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Added 6 mins ago
FH
Assistant Director, People & Culture
Fairmont Hotels & Resorts
Jasper, AB
- Full-time
…something truly special. If you are a passionate, energetic people leader who thrives in moments of change and opportunity, we want to hear from…
Added 6 mins ago
J
Quality Assurance Analyst (COPY) (COPY)
JobsMedia.io
Longueuil, QC
- Full-time
…technological processes. Reporting to the Deputy Director of Information Technologies, you will evolve in an environment where collaboration, continuous improvement and the user experience…
Added 6 mins ago
SA
Accountant II
Southern Alberta Institute of Technology (SAIT)
Calgary, AB · Greater Calgary Metropolitan Area
- Temporary
…internal and external stakeholders, communicates technical information in clear, practical terms, supports audit inquiries, and provides training, mentoring, and current process…
Added 6 mins ago
PC
Internal Audit Senior Manager
PwC Canada
Toronto, ON
- Full-time
…every one of us at PwC needs to be an authentic and inclusive leader, at all grades/levels and in all lines of service. To help us achieve this we have the PwC Professional; our global…
Added 6 mins ago
S
Traffic Signal Design – Electrical CAD Technologist
SYSTRA
Toronto, ON
- Full-time
SYSTRA Canada is part of the SYSTRA group, an international consulting and engineering group, a world leader in the design of transport infrastructures. SYSTRA Canada is an engineering and…
Added 7 mins ago
Manager, Commercial Expansion
Tailscale
Toronto, ON
As our first sales leader in Toronto, you’ll help establish our new sales hub, hire and develop talent, and build a repeatable expansion sales motion. This is a hands-on opportunity to…
Added 7 mins ago
Manager, Commercial Expansion
Tailscale
Vancouver, BC
As our first sales leader in Vancouver, you’ll help establish our new sales hub, hire and develop talent, and build a repeatable expansion sales motion. This is a hands-on opportunity to…
Added 36 mins ago
R
Business Analyst - Expert
Raise
Toronto, ON
- Full-time
…our top clients. After establishing themselves as an industry leader, they’re now expanding their team to meet rising demand. We’re hiring right now; if you’re interested, apply below for…
Added 36 mins ago
BC
Service Centre Manager - Speedy Glass
Belron Canada inc
Hanover, ON
- Full-time
Automotive glass technology is helping transform how we experience the road. At Belron Canada, the home office of Speedy Glass, Lebeau vitres d’auto and Vanfax we take this seriously, which…
Added 36 mins ago
V|
Logistics Specialist
Veolia | North America
Oakville, ON
- Full-time
Veolia's Water Technology Business brings together a dedicated team of experienced professionals committed to tackling the world’s most complex challenges related to water scarcity,…
Added 36 mins ago
J
Quality Assurance Analyst (COPY)
JobsMedia.io
Laval, QC
- Full-time
…technological processes. Reporting to the Deputy Director of Information Technologies, you will evolve in an environment where collaboration, continuous improvement and the user experience…
Added 36 mins ago
J
Quality Assurance Analyst
JobsMedia.io
Quebec, QC
- Full-time
…technological processes. Reporting to the Deputy Director of Information Technologies, you will evolve in an environment where collaboration, continuous improvement and the user experience…
Added 36 mins ago
MC
Senior Sales Representative - KYC Solutions
Moody's Corporation
Toronto, ON
- Full-time
Our KYC/AML Banking team helps financial institutions address critical compliance, risk, data, and operational challenges. We work with banks to modernize how they manage customer and…
Added 36 mins ago
HT
Technical Trainer
Husky Technologies
Bolton, ON
- Full-time
…with us as we pursue our ambitious growth strategy. We are a leader in developing state-of-the-art technology and it is this technology base that uniquely positions us to serve customers…
Added 36 mins ago
HT
Director, Finance (CSM)
Husky Technologies
Bolton, ON
- Full-time
…with us as we pursue our ambitious growth strategy. We are a leader in developing state-of-the-art technology and it is this technology base that uniquely positions us to serve customers…
Added 36 mins ago
UO
Clinical Trial Systems Lead, Calgary Centre for Clinical Research
University of Calgary
Calgary, AB
- Full-time
A Bachelor's or Master's degree in health sciences, information technology, research administration, or related area, and/or equivalent combination of experience/training
Added 36 mins ago
T
Manufacturing System Engineer
Trioworld
Ajax, ON
- $95,000 to $130,000 CAD / year
- Full-time
…automation, SCADA systems, and software development to join our team. The successful candidate will be responsible for designing, implementing, and supporting manufacturing automation and…
Added 36 mins ago
V|
Administrative Assistant
Veolia | North America
AB · Edmonton, AB
- Full-time
Veolia's Water Technology Business brings together a dedicated team of experienced professionals committed to tackling the world’s most complex challenges related to water scarcity,…
Added 37 mins ago
X
VP, Communications, Brand & Marketing
Xanadu
Toronto, ON
- Full-time
Achieving this mission requires exceptional technology, talented people, and the ability to communicate clearly why our work matters. We are seeking a VP, Communications, Brand & Marketing…
Added 51 mins ago
MC
Senior Small Business Advisor
Meridian Credit Union
Barrie, ON
- $68,800 to $100,000 CAD / year
- Full-time
…collaborate, innovate and build effective relationships with your team, your colleagues and your leader which is very important…
Added 51 mins ago
A
Director, Stations
AECOM
Mississauga, ON
- Full-time
…your bold ideas and big dreams and become part of a global team of over 50,000 planners, designers, engineers, scientists, digital innovators, program and construction managers and other…
Added 52 mins ago
AT
Class 1 Truck Driver
Arrow Transportation Systems Inc.
Grande Prairie, AB
- Full-time
In Business since 1919 and still growing, Arrow is a leader in bulk commodity hauling, reload operations, freight management, logistics, consulting, and technology with operations…
Added 52 mins ago
W
(CAN) Senior Director, Digital Strategy and Media
Walmart
Mississauga, ON
- Full-time
Serve as a senior marketing leader partnering with eCommerce, Merchandising, Membership, Walmart Connect, Analytics, Finance, Product, and Technology to align growth priorities, roadmaps,…
Added 1 hour ago
NS
Sr. Account Manager, Public Relations
North Strategic
Toronto, ON
- $80,000 to $90,000 CAD / year
- Contract
…social and digital, establishing itself as a Canadian agency…
Added 1 hour ago
HC
Coordinator, Field Placement, ECS/SWSS - UGH - FT Support
Humber College
Toronto, ON
- Full-time
…excellence, and in doing so, we redefine what it means to be a leader in providing an education combining theory and practice. Join…

