Mid-Market Account Executive
Own the outbound sales cycle for mid-market merchants, building pipeline, developing multi-product solutions, and closing complex deals. The role requires at least five years of full-cycle B2B sales experience, strong outbound prospecting ability, consultative selling skills, and Salesforce proficiency.
About the job
Responsibilities
- Own the full outbound sales cycle—from prospecting to negotiation to close—with 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 needs.
- Partner with Business Development on lead flow while independently driving net-new logo acquisition.
- Conduct discovery, demos, and negotiations across multi-stakeholder deals.
- Act as a consultant and trusted advisor, flexing across BDR, AE, and AM responsibilities when needed.
- Collaborate with Product, Marketing, Implementation, and Operations to deliver cohesive solutions.
- Maintain disciplined pipeline management and forecasting accuracy in Salesforce.
- Consistently hit and exceed monthly and quarterly revenue goals.
Requirements
- 5+ years of full-cycle B2B sales experience with consistent quota achievement.
- Proven success in outbound prospecting and net-new business creation; SaaS or fintech experience 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, including diagnosing business challenges and mapping tailored solutions.
- A resilient, creative, and results-driven hunter’s mindset.
- Ability to work independently while contributing to a team-oriented environment.
- Advanced proficiency with Salesforce and modern sales tools.
- BA/BS degree or equivalent experience.
Benefits
- Remote work
- Medical insurance
- Flexible time off
- Retirement savings plans
- Modern family planning benefits
Skills
B2B Sales, Outbound Prospecting, Salesforce, Consultative Selling, Pipeline Management, Sales Negotiation, SaaS, Fintech, Social Selling, Sales Forecasting
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