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Small Business Account Executive II

Returnly - Remote - Remote

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Salary: USD 142,000 - 200,000 / annual

Affirm is seeking an experienced Account Executive to own the full sales cycle for complex, high-growth merchants in the upper SMB and Mid-Market segment. You will operate as the general manager of a defined territory, managing a portfolio of merchants with up to $300M in annual sales. Key Responsibilities: - Own a defined territory and revenue plan, developing account strategy, prioritization models, and pipeline execution to achieve signed GMV and revenue targets. - Generate net-new pipeline through research, targeted outbound, partner channels, events, and referrals to create qualified opportunities. - Lead executive discovery with founders, C-suite executives, and senior leaders across Finance, E-commerce, Product, Technology, Operations, and Marketing to understand strategic priorities and decision criteria. - Set strategy for complex opportunities, independently determining account plans, stakeholder engagement, competitive positioning, and path to close. - Build quantified business cases translating merchant data into clear recommendations supported by expected conversion, AOV, CAC, repeat purchase, GMV, revenue, and unit economics. - Design merchant solutions in partnership with Sales Engineering and Onboarding, defining product configuration, integration paths, rollout strategy, and customer experience. - Navigate complex buying processes by building champions, mapping stakeholders, aligning economic buyers and technical evaluators, and managing procurement, security, legal, and risk requirements. - Lead commercial negotiations, developing deal strategy, positioning differentiated value, and negotiating pricing, terms, and partnership structure while protecting Affirm's financial interests. - Develop recommendations for non-standard partnerships using sound commercial judgment to structure custom pricing, contractual terms, and implementation investments. - Lead cross-functional deal teams without direct authority, establishing clear owners, operating cadence, decision points, and escalation paths. - Own the path from signature to launch, remaining accountable for successful handoff and project-managing critical launch dependencies. - Maintain forecast and operating discipline, keeping Salesforce current, accurately assessing deal stage and risk, and providing reliable forecasts. - Represent the market internally, bringing structured merchant, industry, and competitive insights to product and business partners. - Raise team performance by sharing effective account strategies, executive messaging, and deal practices. Requirements: - 4+ years of quota-carrying, full-cycle closing experience in B2B SaaS, fintech, payments, e-commerce, or complex technology environments. - Demonstrated record of meeting or exceeding revenue targets and creating self-sourced pipeline in new-logo acquisition roles. - Experience leading complex, multi-stakeholder sales cycles and building relationships with executive and functional decision-makers. - Strong consultative discovery, objection handling, negotiation, and closing skills with ability to establish clear decision processes. - Ability to analyze merchant and market data, develop quantified business cases, and communicate financial and strategic value credibly. - Experience coordinating legal, risk, technical, pricing, operational, and implementation stakeholders to resolve barriers and close business. - Strong territory planning, pipeline management, CRM discipline, and forecasting capabilities. - Excellent written and verbal communication, including executive presentations and concise internal updates. - High ownership, sound judgment, resilience, and ability to operate effectively in fast-changing environments with multiple priorities. Nice to Have: - Experience selling payment, lending, commerce, or financial software requiring technical integration and commercial structuring. - Familiarity with e-commerce platforms, APIs, payment flows, implementation requirements, and merchant economics. - Experience with structured sales methodologies (MEDDPICC, Challenger, Sandler). - Prior business development or high-volume prospecting experience. - Bachelor's degree or equivalent practical experience.

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