About this role.
Tailscale is seeking a founding Director of Strategic Sales to build and lead a new organization focused on winning Fortune 1000 enterprises. This role blends hands-on selling with team building, requiring the ability to close complex, multi-stakeholder deals while recruiting and coaching a team of Strategic Account Executives. You will work closely with executive leadership, product, engineering, and marketing to define the strategic sales motion and playbooks. This is a high-impact, high-visibility role for an experienced sales leader who thrives on building from the ground up.
Role DNA
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Job Complexity
5/5Pace & Pressure
5/5Autonomy Level
5/5Communication Load
5/5Salary analysis
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Core skills
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Cover letter sample
Dear Hiring Manager,
I am thrilled to apply for the Director, Strategic Sales role at Tailscale. Your mission to build a secure and simple internet aligns perfectly with my passion for solving complex connectivity challenges at enterprise scale. With over a decade of experience in strategic sales leadership, I have successfully built and scaled enterprise sales teams while personally closing six-figure and seven-figure deals with Fortune 500 accounts. I am particularly drawn to the opportunity to define a new go-to-market motion and act as a player-coach, which matches my strengths in both direct selling and team development. I look forward to bringing my expertise in enterprise networking, SaaS, and executive relationship building to help Tailscale win the largest enterprises in the world.
Sincerely,
[Your Name]
Sample interview questions
In my previous role, I was tasked with launching a strategic sales team for a cybersecurity startup. I started by analyzing our existing customer base to identify ideal profiles for strategic accounts. I then defined a focused territory plan and developed a repeatable outbound playbook. For recruiting, I prioritized candidates with both hunter mentality and deep enterprise network security knowledge. Within six months, we had hired five AEs and closed our first three Fortune 500 logos, which validated our model and helped us scale.
I approach complex deals by first mapping the buying committee and understanding each stakeholder's unique priorities. I establish executive-level champions and ensure that technical and business value are aligned through tailored presentations and proof-of-value activities. I also coordinate with internal teams, such as legal and security, to preempt objections. Finally, I maintain regular communication through a clear cadence of status updates, ensuring that all stakeholders are aligned and moving toward a mutually beneficial agreement.
I would start by using the product myself and understanding its technical differentiators. I'd bring in subject matter experts from our engineering and customer engineering teams for deep-dive sessions with the customer's technical staff. I would also share relevant case studies from other technical communities and be transparent about product capabilities and limitations. By genuinely understanding the technical challenges and speaking the language of developers, I can build credibility and position Tailscale as a trusted partner.
In the first year, I would focus on leading indicators like the number of target strategic accounts engaged, pipeline value, and conversion rates from first meeting to opportunity. Also important are activity metrics such as outbound touches and executive meetings held. Financial metrics include new ARR from strategic accounts, average deal size, and sales cycle length. Additionally, I would track team ramp-up time and employee satisfaction to ensure sustainable growth without burning out the team.
I once lost a major deal due to a lack of alignment between the economic buyer and the end-user champion. The champion was highly engaged, but the economic buyer didn't see a strong ROI case. I learned that I need to engage the economic buyer early in the process and tailor the value proposition to their financial metrics. After that, I always built a detailed ROI model and presented it to the economic buyer in the first or second meeting. This approach significantly increased my win rate in similar enterprise deals.
About Tailscale
Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We’re building a future for the Internet that’s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we’re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.
About the Role
Tailscale is redefining secure networking by making it simple for organizations to securely connect people, devices, and workloads anywhere in the world.
At Tailscale, we’re solving one of the most fundamental challenges in modern infrastructure: secure connectivity. Our product is loved by developers, trusted by IT and security teams, and rapidly expanding within some of the world’s largest organizations. As adoption accelerates, we’re investing in a Strategic Sales motion that matches the scale of our ambition. If you’re excited by the opportunity to build, lead, and sell and want to define how a category-leading company wins the largest enterprises in the world, we’d love to talk.
As we continue moving up-market, we’re launching a new Strategic Sales organization focused exclusively on the world’s largest enterprises. We’re looking for a founding Director of Strategic Sales to help build one of the most important growth initiatives at Tailscale. This is a rare opportunity to define how we engage Fortune 1000 customers, establish a new go-to-market motion, recruit an elite team, and help shape the future of Enterprise Sales at Tailscale.
This is not a traditional frontline management role.
You’ll be a seller, coach, and builder, personally leading many of Tailscale’s largest strategic opportunities while building a high-performing team of Strategic Account Executives focused on organizations with more than 10,000 employees.