Tailscale

Manager, Commercial Expansion

Vancouver, BC, Canada

$268,000 - $335,000 CAD

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Job details

Pay: $268,000 - $335,000 CAD
Experience: At least 1 year of people management experience in a B2B SaaS sales environment
Posting language: English
Posted: Nov 6, 2026

Original job description

Thank you for considering Tailscale. If this job description resonates with you, please apply. Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. We encourage you to help us break that statistic!

About Tailscale

Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We're building a future for the Internet that's easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.

About the Role

We’re looking for a thoughtful, curious, and driven Sales Manager to lead a team of Commercial Account Executives focused on growing existing customer relationships. You’ll coach and develop reps, own team performance, and help them navigate both fast-moving expansion opportunities and larger, more complex deals.

As our first sales leader in Vancouver, you’ll help establish our new sales hub, hire and develop talent, and build a repeatable expansion sales motion. This is a hands-on opportunity to shape a growing team and help more customers realize the value of Tailscale.

Key Responsibilities

Help establish Tailscale’s new sales hub, hire and onboard Commercial Expansion AEs, and create a culture of curiosity, accountability, and shared success
Drive expansion revenue, maintain a healthy pipeline, and deliver accurate forecasts
Prospect alongside reps, join customer conversations, and help navigate pivotal deals - from fast-moving expansions to larger, more complex opportunities
Turn call reviews, role plays, and deal strategy sessions into practical coaching that sharpens skills and supports career growth
Build and refine a repeatable expansion playbook, using sales data and customer insights to test approaches and scale what works
Develop a deep understanding of Tailscale’s value and partner with Customer Success, Marketing, Product, Sales Engineering, and Partnerships to grow adoption

What We Are Looking For

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 the sales process, including 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 both technical and nontechnical stakeholders
A 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 our Vancouver office three days per week

As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale's compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire's base salary. Individual offers may vary based on experience and skill set.

For this position, our pay ranges reflect target OTE (on target earnings), inclusive of base salary and variable compensation tied to the attainment of quarterly sales targets.

CAN Pay Range (OTE)

$268,000 - $335,000 CAD

What We Offer

An inclusive, flexible environment where you can be your authentic self. We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.
A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).
Comprehensive group benefits with no waiting period. Take advantage of coverage for health, vision, dental, and more for you and your family!
Remote first company - most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.
Employer-funded retirement contributions. Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.
Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.
Support for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.
Paid time off and a healthy work-life integration. Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!
A build-your-own home office setup. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.
Paid parental leave program. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).

Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.

Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.

Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit https://tailscale.com/scam-awareness.

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More about this job

Responsibilities

Lead and develop a team of Commercial Account Executives to drive expansion revenue and maintain a healthy sales pipeline. Establish a new sales hub in Vancouver while building repeatable sales motions and fostering a culture of accountability.

Requirements

Requires at least 1 year of people management experience within a B2B SaaS sales environment. Candidates must demonstrate strong coaching abilities, data-driven decision-making skills, and the capacity to work from the Vancouver office three days per week.

Skills

People management
B2B SaaS sales
Sales coaching
Account management
Pipeline management
Sales forecasting
Prospecting
Deal strategy
Data-driven decision-making
Communication skills
Team leadership
Customer success
Sales enablement
Strategic planning
Hiring
Onboarding

Benefits

Equity incentive plan
Variable commission
Comprehensive group benefits
Health insurance
Vision insurance
Dental insurance
Professional development stipend
Paid time off
Home internet reimbursement
Workstation customization stipend
Paid parental leave

Visa sponsorship

Not detected in the job text

Keywords

B2B SaaS
Account Executive
Sales Management
Expansion Sales
Pipeline Management
Sales Forecasting
Coaching
Customer Success
Sales Engineering
Partnerships
Vancouver
Hybrid Work
Equity
Commission
Professional Development
Parental Leave
Team Leadership
Sales Hub
Accountability
Data-driven
Prospecting
Qualification
Closing
Stakeholder Engagement
Continuous Improvement

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