Director of Sales

AfterShip; Toronto; Remote; CAD 200,000 - 225,000; Full time

Job summary

AfterShip is seeking a Director of Sales to lead and scale its sales team during a pivotal growth phase. The role focuses on driving revenue targets, standardizing processes, and collaborating across functions to enhance pipeline velocity. Ideal candidates have significant B2B SaaS sales experience and proven leadership skills, aiming to shape the company's go-to-market strategy.

Benefits

Competitive compensation

Healthcare coverage from day 1

Retirement plans with company match

Annual learning and wellness benefit

Flexible work setup

Qualifications

• 7+ years in B2B SaaS sales, including 3+ years leading teams.
• Proven success managing and scaling sales teams of 15+.
• Strong executive presence, highly collaborative, and data-driven.

Responsibilities

• Lead and scale a sales team of 10+.
• Drive attainment across new business sales quota.
• Implement scalable sales methodologies.

Skills

B2B SaaS sales

team management

scalable sales methodologies

outbound sales

cross-functional collaboration

Tools

HubSpot CRM

outbound tools

Job description

Join to apply for the Director of Sales role at AfterShip

Join to apply for the Director of Sales role at AfterShip

About Us

AfterShip, recognized as a Great Place to Work Certified company, is at the forefront of transforming the global eCommerce landscape. Our mission is to empower eCommerce retailers to create and manage the world's best online shopping experiences. Powering over 4.4 billion shipment trackings for over 20,000 global brands like Samsung, GymShark, Dr. Squatch, Citizen, Mejuri and Aesop, AfterShip revolutionizes how businesses engage with customers after purchase. We are pioneering AI-driven post-purchase solutions, from smart shipment tracking and returns management to personalized product recommendations and AI-powered delivery estimates.

About Us

AfterShip, recognized as a Great Place to Work Certified company, is at the forefront of transforming the global eCommerce landscape. Our mission is to empower eCommerce retailers to create and manage the world's best online shopping experiences. Powering over 4.4 billion shipment trackings for over 20,000 global brands like Samsung, GymShark, Dr. Squatch, Citizen, Mejuri and Aesop, AfterShip revolutionizes how businesses engage with customers after purchase. We are pioneering AI-driven post-purchase solutions, from smart shipment tracking and returns management to personalized product recommendations and AI-powered delivery estimates.

Having secured a $66 million Series B in 2021, we are accelerating our growth and continuing to shape the future of eCommerce.

At AfterShip, we are building a diverse and high-performing culture that encourages collaboration and experimentation on a global scale. Even as a company with over 10 years under our belt and 450 AfterShippers across our 8 global offices, we embrace a dynamic and agile approach to our work.

We operate with a flat team structure, where you will have opportunities to contribute your ideas and take ownership over your work to create meaningful impact for the business and the customers we serve. If you're looking for a vehicle to achieve your professional goals and work alongside fantastic teams, we invite you to join us.

Your Mission:

As Director of Sales at AfterShip, you'll take on a high-impact leadership role during a defining phase of our growth. You'll own the business' new revenue target and lead a team spanning North America and Europe, focused on scaling our go-to-market strategy for mid-market and enterprise customers.

Your mission is to drive momentum, structure, and consistency across the Sales org. You'll implement a standardized sales process, launch a high-performing outbound motion, and align cross-functional teams around clear messaging and enablement strategies. This role is essential to our next stage of growth, reporting directly to the Vice President of Revenue and helping shape the future of how AfterShip sells.

This is a remote-first role with some flexibility required to collaborate across time zones. Occasional travel (up to 20%, fully expensed) may be required for customer meetings, leadership offsites, or strategic initiatives.

