Senior Enterprise Sales Representative

0011 Checkout LLC; New York (NY); On-site; USD 325,000 - 438,600; Full time

Benefits offered by this job

Health, vision, and dental insurance

401k

Vacation and sick/safe time

Learning days

Volunteer days

Job summary

0011 Checkout LLC is seeking an Enterprise Sales Representative to manage the full sales cycle for new enterprise accounts in New York. You will engage with C-suite executives and drive high-value deals across the US.

The ideal candidate should possess entrepreneurial drive, strategic acumen, and strong communication skills. Compensation ranges from $325,000 to $438,600, with additional benefits such as health insurance, 401k, and vacation time.

Qualifications

• Entrepreneurial drive with self-starter mentality.
• Strong analytical skills and data-driven mindset.
• Ability to adjust strategies based on results.

Responsibilities

• Manage the entire sales cycle for Enterprise accounts.
• Build long-term customer relationships with tailored solutions.
• Lead complex negotiations and close deals effectively.
• Track sales performance and adapt strategies.

Skills

Strategic prospecting

Customer engagement

Negotiation

Sales performance analysis

Stakeholder management

Strong communication

Job description

Overview

Enterprise Sales Representative – responsible for end‑to‑end management of the new logo sales cycle within a territory of Enterprise accounts, driving high‑value deals and expanding Checkout.com’s presence across the US.

Key Responsibilities

• Strategically prospect and plan accounts to identify and target high‑probability new logo opportunities, leveraging deep intelligence, networks, and disciplined execution to build pipeline.
• Engage with customers consultatively to build long‑term, trust‑based relationships, focusing on understanding their challenges and proposing tailored, high‑value solutions.
• 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, handle objections, creatively address concerns and steer complex deals to successful closure.
• Track and analyze sales performance, own results independently, continuously learn industry trends, and leverage feedback to improve and grow.

Core Competencies & Traits

• Entrepreneurial Drive – persistent, self‑starter mentality, operating territory as an owned business with strong accountability and urgency.
• Strategic Acumen – analytical, data‑driven; rapidly learning and applying complex insights to account planning and leveraging new technologies like AI.
• Learning Mindset – actively seek feedback, demonstrate growth mindset, dynamically adjust strategies based on results and evolving information.
• Stakeholder Management – confident in engaging with C‑suite executives; highly organized and able to prioritize shifting workloads effectively.
• Communication – strong written and verbal skills.

Salary & Benefits

US law requires Checkout.com to include a reasonable estimated salary range for this position. The estimated range for this level (Senior Sales Manager) includes both the annual base salary and sales commission: $325,000 USD to $438,600 USD.

Additional benefits include health, vision, dental insurance, 401k, vacation and sick/safe time, learning days and volunteer days.