Senior Director, Deal Strategy Execution (R6259)

Job Description:

The Head of Deal Strategy and Execution (DSE) owns the operating model that turns Shield AI’s most complex, highest-value domestic and international opportunities into repeatable, executable transactions. This is not a traditional deal desk. It is a strategic deal architecture and execution function: a force multiplier for the field that helps teams build winning deal structures, terms, and negotiation approaches faster, accelerate cross-functional decisions, protect margin and risk posture, and convert successful one-off transactions into reusable plays.

The role exists because Shield AI’s opportunity set is increasingly defined by complex government and international transactions where a product sale alone is insufficient. Customers require combinations of autonomous platforms, software subscriptions, payloads, training, field services, integration, sustainment, and partner-led delivery. Each transaction introduces unique constraints around product maturity, delivery capacity, exportability, contracting pathway, pricing, and risk, and the company needs a single operating mechanism that translates all of it into viable, approvable, and scalable transactions.

This is a leadership role. The Head of DSE builds and directs three functions: Regional Deal Strategists embedded with BD teams, a central Business Proposals function, and an Architecture and Packaging capability. The constant is the operating principle: standardize what can be standardized, and elevate and deliberately govern what must be bespoke.

What you'll do:

• Team charter and operating model. Set engagement criteria, service levels, decision rights, approval thresholds, and the escalation framework. Define when DSE engages: a priority or non-standard opportunity involving complex configuration, international scope, a partner-led construct, a packaged offering, or an exception request.
• Cross-functional deal governance. Chair cross-functional deal reviews and ensure executives receive clear decisions, trade-offs, and recommendations. Convene BD Ops, Sales, Product, Finance, Legal, Contracts, Delivery, and Partnerships around a structured process rather than disconnected approval gates.
• Strategic deal architecture. Own the quality of deal strategy on priority pursuits: customer value hypothesis, solution configuration, commercial construct, pricing posture, terms, partner path, negotiation approach, and close plan. Challenge weak qualification and help account teams exit or reframe low-probability pursuits.
• Modular deal catalog and packaging. Direct the build and maintenance of the authoritative capability catalog: approved configurations, modular bundles, eligibility criteria, deployment assumptions, exclusions, dependencies, pricing guardrails, discount and volume logic, and delivery handoffs across hardware, software, subscriptions, services, training, sustainment, and integration.
• Deal plays and repeatability. Establish the deal-play roadmap aligned to GTM priorities, product maturity, and international growth. Turn wins, losses, and delivery outcomes into qualification tools, discovery guides, value narratives, proposal modules, negotiation guidance, and win-wire content the field can reuse in the flow of work.
• Exception governance. Govern pricing, terms, and delivery exceptions through clear thresholds and fast escalation, not bureaucracy. Serve as the escalation point for deal strategy conflict, cross-functional ambiguity, and strategic exceptions.
• Measurement and continuous improvement. Measure business impact: cycle time, deal velocity, win rate on strategic pursuits, gross-margin protection, exception volume, reuse rate, and delivery outcomes. Lead postmortems on won and lost strategic business and feed the lessons back into the pre-sales motion.
• Team leadership and role boundaries. Build and lead Regional Deal Strategists, the Business Proposals team, and the Architecture and Packaging function. Hold the line on the boundary that matters most: the Regional Deal Strategist owns the deal, and the Proposal Manager owns the submission.
• Enablement and incentives. Partner with the GTM Enablement Lead on trainings and enablement, and work with Rev Ops and Business Ops on buying-program and product and deal-structure related SPIFFs.

