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Core Competencies
Role fitCore Competencies
Use this summary to align your resume positioning with the role.
Demonstrates expertise in B2B SaaS sales management, focusing on coaching and developing Account Executives while driving expansion revenue through data-driven decision-making and effective pipeline management.
Highest-signal resume keywords
People Management ExperienceCoaching And DevelopmentPipeline ManagementData-Driven Decision-MakingExcellent Communication Skills
ATS Keywords
Tailor your resumeApplicant Tracking System Keywords
Tip: use these terms in your resume and cover letter to boost ATS matches.
Hard Skills
B2B SaaS SalesProspectingDiscoveryQualificationClosingSales ForecastingSales Data AnalysisAccount ManagementPerformance MetricsSales Playbook Development
Soft Skills
CuriosityProactive MindsetAccountabilityContinuous ImprovementTeam Motivation
Industry Keywords
Sales HubExpansion RevenueCustomer SuccessHigh-Velocity Sales EnvironmentQuota-Carrying Sales Professionals
About the role
Key responsibilities & impact- Establish Tailscale’s new Toronto sales hub
- Hire and onboard Commercial Expansion Account Executives
- Create 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, complex opportunities
- Coach representatives through call reviews, role plays, and deal strategy sessions
- Build and refine a repeatable expansion playbook using sales data and customer insights
- Develop deep understanding of Tailscale’s value and 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 for engaging technical and nontechnical stakeholders
- Curious, proactive mindset with bias for action and passion for continuous improvement
- Willingness to travel approximately once per quarter
- Ability to work from the Toronto office three days per week
Benefits
Comp & perks- Inclusive, flexible environment supporting authenticity and work-life integration
- Competitive total compensation package including 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
- Remote-first company with corporate co-working program, virtual and 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 choice of Mac or PC
- Monthly home internet reimbursement
- $500 USD home office workstation customization allowance
- Paid parental leave top-ups: 20 weeks for birthing parents and 16 weeks for non-birthing parents