Strategic Enterprise Account Executive

atTailscaleRemoteUS flagUnited StatesFull-timeAccount ExecutiveMid-levelSenior$350k/year

Posted Oct 17

This is a fully remote position, open to applicants in United States.

📋 Description

• Take charge of account strategy by developing account plans that span across business units, regions, and various use cases.

• Generate pipeline through tailored outbound prospecting and coordinated account-based campaigns in collaboration with SDRs and Marketing.

• Manage intricate opportunities through negotiation and closure, which may involve lengthy sales cycles, competitive pursuits, and complex purchasing processes.

• Establish executive relationships with CIOs, CISOs, CTOs, and senior leaders in both technical and business domains.

• Cultivate champions within client organizations.

• Collaborate with Customer Engineering, GTM Engineering, Customer Success, Product, Engineering, executive leadership, Legal, and Finance to secure and expand strategic accounts.

• Experiment with sales strategies, share effective practices, and relay customer feedback to product and enterprise strategy teams.

• Maintain clear qualification processes, accurate forecasts, and actionable account and opportunity plans.

• Manage a focused portfolio of organizations that employ over 10,000 individuals, including Fortune 1000 and Global 2000 companies.

• Guide opportunities from initial contact to closure and expansion.

• Formulate outbound strategies and assist in the creation of the strategic sales playbook.


⛳️ Requirements

• A minimum of 5 years of proven success as a top-performing enterprise or strategic seller in early-stage, high-growth environments.

• Demonstrated success in selling to organizations with more than 10,000 employees.

• Proven ability to close complex SaaS deals worth six to seven figures.

• A consistent record of achieving or surpassing annual performance targets, with evidence of year-over-year growth and sustained results.

• Capability to gain executive trust, engage technical stakeholders, and navigate procurement, legal, and financial evaluations.

• Strong business acumen, effective written and verbal communication, and a collaborative, accountable work style.

• Comfort with ambiguity and a passion for establishing a sales motion while meeting quota requirements.

• Proven commitment to maintaining CRM hygiene, including effective opportunity management, pipeline tracking, and reliable forecasting.

• Demonstrated ability to lead value-based sales discussions and quantify business impact to create compelling ROI-driven business cases.

• Strong technical knowledge.

• Preferred: experience as an early sales hire or in developing a new enterprise sales motion.

• A background in infrastructure, networking, cybersecurity, developer tools, or cloud software is a plus.


🏝️ Benefits

• Competitive base salary, equity incentive plan, and variable commission for roles based on quota.

• Inclusive and flexible work environment.

• Comprehensive health, vision, dental, and other group benefits without any waiting period.

• Remote-first work culture.

• Opportunities for virtual and in-person social events.

• Corporate co-working program available.

• Employer-funded retirement contributions that match employee contributions dollar-for-dollar, up to 0.75% of eligible compensation annually.

• Annual company retreat and team off-site gatherings.

• Options for team travel and distributed collaboration.

• $1,500 USD annually allocated for professional development.

• Access to mentorship, coaching, and opportunities for internal promotion.

• Flexible paid time off program.

• Provision of a company-owned laptop (Mac or PC).

• Monthly reimbursement for home internet expenses.

• $500 USD allowance for home office/workstation customization.

• Paid parental leave top-ups: 20 weeks for birthing parents and 16 weeks for non-birthing parents.

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