Strategic Enterprise Account Executive (Remote)

WinsAbove; United States; Remote; USD 315,000 - 385,000; Full time

Benefits offered by this job

Remote first

Equity

Base + incentives

Home office stipend

Professional development allowance

Paid time off

Parental leave

Job summary

Tailscale is building a Strategic Sales team to support our next growth phase. As a founding Strategic Account Executive, you’ll own a focused portfolio of organizations with 10,000+ employees, including Fortune 1000 and Global 2000 companies.

You’ll lead complex opportunities from initial engagement through close and expansion, building executive relationships and aligning customer priorities with Tailscale’s capabilities. This remote-first role reports to the Director of Strategic Sales.

Qualifications

• 5+ years of success as a top-performing enterprise or strategic seller in early stage, high-growth environments.
• Proven success selling to organizations with 10,000+ employees and closing complex six and seven-figure SaaS deals.
• Proven track record of consistently achieving or exceeding annual performance targets, with demonstrated YoY growth and sustained results.
• The ability to earn executive trust, engage technical stakeholders, and navigate procurement, legal, and financial reviews.
• Strong business judgment, clear written and verbal communication, and a collaborative, accountable approach.
• Comfort with ambiguity and enthusiasm for building a sales motion while carrying a quota.
• Demonstrated commitment to CRM hygiene, including accurate opportunity management, pipeline tracking, and forecast reliability.
• Proven ability to lead value-based sales conversations and quantify business impact to build compelling ROI-driven business cases.

Responsibilities

• Own account strategy: Build account plans that connect customer priorities with opportunities across business units, geographies, and use cases.
• Create pipeline: Drive personalized outbound prospecting, partnering with SDRs and Marketing on coordinated account-based campaigns.
• Lead complex deals: Manage opportunities through negotiation and close, navigating long sales cycles, competitive pursuits, and complex buying processes.
• Build executive relationships: Earn trust with CIOs, CISOs, CTOs, and senior technical and business leaders while developing champions across the organization.
• Bring the right team together: Partner with Customer Engineering, GTM Engineering, Customer Success, Product, Engineering, executive leadership, Legal, and Finance to win and grow strategic accounts.
• Shape the playbook: Test approaches, share what works, and bring customer feedback to teams shaping Tailscale’s product and enterprise strategy.
• Execute with discipline: Maintain clear qualification, accurate forecasts, and actionable account and opportunity plans.

Skills

Enterprise selling

Executive relationships

CRM hygiene

Forecasting

Negotiation

Communication

Job description

Tailscale is building a Strategic Sales team to support our next growth phase. As a founding Strategic Account Executive, you’ll own a focused portfolio of organizations with 10,000+ employees, including Fortune 1000 and Global 2000 companies.

You’ll lead complex opportunities from initial engagement through close and expansion, building executive relationships and aligning customer priorities with Tailscale’s capabilities. This remote-first role reports to the Director of Strategic Sales.