What You'll DoThe Vice-President, Software Sales - CRM is the senior revenue leader for DP360 CRM owning Bookings attainment and Performance Management, across the CRM platform with DP360.
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, post-sale performance management, customer retention and cross-functional alignment with Product and Finance.
The VP is expected to be in the field coaching deals, running QBRs across both sales and customer success motions, and holding the team to a consistent standard of execution from first pipeline touch through renewal. Equal parts strategist and operator, this leader will bring structure, accountability and competitive intensity to a team positioned to win share in a large, CRM market across powersports, RV, marine and commercial truck dealer networks, while protecting and growing revenue within the existing book of business.
Revenue Ownership & Bookings Attainment- Own ARR Bookings targets for DP360 CRM holding the team of quota-carrying reps 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 DP360 CRM 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 the entire quota-carrying sales team.
Sales Team Leadership & Coaching- Lead, develop and retain the full team of DP360 CRM quota-carrying Account Executives and supporting SDRs 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 the DP360 CRM sales motion.
Performance Management & Customer Success- Own the Performance Management (Customer Success) function for DP360 CRM setting the standard for onboarding, adoption and utilization across the dealer and operator base.
- Establish and enforce a minimum 3x pipeline coverage ratio, holding managers and reps accountable to territory-level prospecting plans, while ensuring Customer Success maintains equally disciplined coverage of at-risk accounts.
- Run regular QBRs with Customer Success leadership to review adoption metrics, escalations, and health scores across the DP360 CRM install base.
- Champion a rigorous qualification methodology (Challenger or equivalent) to improve deal quality upstream and set new accounts up for a successful, low-churn first year.
Go-to-Market Strategy & Cross-Functional Alignment- 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.
- Track the competitive landscape closely including DMS integration partners, appraisal and lead-generation platforms, and adjacent CRM entrants and translate competitive intelligence into sales positioning and win/loss improvements.
- Represent DP360 CRM commercial leadership in executive reviews, and cross-BU strategic planning sessions.
Client Retention & Renewals- Own Gross and Net Revenue Retention as headline metrics building a proactive, data-driven renewal motion rather than a reactive save process.
- Build and enforce a health-scoring and early-warning system that flags at-risk accounts well ahead of renewal and hold Customer Success accountable to structured save plays.
- Identify expansion and upsell opportunity within the existing book including AI and add-on module attach and hold the team accountable to a disciplined renewal and expansion cadence.
What We're Looking For- 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 over a team of quota-carrying reps.
- 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, with direct ownership of both new-logo acquisition and post-sale retention within the same organization.
- 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.
- Demonstrated ownership of retention and renewal outcomes (GRR/NRR) in a subscription SaaS business, not just new bookings.
- Executive presence and communication skills comfortable presenting to GM, C-suite, and board-level audiences.
Bonus Points:- Experience leading a combined sales and customer success organization under a single P&L, with accountability for both acquisition and retention.
- Background selling into dealership verticals: automotive, powersports, RV, marine, equipment, or adjacent industries.
- Familiarity with dealer CRM, DMS integrations, and the competitive landscape of dealer-facing sales and marketing software.
- Track record of building health-scoring, early-warning, or save-play programs that measurably improved retention.
- 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.
So come and join our team - because every role is a big role in our plans to go big.
Department Software Locations Toronto, ON
