Customer Account Executive

Tailscale

Customer Account Executive expanding and renewing accounts for Tailscale’s secure networking software. Driving upsells, adoption, forecasting, and pipeline growth from Toronto under a hybrid work model.

Posted 8/7/2026full-timeToronto • 🇨🇦 CanadaMid-LevelSeniorWebsite

Core Competencies

Role fit

Core Competencies

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

Demonstrates expertise in customer engagement and upselling within a high-growth software environment, with a strong focus on pipeline management and collaboration across teams. Proven ability to educate clients on product value and drive revenue through effective forecasting and account management.

Highest-signal resume keywords

Quota-Carrying ExperienceTechnical Product SalesCustomer EngagementPipeline ManagementCollaboration with Sales Engineering

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

UpsellingRenewalsForecastingAccount ManagementQuota Achievement

Soft Skills

Proactive ApproachPresentation SkillsCollaboration

Tools & Technologies

Gong

Industry Keywords

Product-Led GrowthCustomer SuccessSolutions EngineeringHigh-Growth Software Startup

About the role

Key responsibilities & impact

Become an expert in how Tailscale helps customers
Build a credible quarterly pipeline through client engagement on 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
Expand and renew current customer accounts, identify additional use cases, and educate clients on new feature releases
Partner with Solutions Engineering and collaborate with Customer Success, Support, Marketing, and Product teams

Requirements

What you’ll need

Up to 1 year of quota-carrying or closing experience in an AE or AM role
Strong desire to join a high-growth software startup
Experience selling developer and/or technical products, especially in a product-led growth 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
Based in Toronto and available to work in-office 3 days per week

Benefits

Comp & perks

Inclusive, flexible environment
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 family
Corporate co-working program and virtual/in-person social events
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
$1500 USD annually for professional development
Mentorship, coaching, and internal promotion opportunities
Flexible paid time off program
Company-owned laptop (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