations
• Professional development and training opportunities

Zone A includes the following locations:

• San Francisco Bay Area - California
• Metro New York City - Connecticut, New Jersey, New York and Pennsylvania

Zone A Pay Range

$240,000—$300,000 USD

Zone B includes the following locations:

• California - outside of San Francisco Bay Area
• Metro Denver / Boulder - Colorado
• Metro District of Columbia - District of Columbia, Maryland, Virginia and West Virginia
• Metro Boston / Cambridge - Massachusetts and New Hampshire
• Metro Austin - Texas
• Metro Seattle - Washington

Zone B Pay Range

$220,000—$275,000 USD

Zone C includes all other locations not listed above, including:

• Alabama, Alaska, Arizona, Arkansas, Delaware, Florida, Georgia, Hawaii, Idaho, Illinois, Indiana, Iowa, Kansas, Kentucky, Louisiana, Maine, Michigan, Minnesota, Mississippi, Missouri, Montana, Nebraska, Nevada, New Mexico, North Carolina, North Dakota, Ohio, Oklahoma, Oregon, Rhode Island, South Carolina, South Dakota, Tennessee, Utah, Vermont, Wisconsin, Wyoming
• Non metro Colorado, Connecticut, Maryland, Massachusetts, New Hampshire, New Jersey, New York, Pennsylvania, Texas, Virginia, Washington, and West Virginia

Zone C Pay Range

$200,000—$250,000 USD

Compensation & Benefits

• Base Salary: The range listed above reflects our standard pay scale and actual pay will vary based on work location, job level, job-related knowledge, skills, and experience.
• Total Rewards: In addition to base pay, this role may be eligible for bonuses, commissions, or equity. SmithRx offers a variety of benefits to help you live well, including: time off programs, medical, dental, vision, mental health support, paid parental leave, life and disability insurance and 401(k).

Individual offers are tailored to your geography, experience, skills, and education. Your recruiter can share more specific details during the hiring process. In the meantime, feel free to explore our comprehensive benefits here.

Headquarters: US
URL: https://openbase.ai/

Head of Growth & Operations — Openbase.ai

Full-time | Remote | Reports directly to the Founder

About Openbase

Openbase.ai is an AI gateway that helps developers and businesses access multiple AI models through one API. We simplify model access, routing, and usage management so teams can focus on building AI products.

Our MVP is ready. We are hiring a hands-on leader to own our go-to-market strategy, day-to-day business execution, and journey from launch to our first 10,000 users.

The opportunity

You will work directly with the founder to turn Openbase into a growing business with repeatable customer acquisition, strong retention, and disciplined operations.

You will own the commercial execution: finding our first customers, testing acquisition channels, improving onboarding, building partnerships, and organizing the people and systems needed to grow.

Our ambition is 10,000 users. Your responsibility is to build a credible, measurable path toward that goal, with clear milestones for activated developers, retained customers, paying accounts, and profitable usage.

What you will own

1. Go-to-market and customer acquisition

• Identify our strongest initial customer segments, including AI startups, independent developers, agencies, and software teams.
• Develop our positioning and explain why developers should choose Openbase.
• Launch and improve acquisition across X, SEO, visibility in AI search engines, developer communities, partnerships, and targeted outbound.
• Test paid campaigns with clear budgets, conversion tracking, and criteria for scaling or stopping.
• Build a growth roadmap with weekly experiments and monthly acquisition targets.

2. Developer activation and retention

• Own the journey from website visit to signup, first successful API request, first payment, and ongoing usage.
• Work with engineering to remove onboarding friction and improve documentation, quickstarts, and integration examples.
• Speak directly with developers to understand why they try Openbase, keep using it, or leave.
• Establish onboarding communications, customer support processes, and reactivation campaigns.
• Turn successful customer implementations into case studies and referrals.

3. Sales and partnerships

• Personally source and close early customers.
• Build a qualified pipeline of startups and businesses with recurring AI usage.
• Develop distribution partnerships with developer tools, AI communities, accelerators, and complementary platforms.
• Coordinate technical evaluations and customer requirements with engineering.
• Build a repeatable sales process as demand grows.

4. Business execution and team management

• Translate company goals into weekly priorities, accountable owners, and delivery dates.
• Recruit and manage freelancers, agencies, and future hires across growth, content, developer relations, and customer success.
• Own marketing budget allocation and evaluate spending against business results.
• Coordinate customer needs with product and engineering priorities.
• Implement practical workflows and automation that reduce manual work.

5. Metrics and commercial performance

• Maintain a dashboard covering acquisition, activation, retention, paying customers, and API usage.
• Track customer acquisition cost, conversion rates, and retention by channel.
• Separate customer spending from provider costs and Openbase’s retained revenue and gross profit.
• Monitor promotional credits and infrastructure costs so growth remains economically sound.
• Give the founder a clear weekly view of results, blockers, and decisions needed.

What we are looking for

• Experience leading growth and commercial execution at an early-stage SaaS, API, developer-tools, or AI infrastructure company.
• Evidence of acquiring users from an early starting point, with specific numbers and your personal contribution.
• Understanding of developer audiences and how technical products earn adoption.
• Ability to understand an API integration, follow documentation, and discuss onboarding issues with engineers.
• Hands-on ability to run experiments, analyze funnels, conduct customer calls, and manage delivery.
• Experience managing budgets and external specialists.
• Strong written English, sound judgment, and comfort working directly with a founder.

Experience with usage-based pricing, developer relations, technical SEO, and AI model platforms is particularly relevant.

Why join

• Direct ownership of Openbase’s launch and growth.
• Close collaboration with the founder and engineering team.
• The opportunity to build the commercial function from its earliest stage.
• Scope to take on broader company leadership as the business grows.

How to apply

Send your CV or LinkedIn profile, together with brief answers to:

1. Which product have you helped grow? Include starting users, ending users, timeframe, budget, and your exact role.
2. Which acquisition channels produced retained or paying customers?
3. How would you approach Openbase’s first 1,000 activated developers?
4. What would you personally execute, and where would you use specialists?
5. What are your location, availability, and compensation expectations?

Include an example of a growth experiment or operating system you built. Share only information you are authorized to disclose.

To apply: https://weworkremotely.com/remote-jobs/openbase-llc-head-of-growth-operations

About Halter At Halter, we’re on a mission to enable farmers and graziers to run the most productive and sustainable operations. Our customers are using Halter to break free from...

About Halter At Halter, we’re on a mission to enable farmers and graziers to run the most productive and sustainable operations. Our customers are using Halter to break free from...

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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