VP of Sales

VP of Sales Location: Toronto/Remote Type: Full-Time, Leadership About 021 Strategic Zero To One Strategic helps Canada’s most innovative startups and scaleups access the full spectrum of non-dilutive funding, from SR&ED tax credits and government grants to growth loans and financing. We’re a fast-growing team of entrepreneurs, engineers, and funding strategists who believe founders shouldn’t have to give up equity to build great companies. Our mission is simple: help innovators turn ideas into impact by unlocking the capital they already qualify for. With growth exceeding 30% month-over-month and new product lines launching, we’re scaling our leadership team to meet rising demand, and we’re looking for someone who can turn strong inbound momentum into a world-class sales engine. The Role We’re hiring a VP of Sales who thrives as a player-coach. Someone who’s equally energized by closing transformative deals and building the systems, structure, and culture that power long-term growth. You’ll take ownership of our go-to-market strategy and lead the next phase of 021 Strategic’s expansion. This means optimizing inbound performance, building outbound capability, mentoring high-performing reps, and shaping how we engage founders and executives of late-stage companies across Canada’s innovation ecosystem. This is both a hands-on and strategic leadership role, ideal for someone who loves driving revenue personally while developing a repeatable process and high-trust team around them. What Success Looks Like You’ve built a repeatable, data-driven revenue engine , not just hit quotas. Founders and CFOs view 021 Strategic as the go-to partner for funding strategy . You’ve hired, developed, and retained a sales team that consistently exceeds targets. Our inbound funnel is structured, prioritized, and forecastable with clear accountability. Sales, Marketing, Partnerships, and Operations work in sync toward shared growth metrics. Key Responsibilities Own revenue growth: Drive acquisition, expansion, and retention targets across all service lines (SR&ED, grants, loans). Lead by example: Manage enterprise and founder-led opportunities end-to-end, modeling consultative selling excellence. Coach & scale the team: Recruit, onboard, and mentor Account Executives and SDRs; implement metrics, pipeline discipline, and sales playbooks. Sales operations: Define forecasting cadence, CRM hygiene (HubSpot), and reporting dashboards to ensure visibility and accountability. Strategic alignment: Collaborate cross-functionally with Marketing, Partnerships, and Finance to align pipeline growth with delivery capacity. Market intelligence: Identify emerging verticals, funding trends, and partnership opportunities that strengthen our market leadership. Leadership: Report directly to the Managing Partner and play an active role in shaping company-wide go-to-market and annual planning. What You Bring 6+ years in B2B sales , ideally in consulting, SaaS, financial services, or funding advisory. 2+ years in a sales leadership or player-coach capacity with a proven ability to build and lead teams. Strong command of consultative, founder-focused selling , you can engage executives, translate value, and close complex service deals. Proven success designing and optimizing sales processes and forecasting systems using HubSpot (or equivalent CRM). Strong business acumen and strategic mindset, you think in terms of growth, efficiency, and impact , not just pipeline volume. A bias for action, humility, and collaboration , you lead by doing and inspire others through performance and clarity. Why Join 021 Strategic Join a company growing 30% month-over-month , backed by a strong inbound funnel and exceptional client base. Shape the future of how Canadian companies access non-dilutive capital through new funding products and tech-enabled services. Work directly with the founders and leadership team — no red tape, just impact. Remote-first, flexible work culture built on trust, autonomy, and shared success. A team that celebrates wins together and values clarity, accountability, and growth. Base Salary: $110K – $140K Variable: $50K – $80K (performance-based, with accelerators) Total OTE: $160K – $210K Equity: Optional small stake (0.1–0.25%) or milestone-based bonus plan #J-18808-Ljbffr