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Added 15 mins ago
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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 15 mins ago
TS
Business Development Representative
Techspirit Solutions Inc
Mississauga, ON
- Full-time
Techspirit Solutions Inc. is seeking an experienced Business Development Representative to drive sales growth across commercial and residential technology solutions, including CCTV, AI…
Added 45 mins ago
NB
Senior Director, IT Delivery and Technology Platforms
National Bank of Canada
Montreal, QC
- Full-time
Lead, engage and develop a team of 3 to 4 technology asset managers by supporting their decisions, development, team leadership and achievement of sustainable results.
Added 45 mins ago
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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
KC
Senior Consultant, ESG Assurance Services
KPMG Canada
Toronto, ON
- Full-time
…balance is how our values show up – in how we work, how we lead, and what we…
Added 1 hour ago
HT
VP, Accounting & Controllership (Husky)
Husky Technologies
Bolton, ON
- Full-time
Husky TechnologiesTM offers a wealth of opportunity for personal growth and development. Most importantly, Husky Technologies TM offers an opportunity to work with – and be challenged by –…
Added 1 hour ago
GD
Design Engineering C4 Systems Associate Specialist
General Dynamics Land Systems–Canada
London, ON
- Contract
Collect supporting data for the development of power budgets, Signal Interface Data (SIDs), subsystem architecture, and subsystem functional diagrams. Collect artifacts for assigned…
Added 1 hour ago
GD
HR Analytics & Compensation Analyst
General Dynamics Land Systems–Canada
London, ON
- Full-time
Lead the development and communication of compensation policies and procedures.
Added 1 hour ago
GD
Specialist, Trainer Maintenance
General Dynamics Land Systems–Canada
London, ON
- Full-time
Conduct the analysis, design, development and maintenance of training material for all training, both operator and maintainer, associated with GDLS-C product lines
Added 1 hour ago
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Electrical Designer
HDR
Richmond Hill, ON
- Full-time
…built environment. This isn’t just a job, it’s a chance to lead innovation, engineer impact, and build a legacy of…
Added 1 hour ago
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Site Civil Section Manager
HDR
Toronto, ON · Richmond Hill, ON
- Full-time
…built environment. This isn’t just a job, it’s a chance to lead innovation, engineer impact, and build a legacy of…
Added 1 hour ago
AM
Director Digital Solutions & Business Growth
Arc Mercer
Barrie, ON
- Full-time
Proven successful completion of a degree or diploma in information technology, computer science, web development, business systems, or other related discipline, or an acceptable equivalent…
Added 1 hour ago
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Partner Enablement Leader
Intuit
Toronto, ON
- Full-time
Recruit, onboard and develop a team of managers and enablement professionals across regions, many of whom will lead their own teams as the function grows.
Added 1 hour ago
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CRM Project Manager
Monks
Toronto, ON
- Full-time
…important feedback on their work and supporting their professional…
Added 2 hours ago
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Business Continuity Manager
CarePartners
Waterloo, ON
- Full-time
…Reporting to the Senior Director of Business Continuity and Development, this role supports the organization’s ability to prepare for, respond to, and recover from disruptions while…
Added 2 hours ago
O&
Sous Chef - Canoe
Oliver & Bonacini
Toronto, ON
- Full-time
…environment as well as experience in recruiting, training, development and overall management of their cooks. Our Sous Chefs are hands on with cooking and managing their…
Added 2 hours ago
PT Supportive Housing Coordinator
Indwell
Kitchener, ON
Ability to take the lead on internal program development and projects.
Added 3 hours ago
FB
Assistant Chef Manager
Farm Boy Inc.
Collingwood, ON
- From $21.5 CAD / hour
- Full-time
You’ll partner with the Department Manager to help lead the delivery of exceptional food and service experiences that reflect Farm Boy’s commitment to the best fresh shopping experience.…
Added 3 hours ago
Retail Sales Associate
Fire & Flower Inc.
Winnipeg, MB
The Retail Sales Associate, under the direction of the Retail Experience Lead, is primarily responsible for greeting customers and providing guidance on where they may find items within the…
Added 3 hours ago
Registered Practical Nurse
Indwell
London, ON
As part of an interdisciplinary team, coordinate, lead and/or facilitate the development and monitoring of supportive care plans in collaboration with an internal and external team of…
Added 3 hours ago
C
Partner Delivery Project Manager
Ciena
Ottawa, ON
- Full-time
…guided by innovation, integrity, and collaboration. Through development opportunities, meaningful work, and flexibility, Ciena supports growth and well-being - on and off the job. Connect…
Added 3 hours ago
DC
Senior Environmental Engineer or Geoscientist
Dillon Consulting Limited
London, ON
- Full-time
We’re looking for a technical leader, trusted advisor and problem solver with a safety-first mindset and the desire to build strong teams to lead Ontario-based contaminated sites projects.
Added 3 hours ago
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AML Operations Officer III
Robertson & Company Ltd.
Toronto, ON
- Contract
Participate in the rollout and development of new processes, systems, and operational enhancements across the department.
Added 3 hours ago
ML
Sr. Health & Safety Manager
Maple Leaf Foods Inc
Mississauga, ON
- $122,000 to $172,000 CAD / year
- Part-time
…compliance with federal and provincial regulations. Develop and lead the rollout of a new safety management platform and modernize standard operating procedures to embed consistent,…
Added 3 hours ago
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Senior New Business Account Executive
Tailscale
Toronto, ON
- Full-time
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…

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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