Enterprise Account Executive Job at Cash App

Enterprise Account Executive

Cash App

Location:
United Kingdom

Category:
Sales

Contract Type:
Not provided

Salary:

Not provided

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Job Description:

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.

Job Responsibility:

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

Requirements:

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

Nice to have:

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

What we offer:

Remote work
medical insurance
flexible time off
retirement savings plans
modern family planning

Additional Information:

Job Posted:
February 17, 2026

Employment Type:

Fulltime

Work Type:

Remote work

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