# Mid-Market Account Executive

**Company:** [Square](https://hotfix.jobs/companies/square)
**Location:** Remote
**Role:** Account Executive
**Experience:** 5+ years
**Skills:** B2B Sales, Outbound Prospecting, Salesforce, Consultative Selling, Pipeline Management, Sales Negotiation, SaaS, Fintech, Social Selling, Sales Forecasting
**Posted:** 2026-08-13

> 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.

## Job Description

## 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

## Similar jobs

- [Strategic Account Executive](https://hotfix.jobs/jobs/a0cdcc4a-0705-4ef5-b948-c6fa6ebb5076) - Datadog - Melbourne, Australia
- [Account Executive](https://hotfix.jobs/jobs/78ca77e5-e16c-49cc-9720-653e4aebfd4d) - Keycard - Remote
- [Sales Executive](https://hotfix.jobs/jobs/2bc5e201-0262-40b4-bf42-d685876fa6f3) - Flexport - Melbourne, Australia
- [Home Care Consultant](https://hotfix.jobs/jobs/2b45b0fc-e1b2-4e37-8df4-fa529ae4ff0a) - Honor - Remote - $41k – $46k/yr
- [Account Executive, Platforms](https://hotfix.jobs/jobs/7809ffff-90a0-416d-ad10-10844d1bedd9) - Stripe - Sydney, Australia

**Apply:** https://hotfix.jobs/jobs/d1070864-9650-4e86-b609-27c0d34caf99
**Canonical:** https://hotfix.jobs/jobs/d1070864-9650-4e86-b609-27c0d34caf99