Director of AI Strategy & Digital Success

We’re seeking a Director of AI Strategy & Digital Success to transform how we support customers through digital, AI-driven engagement. This role will own strategic initiatives and serve as the architect of an AI-first engagement engine designed to drive retention and product adoption at scale.

We need someone who can operate independently from day one and perform at a high level with minimal oversight, with the expectation that a team will be built under them over time. We’re targeting director-level capability now, even though the role won’t include direct reports initially, with leadership responsibilities expanding long-term.

The ideal candidate will show that “low touch” doesn’t mean “low value,” using generative AI and automation to deliver a seamless, personalized, high-impact experience to thousands of customers at once.

This position is open to both Plano, TX and Austin, TX., Digital strategy and implementation

• Scale the human touch: design and deploy AI-driven playbooks that automate routine success motions, including onboarding, product engagement and adoption, health checks, while maintaining a personalized feel
• Predictive churn modeling: integrate predictive AI models that identify ‘at-risk’ signals before they become churn realities.
• GenAI content engine: partner with the success team to oversee the creation of dynamic, AI-generated campaigns and automated email flows tailored to specific personas and behaviors.

Scaled engagement operations

• Digital journey mapping: build end-to-end digital journeys that guide customers from initial implementation to ‘value realization’ without requiring a dedicated CSM.
• In-App orchestration: lead strategy for in-product messaging and self-service capabilities to resolve queries and drive feature adoption.
• Partner with IT and Product teams to ensure seamless deployment and adoption of the Customer Success platform.

Revenue & retention accountability

• Expansion mapping: use AI and automation to identify ‘ready-to-buy’ signals, creating automated lead generation paths.

Change Management & Enablement

• Drive organizational change through training, communication, and stakeholder engagement.
• Foster a culture of continuous improvement and innovation.

Analytics & Reporting

• Define KPIs and dashboards to measure success of digital initiatives and customer outcomes, including churn and adoption.
• Segment customers by risk, maturity, persona, and behavior.
• Provide insights into leadership on trends, risks, and opportunities for improvement.
• Use data to identify systemic churn drivers and design scalable interventions to support key elements of retention strategy, particularly in mid-low market customers.

Partner with the cross-functional team to:

• Track engagement and usage signals
• Measure impact of digital programs on retention.

• Experience with technology platforms like Salesforce, Gainsight, or the newest AI-first Customer Success Platforms.
• 10+ years of experience in Customer Success, Success Transformation, or SaaS operations.
• Proven track record of leading technology implementations and process improvements in a SaaS environment driving successful outcomes.
• Strong understanding of customer success metrics, lifecycle management, and SaaS business models.
• Excellent leadership, communication, and stakeholder management skills.

Preferred Skills

• Knowledge of automation, AI-driven customer engagement, and data analytics.
• Ability to manage cross-functional projects and influence at all organizational levels.
• Background in Educational Technology.
• Prior management or team-lead experience preferred, as this role is expected to evolve into a leadership position with direct reports., Leads business development and capture activities for Latin American defense and government customers. Identifies opportunities, analyzes customer and competitor needs, builds senior stakeholder relationships, coordinates bids and proposals, shapes requirements, manages campaign plans, and supports trade shows and customer engagements. Requires extensive aerospace or defense experience, regional customer expertise, cross-cultural fluency, knowledge of U.S. and international defense sales frameworks, export controls, local partnerships, and English proficiency; Spanish and Portuguese are preferred. Top Skills: CRMDirect Commercial Sales (Dcs)EarForeign Military Sales (Fms)ItarPipeline Management ToolsUncrewed Air Systems

Remote or Hybrid Hiring Remotely in US 145K-181K Annually Expert/Leader Remote or Hybrid Hiring Remotely in US 145K-181K Annually Expert/Leader Leads AI-driven customer success strategy, scaling onboarding, engagement, health checks, retention, adoption, and expansion through automation and digital journeys. Owns predictive churn modeling, AI-generated campaigns, in-app orchestration, customer segmentation, KPI dashboards, and cross-functional implementation. Drives organizational change, stakeholder enablement, and continuous improvement while building the foundation for a future customer success leadership team., * Comprehensive Insurance Coverage (including Medical, Dental, Vision, Pharmacy benefits, Life Insurance and AD&D)

• Flexible Spending Accounts and Health Savings Accounts
• Short-Term Disability and Long-Term Disability
• Comprehensive 401(k) plan
• Generous Parental Leave
• Unrestricted paid time off (known as Discretionary Time Off - DTO)
• Wellness Program, including ClassPass & Employee Assistance Program
• Tuition Reimbursement
• Optional Benefits: Pet Insurance, Identity Theft Protection, Student Debt Repayment Program and Prepaid Legal coverage

A reasonable estimate of the base compensation range for this position is $144,500 - $180,600 USD. This compensation range is specific to the United States and it incorporates many factors including but not limited to an applicant’s skills and prior relevant experience and training; licensures, degrees, and certifications; internal equity; internal pay ranges; and market data/range parameters. EEO CommitmentEEO Commitment, An Hour Ago Remote or Hybrid 173K-312K Annually Senior level 173K-312K Annually Senior level Fintech * Payments * Software * Financial Services Lead Sales Development across North America and the UK, owning top-of-funnel pipeline, regional alignment, performance reporting, upmarket expansion, cross-functional partnerships, talent development, and technology-enabled productivity. The role manages teams and managers, establishes scalable inbound and outbound motions, partners with Marketing, Sales, Finance, and Strategy, and drives revenue-focused planning, qualification, and conversion. Top Skills: AIAnalyticsAutomationReporting Tools Dynatrace

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With a business-friendly climate and research universities like CU Boulder and Colorado State, Colorado has made a name for itself as a startup ecosystem. The state boasts a skilled workforce and high quality of life thanks to its affordable housing, vibrant cultural scene and unparalleled opportunities for outdoor recreation. Colorado is also home to the National Renewable Energy Laboratory, helping cement its status as a hub for renewable energy innovation.

Key Facts About Colorado Tech

• Number of Tech Workers: 260,000; 8.5% of overall workforce (2024 CompTIA survey)
• Major Tech Employers: Lockheed Martin, Century Link, Comcast, BAE Systems, Level 3
• Key Industries: Software, artificial intelligence, aerospace, e-commerce, fintech, healthtech
• Funding Landscape: $4.9 billion in VC funding in 2024 (Pitchbook)
• Notable Investors: Access Venture Partners, Ridgeline Ventures, Techstars, Blackhorn Ventures
• Research Centers and Universities: Colorado School of Mines, University of Colorado Boulder, University of Denver, Colorado State University, Mesa Laboratory, Space Science Institute, National Center for Atmospheric Research, National Renewable Energy Laboratory, Gottlieb Institute