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Checkout.com is seeking two (2) Deal Management Specialists to join our growing Revenue Operations team, based in either our New York City or Atlanta office. Sitting within the Commercial department, these roles are critical to driving our regional and global growth. This is a role for a builder — someone who thrives at the intersection of commercial operations and systems thinking. You won't just support the status quo — you will own the deal pipeline end-to-end, drive cross-functional relationships, and actively evolve how we work. We are looking for highly motivated, detail-oriented professionals who are energized by leveraging AI and automation to eliminate friction and build for scale. The ideal candidate is a self-starter who thrives in an entrepreneurial, fast-paced environment and can work autonomously to exceed expectations.
Responsibilities
Drive and adapt the execution of new sales operations workflows — designing lean, scalable processes that allow our Sales teams to spend less time on admin and more time winning deals.
Provide proactive, end-to-end support to the Sales team and our merchants to navigate and accelerate the onboarding process.
Act as a strategic partner to the business, finding innovative solutions to meet client needs while strictly adhering to Checkout.com's internal risk and compliance policies.
Manage and resolve inbound requests from the Sales team regarding client onboarding or complex profile reviews.
Maintain accurate, up-to-date documentation for complex deal structures and contracts, including the creation and review of customer agreements.
Go beyond reporting — extract specific insights that drive immediate deal decisions, identify gaps in the commercial process, and propose the fix before the problem scales.
Lead the rollout and iteration of AI-powered workflows — deploying AI prompts and automations that reduce rep admin time, improve deal velocity, and increase operational efficiency across the pipeline.
Build and maintain trusted relationships with multidisciplinary internal teams, including Sales, Customer Onboarding, Legal, Risk, and Finance.
Lead impactful projects aimed at improving and automating current processes. You'll define project scopes, set clear milestones, and ship operational improvements on time.
Act as a mentor and support the onboarding of new colleagues as our US operations continue to scale.
Requirements
2–4 years of experience in sales operations, deal desk, revenue operations, financial analysis, or a similar commercial operations role in a high-growth environment.
We're open to your background — whether you come from Deal Desk, RevOps, Finance, or a technical project management role, you love building systems and processes that actually work.
You hate manual, repetitive tasks. You're highly comfortable with AI tools and have hands-on experience (or a strong appetite to learn) deploying AI prompts and automations to optimize workflows.
You have a CRM mindset — proficient in Salesforce or similar tools — and understand how systems connect to drive business outcomes. You don't just use tools; you evolve them.
An uncompromising eye for accuracy, particularly regarding data, legal contracts, and deal structures.
Superb communication and interpersonal skills, with the confidence to manage and influence senior, multidisciplinary stakeholders. You can explain a workflow update to a salesperson just as easily as you can discuss a logic flow with an operations lead.
A self-starter who can take a vague operational request and turn it into a functional project plan with clear deadlines.
Fast learner, humble, hungry to grow, and genuinely motivated by new challenges.
Nice-to-haves
Familiarity with the payment processing/fintech industry
Hands-on experience with Salesforce
Benefits
Hybrid working model offers flexibility, with three days per week in the office to support collaboration and connection.
