Senior Account Executive, Mid-Market

About the role

You will own the complete outbound sales cycle for mid-market merchants across diverse industries, building and shaping a robust pipeline from initial prospecting to final close. You will leverage a consultative, strategic approach to develop multi-product solutions that align with the unique needs of each seller. You will act as a trusted advisor, seamlessly flexing between business development, account management, and discovery to drive complex deals forward. You will build and maintain high-quality pipelines through creative outbound strategies, targeted campaigns, and disciplined social selling. You will conduct high-impact discovery sessions, deliver compelling demonstrations, and execute decisive negotiations across multiple stakeholders. You will collaborate closely with cross-functional teams including Product, Marketing, Implementation, and Operations to ensure cohesive solution delivery. You will consistently hit and exceed ambitious revenue targets on a monthly and quarterly basis.

Key facts

What you'll do

Conduct in-depth discovery sessions to diagnose business challenges and map tailored solutions for mid-market merchants.

Develop and manage a full-funnel pipeline using strategic cold outreach, creative campaigns, and targeted outreach initiatives.

Own the end-to-end sales process, including prospecting, qualification, negotiation, and final close for complex deals.

Leverage consultative selling techniques to uncover needs and position Square and Afterpay as integrated, omnichannel solutions.

Partner with Business Development on lead flow while independently driving net-new logo acquisition and expansion.

Deliver personalized product demonstrations and handle objections with clarity, confidence, and strategic framing.

Collaborate cross-functionally with Product, Marketing, Implementation, and Operations to align on solution design and delivery.

Maintain precise pipeline management and forecasting accuracy within Salesforce to support revenue planning.

Execute targeted social selling and digital outreach to build relationships and surface new opportunities.

Articulate the value of Square's ecosystem, including financial services tools that enable lending and cash flow management.

Design and run creative outbound strategies to reach merchants who are not actively seeking new solutions.

Negotiate contract terms and commercial details to secure mutually beneficial agreements across multi-threaded deals.

Champion seller success by ensuring that solutions drive meaningful value, increase order sizes, and improve competitiveness.

Maintain a high level of organization and discipline to consistently exceed monthly and quarterly revenue goals.

Requirements

3+ years of full-cycle B2B sales experience with a track record of consistent quota achievement.

Proven success in outbound prospecting and net-new business creation, with SaaS or fintech experience strongly preferred.

Experience closing complex, multi-threaded deals that involve longer sales cycles and multiple decision-makers.

Ability to build pipeline from scratch using strategic, targeted outreach and creative engagement methods.

Exceptional communication, presentation, and negotiation skills across phone, video, and written channels.

Strong consultative selling skills, including the ability to diagnose business challenges and map tailored solutions.

A hunter's mindset characterized by resilience, creativity, and an unwavering drive to win new business.

Ability to work independently with minimal supervision while managing multiple priorities in a fast-paced environment.

Demonstrated ability to manage and maintain high-quality CRM records and forecasting accuracy in Salesforce.

Comfort engaging with enterprise-level stakeholders and aligning solutions to large, complex operations.

Experience selling integrated, omnichannel solutions that span payments, inventory, appointments, loyalty, and financial services.

Commitment to ethical sales practices and compliance with all relevant regulations and internal policies.

Willingness to travel within the Toronto area as required for customer meetings and cross-functional collaboration.

Nice to have

Experience selling to mid-market customers in the retail, ecommerce, or services sectors.

Familiarity with Afterpay and its role within the broader Square ecosystem.

Background in business development or inside sales roles that require high-volume outbound activity.

Experience using Salesforce, HubSpot, or similar CRM platforms for pipeline management.

Comfort with financial services products such as lending, payment processing, and cash flow tools.

Practical notes

Hours may vary to accommodate client time zones and business needs.

Travel within the Toronto region may be required for in-person meetings and cross-functional work.

Visa sponsorship may be considered for eligible candidates based on role requirements and client needs.

Deadlines for applications may apply, and early submission is encouraged to ensure full consideration.