Matador AI, Product Specialist

Trader Interactive•Toronto, ON

92d•Remote

About The Position

Matador AI, Product Specialist at Trader Interactive. Trader Interactive is a group of go-getters focused on making buying and selling a great experience through innovation and a people-first approach. They offer big career opportunities and a supportive, inclusive work environment within a global group of digital marketplace businesses. The role is a quota-carrying, new-business hunter responsible for acquiring new logos across Commercial Truck, Marine, Equipment, and Recreational markets by selling Conversational AI solutions. This is a full-cycle sales role involving prospecting, pipeline generation, discovery, demonstration, negotiation, and closing deals. The Product Specialist will work with SDR support, channel and referral partnerships, and self-sourced outbound activity to drive revenue growth in their assigned territory. This role is modeled after best-in-class SaaS acquisition motions and is structured for individuals who thrive in complex, consultative sales environments and enjoy building new customer relationships.

Requirements

3–5+ years of quota-carrying SaaS sales experience in a full-cycle Account Executive or equivalent role.
Demonstrated track record of consistent quota attainment at or above 100%.
Experience selling operational or vertical SaaS solutions to SMB and mid-market customers ($15K–$75K ACV).
Strong command of consultative selling methodologies (Challenger or equivalent).
Proven ability to self-source pipeline through outbound prospecting in addition to working inbound and partner-referred leads.
Excellent discovery, presentation, and negotiation skills with comfort presenting to C-suite and ownership-level buyers.
Data-literate and CRM-disciplined — experience maintaining accurate pipeline in Salesforce, HubSpot or equivalent.

Nice To Haves

Experience selling into automotive, powersports, RV, marine, or equipment dealership verticals.
Familiarity with CRM platforms, dealership management systems (DMS), or Conversational AI/messaging products.
Background selling within a SaaS portfolio (e.g., Coupa, Anaplan, DealerSocket, VinSolutions, vAuto).
Experience working in a channel-assisted or partner co-sell sales environment.
Comfort with product-led growth motions and shorter, transactional deal cycles alongside complex enterprise sales.

Responsibilities

Execute a balanced prospecting motion across self-sourced outbound, SDR qualified inbound, and channel/referral-sourced leads.
Build and maintain a minimum 3x pipeline coverage ratio against quota at all times.
Develop territory and account-level prospecting plans targeting Commercial (powersports, RV, marine, construction equipment) and Recreational verticals.
Leverage referral networks within the broader Trader Interactive ecosystem to identify cross-sell and co-sell opportunities.
Partner closely with SDR team to refine messaging, qualify inbound interest and convert MQLs to SQLs efficiently.
Own the full sales cycle from initial discovery call through signed contract, typically 60-120 days depending on deal complexity.
Conduct compelling discovery sessions to understand dealership workflow, technology gaps and performance objectives.
Deliver tailored product demonstrations of Matador Conversational AI tools to dealership operators, GMs, and ownership groups.
Build multi-threaded relationships with economic buyers, champions and end users within prospect accounts.
Develop and deliver ROI-based business cases and proposals aligned to each prospect's operational metrics and KPIs.
Manage deal progression in CRM with accurate forecasting, stage discipline and pipeline hygiene at all times.
Develop and nurture relationships with referral partners, OEM contacts and adjacent Trader Interactive business units to drive inbound deal flow.
Coordinate with channel partners on joint pipeline reviews, co-selling motions and shared account strategies.
Act as a Matador brand ambassador at industry events, dealer associations and trade shows within target verticals.
Feed competitive intelligence, objection patterns and prospect feedback to Product, Marketing, Marketplace Sales and Leadership teams on a structured basis.
Support go-to-market initiatives including beta launches, product releases and vertical-specific marketing campaigns.
Partner with Marketing to refine ICP targeting, messaging and campaign effectiveness based on field insights.