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Added 14 mins ago
LC
HMR Assistant Department Manager Full Time Day
Loblaw Companies Limited
Halifax, NS
- Full-time
…products and deals our team members are there to give excellent customer service and memorable experiences. Our Assistant Department Managers are dedicated people leaders who navigate us to…
Added 59 mins ago
S-
Assistant Manager
Showcase - Home of the Hottest Trends
Rocky View No 44, AB · Rocky View County, AB
- Full-time
Showcase "Home of the Hottest Trends", voted one of Canada's "Best Managed Companies" 2021 and the world's largest retailer of its kind is hiring for Assistant Manager!
Added 1 hour ago
SC
Marketing Specialist
Sustainability consulting
Canada
- Full-time
…and execute marketing initiatives that drive brand awareness, customer engagement, and business growth. This role is responsible for managing campaigns, analyzing market trends, and…
Added 2 hours ago
T
Account Manager
TransPerfect
Montreal, QC
- Full-time
…marketing, AI strategy and implementation, SEO, and multilingual customer support. Every client partnership is backed by industry-leading technology and a consultative approach designed to…
Added 2 hours ago
T
Account Manager
TransPerfect
Toronto, ON
- Full-time
…marketing, AI strategy and implementation, SEO, and multilingual customer support. Every client partnership is backed by industry-leading technology and a consultative approach designed to…
Added 3 hours ago
GD
GARAGE - Seasonal Sales Associate - Woodgrove Centre
Groupe Dynamite, Inc Garage
Nanaimo, BC
- Part-time
Reporting to the Store Manager, you’ll be the face of our brand. As a Seasonal Sales Associate, your focus is creating an elevated shopping experience - whether it’s styling customers in…
Added 3 hours ago
BM
Assistant Manager, Alpine Race & Freestyle - Full Time
Blue Mountain Resort
The Blue Mountains, ON
- Full-time
The Assistant Manager, Race sets the cultural tone for creating revolutionary guest experiences while uniting their team around purpose and fun. The Assistant Manager, Race & Freestyle,…
Added 3 hours ago
Produce - Supervisor Produce TF Belmont
Sobeys Capital Incorporated or a Franchise/Affiliate / ou une franchise/société affiliée
Langford, BC
The Produce Supervisor is responsible to ensure a superior customer service experience by coaching, and developing friendly, well-trained staff. The Supervisor will supervise the department…
Added 4 hours ago
MP
Funeral Director, Funeral Services
Mount Pleasant Group
Pickering, ON
- $41.4 to $46.43 CAD / hour
- Full-time
Added 4 hours ago
LC
Assistant Front Store Manager, Hourly Part Time Day
Loblaw Companies Limited
Oshawa, ON
- Part-time
Join a locally owned and operated store to help deliver health, beauty and convenience services in your community, and keep the customer at the centre of everything you do.
Added 4 hours ago
LC
Assistant Front Store Manager, Hourly Full Time Flexible Shifts
Loblaw Companies Limited
Oshawa, ON
- Full-time
Join a locally owned and operated store to help deliver health, beauty and convenience services in your community, and keep the customer at the centre of everything you do.
Added 6 hours ago
U
Représentant des ventes – Région d’Ottawa, ON et Gatineau, QC
USG
Montreal, QC
- Other
Added 6 hours ago
BC
Marketing Specialist
BIOAGRINEC CONSULTING & RECRUTEMENT
Canada
- Full-time
…and execute marketing initiatives that drive brand awareness, customer engagement, and business growth. This role is responsible for managing campaigns, analyzing market trends, and…
Added 6 hours ago
SD
Assistant Front Store Manager, Hourly Full Time Flexible Shifts
Shoppers Drug Mart
Oshawa, ON
- Full-time
Join a locally owned and operated store to help deliver health, beauty and convenience services in your community, and keep the customer at the centre of everything you do.
Added 6 hours ago
SD
Assistant Front Store Manager, Hourly Part Time Day
Shoppers Drug Mart
Oshawa, ON
- Part-time
Join a locally owned and operated store to help deliver health, beauty and convenience services in your community, and keep the customer at the centre of everything you do.
Added 6 hours ago
SN
Seasonal Team Member, CrossIron Mills
Saje Natural Wellness | Retail
AB · Rocky View County, Alberta
- Contract
…individuals who have drive and warmth, agility and passion, and keep customer experience at the centre of everything they do.</p><p>At Saje, you’ll connect with a dynamic community…
Added 7 hours ago
CO
Temporary Technical Lead (Housing Accelerator Fund) Up to 18 Months
City of Saint John
Saint John, NB
- Temporary
Under the general supervision of the HAF Project Manager, you will be part of a high-caliber cross functional team leading the E-Permitting Initiative under the City of Saint John Housing…
Added 7 hours ago
CO
Human Resources Generalist
City of Saint John
Saint John, NB
- Full-time
Respond to employee and manager inquiries regarding pay, benefits, and employment-related documentation.
Added 7 hours ago
SI
Sales Associate
Staples Inc.
Penticton, BC
- Part-time
Deliver exceptional customer service and enhance customer engagement and satisfaction.
Added 7 hours ago
TL
Manager, Commercial Expansion
Teli Labs
Vancouver, BC
- Full-time
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 8 hours ago
Area Manager II, YYZ4
Amazon
Brampton, ON
As an Area Manager II at an Amazon fulfillment center, you'll act as a strategic leader overseeing upto 80 associates while driving department level operational improvements. You'll conduct…
Added 8 hours ago
F
Project Manager
FISPAN
Vancouver, BC
- Full-time
Work with internal/external customer teams to assess business and implementation risks, guide the technical integration process, assist with technical problem solving, and manage internal…
Added 8 hours ago
SI
Sales Associate
Staples Inc.
Yellowknife, NT
- Full-time
Deliver exceptional customer service and enhance customer engagement and satisfaction.
Added 9 hours ago
SD
Assistant Front Store Manager, Hourly Part Time Flexible Shifts Greenlight Requisition
Shoppers Drug Mart
Newmarket, ON
- Part-time
Join a locally owned and operated store to help deliver health, beauty and convenience services in your community, and keep the customer at the centre of everything you do.
Added 10 hours ago
L
Assistant Manager, Guest Experience | Rideau Centre
lululemon
Ottawa, ON
- Full-time
The Assistant Manager, Guest Experience role is an essential part of the store leadership team, ensuring our team members and guests (i.e., customers) receive a quality experience in our…

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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