Territory Account Executive - Kelowna, Okanagan BC

Territory Account Executive - Kelowna, Okanagan BC
Since we opened our doors in 2009, the world of commerce has evolved immensely. Square expanded into software, building integrated, omnichannel solutions that help sellers sell online, manage inventory, offer buy‑now‑pay‑later functionality, book appointments, engage loyal buyers, and hire and pay staff. We embed financial services tools at the point of sale so merchants can access a business loan and manage cash flow all in one place.

The Role
As a 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.

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.

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

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.

Compensation
Block takes a market‑based approach to pay, and pay may vary depending on your location. U.S. locations are categorized into one of four zones based on a cost of labor index for that geographic area. The successful candidate’s starting pay will be determined based on job‑related skills, experience, qualifications, work location, and market conditions. These ranges may be modified in the future.

Zone A: $159,900 - $239,900
Zone B: $159,900 - $239,900

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