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Tailscale

Senior Customer Account Executive

Tailscale

. Help expand and renew current customer accounts .

Posted 10/15/2026full-timeToronto • CanadaSeniorWebsite

Core Competencies

Role fit
Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates expertise in customer account management, focusing on upselling and renewals while ensuring successful adoption of Tailscale's solutions. Proven ability to collaborate with cross-functional teams and deliver accurate forecasting and revenue results.

Highest-signal resume keywords
Account ManagementUpsellingCustomer EducationPipeline ManagementQuota Achievement

ATS Keywords

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Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills
Closing ExperienceSales StrategyTechnical Product SalesForecastingRevenue Delivery
Soft Skills
Proactive ApproachCollaborationPresentation SkillsCustomer Engagement
Tools & Technologies
GongSales Tools
Industry Keywords
Product-Led GrowthCustomer SuccessSolutions EngineeringHigh-Growth Software Startup

About the role

Key responsibilities & impact
  • Help expand and renew current customer accounts
  • Find additional use cases and educate customers on new feature releases
  • Ensure successful adoption of Tailscale across existing customer accounts
  • Partner with Solutions Engineering and collaborate with Customer Success, Support, Marketing, and Product teams
  • Become an expert in how Tailscale helps customers
  • Build a credible quarterly pipeline through upsells and renewals
  • Own upsell and renewal targets across assigned accounts
  • Educate customers on Tailscale's value throughout evaluation and adoption
  • Generate short-term results while maintaining annual pipeline coverage
  • Provide accurate weekly forecasting and revenue delivery
  • Create mutual action and success plans with prospective and existing customers
  • Participate in video-recorded customer meetings for training, collaboration, and quality improvement

Requirements

What you’ll need
  • 2+ years of closing experience in an AE or an AM role
  • Strong desire to join a high-growth software startup
  • Experience selling developer and/or technical products, especially in a product-led growth (PLG) motion
  • Experience presenting to senior managers and executives
  • Ability to manage many opportunities simultaneously at various stages
  • Strong track record of meeting and exceeding quota
  • Experience using Gong or similar tools to collaborate internally and manage pipeline
  • Experience partnering with Sales Engineering, Support, and Customer Success teams
  • Proactive approach from lead to close
  • Hybrid required: based in Toronto and working 3 days per week in-office

Benefits

Comp & perks
  • Base salary, equity incentive plan, and variable commission for quota-based roles
  • Comprehensive group benefits with no waiting period, including health, vision, and dental coverage for employees and families
  • Flexible work environment and flexible paid time off
  • Remote-first company with virtual and in-person social events
  • Corporate co-working program through WeWork or similar spaces
  • Employer-funded retirement contributions matching employee contributions dollar-for-dollar, up to 0.75% of eligible compensation annually
  • Annual company retreat and team off-sites
  • $1,500 USD annually for professional development
  • Mentorship, coaching, and internal promotion opportunities
  • Company-owned laptop choice of Mac or PC
  • Monthly home internet reimbursement
  • $500 USD workstation customization allowance
  • Paid parental leave top-ups: 20 weeks for birthing parents and 16 weeks for non-birthing parents