Enterprise Sales Executive - San Francisco

Checkout Ltd; San Francisco (CA); On-site; USD 150,000 - 210,000; Full time

Job summary

Checkout.com is expanding its US GTM with an Enterprise Sales Executive who will own the end-to-end new logo sales cycle across enterprise accounts. You will build pipeline, engage with merchants, and lead complex deals in a fast-growing fintech environment.

The role emphasizes data-driven selling, strategic account planning, and long-term relationships with high-value clients, supported by strong commissions and clear growth opportunities.

Qualifications

• Experience in enterprise/large account sales and complex deals.
• Strong strategic planning and pipeline management.
• Comfort engaging C-suite and negotiating with executives.
• Data-driven GTM mindset and business acumen.

Responsibilities

• Strategically prospect and plan accounts to identify high-probability new logo opportunities and build pipeline.
• Engage with customers consultatively to build long-term, trust-based relationships and propose tailored solutions.
• Lead deals by coordinating internal resources, building quantitative business cases, and delivering impactful presentations.
• Close negotiations and drive complex deals to successful closure.
• Track and analyze sales performance, learn industry trends, and adapt strategies accordingly.

Skills

Entrepreneurial drive

Strategic acumen

Learning mindset

Stakeholder management

Organization

Communication skills

Job description

Company Description

We’re Checkout.com. You might not know our name, but companies like eBay, Spotify, Klarna, Uber, and Sony do, because we’re behind many of the digital experiences you use every day.

We are where the world checks out, enabling over 10 billion transactions yearly for more than one billion global shoppers. Whether you want to book a holiday, order food, renew a subscription, or check out online, there’s a good chance our tech powers the payments behind the scenes. Our platform helps the most ambitious businesses deliver effortless digital experiences, at scale. If you want to do career-defining work, you’ve come to the right place. We move fast, think globally, and believe great teams are built by hiring exceptional people with conviction, curiosity, and the desire to make an impact. With 20 offices across six continents and London as our HQ, we’re shaping the future of fintech – and we’re just getting started.

Are you seeking an opportunity to make a significant impact within one of the world's fastest-growing fintechs? At Checkout.com, we pride ourselves on being the invisible layer powering the payment solutions for some of the world's largest brands, such as Klarna, Sony, and eBay.

This Enterprise Sales Executive role is for a driven and strategically minded professional with a passion for winning complex new business. We are rapidly expanding our Go-To-Market (GTM) team in the US, recognizing this market as our #1 priority with the biggest total addressable market. This is a high-growth, high-reward environment where you'll contribute directly to our expansion by working with innovative Enterprise clients across the US landscape. In this role, you'll be empowered to run your own strategies and hypotheses with best-in-class commissions. We seek smart, hardworking individuals who thrive on challenge, embodying tenacity and a strong sense of urgency. Whether you come from tech sales, banking, consulting, or another results-driven field, this is your chance to make a significant impact and grow quickly in a competitive space.

The ideal candidate approaches business development and go-to-market in an analytical and data-driven manner, and is a creative problem-solver. You will be required to think outside the box, to help build deep and meaningful relationships with merchants and to be highly organised.

What You Will Do (Key Responsibilities):

As an Enterprise Sales Executive, you will be responsible for end-to-end management of the new logo sales cycle within a territory of Enterprise accounts. Your responsibilities will include:

• Strategically prospect and plan accounts to identify and target high-probability new logo opportunities, leveraging deep intelligence, networks, and disciplined execution to build pipeline. High-performing reps excel at identifying leads, evaluating their potential, choosing targets, and creating an outbound strategy to reach them.
• Engage with customers consultatively to build long-term, trust-based relationships, focusing on understanding their challenges and proposing tailored, high-value solutions. You’ll leverage our proven sales methodology, industry, and product knowledge.
• Deal leadership: Orchestrate and lead deals by coordinating internal resources, building quantitative business cases, delivering impactful presentations, and proactively solving problems to drive opportunities forward.
• Closing: Lead negotiations, handling objections, creatively addressing concerns and steering complex deals to successful closure.
• Track and analyze your sales performance, owning results independently, continuously learning industry trends, and leveraging feedback to improve and grow.

Core Competencies & Traits We Value:

• Entrepreneurial Drive: Possess a persistent, self-starter mentality, operating your territory as an owned business with strong accountability and urgency.
• Strategic Acumen: Analytical and data-driven. Exhibit high intellectual curiosity, rapidly learning and applying complex strategic insights to account planning and leveraging new technologies like AI for accelerated performance.
• Learning: Actively seek feedback, demonstrate a growth mindset, and dynamically adjust strategies based on results and evolving information.
• Confident in stakeholder management, including engagement with C-suite executives.
• Highly organised and able to prioritise shifting workloads and responsibilities effectively.
• Strong written and verbal communication skills.

Additional Information

Bring all of you to work

We create the conditions for high performers to thrive, through real ownership, fewer blockers, and work that makes a difference from day one.

Here, you’ll move fast, take on meaningful challenges, and be recognized for the impact you deliver. It’s a place where ambition gets met with opportunity, and where your growth is in your hands.

We work as one team, and we back each other to succeed. So whatever your background or identity, if you’re ready to grow and make a difference, you’ll be right at home here.

It’s important we set you up for success and make our process as accessible as possible. So let us know in your application, or tell your recruiter directly, if you need anything to make your experience or working environment more comfortable.

Life at Checkout.com

We understand that work is just one part of your life. Our hybrid working model offers flexibility, with three days per week in the office to support collaboration and connection.

Curious about what it’s like to be part of our team? Visit our Careers Page to learn more about our culture, open roles, and what drives us.

For a closer look at daily life at Checkout.com, follow us on LinkedIn and Instagram