Mid Market Account Executive

Square; Greater London; On-site; GBP 75,000 - 120,000; Full time

Job summary

Square is hiring a Mid Market Account Executive on the Outbound Team to bring Square’s ecosystem to new SMB and mid-market merchants. You will run sophisticated, multi-product deals from first touch to close, blending hunter instincts with consultative depth and strategic execution.

If you’re a proven closer who thrives in outbound environments and consistently hits ambitious targets, this is your role at Square.

Qualifications

• 4+ years in B2B sales with quota
• Outbound prospecting success, net-new business
• Experience closing multi-threaded deals
• Ability to build pipeline from scratch
• Exceptional communication, presentation, and negotiation skills
• Strong consultative selling to map tailored solutions
• Hunter mindset with resilience and drive
• Ability to work independently within a team
• Advanced proficiency with Salesforce and sales tools
• BA/BS degree or equivalent experience

Responsibilities

• Own the full outbound sales cycle from prospecting to close for SMB and mid-market
• Build and manage a high-quality pipeline via cold outreach and targeted campaigns
• Develop multi-product solutions across Square’s ecosystem for each merchant
• Partner with Business Development on lead flow and net-new logos
• Conduct discovery, demos, and negotiations with multi-stakeholder buyers
• Act as a consultant and trusted advisor across BDR, AE, AM roles as needed
• Collaborate cross-functionally with Product, Marketing, Implementation, and Ops
• Maintain disciplined pipeline management and forecasting in Salesforce
• Hit and exceed monthly and quarterly revenue targets

Skills

Full-cycle B2B sales

Outbound prospecting

Closing complex deals

Pipeline building

Communication & negotiation

Consultative selling

Hunter mindset

Independent working

Salesforce proficiency

BA/BS degree or equivalent

Education

BA/BS degree or equivalent

Tools

Salesforce

Job description

Since we opened our doors in 2009, the world of commerce has evolved immensely, and so has Square. After enabling anyone to take payments and never miss a sale, we saw sellers stymied by disparate, outmoded products and tools that wouldn't work together.

So we expanded into software and started building integrated, omnichannel solutions – to help sellers sell online, manage inventory, offer buy now, pay later functionality, book appointments, engage loyal buyers, and hire and pay staff. Across it all, we've embedded financial services tools at the point of sale, so merchants can access a business loan and manage their cash flow in one place. Afterpay furthers our goal to provide omnichannel tools that unlock meaningful value and growth, enabling sellers to capture the next generation shopper, increase order sizes, and compete at a larger scale.

Today, we are a partner to sellers of all sizes – large, enterprise-scale businesses with complex operations, sellers just starting, as well as merchants who began selling with Square and have grown larger over time. As our sellers grow, so do our solutions. There is a massive opportunity in front of us. We're building a significant, meaningful, and lasting business, and we are helping sellers worldwide do the same.

The Role

At Square, we’re re-imagining how small and midsize businesses grow. As a Mid Market Account Executive on our Outbound Team, you’ll bring Square’s ecosystem to new sellers across diverse industries by building, shaping, and closing your own pipeline. You’ll run sophisticated, multi-product deals from the first touch to final close — blending hunter instincts, consultative depth, and strategic execution.

If you’re an experienced closer who thrives in outbound environments, loves solving meaningful business challenges, and consistently delivers against ambitious targets — this is your role.

You Will

• Own the full outbound sales cycle — from prospecting to negotiation to close — with SMB and mid-market merchants.
• Build and manage a high-quality pipeline through cold outreach, social selling, targeted campaigns, and creative outbound strategies.
• Develop multi-product solutions across Square’s ecosystem and tailor them to each merchant’s unique needs.
• Partner with Business Development on lead flow while independently driving net-new logo acquisition.
• Conduct high-impact discovery, demos, and negotiations with decisiveness across multi-stakeholder deals.
• Act as a consultant and trusted advisor — seamlessly flexing across BDR, AE, and AM responsibilities when needed.
• Collaborate cross-functionally with Product, Marketing, Implementation, and Operations to deliver cohesive solutions.
• Maintain disciplined pipeline management and forecasting accuracy in Salesforce.
• Consistently hit and exceed revenue goals — monthly and quarterly.

You Have

• 4+ years of full-cycle B2B sales experience with consistent quota achievement.
• Proven success in outbound prospecting and net-new business creation (SaaS or fintech preferred).
• Experience closing complex, multi-threaded deals with longer sales cycles.
• Ability to build pipeline from scratch using targeted, strategic outreach.
• Exceptional communication, presentation, and negotiation skills across phone, video, and written channels.
• Strong consultative selling skills — diagnose business challenges and map tailored solutions.
• A hunter’s mindset — resilient, creative, and driven to win.
• Ability to work independently while contributing to a team-first environment.
• Advanced proficiency with Salesforce and modern sales tools.
• BA/BS degree or equivalent experience.

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.