Senior Specialist, Bid Management & Assurance

Company Description

We’re Checkout.com – you might not know our name, but companies like eBay, ASOS, Klarna, Uber Eats, and Sony do. That moment when you check out online? We make it happen. Checkout.com is where the world checks out. Our global network powers billions of transactions every year, making money move without making a fuss. We spent years perfecting a service most people will never notice. Because when digital payments just work, businesses grow, customers stay, and no one stops to think about why. With 19 offices spanning six continents, we feel at home everywhere – but London is our HQ. Wherever our people work their magic, they’re fast‑moving, performance‑obsessed, and driven by being better every day. Ideal. Because a role here isn’t just another job; it’s a career‑defining opportunity to build the future of fintech.

Job Description

About the role

At Checkout.com, our Bids Team acts as both a trusted enabler and a commercial accelerator for our global organization, supporting the enterprise sales cycle through industry‑leading proposals and merchant assurance responses. We are maturing the team to formalize ownership of the merchant assurance workstream, creating a unique opportunity for a driven professional to lead on this initiative and to partner with our global bid managers in support critical commercial activities within the payments space.

Your Mission

As a Senior Specialist, you will primarily own and strengthen our merchant assurance response engine so it scales seamlessly with Checkout.com’s continued growth. You will spearhead our adoption of AI within this subdomain, leveraging AI‑based interfaces for intelligent content management, requirements ingestion, and the surfacing of multi‑disciplinary content (Information Security, Data Protection, Compliance, etc.). By developing the base we have in place today, you will build and maintain an accurate and reliable source of truth, which will build trust and credibility with merchants throughout the enterprise sales cycle. Your work will ensure our due diligence responses are operationally sound, robust, and provide assurance to our merchants, regardless of volume or geography.

Who You Are

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.

What You Will Do

• 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 optimise 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.

What You Will Bring

• 3–5 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 organisational 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.

Bring all of you to work

We create the conditions for high performers to thrive – through real ownership, fewer blockers, and work that makes a difference from day one. Here, you’ll move fast, take on meaningful challenges, and be recognised for the impact you deliver. It’s a place where ambition gets met with opportunity – and where your growth is in your hands. We work as one team, and we back each other to succeed. So whatever your background or identity, if you’re ready to grow and make a difference, you’ll be right at home here.

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

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 to learn more about our culture, open roles, and what drives us. For a closer look at daily life at Checkout.com, follow us on LinkedIn and Instagram.