Director of AI Strategy

*Candidates must be located in Charlotte, NC or willing to relocate. The position requires in-person attendance at least 3 days a week (ideally Tuesday-Thursday) in our Charlotte, NC office*  

About LendingTree:

LendingTree (NASDAQ: TREE) is the nation's leading digital marketplace, where consumers can find and compare a wide variety of products—from home loans to insurance, personal loans, credit cards, and more. Our mission is to empower consumers to take control of their financial lives by providing the information and tools they need to make informed decisions. We are a fast-paced, innovation-driven company that is committed to leveraging the latest technologies, including AI, to create a seamless and personalized consumer experience. 

The Opportunity

LendingTree is seeking a strategic leader to drive our enterprise AI vision. Reporting to the Head of Strategy, you’ll partner across product, technology, operations, and executive leadership to identify, prioritize, and accelerate the most impactful AI initiatives that transform how we operate and how we serve customers. You’ll shape our long-term roadmap, embed AI into core business functions, and ensure our investments deliver measurable results. This role requires a strong balance of technical expertise, leadership and product-oriented execution. 

This is a high-impact, high-visibility individual contributor role—ideal for a systems-thinker who thrives on influence without authority. You’ll act as the connective tissue across multiple organizations to build consensus across diverse stakeholders, and drive execution through collaboration, not command. Success hinges on your ability to connect strategy with delivery, embed AI in core operations, and transform LendingTree into a truly AI-first company. 

We’re not just using AI—we’re redefining what financial empowerment looks like in an AI-first world. You’ll play a key role in helping consumers get smarter, faster financial outcomes—powered by intelligent, ethical AI. 

What Success Looks Like in this Role:

• AI becomes a business accelerant—not just a technical capability. 
  You champion the use of AI as a strategic lever to drive growth, efficiency, and customer value across all business units. You stay abreast of the latest AI trends and technologies, fostering a culture of continuous innovation. 

• AI investments deliver measurable outcomes. 
  You define success metrics, track impact, and clearly communicate the ROI of AI initiatives to leadership and the board. 

• LendingTree shifts toward AI-first ways of working. 
  You embed AI adoption into the company’s DNA—through playbooks, training, cultural shifts, and visible wins that build confidence and momentum. 

• AI opportunities are continuously surfaced, prioritized, and executed with discipline. 
  You build a robust AI intake pipeline, lead initiative evaluation, and oversee delivery—balancing agility with program management rigor. 

• AI capabilities are optimized for performance, token efficiency, and responsible deployment. 
  You consult on architecture and model selection, applying a deep understanding of tokenomics, latency tradeoffs, and guardrail design to ensure our AI solutions are cost-effective, scalable, and aligned with business goals. 

• AI execution is safe, scalable, and aligned with our values. 
  You proactively navigate risk, governance, and ethical considerations in close partnership with Legal, Compliance, and InfoSec. 

• LendingTree is recognized externally as a responsible and innovative AI leader. 
  You collaborate with Government Relations to shape responsible AI policy and represent LendingTree in external forums, amplifying our voice in industry conversations and regulatory dialogues. 

Required Qualifications

• 10+ years in technology strategy, digital transformation, or innovation leadership, with 3+ years focused on AI strategy or implementation 

• Bachelor's degree in Computer Science, Engineering, AI or a related field.  

• High EQ and collaborative leadership style: you know how to work with scientists, engineers, and execs without friction. 

• Strong technical understanding of AI technologies (e.g., NLP, LLMs, ML platforms), token economics, and implementation tradeoffs 

• Proven success driving change across cross-functional teams  

• Executive presence; experienced in communicating technical concepts to C-level audiences 

• Experience applying AI in financial services, fintech, or a similarly regulated, data-rich environment 

Preferred Qualifications

• 7+ years of experience in AI, machine learning, or data science, with a proven track record of leading AI initiatives. 

• Advanced degree (MBA, MS in AI/ML, or similar) 

• Familiarity with AI governance frameworks in regulated industries 

• Experience with portfolio planning, ROI modeling, or initiative triage 

• Hands-on experience with LLMs (OpenAI, Bedrock, Llama), vector databases (Pinecone, Weviate) and Agentic Frameworks preferable 

• Formal training in change management or product development methodologies 

THE COMPANY 

LendingTree is the nation’s largest online lending marketplace. That means we connect customers with multiple lenders, so they find the best deals on loans, credit cards, savings accounts and insurance. Our goal is to help people save money, and we believe the best way to do that is by giving them a way to shop for loans and compare lenders, so they make their best financial choices. 

Our CEO Doug Lebda founded the company in 1996 after a frustrating house-hunting experience. In those days, we mostly helped people find good mortgage deals. Now, we help consumers find their best in personal loans, auto loans, business loans, student loans, credit cards, savings accounts, home equity loans and more. 

What else you should know

• We’re a publicly-traded company (TREE). 

• We’ve welcomed several other companies into the LendingTree family to augment our efforts at helping borrowers make their most sensible financial choices. 

• We’ve built the LendingTree app and My LendingTree dashboard to give consumers tools to manage and monitor their financial health.   

CULTURE 

We’re a fast-paced company with an entrepreneurial bend. We work hard and test our products often. We’re collaborative, ambitious, candid and high-energy. Our teammates are some of the brightest, most talented people you’ll ever work with. We care more about your smarts than we do about the kinds of clothes you wear (but please, do wear clothes to work!), and we’re pretty good about rewarding innovation, creativity and the knack for just getting stuff done (we even have an award for employees called the GSD, “Get Stuff Done”).  

Come work with us! 

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