Head of Billing Sales & Growth (AMER)

Stripe, Inc.; Chicago (IL); On-site; USD 330,000 - 495,000; Full time

Benefits offered by this job

Equity

401(k) plan

Medical, dental, and vision benefits

Wellness stipends

Job summary

Stripe, Inc. in the AMER region seeks a strategic Head of Grower Sales (Billing) to lead and scale a team of Account Executives, shaping go-to-market plans and driving expansion and retention of Stripe Billing. You will partner with product, finance, and marketing to close high-value deals.

You will coach leaders, own forecasts, and build executive relationships with customers. The role requires 10+ years in SaaS sales leadership, finance/revenue domain experience, and a hands-on, collaborative

Qualifications

• 10+ years of sales leadership experience, launching and growing high-functioning sales teams/products.
• 12+ years of experience in hyper-growth SaaS environments across the AMER region.
• Industry experience in finance, revenue management, financial services, or similar software services.
• Proven ability to be a self‑starter, capable of driving business results without significant supervision.
• Ability to understand complex technical requirements and craft solutions across multiple stakeholders.
• Enthusiastic “roll up your sleeves” mentality.
• Excellent verbal and written communication skills.
• Strong presentation skills, particularly for in-person meetings with multiple stakeholders.
• Proven ability to lead complex negotiations involving bespoke agreements with startup, SMB, and Commercial businesses.

Responsibilities

• Recruit, develop and lead a team of product sales executives focused on expansion and retention of our largest Billing Users.
• Create go-to-market plans and solutions to meet our customer needs, in collaboration with Product, Sales, Finance and Marketing stakeholders.
• Manage day-to-day operations, with a focus on performance against key sales metrics.
• Be accountable for driving revenue, increasing attach rates, and new client acquisition at high rates of growth.
• Coach and guide the team in developing consultative and solution-based sales skills through all facets of the sales cycle.
• Get hands on engaged in the largest, most strategic opportunities, leading executive relationships and helping the team win new customers.
• Inspire, motivate, and enable individual development to promote career growth of direct reports.
• Lead with clarity and context with a compelling plan in line with Stripe’s direction.
• Create structure and focus for GTM ideas and product sales campaigns that the product team is exploring. Drive execution and measurement. Analyse results and make recommendations for action in a timely manner.
• Constantly innovate and improve programs and program management mechanisms, suggesting new ideas, sharing best practices, and improving the business and customer engagement model.

Skills

Sales leadership

SaaS

Executive relationships

Strategic planning

Cross-functional collaboration

Negotiation

Presentation skills

Self-starter

Job description

Stripe, Inc. in the AMER region seeks a strategic Head of Grower Sales (Billing) to lead and scale a team of Account Executives, shaping go-to-market plans and driving expansion and retention of Stripe Billing. You will partner with product, finance, and marketing to close high-value deals.

You will coach leaders, own forecasts, and build executive relationships with customers. The role requires 10+ years in SaaS sales leadership, finance/revenue domain experience, and a hands-on, collaborative