VP Revenue
Location: Toronto, ON (preferred)
Reports to: CEO
Direct Reports: Sales and Customer Success teams
About the Role
Red Pepper Digital is building the essential adtech platform for promotion-led commerce — combining pre-shop engagement, shopper insights, and AI-driven personalisation to drive conversion, basket size, and customer lifetime value for grocery and retail operators across North America.
Our platform — digital promotions, retail media, and data infrastructure — is built to be core retailer infrastructure: embedded, recurring, and high-margin by design. The next phase is extending that model beyond our Grocery cornerstone into Retail and Trade, building the unified ecosystem that makes RPD indispensable at scale.
This is the commercial leadership role that drives it — owning revenue, retention, and commercial architecture, and shaping which verticals we enter next. This is a builder's role for someone who wants to shape a category, not run a playbook.
Key Responsibilities
Revenue Growth
- Own the North American sales number across new logos, expansions, and renewals.
- Build and manage a disciplined pipeline with accurate forecasting and stage governance.
- Drive a consultative, insight-led sales motion across retailer and brand buyer personas.
Commercial Structure & Packaging
- Own pricing strategy, packaging architecture, and commercial model design.
- Develop tiered offering structures that serve independent grocery operators while scaling into broader Retail and Trade/Manufacturing segments.
- Work with Product and the CEO to ensure packaging reflects platform capability and market positioning.
- Lead commercial negotiations on strategic deals, setting precedent for scalable contract structures.
Customer Success
- Lead a Customer Success function focused on adoption, ROI realisation, and retention.
- Build strong executive relationships across the retailer and brand customer base.
- Establish health scoring and proactive intervention practices to protect and grow NRR.
Vertical Expansion
- Maintain and grow RPD's core independent and regional grocery segment.
- Extend the commercial motion into broader retail verticals where the RPD platform has clear application.
- Identify vertical-specific packaging, pricing, and partnership requirements for each new segment.
Go-to-Market Leadership
- Partner with the CEO on overall go-to-market strategy, market positioning, and competitive response.
- Collaborate with Marketing to align campaigns, content, and demand generation to pipeline stage and vertical priorities.
- Represent RPD at industry events, trade conferences, and brand/CPG forums.
Team & Culture
- Recruit, develop, and retain a high-performing Sales and Customer Success team.
- Establish a performance culture with clear KPIs, coaching rhythms, and accountability.
Ideal Candidate Profile
- 10+ years of experience in B2B SaaS or retail technology, with at least 5 years in senior sales leadership.
- Proven track record owning a revenue number in the $10M–$30M ARR range.
- Experience across multiple buyer types — retailers, grocery operators, CPG/FMCG brands, or Trade/Manufacturing — strongly preferred.
- Demonstrated ability to build and evolve commercial models, including packaging, pricing, and deal structures — not just selling into existing frameworks.
- Track record of opening new verticals or segments, not just optimising an existing territory.
- Builder mentality — comfortable operating in a scale-up environment where process, structure, and playbooks are still being established.
- Strong executive presence with the ability to engage C-suite and ownership-level buyers across both retailer and brand organizations.
- A deep North American network is considered a strong asset.
Why This Role
RPD's platform sits at the intersection of retail media, shopper data, and digital engagement — a space attracting significant investment and consolidation.
The person in this role won't inherit a mature sales machine; they'll build one, with real influence over product direction, commercial architecture, and which markets RPD enters next.
For the right commercial leader, it's a rare opportunity to shape a category.
Pay: $180,000.00-$300,000.00 per year
Work Location: Remote
