The Role At Square, we're re-imagining how mid-market businesses grow.
As an SMB 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 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.
- Partner with Business Development on lead flow while independently driving net-new logo acquisition.
- 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 - 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 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.
- BA/BS degree or equivalent experience.
Block takes a market-based approach to pay, and pay may vary depending on your location. Canada locations are categorized into one of two 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.
OTE for this role is:
$120,000 - $150,000 CAD
Block is a globally distributed company and this role will require working with other employees in multiple time zones. You may be required to perform work outside of normal business as part of this role.
Block takes a market-based approach to pay, and pay may vary depending on your location. Canada locations are categorized into one of two 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:
$84,168 - $126,252 CAD
Zone B:
$84,168 - $126,252 CAD
Application Guidelines Candidates may submit up to 9 active applications within a 60-day period. Reapplications to the same role are accepted 90 days after a previous application has been reviewed.
Use of AI in Our Hiring Process We may use automated AI tools to evaluate job applications for efficiency and consistency. These tools comply with local regulations, including bias audits, and we handle all personal data in accordance with state and local privacy laws.
Contact us here with hiring practice or data usage questions.
Every benefit we offer is designed with one goal: empowering you to do the best work of your career while building the life you want. Remote work, medical insurance, flexible time off, retirement savings plans, and modern family planning are just some of our offering. Check out our other benefits at Block.
