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Added 1 min ago
Retail Assistant Brand Manager, Sandro/Maje, (Holt Renfrew Ogilvy, Montreal)
SMCP NORTH AMERICA (US, CANADA)
Montreal, QC
…innovation and sustainability come together. As we continue to lead the accessible luxury market, we focus on growth, stability, and prioritizing internal mobility for our people. With a…
Added 16 mins ago
J
Major Account Manager
JobsMedia.io
Mascouche, QC
- Full-time
Lead negotiations related to the renewal of contractual agreements and ensure the sustained profitability of the accounts under their responsibility
Added 16 mins ago
N
Growth Operations Manager
nesto
Toronto, ON
- Full-time
…required to wield influence to win challenging business cases and lead the change management for the changes you are implementing. Underpinned by a strong sense of ownership, your willpower…
Added 16 mins ago
TS
Business Development Representative
Techspirit Solutions Inc
Mississauga, ON
- Full-time
Added 16 mins ago
CH
Unit Manager
Covenant Health Canada
AB · Edmonton, AB
- Full-time
…engaging and collaborative Unit Manager, Pharmacy Services to lead and support pharmacy services here at the Misericordia Community Hospital and Villa Caritas. In this key leadership role,…
Added 16 mins ago
CH
Lead
Covenant Health Canada
AB · Edmonton, AB
- Full-time
…Health is currently recruiting for a Connect Care reporting lead who will work closely with other team members, managers, and leaders from other teams to provide evidence and develop…
Added 16 mins ago
CH
Licensed Practical Nurse
Covenant Health Canada
AB · Edmonton, AB
- Full-time
…patients/residents and families. The LPN must be able to team lead effectively on their own. The LPN works to the full scope of practice in providing safe, quality care in accordance with…
Added 16 mins ago
Global Supply Chain Manager
Intertape Polymer Group (IPG)
Truro, NS
Work with your team to analyze and continuously improve supply chain workflows and warehouse processes, focusing on maximizing efficiency, reducing lead times, and minimizing costs.
Added 16 mins ago
Brand Manager
Sofina Foods Inc
Markham, ON
Lead packaging design development and artwork approval processes.
Added 31 mins ago
NM
Agriculture Equipment Technician
Nelson Motors and Equipment
Avonlea, SK
- Full-time
We're looking for Agricultural Equipment Technicians who lead by example, support a strong team environment, and deliver service excellence that reflects our promise of reliable,…
Added 31 mins ago
NM
Corporate Precision Agriculture Manager
Nelson Motors and Equipment
Avonlea, SK
- Full-time
…other aligned technology, strengthen the customer experience, lead consistent processes, and team development across all five of our locations. This position can be based out of any one of…
Added 45 mins ago
A
Senior Delivery Manager, Temporary
Aviso
Toronto, ON
- Temporary
…consisting of the Product Owner, Product Designer, and Technology Lead. The role is accountable for driving alignment across squads and stakeholders, ensuring roadmaps, priorities,…
Added 45 mins ago
NB
Senior Director, IT Delivery and Technology Platforms
National Bank of Canada
Montreal, QC
- Full-time
You will lead 3 to 4 managers accountable for technology assets and influence an organization of approximately 50 to 75 people. The portfolio’s exact scope will be established based on…
Added 45 mins ago
J
CLSU Manager (Commercial Support) - Insurance
JobsMedia.io
Toronto, ON
- Full-time
🔑 People Leadership: Lead, coach, and inspire a dedicated team of commercial support staff.
Added 45 mins ago
J
Commercial Insurance Director
JobsMedia.io
Toronto, ON
- Full-time
🚀 Lead a High-Impact Team: Take ownership of a commercial operation supporting complex mid-market and large commercial business.
Added 46 mins ago
J&
Team Leader (McArthur Glen Outlets)
JACK & JONES
Richmond, BC
- Part-time
Lead and inspire a team to create an energetic and positive shopping experience.
Added 46 mins ago
M&
Jr Weld Technician
Mitchell & Associates
Vaughan, ON
- Full-time
Job Summary: Promote a high performance safety culture, lead the production of quality parts, and ensure required efficiency targets are achieved by maintaining equipment on a daily basis…
Added 46 mins ago
RM
Supervisor, Centralized Scheduling
Ross Memorial Hospital
Kawartha Lakes, ON · Lindsay, ON
- Full-time
Ross Memorial Hospital is seeking a skilled, analytical, and solutions-oriented Supervisor, Scheduling to lead the effective operation and ongoing improvement of our Scheduling Department.
Added 46 mins ago
HT
Buyer (Contract)
Husky Technologies
Bolton, ON
- Full-time
…passion of our people around the world and their desire to lead change. At the same time, we are not afraid to expect a lot and strive for leadership in all of our key markets. We are a…
Added 46 mins ago
CL
Senior Cloud DevOps Engineer
Charger Logistics Inc
Brampton, ON
- Full-time
Lead cloud migration strategies and multi-region infrastructure design.
Added 46 mins ago
M
AVP, AI
Manulife
Toronto, ON
- Full-time
Lead end-to-end delivery of AI solutions for Risk, Legal, Procurement, Compliance, and other Group Functions – from opportunity shaping and design through deployment, adoption, and value…
Added 1 hour ago
NC
Instructor, Speech-Language Pathologist
NorQuest College
Edmonton, AB
- Full-time
Added 1 hour ago
T
TikTok Commerce - Senior Category Manager
TikTok
Toronto, ON
- Full-time
We strive to do great things with great people. We lead with curiosity, humility, and a desire to make impact in a rapidly growing tech company. Every challenge is an opportunity to learn…
Added 1 hour ago
AH
Primary Care Paramedic
Alberta Health Services
Grande Cache, AB
- Temporary
…airway adjuncts, and semi-automated defibrillation. You may also lead the BLS crew in delivering clinical care during patient transport or at emergency scenes. You will assist with ensuring…
Added 1 hour ago
JC
Store Manager
JYSK Canada
Moose Jaw, SK
- Full-time
…and development of the management and store team. You will lead, manage, and ensure the maximization of sales growth in your store. You will also be accountable for the loss prevention…

