# Senior Account Executive, Mid-Market

**Company:** [Square](https://hotfix.jobs/companies/square)
**Location:** Remote
**Role:** Account Executive
**Salary:** CA$152k – CA$229k/yr
**Experience:** 3+ years
**Skills:** B2B Sales, Outbound Prospecting, Consultative Selling, Pipeline Management, Salesforce, Negotiation, SaaS, Fintech, Social Selling, Sales Forecasting, Lead Generation, Multilingual Sales
**Posted:** 2026-08-05

> Owns the full outbound sales cycle for mid-market merchants, developing tailored multi-product solutions and closing complex, multi-stakeholder deals. Requires 3+ years of full-cycle B2B sales experience, consistent quota achievement, Salesforce proficiency, and fluency in French and English.

## Job Description

## Responsibilities

- Own the full outbound sales cycle—from prospecting and negotiation through 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

- 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 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 and the ability to map tailored solutions to business challenges.
- Resilient, creative, and driven approach to winning business.
- 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.
- Ability to sell in both French and English.

## Compensation and Benefits

- OTE: **$152,300–$228,500 CAD**.
- Benefits include remote work, medical insurance, flexible time off, retirement savings plans, and modern family planning benefits.

## Similar jobs

- [Account Executive, Enterprise](https://hotfix.jobs/jobs/aa083b34-1412-45dd-872c-0777a79dcead) - Snowflake - Remote - $156k – $205k/yr
- [Senior Account Executive](https://hotfix.jobs/jobs/73bea008-c1c9-4394-aaee-81aa8416b967) - Dropbox - Remote - $167k – $254k/yr
- [Enterprise Account Executive, Observability](https://hotfix.jobs/jobs/0c62f13a-c63a-4388-9d82-9eb1b0f62764) - Snowflake - Remote - $134k – $176k/yr
- [Senior Account Executive](https://hotfix.jobs/jobs/7f0bccad-e9f0-4d0e-8ee5-ec22bab605ab) - Cohere - Remote - CA$315k – CA$430k/yr
- [Senior Account Executive](https://hotfix.jobs/jobs/e4e221e1-5567-45f7-a8b1-0f4ebc0ee4b1) - Cohere - Remote - CA$315k – CA$430k/yr

**Apply:** https://hotfix.jobs/jobs/acc3346a-ae32-41fc-990c-70530f6aad61
**Canonical:** https://hotfix.jobs/jobs/acc3346a-ae32-41fc-990c-70530f6aad61