Senior New Business Account Executive

Tailscale; Toronto; Hybrid; CAD 181,000 - 221,000; Full time

Benefits offered by this job

Remote-first environment

Equity and variable commission

Comprehensive benefits

Retirement contributions matching

Professional development funds

Job summary

Tailscale is seeking an ambitious New Business Account Executive to own the full sales cycle from prospecting to purchase. You will handle inbound leads, source a third of your own pipeline, and aim to earn customer trust at every step. The role is based in Toronto with hybrid work (3 days in-office).

You will engage with engineering leaders at innovative companies, travel to events when needed, and contribute to building a scalable sales playbook in a fast-growing startup environment.

Qualifications

• 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.
• Technical background or curiosity in technology.
• Excellent communication and presentation skills.
• Proactive from lead to close and able to justify why you’re the best candidate.

Responsibilities

• Win new business by educating prospects about our services and helping them succeed with Tailscale.
• Experiment and move quickly by analyzing market landscapes and customer trends to inform campaigns.
• Travel to or organize local events and participate in industry events to evangelize Tailscale.
• Support customers across all time zones and manage activities, pipeline, and forecast in Gong and Salesforce.

Skills

Prospecting

Closing

Technical curiosity

Communication

Self-sourcing

Tools

Gong

Salesforce

Job description

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 note, you must reside in the Canada to be considered for this position. We are not currently providing relocation support for this role. If you intended to apply for employment in another country where we are hiring, please return to our careers page and apply to the correct country’s job post for this role.

Please note, you must legally be able to work in the Canada to be considered for this position. We are not currently able to provide immigration support for this role. If you intended to apply for employment in another country where we are hiring, please return to our careers page and apply to the correct country’s job post for this role.