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 - working the deal from within, before it closes, to pressure-test the rollout plan, align internal stakeholders, and make sure the economics being agreed with the customer match what Solutions, Product, Delivery, and Finance can realistically stand behind. This is not a delivery-phase project manager brought in after the ink is dry. The role reports directly to the VP of Enterprise Sales.
Key Responsibilities
- Pre-signature deal engagement & rollout readiness: Build the internal rollout and implementation plan in parallel with commercial negotiation; ensure delivery feasibility informs the deal; flag misalignment early.
- Deal orchestration: Project-manage large, complex enterprise deals end-to-end; maintain clear deal plans (milestones, owners, dependencies, RAID); 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 and hold healthy working boundaries; build trusted relationships to challenge and push back constructively.
- Cross-functional alignment: Bring together functions with different incentives; run structured deal reviews and working sessions that drive decisions.
- Commercial input: Understand deal economics to flag commercial risk and margin exposure; contribute to pricing, packaging, and contract structuring.
- Process and governance: Maintain documentation; improve deal management playbooks; provide regular status reports to the VP, Enterprise Sales.
What Success Looks Like
- Deals reach signature with internal alignment already secured — delivery, pricing, and scope have been stress-tested before the customer signs, not after.
- Large deals move through the pipeline predictably, with fewer last-minute surprises and faster time-to-close.
- Cross-functional teams describe deal coordination as clear, well-paced, and low-friction.
- Commercial and delivery risks are surfaced early, not at the point of signature.
- The VP, Enterprise Sales has full visibility of deal status, risk, and rollout readiness at any point in the cycle.
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.
