Enterprise Account Executive - Remote, High-Impact Deals

WinsAbove; New York (NY); Remote; USD 250,000 - 300,000; Full time

Benefits offered by this job

Equity

Remote work

Professional development

Paid time off

Parental leave

Retirement match

Job summary

Tailscale, a fast-growing, fully distributed company, is seeking an Enterprise Account Executive to drive net-new acquisition and expansion for top enterprise clients. You will partner with Solutions Engineering, Customer Success, and Product teams to secure deals and expand usage of our secure connectivity platform.

You will manage complex multi-stakeholder deals, translate technical value into business impact, and own the full sales cycle from prospecting to close, with emphasis on

Qualifications

• 5+ years of closing experience in a sales role.
• Experience 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 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.

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.

Skills

Enterprise sales

Account planning

Stakeholder mgmt

Outreach prospecting

Complex negotiations

Technical credibility

Gong experience

Tools

Gong

Job description

Tailscale, a fast-growing, fully distributed company, is seeking an Enterprise Account Executive to drive net-new acquisition and expansion for top enterprise clients. You will partner with Solutions Engineering, Customer Success, and Product teams to secure deals and expand usage of our secure connectivity platform.

You will manage complex multi-stakeholder deals, translate technical value into business impact, and own the full sales cycle from prospecting to close, with emphasis on