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Added 19 mins ago
Manager, Commercial Expansion
Tailscale
Toronto, ON
…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…
Added 19 mins ago
Manager, Commercial Expansion
Tailscale
Vancouver, BC
…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…
Added 34 mins ago
General Manager
Five Guys
St. John's, NL
Access to virtual healthcare through TELUS Health
Added 49 mins ago
D
Marketing Coordinator, Quebec
Dormez-vous
Pointe-Claire, QC
- Full-time
Identify issues requiring a decision from the Marketing Manager, provide relevant context, and recommend solutions to support timely decision-making
Added 49 mins ago
FH
Executive Chef
Fairmont Hotels & Resorts
Vancouver, BC
- Full-time
Exclusive access to the Pacific Northwest Food & Beverage Discount Program, offering 50% off at participating dining destinations in Vancouver, Victoria, and Whistler.
Added 49 mins ago
Assistant Branch Manager (Enderby Branch)
First West
Enderby, BC
…support you with award-winning in-house training programs, access to LinkedIn Learning, and reimbursement for external courses to help you get…
Added 1 hour ago
A
Executive Chef
AccorHotel
Vancouver, BC
- Full-time
Exclusive access to the Pacific Northwest Food & Beverage Discount Program, offering 50% off at participating dining destinations in Vancouver, Victoria, and Whistler.
Added 1 hour ago
R-
Specialist, CRM & Lifecycle Marketing
RCL - Reitmans Canada Ltd/Ltée
Montreal, QC
- Full-time
As Specialist, CRM & Lifecycle Marketing, reporting into the Manager, Customer Activation, you plan, brief, and execute direct-to-customer activations and direct messaging campaigns for one…
Added 1 hour ago
R-
Store Manager - Corner Brook Plaza
RCL - Reitmans Canada Ltd/Ltée
Corner Brook, NL
- Full-time
Reporting to the Regional Manager, join a team where your leadership will truly have an impact! As a Store Manager, you’ll be at the heart of the action: leading and inspiring your team,…
Added 1 hour ago
R-
Store Manager - Southgate Centre
RCL - Reitmans Canada Ltd/Ltée
AB · Edmonton, AB
- Full-time
Reporting to the Regional Manager, join a team where your leadership will truly have an impact! As a Store Manager, you’ll be at the heart of the action: leading and inspiring your team,…
Added 1 hour ago
B
Mortgage Specialist
BMO
Montreal, QC
- Full-time
Documents updates in BMO’s internal systems to ensure employees have access to the status of outstanding customer opportunities, transactions, and problems / issues.
Added 1 hour ago
R-
Assistant Store Manager - RioCan Orleans
RCL - Reitmans Canada Ltd/Ltée
Ottawa, ON
- Full-time
Reporting to the Store Manager, join a team where your leadership will truly make an impact! As an Assistant Store Manager, you’ll help drive daily operations while motivating your team,…
Added 1 hour ago
C
Senior Architectural Estimator
CertainTeed
Woodbridge, ON
- Full-time
Coordinate quotation strategy with Estimating Manager as needed.
Added 1 hour ago
N
SaaS Implementation Project Manager
Nakisa
Montreal, QC
- Full-time
As a SaaS Implementation Project Manager, you will be responsible for management, supervision, and implementation of Nakisa SaaS solutions for our clients. Leading the project from…
Added 2 hours ago
SI
Kitchen Manager
Service Inspired Restaurants
Toronto, ON
- Other
Comprehensive Benefits: Access a range of health and wellness benefits tailored for you.
Added 2 hours ago
SI
Kitchen Manager
Service Inspired Restaurants
Mississauga, ON
- Other
Comprehensive Benefits: Access a range of health and wellness benefits tailored for you.
Added 2 hours ago
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Packaging Supervisor
Sleeman Breweries Ltd.
Vernon, BC
- Full-time
At Sleeman Breweries, you’ll have access to benefits that support you today and help you plan for tomorrow:
Added 2 hours ago
M
Spécialiste principal, Économie de la santé et étude des résultats thérapeutiques / Senior Specialist, Health Economics Outcomes Research
MSD
Kirkland, QC
- Full-time
Budget Impact Analysis, Leadership, Market Access, Pharmaceutical Products
Added 2 hours ago
AC
Distribution Account Manager, Canada
Axis Communications
Toronto, ON · Canada - ON - Toronto
- Full-time
Professional Development: Access to continuous learning opportunities, training programs, and tuition reimbursement to support your career growth
Added 2 hours ago
R
Manager, Sales Tax Advisory, Sales and Use Tax
Ryan
Mississauga, ON
- Full-time
Monthly Gym Membership OR Gym Equipment Reimbursement
Added 3 hours ago
RC
Manager, Sales Tax Advisory, Sales and Use Tax
Ryan Companies US, Inc.
Mississauga, ON
- Full-time
Monthly Gym Membership OR Gym Equipment Reimbursement
Added 3 hours ago
SP
Concierge
Southwest Properties
Halifax, NS
- Full-time
Educational Reimbursement for Eligible Employees/Programs
Added 3 hours ago
R(
Store Manager - Corner Brook Plaza
Reitmans (Canada) Ltée/Ltd
Corner Brook, NL
- Full-time
Reporting to the Regional Manager, join a team where your leadership will truly have an impact! As a Store Manager, you’ll be at the heart of the action: leading and inspiring your team,…
Added 3 hours ago
R
Manager, Sales Tax Advisory, Sales and Use Tax
Ryan
Mississauga, ON
- Full-time
Monthly Gym Membership OR Gym Equipment Reimbursement
Added 3 hours ago
P
Bilingual Case Manager – Patient Support Programs
PSPSync
Canada
- Full-time
- Contract
As a Case Manager at PSPSync, you will be the primary point of contact for patients enrolled in our PSPs. You will navigate patients through complex treatment pathways, manage reimbursement…

Tailscale

Manager, Commercial Expansion

Toronto, ON, 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 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 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 Toronto 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.

CAN Pay Range

$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

The manager will lead a team of Commercial Account Executives to drive expansion revenue and establish a new sales hub in Toronto. Responsibilities include coaching reps, managing pipelines, and building a repeatable expansion sales playbook.

Requirements

Candidates must have at least one year of people management experience in a B2B SaaS sales environment. Strong skills in sales processes, data-driven coaching, and the ability to work from the Toronto office are required.

Skills

People management
B2B SaaS sales
Sales coaching
Pipeline management
Account executive development
Data-driven decision-making
Sales strategy
Prospecting
Discovery
Qualification
Closing
Communication skills
Stakeholder engagement
Team leadership
Sales forecasting

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
Sales Management
Account Executive
Commercial Expansion
Pipeline Management
Sales Forecasting
Coaching
Prospecting
Customer Success
Sales Engineering
Partnerships
Data-driven
Toronto
Hybrid
Equity
Commission
Professional Development
Parental Leave
Networking
Account Management

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