Enterprise Sales Representative

Checkout.com•New York, NY

11h•Hybrid

About The Position

Checkout.com is seeking a driven and strategically minded Enterprise Sales Representative to join its rapidly expanding Go-To-Market (GTM) team in the US. This role is crucial for the company's #1 priority market, offering a high-growth, high-reward environment where the representative will contribute directly to expansion by working with innovative Enterprise clients across the US. The ideal candidate will be empowered to run their own strategies and hypotheses with best-in-class commissions, and should be a smart, hardworking individual who thrives on challenge, embodying tenacity and a strong sense of urgency. Whether coming from tech sales, banking, consulting, or another results-driven field, this is an opportunity 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, is a creative problem-solver, thinks outside the box, helps build deep and meaningful relationships with merchants, and is highly organized.

Requirements

Entrepreneurial Drive: Persistent, self-starter mentality, operating 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.

Responsibilities

End-to-end management of the new logo sales cycle within a territory of Enterprise accounts.
Strategically prospect and plan accounts to identify and target high-probability new logo opportunities, leveraging deep intelligence, networks, and disciplined execution to build pipeline.
Identify leads, evaluate their potential, choose targets, and create 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.
Leverage proven sales methodology, industry, and product knowledge.
Orchestrate and lead deals by coordinating internal resources, building quantitative business cases, delivering impactful presentations, and proactively solving problems to drive opportunities forward.
Lead negotiations, handling objections, creatively addressing concerns and steering complex deals to successful closure.
Track and analyze sales performance, owning results independently, continuously learning industry trends, and leveraging feedback to improve and grow.