Senior Sales Account Executive
Square · United States
- Hybrid
- Full-time
- $180,000 / year
- United States
Job highlights
- Sell Square's ecosystem to new SMB/mid-market sellers.
- Manage full outbound sales cycle from prospecting to close.
- Develop tailored multi-product solutions for merchants.
- Achieve and exceed ambitious monthly/quarterly revenue goals.
- Collaborate cross-functionally for cohesive merchant solutions.
About the role
About Square
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 Senior Sales 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.
What You'll Do
- 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.
What You'll Need
- 3+ 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.
Key skills/competency
- B2B Sales
- Account Executive
- Outbound Sales
- SaaS Sales
- Fintech Sales
- Pipeline Management
- Salesforce
- Consultative Selling
- Negotiation Skills
- Quota Achievement
Skills & topics
- Senior Sales Account Executive
- Sales
- Account Management
- B2B Sales
- SaaS
- Fintech
- Outbound Sales
- Salesforce
- SMB
- Mid-Market
How to get hired
- Tailor your resume: Highlight B2B sales experience, quota achievement, and outbound prospecting success, using keywords like SaaS, fintech, and Salesforce.
- Showcase your skills: Emphasize your hunter's mindset, consultative selling abilities, and experience closing complex deals.
- Prepare for interviews: Be ready to discuss your sales strategies, how you build pipelines, and your negotiation techniques.
- Understand Square's mission: Research Square's ecosystem and demonstrate how you can help SMBs and mid-market businesses grow.
- Network strategically: Connect with Square employees on LinkedIn to gain insights into the company culture and hiring process.
Technical preparation
Behavioral questions
Frequently asked questions
- What does a Senior Sales Account Executive at Square do?
- As a Senior Sales Account Executive at Square, you will own the full outbound sales cycle, from prospecting to closing deals with SMB and mid-market merchants. You'll build and manage a pipeline, develop multi-product solutions, and consistently hit revenue goals.
- What experience is required for the Senior Sales Account Executive role at Square?
- We require 3+ 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), and experience closing complex, multi-threaded deals.
- How does Square handle AI in its hiring process for Sales Account Executives?
- Square may use automated AI tools to evaluate job applications for efficiency and consistency, ensuring compliance with local regulations, including bias audits. All personal data is handled in accordance with state and local privacy laws.
- What is the compensation for a Senior Sales Account Executive at Square?
- Square takes a market-based approach to pay, with compensation potentially varying by location. The salary ranges are categorized into zones (A, B, C, D) and include target variable compensation. Exact figures will depend on skills, experience, qualifications, and work location.
- Can I apply for multiple roles at Square as a Sales Account Executive?
- Yes, candidates can 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.
- What are the key responsibilities of an outbound sales role at Square?
- Key responsibilities include owning the full outbound sales cycle, building pipeline through cold outreach and campaigns, developing tailored multi-product solutions, conducting discovery and negotiations, and maintaining accurate forecasting.
- What kind of sales tools does Square use for its Sales Account Executives?
- Advanced proficiency with Salesforce and modern sales tools is required for this role. This includes tools used for prospecting, social selling, campaign management, and pipeline management.
- Does Square offer remote work options for Senior Sales Account Executives?
- The job description mentions 'Remote work' as one of the benefits offered, indicating that this role may have remote work options, though specific arrangements depend on team and company policies.