• Serve as a strategic partner to a portfolio of employer clients and brokers • Retain and grow business while delivering an exceptional customer experience • Collaborate closely with underwriting, sales, service, and other internal partners • Develop business strategies, implement solutions, and support clients throughout the lifecycle of their benefits programs • Establish and maintain cooperative relationships with clients, brokers and internal business partners • Efficiently implement new business, address service inquires and provide consultative support • Periodically present the financial components of re-rates, providing clients premium and claim comparison analysis on both participating and non-participating employees

• Develop and manage a named account list • Achieve and exceed revenue targets and other key sales metrics • Effectively work cross-functionally across the organization • Build strong, long-term relationships with key decision-makers • Conduct product demonstrations and presentations • Develop our sales playbook to enable scaling

• Drive new business development within the broker-dealer market through proactive prospecting, pipeline generation, and strategic account engagement. • Identify, qualify, and close complex, high-value, multi-year sales opportunities. • Develop and execute territory plans focused on broker-dealers and adjacent financial services organizations. • Build and maintain trusted relationships with C-level executives and senior decision-makers to uncover business priorities and growth opportunities. • Apply a consultative, value-based sales approach to understand customer challenges and align solutions with business objectives. • Create compelling business cases, proposals, and presentations tailored to client needs and strategic initiatives. • Leverage industry expertise in fraud, identity, and risk management solutions to position differentiated offerings and drive competitive wins. • Manage and expand a portfolio of existing accounts by identifying upsell and cross-sell opportunities that enhance client outcomes. • Own revenue performance against assigned sales quotas, including accountability for pipeline creation, forecasting, and deal conversion. • Partner closely with Product, Data Science, Professional Services, and other internal stakeholders to design and deliver integrated client solutions. • Maintain accurate sales forecasts, pipeline activity, and account plans within CRM systems.

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.