Current priorities:

• The agenda below reflects the founding priorities. Expect it to evolve as the organization matures.
• Stand up the organization. Charter, engagement criteria, decision rights, escalation paths, and service levels, published so the field knows when and how to engage DSE.
• Deal intake and triage. A structured intake that captures customer mission, use case, configuration, value, funding, timeline, procurement path, geography, export considerations, partners, delivery needs, and requested exceptions early, before heavy internal resources are committed.
• Modular capability catalog. Standard configurations and modular bundles across products, subscriptions, hardware, services, training, sustainment, integration, and partner components, with eligibility criteria, deployment assumptions, exclusions, and handoff requirements.
• Deal plays for priority segments. Repeatable plays for priority customer segments, use cases, geographies, routes to market, and partner motions, with approved pricing guidance and negotiation positions.
• Pre-sales inspection. Premortem discipline in the form of Opportunity Reviews and Management Reviews, with DSE review and approval prior to formal MRs.
• Post-deal learning. Postmortems on wins, losses, and delivery outcomes that feed back into product packaging, pricing, playbooks, training, and governance.

How the role operates:

• Advisory, not administrative. The team shapes stronger deals; it does not merely route requests for signatures. A desk that only passes work to executives fails to create speed or leverage.
• Clear guardrails. Publish price floors, discount bands, authority limits, eligibility rules, standard terms, and escalation triggers. Decisions within established guardrails are delegated; true strategic exceptions are escalated with a concise recommendation, alternatives, and quantified trade-offs.
• Speed by design. Service-level expectations with most standard reviews resolved same day or next business day. Urgency is governed by intake quality, not informal escalation.
• One source of truth. Centralize product and package definitions, deal-structure precedents, templates, approval outcomes, and lessons learned in a searchable repository, usable in the flow of work: inside CRM, opportunity reviews, proposal workflows, and account planning.
• Cross-functional accountability. Functional experts retain their authorities. DSE owns orchestration, deal-strategy coherence, pace, and knowledge capture.
• Decision rights. The role owns the recommendation and the orchestration. The CRO owns the strategic decision. Account teams own the customer relationship and the close.
• Measurement. The organization is evaluated on velocity, economics, execution quality, and reuse, not merely the number of tickets processed.
• Advisory, not administrative. The team shapes stronger deals; it does not merely route requests for signatures. A desk that only passes work to executives fails to create speed or leverage.
• Clear guardrails. Publish price floors, discount bands, authority limits, eligibility rules, standard terms, and escalation triggers. Decisions within established guardrails are delegated; true strategic exceptions are escalated with a concise recommendation, alternatives, and quantified trade-offs.
• Speed by design. Service-level expectations with most standard reviews resolved same day or next business day. Urgency is governed by intake quality, not informal escalation.
• One source of truth. Centralize product and package definitions, deal-structure precedents, templates, approval outcomes, and lessons learned in a searchable repository, usable in the flow of work: inside CRM, opportunity reviews, proposal workflows, and account planning.
• Cross-functional accountability. Functional experts retain their authorities. DSE owns orchestration, deal-strategy coherence, pace, and knowledge capture.
• Decision rights. The role owns the recommendation and the orchestration. The CRO owns the strategic decision. Account teams own the customer relationship and the close.
• Measurement. The organization is evaluated on velocity, economics, execution quality, and reuse, not merely the number of tickets processed.

Required qualifications:

Experience
• 10+ years in revenue, commercial, or deal or sales leadership roles in B2B technology, with material time structuring complex, mixed software and hardware transactions.
• Demonstrated experience building or leading a deal desk, deal strategy, or commercial structuring function, and elevating it from an approval queue into a strategic capability.
• Deep familiarity with international government contracting, international sales, and partner-led motions. Comfort with export considerations, contracting pathways, long cycles, complex stakeholders, and program-driven buyers is required.
• Defense, dual-use, or public-sector commercial exposure strongly preferred.
• Experience hiring and developing high-performing teams of strategists and proposal professionals.
Skills and disposition
• Deal architect. Thinks in commercial constructs, pricing logic, and negotiation posture, and translates technical capability into viable, approvable transactions.
• Cross-functional orchestrator. Aligns sales, finance, legal, product, and delivery around decisions without claiming their authority.
• Negotiation craft. Has personally shaped and negotiated high-value, non-standard transactions to close.
• Writes well. Produces executive-ready deal briefs, decision memos, and value narratives that compress complexity without losing it.
• Standardizer by instinct. Converts one-off wins into reusable plays, templates, and guardrails.
• Calibrated on the line between governing exceptions and adding bureaucracy. Stays on the governance side.