Director, Customer Support Automation

Hi, we’re Underdog!

We’re the fastest-growing sports gaming company ever.

We build innovative games and products for American sports fans.

Founded in 2020, our team built four of today’s most widely played fantasy games and recently launched our Underdog Sportsbook. We are the only sportsbook to ever launch on our own home grown technology, which allows us to build different and innovative experiences. We believe there’s so much more to be built for sports fans, and we’ll continue to win by building the best products and experiences for our customers.

The opportunity in front of us to become the biggest company in our space is massive; after all, we’re currently sitting in the fastest-growing consumer industry in the U.S. In just over two years, we reached a nearly $500 million valuation through some of the best investors in the game, including Mark Cuban, Kevin Durant, BlackRock, and SV Angel. We are many times larger now and our growth is not slowing down.

At Underdog, we believe that sports are for everyone and are building a tomorrow for every fan. Want to help create that future? Join us.

About the role and why it’s unique:

• Lead the development and execution of the strategic vision for AI-driven customer engagement solutions.
• Spearhead the design, enhancement, and integration of chatbot technologies to transform customer service operations.
• Develop and execute a comprehensive roadmap for chatbot initiatives, incorporating AI, NLP, and ML to optimize customer interactions.
• Identify emerging trends in AI and chatbot technologies, translating insights into actionable strategies for competitive advantage.
• Collaborate with cross-functional teams (engineering, product, customer service) to integrate chatbot solutions into existing systems.
• Monitor key performance indicators (KPIs) and use data-driven insights to continuously improve chatbot effectiveness.
• Report to senior leadership on progress, challenges, and opportunities in customer engagement automation.

Who you are:

• Bachelor’s degree in Computer Science, Information Technology, or a related field is required; an advanced degree (MBA, MS in AI/ML, etc.) is preferred.
• 5+ years of experience in managing chatbot platforms, AI technologies, or digital customer experience initiatives, including significant leadership roles.
• Proven track record in optimizing customer service processes and implementing large-scale AI solutions.
• Deep familiarity with chatbot platforms, particularly Intercom, and advanced knowledge of AI-driven customer support technologies.
• Strong understanding of natural language processing, machine learning, and data analytics.
• Demonstrated ability to lead cross-functional teams and drive strategic initiatives in a fast-paced, dynamic environment.
• Proven experience working with senior leadership and multiple stakeholders to align technology initiatives with business strategies.

Our target starting base salary range for this position is between $156,000 and $175,500, plus target equity. The starting base salary will depend on a number of factors including the candidate’s skills and experience, among other things.

What we can offer you:

• Unlimited PTO (we're extremely flexible with the exception of the first few weeks before & into the NFL season)
• 16 weeks of fully paid parental leave
• A $500 home office allowance
• A connected virtual first culture with a highly engaged distributed workforce
• 5% 401k match, FSA, company paid health, dental, vision plan options for employees and dependents

#LI-REMOTE

This position may require sports betting licensure based on certain state regulations.

Underdog is an equal opportunity employer and doesn't discriminate on the basis of creed, race, sexual orientation, gender, age, disability status, or any other defining characteristic.