Customer Account Executive

WinsAbove; Toronto; Hybrid; CAD 142,000 - 193,000; Full time

Benefits offered by this job

Flexible environment

Equity incentive plan

Health benefits

Remote-first culture

Retirement contributions

Professional development funds

Paid time off

Home office setup

Job summary

Tailscale, a fully distributed developer‑security company, is seeking a Customer Account Executive in Toronto. You will drive upsells and renewals, educate customers on new features, and ensure adoption across existing accounts.

Collaborate with Solutions Engineering, Customer Success, Support, Marketing, and Product to expand usage and revenue. The role requires remote-friendly, hybrid work in Toronto with a focus on building a strong pipeline and meeting quota.

Qualifications

• 1 year or less quota-carrying or closing experience.
• Experience selling developer/technical products.
• Experience presenting to senior managers and executives.
• Ability to manage multiple opportunities concurrently.
• Familiar with Gong or similar tools.
• Collaborates with Sales Engineering, support, and customer success.
• Proactive from lead to close; identify hiring manager.
• Role is based in Toronto with hybrid work (3 days in-office).

Responsibilities

• Become an expert in how Tailscale helps customers.
• Build a credible pipeline each quarter by upsells and renewals.
• Own an upsell and renewal number across your accounts.
• Educate customers on the value of Tailscale throughout the evaluation and adoption cycle.
• Generate short-term results while maintaining annual pipeline coverage.
• Provide accurate weekly forecasting and revenue delivery.
• Create mutual action/success plans with customers to expand usage.
• Participate in video-recorded customer meetings for training and quality.

Skills

Quota carrying

Software sales

Executive presentation

Pipeline management

Gong experience

Sales engineering partner

Proactive outreach

Hybrid work Toronto

Tools

Gong

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

Join our rapidly growing Sales team where you will play an important role at one of the fastest growing companies in the Developer Security space.

As a Customer Account Executive, you will be responsible for helping expand and renew current customer accounts. You will focus on finding additional use cases, educating the client base on new feature releases, and ensuring the successful adoption of Tailscale across all of your existing customer accounts. You will partner closely with the Solutions Engineering team, as well as collaborate with the Customer Success, Support, Marketing, and Product teams.

We're an energetic company with a wide variety of backgrounds. We coach each other, share feedback, and collaborate to maximize our performance and earning potential, all the while aligning with our customers' needs.

Key Responsibilities

• Become an expert in how Tailscale helps our customers.
• Build a credible pipeline every quarter by engaging with clients on upsells and renewals.
• Own an upsell and renewal number across your accounts.
• Help educate customers on the value of Tailscale throughout the evaluation & adoption cycle.
• Generate short-term results while maintaining annual pipeline coverage.
• Provide accurate weekly forecasting & revenue delivery.
• Create mutual action/success plans with prospective and existing customers where appropriate to help them evaluate and expand their usage of the Tailscale product.
• Participation in video-recorded customer meetings is a core part of this role. Recordings are used for training, collaboration, and quality improvement.

What We Are Looking For

• Up to 1 year of quota-carrying or closing experience, in an AE or an AM role
• A strong desire to join a high-growth software startup in a fully remote role
• Has sold developer and/or technical products, especially in a product-led growth (PLG) motion
• Experience presenting to senior managers and executives
• The ability to manage many opportunities simultaneously at various stages, coupled with a strong track record of meeting and exceeding quota
• Experience using Gong, or similar, to collaborate internally and manage pipeline
• Experience partnering with a Sales Engineering team, support, and customer success team to drive positive outcomes for clients
• 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.
• This role is based in Toronto and is hybrid required (3 days/week in-office).

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)

$167,500 — $167,500 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.

The hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.