Checkout.com

Senior Enterprise Sales Executive

Checkout.com$285K — $335K *
Enterprise Technology
Less than 5 years of experience
Job Overview by Ladders

Qualifications

  • 5-7 years of experience in enterprise sales or relevant industries
  • Proven track record in winning complex new business deals
  • Ability to engage consultatively with C-suite executives
  • Strong analytical skills and data-driven approach
  • Excellent communication and organizational skills

Responsibilities

  • Strategically prospect and plan accounts to identify new logo opportunities
  • Engage consultatively with customers to build trust-based relationships
  • Lead deals by coordinating resources and building business cases
  • Negotiate and close complex sales with a creative approach to objections
  • Track, analyze sales performance, and leverage feedback for growth

Benefits

  • Health, vision, and dental insurance
  • 401(k) plan with employer matching
  • Generous vacation and sick leave policies
  • Learning days for professional development
  • Volunteer days to support community engagement
  • Hybrid working model for better work-life balance
Full Job Description
Senior Enterprise Sales Executive

This Enterprise Sales Representative 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 youll contribute directly to our expansion by working with innovative Enterprise clients across the US landscape. In this role, youll 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 Representative, 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. Youll 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.


US law requires Checkout.com to include in job postings a reasonable estimated salary range for this position. However, final salaries may vary subject to several factors, such as a candidates level, relevant experience, qualifications, skills and proficiency for the role. Please note that this information is provided for those in Atlanta only, and this role is open to candidates outside of Atlanta as well.

We are hiring at multiple levels within our sales team, the estimated range for this level includes both the annual base salary and sales commission:
  • Senior Sales Manager: $285,200 USD to $335,600 USD.


Our competitive salaries are just one component of Checkout.coms total compensation package. Additional benefits include: health, vision, dental insurance, 401k, vacation and sick and safe time, learning days and volunteer days.

Additional Information

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 its 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

About Checkout.com

Checkout.com is a global payment processing company that allows businesses to accept payments from customers all over the world. The company was founded in 2012 and has since grown to become one of the largest payment processors in the world. Checkout.com offers a range of payment solutions, including credit and debit card processing, alternative payment methods, and more. The company is known for its innovative technology and its ability to process payments quickly and securely. Checkout.com is headquartered in London, England, and has offices in several other countries around the world.
Learn more about Checkout.com
Size
1,000 employees
Industry
Founded
2012

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