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Underdog Fantasy

Director, Customer Support Automation

Sorry, this job was removed at 06:11 p.m. (PST) on Monday, Apr 21, 2025
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Remote
2 Locations
Remote
2 Locations
We’re Underdog.

The fastest-growing sports gaming company – ever.

We build innovative games, products, and experiences for American sports fans.

We’re here to shake up the fastest growing industry with bold ideas, custom-built tech, and the drive to win.

Founded in 2020, our team has built four of today’s most widely played fantasy games and launched the Underdog Sportsbook – built entirely in-house with our own technology. That means we control our product, move fast, and create experiences you won’t find anywhere else. 

In just over two years, we’ve reached over a $1.2 billion valuation, with investors like BlackRock, Spark Capital, SV Angel, Mark Cuban, Kevin Durant, and Adam Schefter. And we’re just getting started.

At Underdog, we believe that sports are for everyone. 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.

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