Head of Strategic Sales

  • Sales
  • Toronto, Canada

Head of Strategic Sales

Job description

Easyship is revolutionizing logistics for eCommerce. With our all-in-one cloud based shipping software, businesses of all shapes and sizes have the tools needed to scale globally. At Easyship we believe in accelerating borderless commerce. We’re proud that a diversity of small business owners, crowdfunding campaigns, and global brands trust Easyship as their gateway to the world.

“We envision a frictionless economy where creators can use one platform to ship products to anyone, anywhere. When you grow, we grow.” Tommaso Tamburnotti, Co Founder.

Easyship is building tomorrow’s logistic infrastructure, today. Our team is continuously looking to reach new heights, whether it’s learning about new technologies or improving your own skillset, Easyship is prepared to empower you to grow. We believe that when we inspire each other, we grow together.

Easyship is recruiting brilliant, curious, and driven individuals to help us scale our innovative technology worldwide. Headquartered in New York with offices in London, Hong Kong, Singapore, Melbourne, Toronto, and Taipei – our team is global and growing. We encourage you to apply if a challenge excites you. If you enjoy the company of talented people. If you would dedicate yourself to a simple mission: to make shipping easy for everyone.

We operate with a global footprint, but we’re still tiny relative to the opportunity ahead, so there is still much to do. Join us and help put borderless commerce within reach of every entrepreneur.

Position Title: Head of Strategic Sales

Reports to: Co-Founder

Location: Toronto, ON

Key Relationships: Sales, Partnerships, Operations, and Customer Success Teams

Job Purpose:

The Head of Strategic Sales will be responsible for leading the Strategic Sales team while focusing on acquiring Enterprise clients and developing a strategy to drive all the revenue generating activities. Reporting to the Co-Founder, you will play a key role in generating new revenue, defining scalable sales processes, and creating efficient programs that drive predictable sales productivity with an emphasis on upselling and customer success

The Head of Strategic Sales will be the driving force for identifying new business opportunities, developing strategic relationships with internal key stakeholders, external business partners, growing and managing existing business, as well as hiring and developing top talent. You will help define a clear vision for how Easyship can capture greater market share within the strategic space and will lead the execution of the plan to enable exponential growth.

Job Responsibilities:

  • Generate, retain, and expand strategic sales revenue globally

  • Hire, train, manage, and mentor a team of Strategic Account Executives, and personally help close large deals.

  • Establish, enforce and improve the sales processes to maximize team efficiency

  • Drive business cadence for forecast calls, functional review meetings, deal review, customer account reviews, weekly team meetings and periodic company-wide kick offs

  • Manage the team via metrics and report on their success

  • Identify and create strong relations with customers through consistent contact; manage customer relationships within assigned accounts to defend and grow the business

  • Collaborate with cross functional teams to identify new opportunities for growth

  • Manage company CRM and provide key data for business decisions


Skills & Personal Qualities:

  • 10 years of sales experience with a minimum 4 years of experience as an enterprise sales leader for SaaS

  • E-commerce and/or technology sales experience required

  • Strong communication and negotiation skills. Present solutions to customers throughout any phase of the deal cycle

  • Excellent leadership skills and ability to inspire others to drive toward common goals

  • Experience with accurately forecasting new sales and revenue recognition using revenue metrics.

  • Ability to work under pressure and multitask in a fast-paced environment


  • Competitive compensation package

  • Company Equity

  • Gym & Wellness Reimbursement

  • Dental, Health & Vision Insurance

  • Generous Vacation Policy

  • Duvet Day - Perfect for those cold winter days, when you don’t want to escape the warmth of your bed!

  • Mental Health Day - You deserve a day off! A chance to recharge and enjoy ‘Me Time’

  • Flexible working approach

  • Unlimited Coffee, Drinks & Healthy Snacks

  • Office PlayStation Games

  • As we expand, the potential to work in one of our international offices

  • Annual Summit in Hong Kong for you to collaborate with the team

You will have the opportunity to work with a global team, filled with smart, ambitious and like minded colleagues. We have built an inclusive culture which supports and enables you to grow. Come and join the Easyship team!