You’ll define territory strategy, build an outbound-first motion, recruit exceptional talent, establish repeatable playbooks, and create the operating cadence that becomes the blueprint for Strategic Sales at Tailscale.
Our Strategic Sales organization will operate like an elite SWAT team, small, highly collaborative, and focused on pursuing a select number of transformational customers. You’ll work alongside Executive Leadership, Product, Engineering, Customer Engineering, Marketing, GTM Engineering, and Customer Success to win the company’s largest opportunities.
Initially, you’ll lead a team of approximately 3–5 Strategic Account Executives while continuing to personally own and close strategic opportunities. As the business grows, you’ll play a central role in scaling both the team and the operating model.
This role reports directly to the Head of Sales and offers the opportunity to build a category-defining Strategic Sales organization from the ground up.
Key Responsibilities
Build a New Business
- Build Tailscale’s Strategic Sales organization from the ground up.
- Design the operating model, territory strategy, account segmentation, and engagement approach.
- Develop repeatable playbooks for winning the world’s largest enterprises.
- Help shape the long-term vision for Strategic Sales as the business scales.
- Partner with executive leadership to influence go-to-market strategy for our largest customers.
Lead From the Front
- Personally own a portfolio of Tailscale’s highest-value strategic accounts.
- Lead complex, multi-stakeholder sales cycles from initial engagement through expansion.
- Develop trusted executive relationships with CIOs, CISOs, CTOs, Chief Architects, Infrastructure leaders, and other senior decision makers.
- Serve as the executive quarterback on the company’s largest strategic pursuits.
- Negotiate complex commercial agreements and drive successful outcomes across technical, financial, legal, and executive stakeholders.
Build an Elite Team
- Recruit, hire, and develop exceptional Strategic Account Executives.
- Initially lead a team of approximately 3–5 Strategic AEs, expanding the organization over time.
- Coach account strategy, executive engagement, negotiation, forecasting, and deal execution.
- Foster a high-performance culture built on accountability, collaboration, curiosity, and continuous learning.
- Build a team recognized for winning the most competitive enterprise opportunities in the market.
Create Pipeline
- Lead an outbound-first sales motion.
- Personally prospect into strategic accounts and build executive relationships.
- Partner with SDRs, Marketing, GTM Engineering, Customer Engineering, and Customer Success to develop account plans for our highest-value prospects.
- Create scalable account planning and outbound strategies that consistently generate executive engagement and qualified pipeline.
- Establish best practices for strategic prospecting, account planning, and executive alignment.
Drive Operational Excellence
- Own account planning, forecasting, pipeline health, and business planning for the Strategic segment.
- Inspect deal strategy and qualification throughout the sales cycle.
- Use data to improve execution, identify trends, and optimize performance.
- Partner closely with Product and Engineering to provide market feedback that influences product direction.
- Build the operating rhythm, metrics, and inspection processes that enable the organization to scale.
What We Are Looking For
- Founding AE at a high growth start-up
- 5+ years as the top sales rep at a high-growth technology company.
- Proven success selling into organizations with 10,000+ employees.
- Demonstrated ability to close complex six-, seven-, and eight-figure SaaS opportunities.
- A consistent track record of building outbound pipeline and winning net-new enterprise customers.
- Executive presence with the ability to engage CIOs, CISOs, CTOs, and senior business executives as trusted advisors.
- Strong business acumen with experience navigating complex buying committees and long enterprise sales cycles.
- Comfortable operating in ambiguity and building new processes where none exist.
- Passionate about building teams, developing people, and creating scalable organizations.
You’ll Thrive Here If You…
- Want to build something rather than inherit it.
- Enjoy leading from the front instead of managing from the sidelines.
- Love hunting transformational opportunities and winning competitive enterprise pursuits.
- Enjoy building outbound strategies as much as closing business.
- Like collaborating across Product, Engineering, Marketing, and Customer Success.
- Are energized by creating playbooks that become the foundation for future growth.
- Want to leave a lasting impact on how a company scales its enterprise business.
As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale’s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire’s base salary. Individual offers may vary based on experience and skill set.
For this position, our pay ranges reflect target OTE (on target earnings), inclusive of base salary and variable compensation tied to the attainment of quarterly sales targets.
Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. We encourage you to help us break that statistic!
What We Offer
- An inclusive, flexible environment where you can be your authentic self. We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.
- A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).
- Comprehensive group benefits with no waiting period. Take advantage of coverage for health, vision, dental, and more for you and your family!
- Remote first company—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.
- 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.
Annual salary information is not provided for this position. Explore salary ranges for similar roles in our Salary Directory ›
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