What You'll Do:

• Lead & scale the team: Manage a sales org of 10 (4 direct reports), with plans to expand
• Own the number: Drive attainment across the entire new business sales quota
• Standardize processes: Implement scalable sales methodologies, qualification frameworks, and deal stages
• Drive outbound: Launch and optimize outbound programs to accelerate pipeline growth
• Enable the team: Align closely with Sales Enablement and Product Marketing on training and messaging
• Collaborate cross-functionally: Partner with Marketing, CS, Product, and RevOps to drive pipeline velocity
• Improve forecasting: Establish a consistent, reliable forecasting model based on leading and lagging indicators
• Represent AfterShip: Serve as a trusted advisor to prospects and customers, especially at the enterprise level
• Influence product direction: Share customer insights to guide our product roadmap and go-to-market strategy
  
  

Who We're Looking For:

• 7+ years in B2B SaaS sales, including 3+ years leading teams in a high-growth environment
• Proven success managing and scaling sales teams of 15+
• Experienced in building repeatable sales processes, outbound motions, and accurate forecasting
• Strong executive presence with the ability to communicate clearly and persuasively
• Highly collaborative; thrives in cross-functional environments and fast-paced cultures
• Curious, analytical, and energized by continuous improvement—"geeky spirit" welcomed
• Familiarity with the eCommerce ecosystem strongly preferred
• Hands-on experience with HubSpot CRM and outbound tools like Outreach or Apollo is a plus
• This remote-first role is open to candidates across North America, ideally in close proximity to Toronto, Austin, Los Angeles, San Francisco, or Seattle
  
  

At AfterShip, we understand that not all applicants will have skills that match the job description exactly. We value diverse experiences and respect that experience comes in many different forms, so even if you feel you may not meet every qualification to a T then we still encourage you to apply. We are always looking for people who can help us continue to raise the bar for our team and who want to join us on our mission.

Why You Should Join Us:

• Great Place to Work Certified: We've been recognized for our inclusive, values-driven culture that celebrates diversity and collaboration.
• Innovative & Inclusive Culture: Started by our software engineer-turned-CEO, AfterShip is built on curiosity, creativity, and collaboration. We're a passionate, global team of problem solvers who put egos aside to innovate together. We take immense pride in fostering a culture that's inclusive, which has allowed us to surround ourselves with the industry's most talented professionals.
• Ambitious Mission with Real Impact: Join us in transforming eCommerce by making buying and selling easier for everyone. It's one of the most dynamic spaces in tech, with limitless opportunities to innovate and grow.
• Thrive & Grow: There's no ceiling to what you can achieve or learn here. We're committed to empowering your career while advancing together as a company.
• Flexible Work Setup: We're a remote-first team, meaning by default that employees work from home or on a hybrid-flexible basis in our hub locations (Toronto, Austin, Barcelona). You're empowered to choose a work setup that works best for you and your team. With flexible hours depending on your time zone, you'll be able to have a schedule that fits your working style and the requirements of your role.
  
  

Perks:

• Competitive compensation
• Remote-first/hybrid-flexible work setups
• Healthcare coverage offered from day 1
• Retirement plans including company match
• Annual learning & wellness benefit
• Monthly book perk
• Career progression & professional development
• In-office lunch and commuter benefits for those located in our hub locations
  
  

We are an equal opportunity employer. In addition, we are committed to providing accommodations for applicants upon request at any stage of the recruitment process in accordance with the legislative requirements of this job's location. Please let us know if you require accommodation due to a disability during any aspect of the recruitment process and we will work with you to address your needs.

Seniority level

• Seniority level

  Director

Employment type

• Employment type

  Full-time

Job function

• Job function

  Sales and Business Development

• Industries

  Software Development

Referrals increase your chances of interviewing at AfterShip by 2x

Get notified about new Sales Director jobs in Toronto, Ontario, Canada.

Toronto, Ontario, Canada CA$200,000.00-CA$225,000.00 17 hours ago

Scarborough, Ontario, Canada 13 hours ago

Director of Sales And Business Development

Mississauga, Ontario, Canada $80,000.00-$90,000.00 12 hours ago

Director of Sales And Business Development

Regional Sales Director Healthcare SaaS OTE ($140-170K), commission uncapped

Whitchurch-Stouffville, Ontario, Canada 2 months ago

We’re unlocking community knowledge in a new way. Experts add insights directly into each article, started with the help of AI.