Tailscale

Senior New Business Account Executive

Toronto, ON, Canada

$201,000 - $201,000 CAD · Full-time

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Job details

Pay: $201,000 - $201,000 CAD
Job type: Full-time
Apply by: Nov 4, 2026
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

Generate new business by prospecting, sourcing pipeline, engaging prospective customers, and managing sales from initial outreach through purchase. Analyze markets and customer trends, promote Tailscale at events, support customers across time zones, and manage sales activities, pipeline, and forecasts in Gong and Salesforce.

Requirements

Candidates need at least two years of prospecting or closing experience in door-to-door or in-person sales, along with experience sourcing opportunities and guiding customers through the full sales cycle with senior technical buyers. The role also calls for ambition to build a sales playbook, technical background or curiosity, and strong communication and presentation skills.

Skills

Prospecting
New Business Development
Full-Cycle Sales
Pipeline Generation
Customer Discovery
Sales Campaigns
Market Analysis
Customer Trend Analysis
Technical Sales
Communication
Presentation
Forecasting
Salesforce
Gong
Customer Relationship Building

Benefits

Equity Incentive Plan
Variable Commission
Health Insurance
Vision Insurance
Dental Insurance
Retirement Contributions
Professional Development Funding
Paid Time Off
Home Office Equipment
Internet Reimbursement
Paid Parental Leave

Visa sponsorship

Not detected in the job text

Keywords

Tailscale
New Business Sales
Account Executive
Prospecting
Pipeline Generation
Inbound Leads
Self-Sourced Opportunities
Full-Cycle Sales
Customer Discovery
Closed-Won Deals
Senior Technical Buyers
VP Engineering
CTO
Head of Platform
CISO
Sales Playbook
Sales Campaigns
Market Analysis
Customer Trends
Industry Events
Gong
Salesforce
Technical Sales
Software Development
Network Security

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