Customer Success Engineer Jobs in Virginia (NOW HIRING)

AI is reshaping every industry on earth, and right now, almost no one has figured out how to govern it at scale. This is the defining challenge of the new technology era we just entered. Trustible exists to meet that challenge. We're building the platform that lets the world's most innovative and complex organizations move fast with AI and prove they're doing it responsibly. The window to get this right is narrow, the stakes are enormous, and we're hiring the people who want to be at the center of it.

We're an AI-native public benefit corporation headquartered in Arlington, Virginia, backed by over $6M in venture funding from investors betting on trustworthy AI as one of the defining infrastructure categories of the decade. We've grown fast, we're winning enterprise customers in some of the most impactful industries in the world, and we're still small enough that a Customer Success Manager here shapes how the entire customer journey works, not one piece of a process someone else designed. If you want to work on a genuinely hard, genuinely new problem at a startup with real traction in the DC area, this is that role.

Trustible sells to CAIOs, CIOs, GCs, and compliance officers, most often inside of regulated enterprises in financial services, healthcare, insurance, defense, and manufacturing. These customers are governing high-stakes AI programs, often across multiple stakeholder groups, and they need a CSM who can operate credibly in that environment from day one.

We're hiring an Enterprise CSM to own the full post-sale customer journey for their customer base: onboarding, implementation, adoption, and renewal. You'll be the primary relationship owner for a portfolio of our largest and most complex accounts – and some small ones too! You'll need to be comfortable running a multi-stakeholder enterprise implementation, technical enough to know when a request needs engineering, and interested enough in AI governance and regulation to be a genuine thought partner to your customers, not just a project manager keeping tasks on track.

This role also reaches beyond traditional CS. You'll help build out our AI Governance Enablement solutions offering, working alongside our founders, policy, and solutions engineering team members to figure out where services and structured solutions can accelerate customer outcomes. You'll run pilots and trials, feed customer signal directly into product roadmap conversations, support product launches with customer-facing enablement, and use AI tools to automate parts of the CSM workflow so the team scales without the experience degrading.

• You'll report directly to the CEO, with regular visibility into company strategy, board reporting, and GTM decisions
• CTO/Co-Founder and engineering, on integrations, configurations, and technical escalations
• CSM, serving other Trustible customers and setting the foundation for the customer journey
• Sales and BD, on renewals, expansion, and pilot-to-contract conversion

• Own onboarding and implementation for enterprise accounts, managing multi-stakeholder rollouts across AI, legal, IT, and business teams
• Serve as the primary point of contact for a portfolio of enterprise customers post-sale, driving adoption, retention, and expansion
• Translate customer needs into configuration and workflow decisions inside the platform, and know precisely when a request needs to be escalated to engineering versus solved within CS
• Advise customers on how to structure their AI governance programs using Trustible, drawing on real fluency in AI risk, regulatory frameworks (EU AI Act, NIST AI RMF, ISO 42001), and cybersecurity/compliance fundamentals
• Manage and support pilots and trials, structuring them around clear activity commitments and conversion criteria
• Feed structured product feedback and customer signal into roadmap discussions, working directly with product and engineering
• Support product launches with customer-facing enablement materials, training, and rollout communication
• Help build and refine Trustible's AI Governance Enablement solutions offering: identifying where packaged services, playbooks, or structured engagements should supplement the core platform
• Identify and use AI tools to automate repetitive parts of the CSM motion (intake synthesis, health scoring, renewal prep, documentation) to improve consistency and free up time for high-value customer work
• Play a primary role in supporting business development on renewal and expansion conversations for your accounts in partnership with sales

• 5+ years of Customer Success experience, with a track record implementing AI or enterprise software solutions inside large, complex organizations
• Prior experience at a governance, risk, or cybersecurity software companies
• Comfort operating in a small, fast-moving team where the CS function is still being built, not inherited
• Demonstrated ability to manage multiple stakeholders within a single enterprise account, including technical, compliance, and executive audiences
• Technical proficiency sufficient to scope integration and configuration needs, and sound judgment about when to bring in engineering
• Working knowledge of AI risk, cybersecurity, or regulatory compliance (EU AI Act, NIST AI RMF, ISO 42001, SOC 2, or similar), or the ability to get fluent fast
• Experience running structured pilots or trials that convert to long-term contracts
• Strong written and verbal communication, comfortable presenting to senior stakeholders including CISOs, General Counsel, and Chief AI Officers

• Experience working directly with regulated industries (financial services, healthcare, insurance, defense/government)
• Familiarity with tools like HubSpot, Notion, or similar CS/GTM stacks
• Experience building or contributing to a services or solutions offering alongside a core software product
• Hands-on experience using AI tools to build workflow automation or internal tooling

• Base salary: $120,000-$140,000, commensurate with experience
• Meaningful equity in an early-stage, venture-backed company
• Health, dental, and vision coverage
• Unlimited PTO
• 401(k)