Field Sales Account Executive Kelowna, Okanagan BC

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 wouldnt 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 weve 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. Were building a significant meaningful and lasting business and we are helping sellers worldwide do the same.

The Role

Location: Kelowna Okanagan BC

At Square were re-imagining how small and midsize businesses grow. As a Sales Account Executive on our Outbound Team youll bring Squares ecosystem to new sellers across diverse industries by building shaping and closing your own pipeline. Youll run sophisticated multi-product deals from the first touch to final close blending hunter instincts consultative depth and strategic execution.

If youre 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 Squares ecosystem and tailor them to each merchants 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 hunters 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.