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Added 5 mins ago
PM
Administrative Secretary 2
Prairie Mountain Health
Brandon, MB
- Full-time
The Administrative Secretary 2 will provide clerical and administrative support functions for all of the staff and clients who receive services from the program that they support. The…
Added 5 mins ago
PM
Clerk III - Health Information
Prairie Mountain Health
Brandon, MB
- Full-time
Completion of a recognized Medical Terminology course or program
Added 5 mins ago
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Project Cost Administrator - 6 Month Contract
Convergint
Calgary, AB
- Contract
College diploma or certificate in Business Administration, Accounting or similar program required; extensive relevant experience will also be considered.
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PM
Health Care Aide
Prairie Mountain Health
Souris, MB
- Full-time
Health Care Aide Certificate from a recognized program
Added 5 mins ago
PM
Health Care Aide
Prairie Mountain Health
Brandon, MB
- Full-time
Health Care Aide Certificate from a recognized program
Added 5 mins ago
PM
Health Care Aide
Prairie Mountain Health
Brandon, MB
- Full-time
Health Care Aide Certificate from a recognized program
Added 5 mins ago
PM
Health Care Aide
Prairie Mountain Health
Dauphin, MB
- Full-time
Health Care Aide Certificate from a recognized program
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Responsable Agile (Scrum Master)
Jobgether
Canada
- Full-time
Establish and support mechanisms that improve delivery velocity, predictability, and value creation while keeping teams focused on meaningful outcomes.
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Technical Support Specialist - Bilingual French
Jobgether
Canada
- Full-time
Home office reimbursement program to support effective remote work.
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IF
Student - Branch Coordinator
iA Financial Group (Industrial Alliance)
Quebec, QC
- $23.5 to $28.75 CAD / hour
- Internship
Support advisors and associates on projects by leveraging tools such as Microsoft Teams and SharePoint;
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IH
Registered Nurse (RN) | Intensive Care Unit (ICU)
Interior Health Authority
Kelowna, BC
- Internship
We offer a range of employee benefits and services to support you at every stage of your career:
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BW
Ambulance Readiness Technician
BC Women's Hospital and Health Centre
Kamloops, BC
- Full-time
…care too – offering health, wellness, development programs to support you – at work and at…
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NG
Construction Surveyor
New Gold Inc.
Emo, ON
- Full-time
Reporting to the Construction Technical Supervisor, the Construction Surveyor provides technical survey support to the Coeur Rainy River Construction team, including construction layout,…
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Assistant Head Nurse
Alberta Health Services
Cold Lake, AB
- Part-time
Completion of an accredited nursing education program. Active or eligible for registration and practice permit with the College of Registered Nurses of Alberta (CRNA). Current Basic Cardiac…
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Accountant, Assurance and Accounting (Fall 2027)
MNP
Chilliwack, BC
- $50,000 to $65,000 CAD / year
- Full-time
Completion of, or working towards, prerequisites for admission into the CPA Professional Education Program (PEP) upon commencement of employment
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TH
Merchandising Execution Associate Part-Time - 7245 Regina Northwest-
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Regina, SK
- Part-time
Read and interpret directions to ensure merchandise is set to the planogram, project instructions, program service requirements and general service guidelines
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IF
Inside sales specialist
iA Financial Group (Industrial Alliance)
Toronto, ON
- Temporary
Are you driven by sales support and relationship management and eager to contribute to the purpose of a company that aims to help its clients feel confident and secure about their future?…
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Recreation Therapy Worker
Interior Health Authority
Ashcroft, BC
- Full-time
…employer-paid training, and an Employee & Family Assistance Program to support you every step of the…
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Registered Nurse (RN) | Intensive Care Unit (ICU)
Interior Health Authority
Kelowna, BC
- Internship
We offer a range of employee benefits and services to support you at every stage of your career:
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Registered Nurse (RN) | Surgical
Interior Health Authority
Kelowna, BC
- Internship
We offer a range of employee benefits and services for eligible positions, to support you at every stage of your career:
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Professional, Engineering, In-Service
Bombardier
Dorval, QC
- Full-time
With our employees’ well-being top of mind, we offer a comprehensive and competitive Benefits Program, which includes the following:
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Specialist, Supply Chain (Systems & Avionics)
Bombardier
Dorval, QC
- Full-time
With our employees’ well-being top of mind, we offer a comprehensive and competitive Benefits Program, which includes the following:
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Registered Nurse- Specialist, Clinical Responder (GTA)
Ontario Health | Santé Ontario
Toronto, ON
- Full-time
Flexible health care or wellness spending accounts, plus an inclusive program to support your well-being.
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IH
Occupational Therapist | Acute and Rehab
Interior Health Authority
Penticton, BC
- Full-time
We are a B.C. top employer and offer welcoming workplaces with a range of benefits and policies to support you at every stage of your career.
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Compensation Analyst - 1-year Contract
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Toronto, ON
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Support process improvement initiatives that enhance program effectiveness, administrative efficiency, and user experience.

