Senior Named Account Sales Director, AI & Enterprise

SimSpace serves as an AI Proving Ground where organizations can confidently train, test, and outmaneuver adversaries in any environment. Trusted by allied governments, militaries, enterprises, and research institutions worldwide, SimSpace enables adaptive, AI-ready defenses that stay ahead of evolving threats. Founded in 2015 by experts from U.S. Cyber Command and MIT Lincoln Laboratory, the platform unifies training, testing, and validation in a realistic, live-fire simulation—helping teams evaluate security investments, optimize performance, and compress cyber readiness cycles from months to days. Why join SimSpace? We are an organization that is focused on building our culture and mindfully enhancing our atmosphere every day which is why we have collaborated on an integral value system. Our governing philosophy of being Human Centered is deeply embedded within our value system. We apply this philosophy to every one of our internal team members, external clients, and their customers. How Do We Work? We believe that people are at the center of everything we do. SimSpace fosters a culture of continuous learning, curiosity, and professional growth. That belief shows up in action: in-house training, internal and external learning platforms, cyber conferences, industry events, and dedicated time for skill development. Our people are empowered to shape their careers - and it shows. Year over year, SimSpace consistently outperforms industry benchmarks in internal mobility, promotions, and total rewards growth. Who Thrives Here? We are a team of innovators, protectors, and problem-solvers. We believe diversity of thought and experience fuels better solutions, and we’re committed to building teams that reflect the communities we serve. Whether you’re remote or office-based, you’ll collaborate with talented colleagues across departments and time zones, united by the mission to create a safer digital world. We invite you to apply today! THE OPPORTUNITY SimSpace is building the AI Proving Grounds: a destructive-safe, non-production environment where organizations evaluate AI agents, tools, teams, and processes before deployment—and continue testing as they evolve. We’re hiring a high-ownership enterprise seller to lead a small portfolio of strategic AI providers and selected AI-leading enterprises. You will work directly with security, AI, and executive teams to identify consequential use cases, shape evaluations around customer outcomes, and carry opportunities from first conversation through close and expansion. This role calls for deep account focus, technical curiosity, and strong commercial judgment. You’ll spend your time building executive access and advancing a small number of important accounts. WHAT YOU’LL DO - Own a deliberately small portfolio—approximately 5–8 named accounts—with tailored account plans, stakeholder maps, and clear next steps. - Engage in model building, evaluation and hill-climbing activities alongside strategic model providers - Build relationships with CISOs and security leaders, AI and engineering leaders, and the management budget owners who can fund the work. - Lead direct, account-specific outreach and develop credible introduction paths through customers, executives, and partners. - Learn how each account is developing and deploying AI agents; identify where security teams need evidence before agents or workflows move into production. - Turn customer priorities into specific evaluation use cases, such as testing agent behavior, security workflows, tools, and teams against realistic adversarial scenarios. - Work with Sales Engineering, Field CISO, Product, and Professional Services to shape the right technical and commercial approach. - Lead structured what-if workshops that surface current, consequential problems and produce written value hypotheses with the right customer stakeholders. - Recommend a Proof of Value only when the management budget owner is engaged, success criteria are agreed, and the decision and procurement paths are understood. - Lead negotiations, security and legal reviews, procurement, and contracting through to a signed agreement. - Protect full-value positioning and keep the forecast grounded in customer evidence, buying commitments, and a clear path to a decision. - Ensure a clean transition to Customer Success, support customer outcomes, and identify opportunities for expansion while remaining primary account owner before, during and after closed-won - Bring structured customer feedback to Product and company leadership without making unsupported roadmap commitments. WHAT SUCCESS LOOKS LIKE - Each assigned account has an actionable plan, a current stakeholder map, and a clear view of its AI initiatives, security priorities, budget ownership, and decision path. - Customer conversations progress from general interest to a validated use case with an accountable owner and a fundable initiative. - Workshops end with written value hypotheses and an agreed next step—or a clear decision to stop pursuing the opportunity. - Proofs of Value have customer-agreed success criteria, an engaged budget owner, a defined timebox, and a scheduled decision meeting. - You create and close meaningful enterprise revenue while maintaining forecast accuracy and pricing discipline. - Customers adopt the capability and can describe the operational value it provides. WHAT YOU’LL BRING - 7+ years of full-cycle enterprise sales experience, with a track record of personally creating and closing complex technical opportunities. - Experience selling cybersecurity, AI infrastructure, cloud, developer platforms, or similarly technical solutions to large organizations. - Strong executive presence with the ability to engage CISOs, technology leaders, AI teams, and economic buyers. - Skill in account planning, executive outreach, multi-threading, discovery, value development, negotiation, and contracting. - The ability to translate technical and operational detail into a clear business case and buying decision. - Comfort working with technical teams to understand customer environments, use cases, evaluation needs, and deployment constraints. - A disciplined approach to qualification: you can distinguish a current, owned, fundable problem from curiosity or general interest. - Experience operating independently in an early-stage or high-growth company, where priorities move quickly and good judgment matters. - Curiosity about AI agents, cybersecurity, adversarial testing, security operations, and how organizations evaluate new technology. - A collaborative, low-ego working style and a reputation for following through. HELPFUL EXPERIENCE - Selling to strategic AI providers, AI labs, hyperscalers, or Fortune 100 technology and enterprise organizations. - Working with AI evaluation, AI security, red teaming, purple teaming, SOC modernization, cyber operations, or simulation. - Building executive relationships through partners,