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Techstars wanted!

Our employees are important to us. We offer market rate salaries along with a supportive and fun work environment. Candidates can expect us to present them with opportunities that best match their talents and desires. We look forward to meeting you and thank you for your interest!

Job Title: Conversational Advertising Sales Representative

Reports to: CEO

Position Overview is a fast growing Chatbot and AI company based in Toronto building automated solutions in the emerging conversational channel (messaging, chat, voice). We have recently launched a new product called BEAM which combines optimal conversational design, powerful natural language processing and machine learning techniques with digital ads to enable an entirely new way of marketing that we call conversational advertising. This solves a critical pain point around engagement and effectiveness in advertising and represents a complete game changer for advertisers and chatbot technology adoption.

We are looking for a sales and business development professional with 4-8 years of experience in Digital Media Sales and/or AdTech sector to join our team. The Manager, Conversational Advertising Sales is responsible for full lifecycle sales into highly strategic accounts (media agencies, ad networks, client direct). This role requires prior digital media or AdTech sales experience, ability to maintain high level relationships and work with a large extended team.

What you’ll do:

  • Develop and execute complete sales strategy with a focus on US and Canada alongside key executive and technical leadership.
  • Prospecting, engage and qualify prospects.
  • Close business with new accounts and structure and negotiate business terms and contracts.
  • Utilize a consultative channel partner sales approach to close opportunities with senior level executives
  • Identify product improvements or new products by remaining current on customer needs, industry trends, market activities, and competitors
  • Manage multiple business initiatives simultaneously
  • Understand company resources and strengths and collaborate with internal team members to develop and sell solutions that address client objectives

Job Skills:

  • 4-8 years work experience in sales for Digital Media Sales, AdTech or MarTech software products.
  • A Self-starter who can work independently and hunt for new opportunities.
  • Performing the entire sales process from hunting for leads, cold calling, nurturing the account and closing
  • Excellent presentation skills and comfortable speaking in client/project meeting
  • Comfortable in a technologically driven environment and have worked with multiple software applications. Bonus for familiarity with AI, chatbots and related technology
  • Strong work ethic with the ability to work flexible hours and over phone with remote clientele
  • Conversational technology knowledge (voice, messaging, chat) with vertical expertise: i.e. Retail, CPG, Advertising/Agency, Government, Financial Services, CRM, Customer Service. Target customers will include mid-sized and large enterprise customers in these domains.
  • Qualifying new opportunities and moving them through the sales cycle. You will also be required to represent the company at various events or business meetings.


  • 4+ years of experience in high performing and progressive teams
  • Mastery of pipeline management and forecast accuracy within a complex solutions environment
  • Extraordinary communication skills across an organization
  • Ability to thrive in an entrepreneurial environment
  • Successful candidates will be: ambitious, resilient, persistent and results oriented, problem solvers.

About Massively

One-to-one at massive scale. Launched in 2014, Massively manages your most important relationships by powering chatbots people actually want to talk to. lives at the intersection of technology, design, and creativity bringing the latest developments in the fields of artificial intelligence and machine learning to marketers to increase their digital brand presence.

To apply, please forward your resume to 

Massively Demo

BMO Ad Unit

Monkey Knife