About Keyloop
Keyloop bridges the gap between dealers, manufacturers, technology suppliers and car buyers. We empower car dealers and manufacturers to fully embrace digital transformation by creating innovative technology that makes selling cars better for our customers, and buying and owning cars better for theirs. We use cutting-edge technology to link our clients’ systems, departments and sites, providing an open technology platform that’s shaping the industry for the future.
Purpose of the Role
The Project Manager, Enterprise Deals, is embedded directly in the Enterprise Sales team's largest and most complex pursuits, ahead of contract signature. The role exists to close the gap between what Sales has proposed commercially and what the business can actually deliver operationally. You will work the deal from within, before it closes, to pressure-test the rollout plan, align internal stakeholders, and ensure the economics being agreed with the customer match what Solutions, Product, Delivery, and Finance can realistically stand behind.
Key Responsibilities
- Pre-signature deal engagement & rollout readiness: Support large enterprise deals ahead of signature, build internal rollout plans in parallel with commercial negotiation, and ensure pricing, scope, and timeline commitments are deliverable.
- Deal orchestration: Project-manage large, complex enterprise deals end-to-end, build and maintain clear deal plans (milestones, dependencies, RAID logs), and act as the single point of coordination across Sales, Solutions Engineering, Legal, Finance, Product, and Services.
- Stakeholder management: Manage multiple senior internal and external stakeholders, set healthy working boundaries, and build relationships that allow you to challenge or push back constructively.
- Cross-functional alignment: Bring together functions with different incentives around a shared deal outcome and run structured deal reviews that drive decisions.
- Commercial input: Understand deal economics to flag commercial risk or margin exposure, and contribute to pricing, packaging, and contract structuring from a delivery-feasibility perspective.
- Process and governance: Maintain rigorous documentation and continuously improve deal management playbooks based on win/loss learnings.
The role reports directly to the VP of Enterprise Sales and operates as a trusted extension of that leadership, providing the opportunity to influence high-level strategy and challenge senior stakeholders across functions.
Essential
- Proven experience managing large, complex, multi-stakeholder commercial deals or bids, ideally in enterprise software or technology sales.
- Formal training or certification in project management fundamentals (e.g. PRINCE2, PMP, APM, or equivalent), or clear evidence of applying that discipline in practice.
- Strong commercial acumen — comfortable discussing pricing, margin, and contract terms with Sales and Finance.
- Excellent stakeholder management skills, with the confidence to manage upwards and hold firm, healthy boundaries with senior leaders.
- Exceptional attention to detail, balanced with the ability to see the bigger picture and prioritise what matters most.
- A natural connector — skilled at cross-functional alignment and bringing people together around a common goal.
- Excellent written and verbal communication, including executive-level summaries and presentations.
- Ability to anticipate delivery and commercial risk before it escalates, and to make sound decisions under pressure in high-uncertainty, multi-stakeholder situations.
Desirable
- Working knowledge of CRM, CPQ, and contract lifecycle management tools.
- Experience in automotive retail technology, DMS, or adjacent B2B SaaS sectors, including familiarity with OEM sales and aftersales journeys.
- Exposure to RFP/bid management processes for complex, competitive enterprise pursuits.
- Experience operating within a PMO, adhering to or defining standards, KPIs, and delivery tooling across a portfolio.
- Familiarity with Generative AI technologies and their application to project management.
