Senior Director, Deal Strategy Execution (R6259)

Shield AI is a venture-backed defense-tech company with the mission of protecting service members and civilians with intelligent systems. Its products include Hivemind autonomy software, V-BAT and X-BAT aircraft, and Aechelon simulation and synthetic reality technologies. With offices and facilities across the U.S., Europe, the Middle East, and Asia-Pacific, Shield AI’s technology actively supports operations worldwide. For more information, visit www.shield.ai. Follow Shield AI on LinkedIn, X, Instagram, and YouTube.

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.

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Full-time regular employee offer package:

Pay within range listed + Bonus + Benefits + Equity

Temporary employee offer package:

Pay within range listed above + temporary benefits package (applicable after 60 days of employment)

Salary compensation is influenced by a wide array of factors including but not limited to skill set, level of experience, licenses and certifications, and specific work location. All offers are contingent on a cleared background and possible reference check. Military fellows and part-time employees are not eligible for benefits. Please speak to your talent acquisition representative for more information.

Shield AI is proud to be an equal opportunity workplace and is an affirmative action employer. We are committed to equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, marital status, disability, gender identity or Veteran status. If you have a disability or special need that requires accommodation, please let us know.