Account Executive, Mid-Market

Since our beginnings in 2009, the world of commerce has evolved tremendously. So has Square. After enabling everyone to accept payments and never miss a sale, we noticed that merchants were being slowed down by disparate and outdated products and tools that do not work together harmoniously. We therefore set out to develop software and created integrated, omnichannel solutions to help merchants sell online, manage their inventory, offer "Buy Now, Pay Later" functionality, book appointments, build customer loyalty, and hire and pay their employees. Throughout all of this, we have integrated financial services tools into the point-of-sale system so that merchants can access a business loan and manage their cash flow in one place. Afterpay contributes to our goal of providing omnichannel tools that generate significant value and growth, allowing merchants to attract the next generation of shoppers, increase order volume, and compete on a larger scale. Today, we are the partner of businesses of all sizes, from large companies with complex operations to sellers just starting out, as well as merchants who began selling with Square and have grown over time. Our solutions evolve at the same pace as our merchants. An incredible opportunity lies ahead of us. We are building an important, meaningful, and sustainable company, and we are helping merchants around the world do the same. The Role At Square, we are reinventing the way mid-market businesses grow. As a Senior Account Executive on our Mid-Market team, you will offer the Square ecosystem to new sellers across various industries. To do this, you will create, shape, and drive your own pipeline to completion. You will manage complex, multi-product contracts from initial contact to signature, blending a hunter's instinct, consultative depth, and strategic execution. If you are an expert at closing sales, thrive in field prospecting environments, enjoy tackling large-scale business challenges, and consistently hit ambitious goals, this position is for you. Your Missions - Manage the entire sales cycle, from prospecting to negotiation and closing, with mid-sized businesses. - Create and manage a high-quality pipeline through cold calling, social selling, targeted campaigns, and creative prospecting strategies. - Develop multi-product solutions encompassing the entire Square ecosystem and adapt them to the specific needs of each merchant. - Collaborate with the business development department on lead flow while independently driving new customer acquisition. - Facilitate discovery, conduct demonstrations, and lead high-impact negotiations with determination within the framework of multi-party contracts. - Serve as a consultant and trusted advisor, seamlessly assuming the responsibilities of business development manager, account executive, and account manager as needed. - Collaborate cross-functionally with Product, Marketing, Implementation, and Operations teams to provide cohesive solutions. - Maintain rigorous pipeline management and ensure forecast accuracy in Salesforce. - Consistently meet and exceed revenue targets on a monthly and quarterly basis. ##### You have - At least 3 years of experience in the full B2B sales cycle, with consistent quota attainment. - Proven results in prospecting and creating new business opportunities (preferably in the SaaS or fintech sector). - Experience closing complex contracts with long sales cycles that require building relationships with multiple stakeholders. - An ability to build a pipeline from scratch through targeted and strategic prospecting. - Excellent communication, presentation, and negotiation skills, whether by phone, video, or in writing. - Strong consultative sales skills: diagnosing business challenges and developing tailored solutions. - A "steel" mindset: you demonstrate resilience, creativity, and determination. - An ability to work independently while contributing to a collaborative environment. - Advanced proficiency in Salesforce and modern sales tools. - A bachelor's degree or equivalent experience. - An ability to sell in both French and English. Block takes a market-based approach to compensation, which may vary depending on the work location. In Canada, sites are divided into two zones based on a labor cost index specific to each geographic area. The starting compensation for the successful candidate will be determined based on their job-related skills, experience, qualifications, work location, and market conditions. These ranges are subject to change in the future. The total compensation for this position is: $152,300 - $228,500 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. Block, Inc. (NYSE: XYZ) builds technology to increase access to the global economy. Each of our brands unlocks different aspects of the economy for more people. Square makes commerce and financial services accessible to sellers. Cash App is the easy way to spend, send, and store money. Afterpay is transforming the way customers manage their spending over time. TIDAL is a music platform that empowers artists to thrive as entrepreneurs. Bitkey is a simple self-custody wallet built for bitcoin. Proto is a suite of bitcoin mining products and services. Together, we’re helping build a financial system that is open to everyone. Privacy Policy