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Strategic Account Executive - Canada Market

RemoteToronto, Ontario, CanadaSales Team

Job description

NOTE: This is a 100% remote position.


Cloud Academy is a hyper-growth upskilling and reskilling SaaS company, focused on enabling enterprise customers to have full transparency and control over their tech workforce skills readiness. In a rapidly changing cloud technical landscape where there is an increasing tech skills gap in the market, combined with the difficulty organizations are facing to retain tech talent and the demands for numerous technical certifications, companies need the ability to manage these skills at scale more than ever. We help over 1000 customers visualize, assess, transform and measure their teams’ tech skills readiness through a unique Skills Intelligence Platform, powered by world-class cloud training content. Companies like Warner Media, Deloitte, JP Morgan Chase, and Walmart trust Cloud Academy with their technical cloud skills readiness at scale, so they can achieve their cloud business goals.

We are a global team, with colleagues in over 14 countries worldwide. We are a diverse team that is innovative, collaborative, pragmatic, and passionate about making an impact. We thrive on a common vision, we obsess about our customers and learners, and we take pride in the quality of our work. Most importantly, we know that individually we are only as good as our teams are, and we always have each others’ backs.

We are seeking driven, highly competent, and creative team players to join us on the next phase of our growth story, as we scale our winning products to help even more customers and learners.


Cloud Academy is looking for a highly motivated, over-achieving hunter who flourishes in a fast-paced, dynamic and international environment. In this role you will partner with enterprise organizations to solve one of their biggest challenges: upskill, develop and constantly retain their tech talent. You will work closely with them to show them how our platform can align with their IT organization and help them build job roles, career paths and specific programs at scale. Your ability to understand and focus on their problems and speak to them will be critical to build a consultative relationship with your customers and work on solutions that show clear ROIs from day one. This is a unique opportunity to join a growing Enterprise SaaS platform that is creating a new software category and working with top brands in several industries, including Financial Services, Technology, Manufacturing, Pharmaceutical and more.

The ideal profile is someone with solid experience and success selling into large, complex enterprise organizations in Canada. This person should have the polish and experience to meet C-level face-to-face and the attitude of a trusted advisor. The Account Executive will drive sales opportunities from identification to close and have the experience and the confidence to manage relations and negotiations in line with the strategic and business priorities of the company. Strategic Account Executives will be hands-on by building a book of opportunities and business while simultaneously meeting prospects and closing business.


  • Conduct individual prospecting and develop/close new sales opportunities for Cloud Academy’s solution

  • Create and deliver accurate forecasts

  • Work side by side with our solution engineering and sales enablement team

  • Sell the Cloud Academy vision to prospects through product demonstrations, video calls, and face-to-face presentations and workshops at CXO, VP and Director level

  • Coordinate and work with extended team members in Product, Content and Marketing

  • Collaborate with Customer Success managers to deliver exceptional results that will ultimately lead to more business

  • Work closely with Customer Success to ensure world class onboarding and customer satisfaction

  • Strategically align with Customer Success and Solutions Engineering to grow/expand existing accounts

Job requirements

  • A minimum 2 years of on-quota, B2B SaaS applications sales experience

  • Proven track record of strategic outreach and sourcing new business accounting for 80+% of your quota attainment

  • Previous experience selling to the Canadian market

  • Previous experience selling business solutions to the e-learning industry is preferred but not mandatory

  • Skilled at negotiating business terms with the IT organization of enterprise organizations and with senior management executives

  • History of consistent quota over-achievement in highly competitive markets

  • Ability to work in a rapidly expanding and changing environment

  • Teamwork and good verbal and written communication skills a must

  • Excellent presentation skills and the ability to effectively articulate our solution’s value proposition as part of an overall business solution.

  • Good skills with Salesforce, Outreach and similar tools is preferred

  • Advanced user of Linkedin and professional social networks such as Twitter

  • Hands-on attitude, ambitious and passionate

  • Great knowledge of the digital space and ability to work with a variety of SaaS tools including Google Suite, Slack and more

  • Solid knowledge and familiarity with cloud, software and data (you are familiar with AWS, Azure, GCP, DevOps, Software Development etc) is a strong plus for this role and definitely a big bonus


  • ​​Competitive benefits, paid time off and salary with uncapped commission

We value diversity and are an equal opportunity employer at Cloud Academy. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.