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CommonShares

CEO – B2B FinTech

CommonShares

. Serve as CEO for Simple Ventures’ next venture .

Posted 11/11/2026full-timeToronto • CanadaSeniorLeadWebsite

Core Competencies

Role fit
Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates extensive experience in building and scaling B2B fintech companies, with a strong focus on customer experience and strategic decision-making. Proven ability to lead high-performing sales teams and develop effective go-to-market strategies in fast-growing environments.

Highest-signal resume keywords
B2B Sales ExperienceExecutive-Level LeadershipFinancial AnalysisGo-To-Market Strategy DevelopmentCustomer Experience Design

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills
Financial AnalysisB2B SalesGo-To-Market StrategySales Process DevelopmentRisk Management
Soft Skills
DecisivenessEffective CommunicationIntellectual CuriosityAccountabilityCrisis Management
Industry Keywords
FintechCustomer-Centric ApproachComplex B2B MarketsRevenue GrowthBrand Ownership

About the role

Key responsibilities & impact
  • Serve as CEO for Simple Ventures’ next venture
  • Build and scale a B2B fintech company from day one
  • Help Canadian businesses navigate complex risks with greater clarity, confidence, and control
  • Modernize business risk management through a technology-enabled, customer-centric approach
  • Win customers and build trust in complex B2B markets
  • Secure major accounts and drive revenue growth
  • Build and lead high-performing sales teams
  • Develop repeatable sales processes and go-to-market strategies
  • Design and deliver an exceptional customer experience
  • Act as the brand owner and face of the business
  • Pitch the business to customers, partners, and press
  • Use financial analysis and key indicators to evaluate and act on strategic opportunities
  • Make timely decisions and keep the organization moving forward

Requirements

What you’ll need
  • 10+ years of experience
  • Most recently executive-level experience with a proven track record of success
  • Experience building and scaling B2B sales
  • Experience winning complex customers
  • Experience establishing repeatable go-to-market strategies
  • Experience in a fast-growing environment
  • Understanding of existential threats in a limited-resources situation
  • Intellectual curiosity
  • Extreme levels of accountability
  • Ability to be incredibly decisive
  • Obsession with designing and delivering an exceptional customer experience
  • Distinct view of being the "brand owner" and face of the business
  • Comfort pitching the business to customers, partners, and press
  • Ability to take action with urgency, energy, and enthusiasm
  • Confidence under pressure and ability to maintain a positive attitude despite setbacks
  • Ability to grow from hardships and manage crises effectively
  • Effective communication in one-on-one, small-group, large-group, and diverse settings
  • Ability to create organization-wide energy and optimism for the future
  • Ability to articulate visions positively and accessibly
  • Ability to create milestones and symbols that rally support and motivate action
  • Ability to persist in accomplishing objectives and exceeding goals despite obstacles
  • Financial analysis and understanding of key indicators
  • Ability to make sound and timely decisions with incomplete information

Benefits

Comp & perks
  • Real ownership in building and scaling a new company from day one
  • Simple Ventures as a highly engaged partner
  • Seed investment support
  • Opportunity to partner with and build a company backed by leaders including founders of Wealthsimple, Shopify, Ada, and MindBeacon