Head of Sales

Mikelle Group; Toronto; On-site; CAD 120,000 - 180,000; Full time

Job summary

Mikelle Group in Toronto is seeking a Head of Sales to build and scale a world-class sales organization for a venture-backed fintech company. You will oversee the Sales Development team and Account Executive programs, shaping systems, processes, and culture to drive a repeatable revenue engine.

Reporting to the CEO, you will transition from founder-led to scalable sales, partnering with experienced operators to set the go-to-market strategy and revenue operations for North America.

Qualifications

• 8+ years of experience in sales, business development, partnerships, or go-to-market leadership.
• 5+ years leading outbound sales or sales development teams.
• Proven track record of hiring, coaching, and scaling BDR/SDR organizations.
• Experience leading Account Executives and/or partner or channel sales programs.
• Strong analytical skills with CRM data and sales metrics to drive performance.
• Hands-on experience with AI-enabled sales tools and modern sales technology.
• Builder's mindset with a passion for scalable systems in a startup.

Responsibilities

• 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, coaching frameworks, and performance metrics.
• 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 with the CEO and leadership to shape go-to-market strategy and revenue operations.

Skills

Sales leadership

Outbound sales

BDR/SDR scaling

CRM analytics

AI-enabled sales tools

Go-to-market

Channel/partner sales

Forecasting

Tools

Salesforce

Job description

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.