Senior Customer Account Executive

Tailscale

Senior Customer Account Executive expanding and renewing accounts for Tailscale's secure networking software. Driving upsells, adoption, forecasting, and customer success in Toronto's hybrid Sales team.

Posted 8/7/2026full-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

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Hard Skills

Closing ExperienceTechnical Product SalesForecastingRevenue DeliveryCustomer Success Strategies

Soft Skills

Proactive ApproachCollaborationPresentation SkillsCommunication

Tools & Technologies

GongSales Engineering Tools

Industry Keywords

Product-Led GrowthCustomer AdoptionHigh-Growth Software StartupClient Outcomes

About the role

Key responsibilities & impact

Expand and renew current customer accounts
Find additional customer use cases
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 for 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 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 a similar tool to collaborate internally and manage pipeline
Experience partnering with Sales Engineering, Support, and Customer Success teams to drive positive client outcomes
Proactive approach from lead to close
Role based in Toronto, with hybrid work preferred at 3 days per week in-office

Benefits

Comp & perks

An inclusive, flexible environment where you can be your authentic self
Competitive total compensation package including 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 you and your family
Remote-first company environment with virtual and in-person social events
Corporate co-working program to visit WeWork or similar spaces
Employer-funded retirement contributions matching employee contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of eligible compensation
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 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