Manager, Commercial Expansion

United States Digital Space LLC; Toronto; Hybrid; CAD 265,000 - 335,000; Full time

Benefits offered by this job

Inclusive environment

Competitive compensation

Comprehensive benefits

Hybrid in-office

Retirement contributions

Professional development budget

Paid time off

Job summary

United States Digital Space LLC is seeking a gritty, thoughtful Sales Manager to lead the Expansion sales team for the Commercial segment in Toronto. You will build the new Toronto hub and lead from the front to create a repeatable sales machine.

The role balances high-velocity opportunities with larger $50k-$100k+ ACV deals and requires a hybrid schedule (3 days in-office) in Toronto.

Qualifications

• Minimum 1+ years of sales management in a B2B SaaS/Software company.
• Aptitude for delivering world-class customer experiences: urgency, curiosity, value.
• Excellent written and verbal communication skills.
• Ability to manage many activities and tasks simultaneously.
• Willingness to travel to industry events quarterly.
• Role based in Toronto with hybrid in-office expectation.

Responsibilities

• Lead a team of account executives from the front.
• Prospect with the team, lead role plays, unblock opportunities, travel to customers.
• Establish and refine best practices for pipeline generation and opportunity management.
• Develop and coach the team using sales data, performance metrics, and enablement.
• Collaborate with marketing, product, sales engineering, and partnerships to create pipeline.

Skills

Sales management

Customer experience

Communication

Multitasking

Travel willingness

Toronto-based

Job description

About the company

the company is building the new Internet 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 the company 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 a gritty, thoughtful, and curious Sales Manager to lead an Expansion (existing customers) sales team focused on the Commercial segment (<750 employees). The Commercial team balances both a high velocity sales motion (7 to 13 opportunities per month) and occasional large opportunities ($50,000-$100,000+ ACV contracts).

You will be the first sales leader to build out our new Toronto sales hub. If you are looking for an opportunity to lead from the front and to build a repeatable sales machine from the ground up, this is it.

Key Responsibilities

• Become an expert in how the company helps our customers
• Lead a team of account executives from the front - prospecting with the team, leading role plays, unblocking critical opportunities, and traveling to customers to build relationships
• Establish and refine best practices for pipeline generation, opportunity management, and customer relationship building
• Develop and coach the team using sales data, performance metrics, and sales enablement
• Work closely with marketing, product, sales engineering, and partnership teams to create pipeline and accelerate opportunities

What We Are Looking For

• 1+ years of sales management experience in a B2B SaaS/Software company
• Aptitude for delivering world-class customer experiences: operate with a sense of urgency, exercise curiosity about customers, and strive to add value in your interactions
• Excellent written and verbal communication skills
• Ability to manage many activities and tasks simultaneously
• Ability to travel to industry events once a quarter
• This role is based in Toronto and is hybrid required (3 days/week in-office).

CAN Pay Range (OTE)

$265,000—$335,000 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. the company 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 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).

the company 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.