Head of SMB Sales

This is a fully remote position, open to applicants in California.

📋 Description

• Lead and manage the North American SMB Sales Team, encompassing BDR, Inbound, and Outbound Account Executive functions.

• Develop and enhance playbooks, processes, tools, and segment strategies to effectively convert and grow merchants at scale.

• Ensure the team meets OKRs and revenue objectives across all sales motions.

• Cultivate team skills, talent, performance, and culture; mentor frontline managers.

• Collaborate with Marketing, Finance, Product, Risk, Legal, Account Management, and other cross-functional teams.

• Oversee and optimize the entire sales process from discovery and qualification to value articulation, negotiation, and closing.

• Enhance forecasting accuracy and maintain pipeline health together with Finance and Sales Ops/Strategy.

• Identify the ideal customer profile, use cases, value propositions, and sales/growth narratives.

• Act as a thought leader in payments and Buy Now Pay Later, representing Afterpay and Cash App to SMB merchants.

• Collect and relay merchant feedback while advocating for clients within the organization.

• Take ownership of revenue outcomes within the North American SMB merchant pipeline.

⛳️ Requirements

• A minimum of 12 years of experience in high-growth settings, leading SMB Sales, BDR, or Account Management teams, ideally within a fast-paced technology or financial services firm, with a focus on high volume and velocity.

• Outstanding leadership capabilities, including talent development, motivating high-performance teams, establishing cross-functional relationships, and coaching/managing frontline managers to achieve results.

• Proven experience in establishing or scaling sales organizations from the ground up, including hiring, onboarding, and developing BDRs, AEs, and frontline managers.

• Demonstrated success in building, operating, and continuously enhancing scalable playbooks.

• Experience collaborating closely with Product and Marketing to enhance conversion rates and improve self-service sign-up, activation, and onboarding processes.

• Strong presence with senior internal leaders, capable of influencing, building trust, asking insightful questions, and exercising sound business judgment.

• Proven track record of leading teams that achieve revenue growth and surpass revenue targets.

• Comfortable with analytics and tools for forecasting, funnel analysis, and pipeline conversion metrics on a large scale.

• Exceptional storytelling abilities and the capacity to create data-driven business cases around value propositions.

• A scrappy and humble mindset, adept at both strategic planning and hands-on pipeline management.

• Openness to travel as needed.

🏝️ Benefits

• Remote work opportunities.

• Comprehensive medical insurance.

• Flexible time off policies.

• Retirement savings plans.

• Modern family planning benefits.