Project Manager, Enterprise Deals

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 ensure 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, with the standing and judgment to challenge senior stakeholders across functions when a deal's internal alignment is at risk.

Key Responsibilities

Pre-signature deal engagement & rollout readiness

• Supporting large enterprise deals ahead of signature, at the point where commercial terms are taking shape but before they are locked in.
• Build the internal rollout and implementation plan for each deal in parallel with the commercial negotiation, so delivery feasibility informs the deal rather than following it.
• Work with Solutions, Product, Delivery, and Finance to confirm that pricing, scope, and timeline commitments being made to the customer are ones the business can actually meet.
• Flag misalignment between what is being proposed externally and what is deliverable internally early enough to influence the deal, not after signature.

Deal orchestration

• Project-manage large, complex enterprise deals end-to-end—from qualification and solutioning through pricing, contracting, and close.
• Build and maintain a clear deal plan for each pursuit: milestones, owners, dependencies, and decision points, with visible risk and status tracking ( RAID ).
• Act as the single point of coordination across Sales, Solutions Engineering, Legal, Finance, Product, and Services for each enterprise deal.
• Apply governance discipline—scoping, planning, RAID logs, decision gates—scaled appropriately to the size and complexity of each pursuit.

Stakeholder management

• Manage multiple senior internal and external stakeholders simultaneously, adapting communication style and cadence to each audience.
• Set and hold healthy working boundaries—protecting timelines and quality standards even under pressure from competing priorities or senior voices.
• Build trusted relationships that allow the role to challenge, escalate, or push back constructively when a deal's alignment is at risk.
• Manage executive communication and reporting on deal status, proactively surfacing risks and driving decisions rather than just reporting on them.

Cross-functional alignment

• Bring together functions with different incentives—Sales, Legal, Finance, Product, Delivery—around a single, shared deal outcome.
• Identify and surface the goal a group didn't know it had in common, and use it to unblock stalled decisions or misaligned priorities.
• Run structured deal reviews, working sessions, and stakeholder check-ins that drive decisions rather than just status updates.
• Bring a working understanding of OEM sales and aftersales dynamics to keep alignment conversations grounded in how automotive retail customers actually operate.

Commercial input

• Understand deal economics well enough to flag commercial risk, margin exposure, or non-standard terms early, in partnership with Deal Desk/Finance.
• Contribute to pricing, packaging, and contract structuring conversations from a delivery-feasibility and risk perspective.
• Support the development of compelling, commercially sound proposals and executive summaries for client-facing submissions.
• Contribute to business cases, SOWs, and estimates, ensuring commercial commitments are grounded in realistic delivery assumptions.

Process and governance

• Maintain rigorous documentation and audit trail across Keyloop systems.
• Continuously improve the deal management and rollout-readiness process, templates, and playbooks based on win/loss learnings.
• Provide regular updates and reports on deal status, risk, and readiness to the VP, Enterprise Sales, and other senior stakeholders.

What We're Looking For

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 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 prioritize 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.

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.