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Added 1 day ago
A
Senior Compensation Partner, Sales & Marketing
Autodesk
Vancouver, BC · Greater Vancouver Metropolitan Area
- Full-time
Prepare Sales-specific communications, quick-reference guides, and manager enablement, including guidance for commission and non-commission employees
Added 1 day ago
A
Senior Compensation Partner, Sales & Marketing
Autodesk
Toronto, ON · Greater Toronto Area, Canada
- Full-time
Prepare Sales-specific communications, quick-reference guides, and manager enablement, including guidance for commission and non-commission employees
Added 1 day ago
A
Analyst, Investment Research and Solutions
ATB
Toronto, ON · Edmonton, AB · Calgary, AB
- Full-time
…responsible for supporting quantitative data collection, peer performance attribution, and research reporting to directly assist our investment advisory and portfolio management teams. The…
Added 1 day ago
IW
Senior Manager, Events
IG Wealth Management
MB · Manitoba, Canada
- Full-time
The Senior Manager, Events & Experience is responsible for leveraging strategic event marketing and experience design to support the sales, distribution, and growth objectives of IG Wealth…
Added 1 day ago
IW
Senior Manager, Events
IG Wealth Management
ON · Ontario, Canada
- Full-time
The Senior Manager, Events & Experience is responsible for leveraging strategic event marketing and experience design to support the sales, distribution, and growth objectives of IG Wealth…
Added 1 day ago
PC
Manager, Financial Services, Digital Banking Operations, Consulting
PwC Canada
Toronto, ON
- Full-time
Demonstrated Manager-level experience in management consulting or a comparable client-facing leadership role, with strong knowledge of operations in Financial Services, particularly…
Added 1 day ago
Manager, Commercial Expansion
Tailscale
Vancouver, BC
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…
Added 1 day ago
AF
Analyst, Investment Research and Solutions
ATB Financial
Toronto, ON
- Volunteer
…responsible for supporting quantitative data collection, peer performance attribution, and research reporting to directly assist our investment advisory and portfolio management teams. The…
Added 1 day ago
K
Senior Customer Success Manager
KORE
Canada
- $93,772 to $118,738 CAD / year
The Strategic Customer Success Manager is responsible for the customer journey, building loyalty, and developing close, long-term client relationships with our strategic customers. In this…
Added 1 day ago
TH
Community Enablement Specialist, Video (Askuity division)
The Home Depot Canada
Toronto, ON
- Full-time
…total rewards may include: semi-annual bonuses tied to business performance; Deferred Profit-Sharing Program to assist with retirement savings; comprehensive paid benefits; a 15% discount…
Added 1 day ago
O
Analytics Engineering & Measurement Student
OLG
Sault Ste. Marie, ON · Toronto, ON · York Mills Office
- Full-time
Reporting to the Sr Manager Strategic Analytics, you will be empowered to:
Added 1 day ago
AC
Distribution Account Manager, Canada
Axis Communications
Toronto, ON · Canada - ON - Toronto
- Full-time
Do you enjoy building strong partnerships and turning relationships into results? As our Distribution Account Manager for Canada, you'll help grow Axis's presence, engagement and advocacy…
Added 2 days ago
MT
Senior Product Manager
Meal Ticket
Canada
- Full-time
Meal Ticket is seeking a Senior Product Manager to own and evolve the TrackMax+ product portfolio, our platform serving the foodservice distribution industry.
Added 2 days ago
P
Manager, Financial Services, Digital Banking Operations, Consulting
PwC
Toronto, ON
- Full-time
Demonstrated Manager-level experience in management consulting or a comparable client-facing leadership role, with strong knowledge of operations in Financial Services, particularly…
Added 2 days ago
UO
Business Solutions Analyst (Shopify)
University of Alberta
Edmonton, AB
- Full-time
…which generates over $8 million annually. Reporting to the Manager of Enterprise Asset Systems within Enterprise Applications, this position works closely with campus store administrators,…
Added 2 days ago
MS
Senior Manager, Sales Enablement and Strategy
Metergy Solutions
Toronto, ON · North York, ON
- $110,000 to $135,000 CAD / year
- Full-time
The Senior Manager, Sales Strategy & Enablement is a strategic and hands-on leader responsible for strengthening how Metergy plans, manages and executes sales across Canada and the United…
Added 2 days ago
TH
Community Enablement Specialist, Video (Askuity division)
The Home Depot
Toronto, ON
- Full-time
The Community Enablement Specialist will plan, develop, and produce scalable content that drives awareness and usage of the Supplier Analytics Program, with a strong focus on video…
Added 2 days ago
T
AVP, Legal - Technology Enablement, Data Analytics and Reporting
TD
Toronto, ON
- Full-time
Generate actionable insights to support decision-making, resource allocation, and performance management
Added 2 days ago
RB
Assistant Branch Manager
Royal Bank of Canada
Fredericton, NB
- Full-time
Partner with your manager to ensure operational effectiveness of the branch and maximize the performance of the team
Added 2 days ago
DC
Executive Director, Marketing & Brand
Diabetes Canada
Toronto, ON · Greater Toronto Area, Canada
- Full-time
Lead strategic prioritization of marketing enablement across the organization, continuously balance competing departmental demands and ensure cohesive alignment among senior stakeholders
Added 2 days ago
Executive Director, Marketing & Brand
Diabetes Canada / National Diabetes Trust
Toronto, ON · ON
Lead strategic prioritization of marketing enablement across the organization, continuously balance competing departmental demands and ensure cohesive alignment among senior stakeholders
Added 2 days ago
AVP, Advisor Experience and Programs
Richardson Wealth Ltd
Toronto, ON
Reporting to the VP National Sales Manager and Head of Advisor Experience, this role serves as a trusted right-hand partner, helping translate strategic priorities into coordinated programs…
Added 2 days ago
Employee Services Supervisor
Pembina Pipeline Corporation
Calgary, AB
The Supervisor will strengthen operational performance through automation, process optimization, technology enablement and data-driven decision-making. This role also leads HR functions,…
Added 2 days ago
Senior Manager, Special Operations (The Pets Table)
HelloFresh
Toronto, ON
The Senior Manager, Special Operations will have the opportunity to shape the growth and strategy of operation functions at The Pets Table. This person will be responsible for managing and…
Added 2 days ago
EC
Manager, Customer Success (Corporate Travel/SaaS)
Emburse Chrome River
Toronto, ON
- Full-time
The Manager, Customer Success - Travel leads a team of Customer Success Managers responsible for helping Travel customers achieve measurable program value, strong adoption, and successful…

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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