Project Manager - Enterprise Sales

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. We provide an open technology platform that’s shaping the industry for the future. We use data to help clients become more efficient, increase profitability and give more customers an amazing experience.

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 right person is assigned into a live opportunity, gets fluent in the deal fast, and drives the internal alignment work - pricing assumptions, resourcing, delivery feasibility, contractual commitments — so that by the time the customer signs, the business has already agreed internally on how it will deliver against what was promised. The role reports directly to the VP of Enterprise Sales and operates as a trusted extension of that leadership.

Key Responsibilities

• Pre-signature deal engagement & rollout readiness: Support large enterprise deals ahead of signature, build internal rollout plans, work with cross-functional teams to confirm feasibility, and flag misalignment early.
• Deal orchestration: Project-manage complex enterprise deals end-to-end, maintain clear deal plans (milestones, owners, dependencies), act as the single point of coordination, and apply governance discipline.
• Stakeholder management: Manage multiple senior internal and external stakeholders, set healthy working boundaries, build trusted relationships to challenge or push back constructively, and manage executive communication.
• Cross-functional alignment: Bring together functions like Sales, Legal, Finance, Product, and Delivery around shared outcomes, identify common goals to unblock decisions, and run structured deal reviews.
• Commercial input: Understand deal economics to flag risk or margin exposure, contribute to pricing and contract structuring, and support the development of proposals.
• Process and governance: Maintain documentation, improve deal management playbooks, and provide regular status reports to senior stakeholders.

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.