Small Business Account Executive II

At the company, we exist for the moments that matter—giving people a clear, predictable way to pay over time, with no hidden fees, no surprises, and no tradeoffs on what matters most.

About the role

The company is seeking an experienced, quota-carrying Account Executive to own the full sales cycle for complex, high-growth merchants across the upper SMB and Mid-Market segment. This portfolio includes merchants with up to $300M in total annual sales and requires a seller who can operate as the general manager of a territory, create demand, engage executive decision-makers, build a quantified business case, structure a compelling commercial solution, and lead the opportunity through contract and launch.

The Account Executive is accountable for new merchant acquisition and the long-term quality of each partnership. The role translates merchant priorities into solutions across the company's products and capabilities, while aligning internal stakeholders across Sales, Merchant Pricing, Product, Partnerships, Risk, Legal, Operations, Implementation, and Merchant Success. Success requires strategic prospecting, strong financial and commercial judgment, fluency in technical and operational requirements, and the ability to create momentum across complex buying groups.

What you will do

• Own a defined territory and revenue plan. Operate as the general manager of a portfolio that includes complex, high-growth merchants with up to $300M in total annual sales. Develop the account strategy, prioritization model, pipeline plan, and execution cadence required to achieve signed GMV and revenue targets.

• Generate and develop net-new pipeline. Research priority merchants, identify relevant business and market triggers, and use targeted outbound, partner channels, events, referrals, and internal resources to create qualified opportunities.

• Lead executive discovery. Engage founders, C-suite executives, and senior leaders across Finance, E-commerce, Product, Technology, Operations, and Marketing to understand strategic priorities, operating constraints, customer economics, and decision criteria.

• Set the strategy for complex opportunities. Independently determine the account plan, stakeholder engagement strategy, competitive positioning, internal resource requirements, negotiation posture, and path to close for each opportunity.

• Build quantified business cases. Translate merchant data and objectives into clear recommendations supported by expected conversion, average order value, customer acquisition, repeat purchase, GMV, revenue, unit economics, and operational impact.

• Design the merchant solution. Partner with Sales Engineering and Onboarding to define the appropriate product configuration, integration path, rollout strategy, and customer experience. Lead opportunities that may require customized payment configurations, e-commerce platform integrations, technical solutioning, or multi-entity implementation planning.

• Navigate complex buying processes. Build champions, map stakeholders, align economic buyers and technical evaluators, manage procurement, security, legal, and risk requirements, and establish a mutual action plan through decision and signature.

• Lead commercial negotiations. Develop deal strategy, position differentiated value, handle objections, and negotiate pricing, terms, and partnership structure. Evaluate merchant requirements against expected GMV, revenue, unit economics, implementation complexity, and risk while protecting the company’s long-term financial interests.

• Develop recommendations for non-standard partnerships. Use sound commercial judgment to structure and present recommendations involving custom pricing, contractual terms, product requirements, implementation investments, or other exceptions requiring internal approval.

• Lead cross-functional deal teams. Lead virtual teams without direct authority by establishing clear owners, operating cadence, decision points, escalation paths, and timelines across Partnerships, Risk, Legal, Implementation, and Merchant Pricing.

• Own the path from signature to launch. Remain accountable for a successful handoff and project-manage critical launch dependencies so signed merchants progress efficiently toward integration and go-live.

• Maintain forecast and operating discipline. Keep Salesforce current, accurately assess deal stage and material risk, provide reliable weekly and quarterly forecasts, and communicate changes early with a clear recovery plan.

• Represent the market internally. Bring structured merchant, industry, and competitive insights to product and business partners, identify recurring barriers, and influence scalable improvements to the company’s products and go-to-market motion.

• Raise team performance. Share effective account strategies, executive messaging, business cases, and deal practices. Contribute to a high-accountability culture focused on customer value, commercial discipline, and measurable outcomes.

What success looks like

• Revenue and GMV attainment. Consistently meet or exceed signed annualized estimated GMV and revenue goals across a portfolio of upper-SMB and Mid-Market merchants.

• Pipeline creation and quality. Maintain sufficient qualified coverage through self-generated and partner-supported pipeline, supported by clear account prioritization, stakeholder access, and actionable next steps.

• Conversion and velocity. Advance qualified opportunities with healthy win rates, disciplined stage progression, and sales cycles appropriate to the size and complexity of each partnership.

• Commercial quality. Structure partnerships that balance merchant value with the company’s revenue, unit economics, implementation requirements, and risk considerations.

• Forecast accuracy. Provide a reliable view of expected outcomes, material risks, decision criteria, and timing based on evidence and confirmed buyer commitments.

• Executive engagement. Establish credibility with senior decision-makers, build effective internal champions, and maintain alignment across complex buying groups.

• Launch quality. Ensure signed merchants transition effectively into implementation and progress toward go-live with aligned scope, owners, technical requirements, and timelines.

• Cross-functional leadership. Create clarity, accountability, and momentum across internal teams while representing both merchant needs and the company’s business requirements.

• Organizational impact. Surface recurring merchant and market insights that improve product capabilities, remove operating barriers, and strengthen the company’s broader go-to-market execution.

What we look for

• 4 or more years of quota-carrying, full-cycle closing experience in B2B SaaS, fintech, payments, e-commerce, or another complex technology environment.

• A demonstrated record of meeting or exceeding revenue targets and creating self-sourced pipeline in a new-logo acquisition role.

• 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, including the ability to establish a clear decision process and mutual action plan.

• Ability to analyze merchant and market data, develop a quantified business case, and communicate financial and strategic value with credibility.

• 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 the ability to operate effectively in a fast-changing environment with multiple priorities.

Preferred experience

• Experience selling payment, lending, commerce, financial software, or other solutions that require technical integration and commercial structuring.

• Familiarity with e-commerce platforms, APIs, payment flows, implementation requirements, and merchant economics.

• Experience using a structured sales methodology such as MEDDPICC, Challenger, or Sandler.

• Prior experience in business development or another role requiring high-volume prospecting and disciplined pipeline creation.

• Bachelor's degree or equivalent practical experience.

Role requirements

• Ability to work effectively in a remote environment and collaborate across functions and time zones.

• Ability to travel periodically for merchant meetings, industry events, and internal team sessions as business needs require.

• Authorization to work in the United States without current or future visa sponsorship.

Remote-first with flexibility built in

The company is proud to be a remote-first company. Most roles can be done from almost anywhere within the country of employment. Some positions may occasionally require in-person work at the company office, and a few are office-based due to the nature of the work. All new hires will be invited to attend an in-person onboarding experience.

Benefits designed for you

Our benefits reflect our commitment to care, transparency, and flexibility. Here are a few highlights:

• Health coverage at no cost: We cover 100% of premiums for employees and their dependents.

• Spending stipends: Monthly stipends support your tech setup, and the ability to choose health and wellness options that are right for you.

• Time off to recharge: Flexible time off and generous holiday calendars help you rest when you need to.

• Own a piece of what you build: Our employee stock purchase plan (ESPP) lets you buy the company stock at a discount.

We’re committed to providing an inclusive interview process, including accommodations for candidates with disabilities. If you need support, we’re happy to help.

For positions based in San Francisco or Los Angeles: the company considers qualified applicants with arrest and conviction records, as required by law.

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