Stripe Verified

Fintech, Payments, Software-as-a-Service (SaaS)

Head of Sales, Billing

New YorkOnsiteFull TimeManager / HeadPosted 2 months ago

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Required skills

Stripe Billing
AMER
Account Executives
Product Marketing
Product
Go-to-market strategy
Sales metrics
Revenue
Attach rates
Client acquisition

Nice to have

AI industry users

Role summary

Stripe is seeking a Head of Grower Sales for Billing to lead and expand a team of Account Executives in the AMER region. This role involves driving revenue growth, retention, and new client acquisition for Stripe's Billing product, a key strategic offering. The Head of Grower Sales will be responsible for coaching, developing, and managing the sales team, collaborating with cross-functional teams (Product, Marketing, Sales Leadership), and engaging in strategic deals and executive-level customer discussions. The ideal candidate is an experienced sales leader with a strong background in hyper-growth SaaS environments, particularly in finance, revenue management, or financial services, and possesses expertise in billing systems, go-to-market strategy, and complex negotiations. A proven ability to build and lead high-performing sales teams and drive business results with minimal supervision is essential.

Who we are

About Stripe

Stripe is a financial infrastructure platform for businesses. Millions of companies - from the world’s largest enterprises to the most ambitious startups - use Stripe to accept payments, grow their revenue, and accelerate new business opportunities. Our mission is to increase the GDP of the internet, and we have a staggering amount of work ahead. That means you have an unprecedented opportunity to put the global economy within everyone's reach while doing the most important work of your career.

About the team

The world is having a monetization moment – every ambitious company is replatforming their billing solution in response to AI. Stripes Billing is a team of deep functional and technical specialists who both lead and advise on deals for one of the most strategically important products in Stripe’s portfolio. Billing Sales is tasked with attacking a $100B market opportunity for automating the entire order to cash process and helping companies not get left behind in the AI era.

What you’ll do

As the Head of Grower Sales (Billing), you will use your leadership and management skills to manage and grow a team of Account Executives to drive expansion and retention of Stripe Billing across the AMER region. You will build and lead a team of sellers, while collaborating with the core sales leadership, marketing, product marketing, and product teams to develop deep product and industry knowledge and drive strategic deals. You will own the coaching, development, and performance of your team, driving the forecast of the business. You will be instrumental in leading in-depth product discussions with existing and prospective customers and building and executing against our go-to-market strategy.

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.

Who you are

You are an adept sales leader, capable of engaging in business-level and technical conversations at multiple levels of the organization. You have a reputation and drive for building strategic relationships with executives (CEO, CFO, and CTO) across the AMER region, including core markets like NA, CA, and LATAM. You excel in building clear plans to grow a region through a high-functioning sales team, with strategic thought leadership and strong management. You see value in competitive situations and enjoy working on products that require both deep product understanding and technical knowledge, especially for AI industry users. You’re as comfortable working with clients as with internal stakeholders (including executives) and are excited to become an expert and share your knowledge. You possess an organized, self-starter mindset and excellent communication skills, with a track record for improving the processes and organizations around you.

Minimum requirements

10+ years of sales leadership experience, launching and growing high-functioning sales teams/products.

15+ 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.

An 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.

Sample Stripe interview questions

1
Discuss failure modes and backward compatibility for a system design.
system designeasy
2
How do you see customer expectations shifting in the coming years?
technicalmedium
3
Discuss your solution, coding approach, problem-solving process, and technical decision-making for the coding challenge.
technicaleasy
4
What are important metrics to analyze to measure pipeline and deal signed health
metrics analyticsdifficult

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