checkout.com - Bid Management Senior Specialist
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Requirements
• This is a senior specialist role requiring strong judgment, structured thinking, the ability to navigate competing priorities across multiple deadlines, and the confidence to challenge constructively. • If you thrive in busy environments (bids/proposals, sales cycles or equivalent.), this is an ideal opportunity to make a meaningful, real-world impact. You will help to define how AI and technology will deliver reliable outcomes, all while developing professionally alongside some of the best minds in the payments industry and laying the groundwork to progress into a more senior bid management role. • Trust, credibility and operational rigour are core tenets of this function and, by extension, are core requirements for this role. • It’s important we set you up for success and make our process as accessible as possible. So let us know in your application, or tell your recruiter directly, if you need anything to make your experience or working environment more comfortable. • Life at Checkout.com http://Checkout.com • We understand that work is just one part of your life. Our hybrid working model offers flexibility, with three days per week in the office to support collaboration and connection. • Curious about what it’s like to be part of our team? Visit our Careers Page https://www.checkout.com/careers to learn more about our culture, open roles, and what drives us. • For a closer look at daily life at Checkout.com http://Checkout.com, follow us on LinkedIn https://www.linkedin.com/company/checkout/life/ and Instagram https://www.instagram.com/checkout_com/
Responsibilities
• Manage and execute end-to-end merchant assurance requests, security questionnaires, and due diligence inquiries from enterprise prospects and existing customers, ensuring absolute accuracy and timely delivery. • Act as the primary architect of the assurance content repository. Adapt, train, and optimize AI-based tools to automate the ingestion of merchant requirements and streamline response generation. • Partner closely with Subject Matter Experts (SMEs) across Information Security, Data Protection, Legal, and Compliance to extract highly technical data and translate it into clear, commercial-ready responses. • Collaborate closely with our team of global Bid Managers to support complex, high-value enterprise RFPs, taking ownership of the risk, security, and compliance sections. • Continuously review and refine the assurance response engine. Identify bottlenecks and design scalable workflows to handle Checkout.com's growing commercial volume without compromising quality or merchant trust. • Confidently navigate competing priorities and constructively challenge stakeholders to ensure our market positioning remains operationally sound. • 4+ years of experience in bid management, proposal writing, sales operations, or technical assurance. • Proven ability to thrive in a high-growth startup/scale-up or a fast-paced, high-volume enterprise environment. You are comfortable with ambiguity and rapid change. • A strong aptitude for navigating technical and technical topics, and you must be comfortable working alongside Information Security, Data Protection, and Compliance teams to translate their expertise into clear, compelling, merchant-facing language. • Exceptional organizational skills and structured thinking. You can seamlessly juggle multiple deadlines, prioritize competing demands, and maintain impeccable attention to detail under pressure. • The confidence and credibility to engage with global, cross-functional teams, regardless of seniority. • Experience with technology: e.g. RFP/content management platforms, AI tools such as cursor and Gemini. More importantly, you bring a forward-thinking mindset and an eagerness to champion the adoption of AI tools to scale this important work.
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