Vice President, Software Sales

Trader Interactive•Toronto, ON

16d

About The Position

Are you ready to be a big part of something big? At Trader Interactive, we make buying and selling a great experience. We’re a group of go-getters who decided they didn’t want to settle for the status quo. We come together as one team to build value and drive innovation across our industries - but we have fun while we do it and make sure our people are always our #1 priority. When it comes to your career, we want to provide big opportunities to help you make a big impact. But for this to be possible, we strive to feel small. Small enough to quickly change tack, small enough to learn from different teams and small enough to connect authentically with leadership. What We Offer: An inclusive and supportive work environment where you can move your career forward and will have the chance to do work that has real, significant impact on the world. The opportunity to be a part of a global group of digital marketplace businesses (CAR Group) located across Australia, Brazil, Chile and South Korea - collectively we have around 2,500 team members worldwide, and our CAR Group Tour means you might just find yourself working in one of those businesses sometime soon. Plenty of flexible leave options and employee benefits including up to 31 days of paid time off in your first year, continuing education with access to LinkedIn Learning, a full benefits package including medical, dental & vision, 401K with company match, and wellness program. The Vice-President, Software Sales is the senior revenue leader for Trader Interactive's Software Business Unit owning Bookings attainment across three distinct product lines: iMotor Websites, Matador AI and Statistical Surveys. Reporting directly to the GM of Software, this leader is accountable for building and scaling a high-performing, metrics-driven sales organization. The VP owns the full revenue motion from pipeline generation and forecasting to rep coaching, territory design and cross-functional alignment with Product and Finance. The VP is expected to be in the field coaching deals, running QBRs, working channels and holding the team to a consistent standard of sales execution. Equal parts strategist and operator, this leader will bring structure, accountability and competitive intensity to a team positioned to capitalize on a greenfield SaaS opportunity across dealership and commercial verticals.

Requirements

8–12+ years of SaaS sales experience, including 3–5+ years in a senior sales leadership role (Director, VP, or equivalent) with direct quota ownership.
Demonstrated track record of leading teams to consistent quota attainment — including building from early-stage and scaling through growth phases.
Deep experience managing full-cycle SaaS sales teams in SMB and mid-market environments ($15K–$100K ACV range).
Strong command of consultative and value-based selling methodologies; Challenger Sales, or equivalent.
Proven ability to build and implement structured coaching frameworks that reduce performance variation and develop sellers at all levels.
Data-literate and operationally rigorous — expertise in Salesforce (or equivalent CRM), pipeline management, and revenue forecasting.
Experience as a cross-functional stakeholder in Product planning and Financial / AOP processes.
Executive presence and communication skills — comfortable presenting to GM, C-suite, and board-level audiences.

Nice To Haves

Experience leading multi-product SaaS sales teams — managing distinct GTM motions, quota structures, and buyer profiles under a unified P&L.
Background selling into dealership verticals: automotive, powersports, RV, marine, equipment, or adjacent industries.
Familiarity with Websites, Digital Advertising, CRM, DMS, Conversational AI/messaging, or survey/analytics SaaS products.
Track record of building or scaling channel and partner co-sell programs that contribute meaningfully to pipeline.
Experience navigating go-to-market initiatives alongside Product, Marketing, and Customer Success in a portfolio SaaS company.
Comfort operating in both greenfield acquisition environments and renewal/expansion revenue contexts.

Responsibilities

Own ARR Bookings targets across iMotor Websites, Matador AI and Statistical Surveys — holding the team accountable to quarterly and annual plan.
Drive consistent revenue execution through disciplined forecasting, pipeline management, and deal inspection at every stage of the funnel.
Develop and manage a consolidated view of Software BU pipeline health, coverage ratios, and conversion velocity to surface risks and opportunities early.
Deliver accurate, stage-disciplined forecasts to the GM and executive leadership on a weekly and monthly cadence.
Build and enforce a culture of forecast hygiene and CRM discipline across all three product sales teams.
Lead, develop, and retain a team of Product Specialists and supporting SDRs across multiple product verticals — building capability, not just managing activity.
Implement a structured coaching and enablement framework designed to reduce performance variation across the sales force and elevate the floor as well as the ceiling.
Conduct regular 1:1s, deal reviews, call coaching, and pipeline inspections with a focus on skill development tied to measurable outcomes.
Identify top performers and create clear career paths; identify underperformers and execute structured improvement plans with urgency.
Partner with Sales Enablement and People teams to design onboarding, ramp programs, and ongoing skills development aligned to each product's sales motion.
Establish and enforce a minimum 3x pipeline coverage ratio across all product lines — holding managers and reps accountable to territory-level prospecting plans.
Own demo-to-conversion targets as a core operating metric; drive systematic improvement through better qualification, discovery process, and demo delivery standards.
Partner with SDR leadership to optimize MQL-to-SQL conversion, inbound routing, and outbound sequencing across all three product verticals.
Champion a rigorous qualification methodology (Challenger or equivalent) to improve deal quality upstream and reduce late-stage churn.
Serve as a key stakeholder in Product planning — bringing structured field intelligence, objection patterns, competitive insights, and ICP feedback into roadmap and prioritization conversations.
Partner with Finance in Annual Operating Plan (AOP) and quota-setting processes — contributing bottom-up insights on territory capacity, market sizing, and achievable ramp timelines.
Collaborate with Marketing on campaign effectiveness, ICP targeting, and vertical-specific messaging to ensure field alignment with demand generation motions.
Work closely with Customer Success leadership to ensure clean post-sale handoffs that protect NRR and set the foundation for expansion.
Represent Software BU sales leadership in executive reviews, board materials, and cross-BU strategic planning sessions.
Develop and scale referral, OEM, and channel partnerships that generate incremental pipeline and expand market reach beyond direct outbound motions.
Coordinate co-sell motions across the broader Trader Interactive ecosystem — identifying cross-BU opportunities and driving coordinated account strategies.
Act as the Software BU's senior commercial presence at industry events, dealer associations, trade shows, and OEM forums.

Benefits

Plenty of flexible leave options and employee benefits including up to 31 days of paid time off in your first year, continuing education with access to LinkedIn Learning, a full benefits package including medical, dental & vision, 401K with company match, and wellness program.

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