Head of Sales

About Kick

Kick aims to streamline tedious tasks for over 35 million US business owners and their accounting firms, enabling them to concentrate on critical priorities. Founded by Conrad Wadowski, after the successful $250M sale of his previous company Teachable, Kick is a rapidly expanding team of top-tier professionals from McKinsey, Shopify, NASA, and more. The company has secured $20M in funding from OpenAI, General Catalyst, and Google Ventures, positioning itself as the leading AI-first accounting platform favored by growing firms.

About the Role

The Head of Sales will oversee and expand a team of 4 Account Executives, crafting scalable and repeatable sales strategies that drive growth from SMB to Enterprise segments, targeting a $100M+ revenue milestone and capturing market share from QuickBooks' $13 billion revenue. This role entails hands-on involvement in deals, designing playbooks, scaling the sales force, and establishing Revenue Operations from the ground up, with a defined career trajectory toward SVP of Revenue overseeing pre- and post-sales functions.

Key Responsibilities

• Create and refine a consistent SMB accountant sales process including discovery, qualification, defined sales stages, conversion metrics, and weekly forecasting rituals.
• Provide live coaching to Account Executives during calls, accompany them on critical sales meetings, and actively manage own sales pipeline to propel team productivity.
• Develop and lead Revenue Operations fundamentals covering pipeline structure, attribution systems, and reporting for leadership and investors.
• Lead the negotiation and closing of initial enterprise contracts with Top 50 accounting firms involving multiple stakeholders.
• Collaborate closely with the Head of Customer to align sales strategies with customer activation data ensuring quality over quantity in deals.
• Incorporate AI-driven sales methodologies that enhance agent capabilities and optimize headcount efficiency as the team expands.

Ideal Candidate Profile

• Minimum 7 years in B2B sales or entrepreneurial roles selling SaaS or services, with at least 3 years managing a sales team.
• Experience building high-velocity sales motions from scratch rather than inheriting established playbooks.
• Proven capability as a hands-on leader who can support deals directly and provide tactical coaching afterward.
• Strong acumen in Revenue Operations, including designing pipeline stages, forecasting approaches, and analyzing conversion metrics.
• Proficiency in adjusting Ideal Customer Profiles or qualification standards based on post-sale activation insights.
• Active user of AI-enhanced sales tools and holds informed opinions on balancing automation and human touch.

Preferred Qualifications

• Background selling to accounting professionals or firms, using platforms like Xero, Gusto, or similar.
• Experience scaling sales teams substantially from small groups to over 15 representatives.
• Developed or implemented AI-native sales technologies beyond basic vendor offerings.
• Professional background combining consulting, banking, or strategic roles alongside frontline sales leadership.

Location & Working Conditions

This full-time position is based in downtown Toronto, requiring onsite attendance five days weekly.

Compensation & Benefits

• Competitive on-target earnings (OTE) at the upper market level plus significant equity in a high-growth early-stage company.
• Performance-based variable compensation linked to new accountant client acquisitions and activated annual recurring revenue.
• Employee-friendly equity options including QSBS eligibility, early exercise rights, and extended exercise periods.
• Comprehensive medical, dental, and vision coverage for employees and their dependents.
• Provision of Apple hardware (laptop and headset), along with health and commuter stipends.
• Regular team gatherings in Palo Alto and access to a dedicated office space in Toronto.

Additional Information

Kick values a diverse, innovative team culture and welcomes applications from candidates with varied backgrounds, even if not all experience requirements are met precisely.