Enterprise Account Executive, Clearpay

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It's a fast-paced business and that's the way we love it. We know that world class talent is the only way to pave our future success, so come and work with some of the brightest minds and be part of the once in a lifetime ride.
The Role
Clearpay is looking for an experienced, commercially minded Enterprise Account Executive with a strong background in complex, consultative new logo sales to join our Mid Market & Enterprise Sales team.
Reporting to the Head of Mid Market and Enterprise Sales, you will be responsible for identifying, engaging, and closing high-value Enterprise and upper Mid Market merchants across the UK. This is a full-cycle, outbound-focused role requiring strong strategic selling skills, executive presence, and the ability to navigate multi-stakeholder buying processes.
You will own your territory end-to-end - from developing your outbound strategy and building pipeline, through to negotiating and closing long-term, mutually beneficial commercial agreements. You will work closely with internal stakeholders across Sales Leadership, Marketing, Product, Legal, Finance, and Implementation to successfully bring complex deals to market.
We are looking for someone who thrives in ambiguity, is comfortable selling at C-suite level, and can clearly articulate Clearpay's differentiated value proposition versus competitors in a highly competitive payments and fintech landscape.
This role is remote and can be based anywhere in the UK
You Will

• Develop and execute a targeted outbound strategy to source and close new Enterprise and upper Mid Market merchants
• Prospect strategically via email, phone, social selling, and account-based approaches to generate high-quality opportunities
• Own and manage the entire sales cycle from initial outreach through to contract negotiation, close, and go-live
• Lead complex, consultative sales conversations with senior executives, commercial leaders, and business owners at target accounts
• Build and maintain a strong pipeline of qualified opportunities, demonstrating rigorous pipeline management and forecasting accuracy
• Identify merchant-specific metrics, business challenges, and value drivers to create compelling, data-led commercial proposals
• Clearly articulate Clearpay's value proposition and USPs, positioning us effectively against competitive alternatives
• Negotiate and close long-term, high-value contracts that drive sustainable growth for both Clearpay and our partners
• Partner cross-functionally with Marketing, Product, Finance, Legal, Risk, and Implementation teams to structure and close deals efficiently
• Drive urgency post-signature to ensure timely onboarding and successful merchant activation
• Be accountable to individual revenue targets and KPIs, demonstrating control and ownership of deals through CRM hygiene and reporting
• Use Salesforce to track sales activity, pipeline progression, forecasting, and outcomes
• Apply defined sales methodologies and repeatable playbooks to progress opportunities and continuously improve performance

You Have

• 8+ years of experience in a quota-carrying, outbound sales role, ideally within Enterprise or upper Mid Market segments
• A proven track record of consistently meeting or exceeding revenue targets in complex, competitive sales environments
• Demonstrated success owning a full 360° sales cycle, from prospecting through to close and activation
• Strong experience selling to senior executives (C-suite, VP, Director level) and navigating multi-stakeholder decision-making processes
• Experience selling within e-commerce, payments, fintech, retail, or adjacent technology verticals
• Excellent commercial acumen with the ability to structure, negotiate, and close sophisticated commercial agreements
• A consultative, value-led selling approach with the ability to tailor messaging to different merchant needs and verticals
• Strong communication, presentation, and negotiation skills, with confidence operating at executive level
• A structured, analytical mindset with the ability to assess complex business opportunities and prioritise effectively
• A self-starter mentality with the resilience and drive to succeed in a fast-paced, high-growth environment
• Experience using Salesforce (or equivalent CRM) to manage pipeline, forecasting, and reporting
• Formal sales methodology and/or negotiation training (e.g. MEDDICC, Challenger, SPIN, Sandler, Gap etc.) is highly desirable
• A collaborative, team-first mindset with a willingness to support broader team and business objectives

We're working to build a more inclusive economy where our customers have equal access to opportunity, and we strive to live by these same values in building our workplace. Block is a proud equal opportunity employer. We work hard to evaluate all employees and job applicants consistently, based solely on the core competencies required of the role at hand, and without regard to any legally protected class. We believe in being fair, and are committed to an inclusive interview experience, including providing reasonable accommodations to disabled applicants throughout the recruitment process. We encourage applicants to share any needed accommodations with their recruiter, who will treat these requests as confidentially as possible. Want to learn more about what we're doing to build an inclusive workplace? Check out our Inclusion & Diversity page
Application Guidelines
Candidates may submit up to 9 active applications within a 60-day period. Reapplications to the same role are accepted 90 days after a previous application has been reviewed.
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Every benefit we offer is designed with one goal: empowering you to do the best work of your career while building the life you want. Remote work, medical insurance, flexible time off, retirement savings plans, and modern family planning are just some of our offering. Check out our other benefits at Block.
Block, Inc. (NYSE: XYZ) builds technology to increase access to the global economy. Each of our brands unlocks different aspects of the economy for more people. Square makes commerce and financial services accessible to sellers. Cash App is the easy way to spend, send, and store money. Afterpay is transforming the way customers manage their spending over time. TIDAL is a music platform that empowers artists to thrive as entrepreneurs. Bitkey is a simple self-custody wallet built for bitcoin. Proto is a suite of bitcoin mining products and services. Together, we're helping build a financial system that is open to everyone.