Role Description At Square, we’re re-imagining how mid-market businesses grow. As a Senior Sales Account Executive on our Mid-Market 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. - 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. Qualifications - 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. - BA/BS degree or equivalent experience. - Ability to sell in both French and English. Requirements - Block takes a market-based approach to pay, and pay may vary depending on your location. - OTE for this role is: $152,300 - $228,500 CAD. Benefits - Remote work. - Medical insurance. - Flexible time off. - Retirement savings plans. - Modern family planning.

• Owning print renewals and identifying top print opportunities each quarter for digital conversion. • Proactively engaging with customers via health check-in calls to understand their needs and uncover digital courseware opportunities. • Conducting sales demos using our digital content platforms like CIMA and ExamReady. • Growing accounts through quarterly check-ins, assessments, sales pitches, demos, and strong closings. • Handing off converted digital accounts to the Customer Success Manager.

• Provides technical expertise and guidance across client engagements through assigned work based on demand, skill alignment, and historical relationships. • Builds credibility through efficient and effective delivery, supported by strong platform expertise. • Leverages knowledge of client system architecture and integrations to implement configuration changes and enhancements effectively. • Provides input on best practices when executing enhancements or configuration changes. • Constructively challenges client assumptions, aligning stakeholders to the most strategic and sustainable outcome—even when it demands a harder path forward. • Provides proactive technical guidance to ensure the client’s environment is stable, efficient, and scalable. • Executes configuration changes and enhancements based on incoming client requests and functional needs. • Advises on system configuration, integrations, and insurance data workflows to improve performance and compliance with best practices. • Configures the Origami platform in accordance with client requirements and conducts unit testing on assigned deliverables to verify functionality. • Documents client-specific configurations, integrations, standard operating procedures, and areas of opportunity. • Produces accurate level-of-effort (LOE) estimates for assigned technical work. • Applies a deep understanding of platform capabilities and configuration options to deliver solutions that align with client needs while maintaining consistency with standard functionality. • Collaborates with Client Success Managers (CSMs) and next-level management to ensure work efforts align with contracted scope; proactively communicates any risks or constraints impacting delivery. • Ensures SLAs and SLOs are met and communicated transparently. • Records hours worked in accordance with Origami's time entry policy. • Supports Client Success management on client success plans, adoption efforts, periodic business reviews, and other success milestones and playbooks. • Partners with Client Success and Sales to support retention, renewals, and expansion opportunities. • Collaborates with Client Success on executive-level reports summarizing technical health, key initiatives, and value delivered. • Partners with Product Management and Service Enablement to provide structured feedback from clients and influence roadmap priorities. • Works with Engineering and Cloud Operations on environment upgrades, migrations, and performance tuning. • Collaborates with Support to ensure the technical health of the account by driving timely resolution of outstanding incidents. • Coordinates with Implementation and Professional Services to ensure smooth handoffs post-deployment.

• Drive success of the company's goals and objectives through achieving individual sales quotas • Build and manage a sales pipeline through prospecting efforts into a geographic territory or within the core verticals • Develop and deliver customized sales presentations and products demonstrations, by phone and via online demo • Develop and negotiate enterprise level proposals and contracts • Forecast sales activity and revenue achievements accurately through proper use of sales tools • Collaborate effectively and engage various pre/post sales resources including Sales Development Representatives, Market Development Representatives, Solutions Engineers, Account Managers, Partner Account Managers, as well as Legal, Security, Professional Services and Customer Support