Sales Assistant jobs in Canada

Before jumping in on all the information about the role and what you can bring to the table, let us introduce ourselves real quick.

We are Insider, a B2B SaaS company that drives growth for its clients around the world. How are we achieving this? We are the #1 AI‑native platform for Customer Experience and Marketing—offers marketers a single platform to deliver unique experiences per person, drive profitable growth, and unleash peak productivity and efficiency. Our platform connects data across channels, predicts future behavior with AI, and individualizes experiences from a single platform.

We have just celebrated our $500M Series E funding round, led by General Atlantic. Before this, we’ve unlocked unicorn status following our Series D round. We are backed by top‑notch investors, including Sequoia Capital, QIA, Riverwood, and Endeavor Catalyst, and trusted by 1200+ brands from high‑growth startups to the most prestigious Fortune 500 companies such as Samsung, Coca‑Cola, Nike, L’Oreal, Singapore Airlines, Virgin, Nestle, Nissan, Lenovo, Puma, IKEA, Allianz, Dominos, CNN, and the list goes on.

Having unlocked unicorn status, Insider was congratulated for becoming one of the only woman‑founded, women‑led B2B SaaS unicorns in the world, to achieve $200M in CARR (Committed Annual Recurring Revenue). Insider was named a leader in The Forrester Wave for Cross‑Channel Campaign Management 2021, and Leader in the IDC MarketScape: Worldwide Omnichannel Marketing Platforms for B2C Enterprises 2023 Assessment. The company has been recognized in The Top 1% of all software companies worldwide in G2’s 2024 Software Awards, and named in The Top 10 Best Software Products with the most #1 rankings alongside other software legends like Google, Zoom, and Monday.com. According to G2’s Spring’24 reports. Insider is also the #1 G2 Leader in 6+ categories, including Customer Data Platforms (CDP), Personalization Engines, Personalization Software, Mobile Marketing, Customer Journey Analytics, and e‑commerce Personalization.

Through our corporate social responsibility initiatives like 100Projects SheCodes, SheLeads, and SheMarkables, our community has committed to scaling its impact into our communities across 27+ countries, spearheading transformative projects in areas such as health, education, farming, animal rights, and increasing the proportional representation of women in STEM careers.

Behind all these achievements, there is an exceptionally talented and passionate team across 27+ countries that moves fast and agile, creates cutting‑edge products, and focuses on making an impact. If you want to join us on this journey, just keep reading.

We’re looking for a Chatbot Sales Specialist to lead growth for Insider’s Support Agent product - our AI‑driven conversational platform that powers intelligent customer interactions at scale.

This is a hybrid role: You’ll act as the Account Executive (AE) for new business acquisition, driving the full sales cycle from prospecting to close.

You’ll also operate as an overlay specialist with Account Directors (ADs) to expand Chatbot adoption within existing accounts.

You’ll combine strong hunting instincts, solution selling expertise, and deep product knowledge to unlock the full potential of Insider’s Chatbot offering in the market.

• New Business (AE Motion):
  • Own end-to-end sales cycle for new logo acquisition for the Chatbot (Support Agent) product.
  • Build and manage a strong pipeline through prospecting, outbound, and industry mapping.
  • Conduct product demos, craft tailored proposals, and lead negotiations to close deals.
  • Collaborate with marketing to run targeted campaigns and events to generate leads.
• Expansion (Overlay Motion):
  • Partner with Account Directors to identify, prioritize, and close cross‑sell / upsell opportunities within existing customers.
  • Bring deep product expertise to customer conversations, driving incremental value realization and adoption.
  • Co‑own forecasting and deal strategy for Chatbot opportunities inside large multi‑solution deals.
• Collaboration & Market Development:
  • Work closely with Solution Consultants (SolCons) on multi‑product or enterprise‑wide opportunities.
  • Partner with Product and Marketing to refine regional messaging and competitive positioning.
  • Provide continuous market feedback on emerging Chatbot trends, competitive landscape, and customer needs.

• 3+ years of SaaS or enterprise sales experience, ideally in CX, AI, or conversational platforms.
• Demonstrated success in both new business acquisition and expansion selling.
• Deep understanding of chatbots, automation workflows, or support agent platforms.
• Ability to articulate business value to senior executives and technical stakeholders alike.
• Proven hunter mindset, self‑driven, and able to manage complex deal cycles independently.
• Fluent in English; regional language proficiency add on.

• Performance Metrics:
  • Attainment of Chatbot‑specific quota (both new business and cross‑sell).
  • Growth in Chatbot adoption within existing enterprise accounts.
  • Contribution to regional pipeline generation, quality, and win rate.
• Compensation Base salary + commission tied to Support Agent ACV attainment.
• Direct quota credit for new business and overlay quota credit for expansion deals.
• High‑impact variable structure rewarding full ownership of pipeline and execution.

We provide equal opportunity in a zero‑discrimination workplace and not just welcome but also embrace everyone without regard to sex, race, color, nationality, religion, gender identity, sexual orientation, disability status, citizenship, or marital status.

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