Full Time | Richmond Hill - ON | Sales

We are looking for a great Director Sales to join Wysdom.AI – a fast-growing company providing the world’s most advanced AI-based cognitive customer care solutions.

Wysdom is a mature full-stack virtual assistant platform that uses machine intelligence for cognitive customer care management over social, web chat, and voice. We give businesses a powerful new way to connect to customers, answer questions, and transact any time, using natural language.

Wysdom provides the framework, the tools, and a massive AI training data corpus to enterprises needing to quickly implement cognitive care. Our experienced team of AI experts continuously trains the system, ensuring businesses provide the best customer experience in whatever channel their customers choose.

We are growing and expanding our team — please join us as a Director Sales based in our King West downtown office.

As a Director Sales, you will:

  • Focus on revenue growth through new logo acquisition. We’re looking for an experienced sales executive with a proven track record of consultative selling of software technology to senior executives at the world’s largest enterprises.
  • Possess thought leadership in the digital domain and have a strong network of professionals in customer experience across the Finance, Insurance and Telecommunications industries, then this job is for you.
  • Demonstrate strategic thinking, analysis and insight abilities to lead in creating effective enterprise account plans that lead to new logo acquisition.
  • Be effective in leading enterprises through evaluation and adoption of complex technology solutions in a 9 – 12 month selling cycle with deal sizes of at least $1MM ARR.
  • Be able to effectively communicate the benefits of Wysdom.AI solutions at all levels of your accounts.

About You

  • You have 8+ years’ experience selling software technology solutions to senior leaders in large enterprises. You should be experienced in deal ARR sizes from $1 million+ and 6– 12-month sales cycles. You should be a seller in the top 10% of the Sales organizations you’ve been part of and have a consistent track record of achieving or exceeding your sales quota
  • You have a demonstrated track record of new enterprise logo acquisition including account planning strategy and execution with an ability to show how you have acquired and grown multiple new logos in multiple years. Experience selling to clients in multiple vertical industries is critical.
  • You demonstrate a career pattern of being able to quickly understand different technologies and an ability to advise complex organizations on how to deploy them effectively.
  • You are experienced and knowledgeable in enterprise selling methodologies and how to leverage them for effective selling.
  • You demonstrate strong selling skills across the entire sales cycle including opportunity analysis, account discovery, proposition presentation, objection handling and offer negotiation.
  • You display extremely strong analytical, verbal and written communication skills. You should be very comfortable presenting to groups of cross-functional C-level executives. This position will regularly interact with the CEO and senior leadership.
  • You are experienced in social selling including leveraging LinkedIn and other networks to reach critical contacts in the accounts you are focused on.
  • You have experience working collaboratively with multiple cross-functional teams to design and implement effective business proposals.
  • You have technology consulting experience with a global business strategy or technology consulting firm is a plus.

Additional Information

  • This position reports to the VP, Sales
  • This position will require travel

About Wysdom.AI

Wysdom.AI is a VC-funded start-up, and is led by an experienced team of serial entrepreneurs with a history of building great teams and products. We offer a terrific work environment in all our offices, full company-paid benefits from your first day, and a stock option program, to ensure you participate in the growth we see ahead. Head here to read more about what it’s like to work at Wysdom.

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