Tailscale - Enterprise Account Executive
Requirements
• 5+ years of closing experience in a sales role • Demonstrated success selling infrastructure, networking, cybersecurity, cloud, developer tools, or other highly technical software solutions • Proven track record of consistently meeting or exceeding quota in an enterprise sales environment • Experience managing complex, multi-stakeholder sales processes involving technical and executive buyers • Ability to engage credibly with both technical practitioners and senior business leaders • Experience collaborating and working with a Sales Engineer on sales cycles • Strong account planning, discovery, and business case development skills • Experience closing six-figure enterprise opportunities is strongly preferred • Experience using Gong, or similar, to collaborate internally and manage pipeline • Location: Remote, but based in or near San Francisco as it supports customers and requires occasional travel/commute within the assigned region. • What Success Looks Like • Consistently exceed quota through a combination of self-generated pipeline, new customer acquisition, and account expansion • Establish trusted advisor relationships with Security, Infrastructure, and Engineering leaders • Successfully drive adoption from initial deployment to broader organizational standardization • Build a predictable pipeline through disciplined prospecting and strategic account development • 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.
Responsibilities
• Own and grow a territory of enterprise organizations, driving both net-new customer acquisition and expansion opportunities • Proactively self-source pipeline through outbound prospecting activities, including cold outreach, strategic account targeting and networking. • Take ownership of the full sales cycle from lead to close • Develop strategic account plans that identify key stakeholders, organizational priorities, technical initiatives, and expansion paths across the account • Build relationships with Security, Infrastructure, Engineering, Compliance, and Executive stakeholders to drive alignment and consensus throughout the buying process • Navigate complex enterprise sales cycles involving multiple decision-makers, procurement processes, security reviews, and legal negotiations • Position Tailscale as a strategic platform for secure connectivity and modern network access by helping customers understand both the technical and business value of the solution • Lead cross-functional account teams consisting of Sales Engineering, Customer Success, Product, Marketing, and Support to deliver exceptional customer outcomes • Drive adoption beyond the initial deployment by identifying opportunities for broader organizational usage and long-term account growth
Benefits
• $250,000—$300,000 USD • 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. • An inclusive, flexible environment where you can be your authentic self. • A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles). • A competitive total compensation package. • Comprehensive group benefits with no waiting period. Take advantage of coverage for health, vision, dental, and more for you and your family! • Comprehensive group benefits with no waiting period. • 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. • Remote first company • 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. • Employer-funded retirement contributions. • 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. • Support for your personal and professional development. • 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! • Paid time off and a healthy work-life integration. • 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. • A build-your-own home office setup. • 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). • Paid parental leave program • 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.
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