Bid Management Senior Specialist

Role Overview

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 formalise 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 supporting critical commercial activities within the payments space.

Mission

As a Senior Bid 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, building 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.

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 optimise AI‑based tools to automate the ingestion of merchant requirements and streamline response generation.
• Partner closely with 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.

Qualifications

• 4+ years of experience in bid management, proposal writing, sales operations or technical assurance.
• Proven ability to thrive in a high‑growth start‑up/scale‑up or a fast‑paced, high‑volume enterprise environment.
• Comfortable with ambiguity and rapid change.
• Strong aptitude for navigating technical topics and working alongside Information Security, Data Protection and Compliance teams to translate their expertise into clear, merchant‑facing language.
• Exceptional organisational skills and structured thinking.
• Ability to juggle multiple deadlines, prioritise competing demands and maintain impeccable attention to detail under pressure.
• 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.
• Forward‑thinking mindset and eagerness to champion the adoption of AI tools to scale this important work.

Benefits

Our hybrid working model offers flexibility, with three days per week in the office to support collaboration and connection.