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Added 10 mins ago
BI
Regional Manager, Retail Insurance
BMO Insurance
Montreal, QC
- Full-time
Provides specialized consulting, analytical and technical support.
Added 10 mins ago
BI
Licensed Insurance Advisor
BMO Insurance
NS · Nova Scotia, Canada
- Full-time
Provide answers to technical questions regarding life insurance necessary for the licensed agents to perform their duties.
Added 14 mins ago
Senior Disaster Recovery Analyst
The Canada Life Assurance Company
Winnipeg, MB · London, ON · Toronto, ON
…executing DR tests and leveraging ServiceNow (SNOW) BCM to maintain technical…
Added 14 mins ago
Manager, Controllership & Projects
Bell
Montreal, QC
Added 25 mins ago
B
Manager, Portfolio Management Group, Private Wealth
BMO
Toronto, ON
- Full-time
Strong technical skills and exposure to portfolio management and trading (Charles River – CRIMS and CRA) and book of record software (FIS – Global Plus) is an asset.
Added 25 mins ago
T
Senior Operations Analyst
TD
Burlington, ON
- Full-time
As a candidate, you are encouraged to ask compensation related questions and have an open dialogue with your recruiter who can provide you more specific details for this role.
Added 25 mins ago
B
Branch Support Specialist
BMO
Toronto, ON
- Full-time
Excellent written and verbal communication skills with the ability to interact effectively with technical and non-technical audiences.
Added 27 mins ago
B
Senior Platform Engineer, AI & Fabrics
BMO
Toronto, ON
- Part-time
…correctness, and collaborates well within your team. You work within technical direction and standards set by the team's Principal Engineers and Leads, contribute to design discussions, and…
Added 28 mins ago
R
Account Executive (Accounting & Bookkeeping)
Relay
Remote, Canada
- Full-time
- Remote
You take a consultative, discovery-led approach and sell on value rather than technical functionality
Added 28 mins ago
R
Account Executive (Accounting & Bookkeeping)
Relay
Remote, Canada
- Full-time
- Remote
You take a consultative, discovery-led approach and sell on value rather than technical functionality
Added 28 mins ago
AC
Ab Initio ETL Developer
Adastra Corporation
Markham, ON
- Full-time
Collaborate with business analysts and data architects to translate business requirements into technical solutions
Added 1 hour ago
C
Full Stack Developer - Golang & Nodejs
CGI
Halifax, NS
- Full-time
…deliver secure, reliable, and high-performing solutions. Beyond technical expertise, we are looking for someone who brings sound engineering judgment, challenges assumptions constructively,…
Added 1 hour ago
C
Sr Product Manager
CGI
Halifax, NS
- Full-time
Own and prioritize the product backlog, balancing business value, technical feasibility, and delivery timelines.
Added 1 hour ago
T
Portfolio Management Consultant, FP
TD
Toronto, ON
- Full-time
As a candidate, you are encouraged to ask compensation related questions and have an open dialogue with your recruiter who can provide you more specific details for this role.
Added 1 hour ago
T
Finance Operations Analyst III
TD
Dieppe, NB
- Full-time
As a candidate, you are encouraged to ask compensation related questions and have an open dialogue with your recruiter who can provide you more specific details for this role.
Added 1 hour ago
T
Data Engineer II
TD
Toronto, ON
- Full-time
As a candidate, you are encouraged to ask compensation related questions and have an open dialogue with your recruiter who can provide you more specific details for this role.
Added 1 hour ago
T
Software Engineer II
TD
Toronto, ON
- Full-time
As a candidate, you are encouraged to ask compensation related questions and have an open dialogue with your recruiter who can provide you more specific details for this role.
Added 1 hour ago
T
Data Engineer II
TD
Toronto, ON
- Full-time
As a candidate, you are encouraged to ask compensation related questions and have an open dialogue with your recruiter who can provide you more specific details for this role.
Added 1 hour ago
T
Software Engineer III
TD
Toronto, ON
- Full-time
…annually. You are encouraged to have an open dialogue with your recruiter who can provide more specific pay details for this…
Added 1 hour ago
T
Security Architect (Distributed Ledger)
TD
Toronto, ON
- Full-time
As a candidate, you are encouraged to ask compensation related questions and have an open dialogue with your recruiter who can provide you more specific details for this role.
Added 1 hour ago
D
Senior Manager, HR Technology & Delivery
dentalcorp
Toronto, ON · Support Centre - Toronto Office
- Full-time
You lead through influence, bring structure to ambiguity, and communicate clear recommendations across technical and non-technical teams. You establish the governance, documentation, and…
Added 1 hour ago
C
Sr. Manager, Production Application Support
CIBC
Toronto, ON
- Full-time
…Application Support you will join CIBC’s AESP department to provide technical expertise for small to medium, complex projects/initiatives as they relate to the implementation and support of…
Added 1 hour ago
C
Cyber Implementation Specialist
CAE
Ottawa, ON
- Full-time
Translate contractual cybersecurity requirements, including CDRLs, DIDs, and Annex F matrices, into implementation plans and technical architectures
Added 1 hour ago
B
Managing Director and Head, Financial Services Group
BMO
Toronto, ON · FCP
- Full-time
Added 1 hour ago
Solutions Architect (Individual Wealth - Application Delivery)
The Canada Life Assurance Company
London, ON · Toronto, ON
…application support. They will play an active role in setting the technical vision and direction for solutions, ensuring consistency with overall enterprise and portfolio architecture.…

Tailscale

Customer Account Executive

Toronto, ON, Canada

$167,500 - $167,500 CAD

Apply About employer

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Job details

Pay: $167,500 - $167,500 CAD
Experience: Up to 1 year of quota-carrying or closing experience, in an AE or an AM 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

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).

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)

$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.

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

The Customer Account Executive is responsible for managing renewals and expanding existing customer accounts by identifying new use cases and driving product adoption. They will collaborate with cross-functional teams, including Sales Engineering and Customer Success, to ensure revenue growth and accurate forecasting.

Requirements

Candidates should have up to 1 year of quota-carrying experience in an AE or AM role, preferably with technical or developer-focused products. Strong skills in pipeline management, executive communication, and a proactive approach to sales are essential for this hybrid role.

Skills

Sales
Account management
Upselling
Renewals
Pipeline management
Forecasting
Revenue delivery
Customer success
Sales engineering
Technical product sales
Product-led growth
Executive presentation
Gong
Customer adoption
Relationship management

Benefits

Equity incentive plan
Variable commission
Comprehensive group benefits
Health insurance
Vision insurance
Dental insurance
Professional development stipend
Paid time off
Home office setup
Home internet reimbursement
Paid parental leave

Visa sponsorship

Not detected in the job text

Keywords

Tailscale
Sales
Account Executive
Developer Security
Product-led growth
PLG
SaaS
Pipeline
Renewals
Upselling
Forecasting
Gong
Sales Engineering
Customer Success
Hybrid
Toronto
Equity
Commission
Software
Technical sales

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