Manager, Commercial Expansion

Tailscale

. Lead a team of Commercial Account Executives focused on growing existing customer relationships .

Posted 11/6/2026full-timeVancouver • CanadaJuniorWebsite

Core Competencies

Role fit

Core Competencies

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

Demonstrates strong leadership in managing and developing a team of Commercial Account Executives within a B2B SaaS sales environment, focusing on driving expansion revenue and maintaining a healthy sales pipeline through data-driven decision-making and effective coaching.

Highest-signal resume keywords

People Management ExperienceB2B SaaS Sales ExpertiseCoaching And Development SkillsData-Driven Decision-MakingPipeline Management

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

ProspectingDiscoveryQualificationClosingSales ForecastingSales Playbook DevelopmentAccount ManagementPerformance Metrics AnalysisSales StrategyQuota Management

Soft Skills

Excellent Communication SkillsCuriosityProactive MindsetAccountabilityTeam Building

Industry Keywords

B2B SalesSaaSCustomer SuccessSales EngineeringMarketing PartnershipsHigh-Velocity Sales EnvironmentContinuous ImprovementOnboardingCoachingCustomer Insights

About the role

Key responsibilities & impact

Lead a team of Commercial Account Executives focused on growing existing customer relationships
Establish Tailscale’s new Vancouver sales hub
Hire, onboard, coach, and develop Commercial Expansion Account Executives
Build a culture of curiosity, accountability, and shared success
Drive expansion revenue, maintain a healthy pipeline, and deliver accurate forecasts
Prospect alongside representatives and join customer conversations
Navigate fast-moving expansions and larger, more complex opportunities
Conduct call reviews, role plays, and deal strategy sessions
Build and refine a repeatable expansion playbook using sales data and customer insights
Partner with Customer Success, Marketing, Product, Sales Engineering, and Partnerships to grow adoption

Requirements

What you’ll need

At least 1 year of people management experience in a B2B SaaS sales environment
Proven ability to coach, develop, and motivate Account Executives or other quota-carrying sales professionals
Strong understanding of prospecting, discovery, qualification, pipeline management, and closing
Experience driving team performance through data-driven decision-making, structured coaching, and clear accountability
Ability to thrive in a fast-paced, high-velocity sales environment while managing multiple priorities
Excellent written and verbal communication skills, with the ability to engage technical and nontechnical stakeholders
Curious, proactive mindset with a bias for action and a passion for continuous improvement
Willingness to travel approximately once per quarter
Ability to work from the Vancouver office three days per week

Benefits

Comp & perks

An inclusive, flexible environment where you can be your authentic self
Competitive total compensation package including an 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 flexible work arrangements, virtual and in-person social events, and corporate co-working program
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
$1,500 USD annually for professional development, plus 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