**VP, Underwriting Operations and Customer Experience Transformation**

Posted 2026-05-05
Remote, USA Full-time Immediate Start

At arenaflex, we're revolutionizing the commercial insurance industry by making it easier and more accessible for small businesses to thrive. As a diverse team of builders, dreamers, and entrepreneurs, we're driven by our core values and operating principles that guide every decision we make. We're seeking an exceptional leader to join our team as the VP, Underwriting Operations and Customer Experience Transformation. This role will be responsible for leading our customer experience journey, delivering effortless experiences that live into our brand promise of being "easy as Pie."

  • *About arenaflex**

arenaflex is a pioneering company that leverages technology to transform how small businesses buy and experience commercial insurance. Our mission is to empower small businesses to thrive by making commercial insurance affordable and as easy as pie. We're a team of innovators, thinkers, and doers who are passionate about making a difference in the lives of our customers.

  • *The Role**

As the VP, Underwriting Operations and Customer Experience Transformation, you will lead our customer experience journey, delivering effortless experiences that live into our brand promise of being "easy as Pie." You will be responsible for developing, building, and leading a best-in-class customer experience that leans into current expectations of users and partners. You will work closely with our leadership team to establish high-impact relationships with key stakeholders, both within and outside the organization.

  • *Key Responsibilities**
  • Lead the development of our customer experience strategy, ensuring it aligns with our brand promise and industry benchmarks.
  • Direct the overarching strategy, scale, and performance of our customer experience, including customer success, agent experiences, and underwriting operations.
  • Establish and manage key relationships with leaders inside and outside the organization to ensure excellent customer experience and outcomes.
  • Develop and implement processes to ensure we are delivering on analytics and data-driven insights.
  • Foster collaboration within the team and across customer lifecycle support areas.
  • Drive teamwork with customer experience in mind, accountable for setting and meeting metrics and deliverables around policy services and customer experience.
  • Develop and drive customer experience strategic initiatives, including managing partners at the highest level and establishing and measuring metrics and extensive business KPIs.
  • *The Right Candidate**
  • Bachelor's Degree in a related field is required.
  • 5 years in a senior operating role leading as a Director, VP, or Executive level for customer-facing organizations.
  • 10 years overall P&C Insurance Industry experience is required.
  • Proven track record of leading senior leaders.
  • Executive presence, business acumen, drive strategy, and deliverable outcomes, and driving results and measuring results is essential.
  • Ability to manage influence through persuasion, negotiation, and consensus building.
  • Ideally combined background of post-sale and sales experience in a high-volume, transactional-focused environment.
  • Advanced knowledge of the insurance industry is required.
  • Knowledge of workers' compensation is highly preferred.
  • Excellent process management and data analysis skills.
  • High ability to use data and metrics for decision making and strategic process mapping.
  • Strong empathy for customers and team members, and a passion for revenue and growth.
  • Deep understanding of value drivers in recurring revenue business models.
  • Analytical and process-oriented mindset.
  • Demonstrated desire for continuous learning and improvement.
  • Enthusiastic and creative leader with the ability to inspire others.
  • Excellent communication and presentation skills.
  • *What We Offer**
  • Competitive cash compensation.
  • A piece of the pie (in the form of equity).
  • Comprehensive health plans.
  • Generous PTO.
  • Future-focused 401k match.
  • Generous parental and caregiver leave.
  • Our core values are more than just a poster on the wall; they're tangibly reflected in our work.
  • *Work Environment and Culture**

arenaflex is a remote-first company, and this role will be based in the United States. We're committed to creating a work environment that's inclusive, diverse, and supportive. We believe in the importance of work-life balance and offer flexible working arrangements to ensure our team members can thrive both personally and professionally.

  • *How to Apply**

If you're a passionate and experienced leader who is driven by a desire to make a difference in the lives of our customers, we'd love to hear from you. Please submit your application, including your resume and a cover letter, to [insert contact information]. We can't wait to hear from you!

  • *Equal Opportunity Employer**

arenaflex is an equal opportunity employer. We do not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity, marital status, age, disability, national or ethnic origin, military service status, citizenship, or other protected characteristic.

  • *E-Verify Program**

arenaflex participates in the E-Verify program. Please click here, here, and here for more information.

  • *Privacy Policy**

arenaflex is committed to protecting your personal data. Please review our Privacy Policy.

  • *Safety First**

arenaflex is committed to your security during the recruitment process. We will never ask you for credit card information or ask you to purchase any equipment during our interview or onboarding process.

  • *Apply Now**

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