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Added 1 min ago
Sales Executive Partnerships - FX Sales
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Montreal, QC
Added 1 hour ago
FT
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- Other
Fountain Tire offers competitive pay, strong leadership, and a chance to build your future. Apply online or in person today at 5505 58 Ave Drayton Valley, AB T7A 1R7!
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Vancouver, BC
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Office Manager
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ON · Ontario, Canada
- Full-time
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Life Insurance Specialist
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Torboy Transfer Station - Republic - TRANSFER STATION/RECYCLING OPERATOR
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Arborist Climber
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Arborist Crew Leader
The Davey Tree Expert Company
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TD
Arborist Climber
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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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