Sales Leader (Fintech)

Location: Remote, Chicago, Illinois, United States

Salary: $318,000–$477,000 annually, including target variable compensation.

Company

hirify.global builds technology and financial services products through brands including Square, Cash App, Afterpay, TIDAL, Bitkey, and Proto.

What you will do

• Scale Square's Central Region Field Sales organization through territory design, go-to-market planning, and operational rigor.
• Lead Sales Managers and Territory Account Executives focused on acquiring and expanding small and midsize businesses.
• Build a performance-oriented culture based on accountability, competitiveness, coaching, and excellence.
• Coach teams in the field, support co-selling, and develop deep expertise in the Square product ecosystem.
• Manage pipeline health, conversion rates, forecasting, and sales productivity to drive predictable growth.
• Partner with Marketing, Sales Operations, Partnerships, and Product while developing sales talent and representing Square in Central markets.

Requirements

• 10+ years of sales experience, including 5+ years leading regional or field sales teams.
• Experience in a high-growth SaaS, fintech, or payments environment.
• Proven success exceeding regional revenue and productivity goals.
• Experience building high-performance teams and cultures grounded in coaching and accountability.
• Strong product acumen and the ability to position complex solutions across multiple product lines.
• Operational expertise in forecasting, pipeline management, KPI tracking, and executive communication.

Culture & Benefits

• Remote work with market-based pay determined by location, skills, experience, qualifications, and market conditions.
• Medical insurance, flexible time off, retirement savings plans, and modern family planning benefits.
• Inclusive hiring practices with reasonable accommodations available during the recruitment process.
• AI tools may be used to evaluate applications in accordance with local regulations and privacy laws.

Hiring process

• Candidates may submit up to 9 active applications within a 60-day period.
• Reapplications to the same role are accepted 90 days after a previous application has been reviewed.