Tailscale

Senior New Business Account Executive

Toronto, ON, Canada

$201,000 - $201,000 CAD

Apply About employer

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Job details

Pay: $201,000 - $201,000 CAD
Experience: 2+ years of prospecting or closing experience in a door-to-door or in-person sales role
Posting language: English
Posted: Oct 5, 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 are looking for ambitious sellers to join our New Business Account Executive team. This is not a “farmer” role. You will be assigned inbound leads via round robin, however you will also be responsible for prospecting and sourcing a third of your own pipeline. You’ll own the sales cycle from prospect to purchase, and work to earn customer trust every step of the way.

Tailscale has a vibrant community across Hacker News, X, and Reddit. We have 100,000+ monthly active users, many of whom are engineering leaders working at the most innovative companies in the world. This is an opportunity to join early at a rapidly growing startup and build the playbook for startup sales.

Key Responsibilities

Win new business. Find your way to the right people at prospective customers, educate them about our services, and help them succeed with Tailscale.
Experiment and move quickly. Analyze market landscapes and customer trends to inform your sales campaigns.
Travel to (or organize) local events and attend large industry events to evangelize Tailscale to prospective customers
Support customers across all time zones
Manage and organize your activities, pipeline, and forecast in Gong and Salesforce

What We Are Looking For

2+ years of prospecting or closing experience in a door-to-door or in-person sales role
Ambition to build (and not just follow) a sales playbook
A technical background or curiosity in technology
Excellent communication and presentation skills
Proactive from lead to close - if this opportunity really excites you, please don’t just apply on the website. Find the hiring manager, prospect thoughtfully, and tell us why you’re the best candidate for this position.
Experience self sourcing opportunities and guiding a customer from discovery all the way through closed won deals, with senior technical buyers (VP Engineering, CTO, Head of Platform, CISO)
This role is based in Toronto and is hybrid required (3 days/week in-office)

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)

$201,000 - $201,000 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

You will be responsible for winning new business by prospecting, sourcing your own pipeline, and managing the full sales cycle from discovery to closed deals. Additionally, you will analyze market trends, attend industry events, and maintain accurate records in Gong and Salesforce.

Requirements

Candidates must have at least 2 years of experience in prospecting or closing roles, ideally with a technical background or strong curiosity. Excellent communication skills and the ability to self-source opportunities with senior technical buyers are essential for this position.

Skills

Sales
Prospecting
Account management
Pipeline management
Sales cycle management
Communication
Presentation skills
Technical curiosity
Negotiation
Lead generation
Forecasting
Strategic planning

Benefits

Health insurance
Dental insurance
Vision insurance
Equity incentive plan
Retirement contributions
Professional development budget
Paid time off
Home office stipend
Internet reimbursement
Paid parental leave

Visa sponsorship

Not detected in the job text

Keywords

Sales
New Business
Account Executive
Prospecting
Pipeline
Gong
Salesforce
SaaS
Technology
Engineering
VP Engineering
CTO
CISO
Startup
Networking
Lead Generation
Market Analysis
Hybrid
Toronto
B2B Sales

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