Head of Sales

We're partnering with an exciting, venture-backed fintech company that's experiencing rapid growth and building the future of merchant operations. Backed by leading venture capital firms from Silicon Valley and Atlanta's fintech ecosystem, the company has strong early momentum and a significant opportunity to scale across North America. By combining payment processing, intelligent workflow automation, and AI-powered operational tools, they're helping businesses simplify payments, streamline reconciliation, reduce operational complexity, and modernize how they manage their financial operations. They're now looking for a Head of Sales to build and scale a world-class sales organization in Toronto. This is a rare opportunity to join at a pivotal stage of growth and help shape the company's go-to-market strategy from the ground up. Reporting directly to the CEO, you'll play a key role in transitioning the business from founder-led sales to a scalable, repeatable revenue engine. Working alongside experienced operators, serial founders, and builders, you'll lead the Sales Development team, oversee the Account Executive function, and establish the systems, processes, and culture that drive sustainable growth. What You'll Do Build, hire, coach, and scale a high-performing BDR team. Lead and develop the Account Executive program and partner channels. Design repeatable sales processes, onboarding programs, coaching frameworks, and performance management systems. Own pipeline generation, outbound strategy, and key sales development metrics. Establish forecasting, pipeline reviews, call coaching, and performance operating rhythms. Leverage AI-powered sales tools and automation to improve prospecting, outreach, coaching, CRM hygiene, and reporting. Partner closely with the CEO and leadership team to shape the company's go-to-market strategy and revenue operations. What We're Looking For 8+ years of experience in sales, business development, partnerships, or go-to-market leadership. 5+ years leading outbound sales or sales development teams. A proven track record of hiring, coaching, and scaling high-performing BDR/SDR organizations. Experience leading Account Executives and/or partner or channel sales programs. Strong analytical skills with experience using CRM data and sales metrics to drive performance. Hands-on experience with AI-enabled sales tools and modern sales technology. A builder's mindset with a passion for developing people, creating scalable systems, and thriving in a fast-paced startup environment. Why Join? Build a sales organization from the ground up and leave a lasting impact. Work directly with experienced founders and executive leadership. Influence the company's sales strategy, culture, and long-term growth. Join a high-growth, venture-backed fintech with exceptional momentum. Competitive compensation, performance incentives, and outstanding career growth opportunities. If you're excited by the opportunity to build, lead, and scale a high-performing sales organization, we'd love to hear from you.

The Head of Sales will build and scale a world-class sales organization in Toronto, transitioning the company from founder-led sales to a repeatable revenue engine. This includes leading the BDR and Account Executive teams while designing sales processes and go-to-market strategies.

Candidates need 8+ years of experience in sales or GTM leadership, with at least 5 years specifically leading outbound sales or BDR teams. A proven track record of scaling high-performing sales organizations and proficiency with AI-enabled sales tools is required.

• Competitive Compensation • Performance Incentives • Career Growth Opportunities

Identified from the job description. Confirm important requirements above.

• Sales Leadership
• Business Development
• Go-To-Market Strategy
• BDR Management
• Account Executive Management
• Pipeline Generation
• Sales Forecasting
• CRM Management
• AI Sales Tools
• Channel Sales
• Performance Management
• Outbound Strategy
• Coaching
• Revenue Operations
• Scaling Sales Organizations
• Analytical Skills

• Sales
• Management & Leadership
• Finance & Accounting
• Technology
• Software

Minimum experience

10+ years

Apply by

Aug 28, 2026

Posting language

English

Working hours

40 hours per week

Seniority

Director

Application method

Direct apply is available