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Nautilus Insurance Company

Territory Sales Director

Company : Nautilus Insurance Company

Location : Chicago, IL, 60661

Job Type : Full Time / Part Time

Date Posted : 14 January 2026

Company Details

Berkley Select delivers professional liability insurance solutions to individuals, businesses, professional services firms, and nonprofit organizations.

As a Berkley company, Berkley Select is staffed with a team of experts with a specific focus on Professional Liability. Berkley Select utilizes individual risk underwriting, loss control, and claims practices to provide superior products and services to its customers.

Berkley Select is a Berkley Company. W. R. Berkley, founded in 1967, is one of the nation’s premier commercial lines property casualty insurance providers. W. R. Berkley Corporation (NYSE: WRB).

Company URL:  https://www.berkleyselect.com

The company is an equal employment opportunity employer.

Responsibilities

As a Territory Sales Director, you will be the face of Berkley Select in your region, driving profitable growth, deepening strategic relationships with broker partners, and expanding our market presence. This is a high-impact, relationship-driven role ideal for a dynamic, self-motivated insurance professional.

Planning & Strategy

  • Develop territory-specific business plans and budgets.
  • Lead annual sales planning with internal teams and broker partners.

Broker Engagement

  • Build and execute strategic growth plans with assigned producers and brokers.
  • Conduct regular business reviews and planning sessions.
  • Identify cross-selling opportunities across product lines.

Territory Development

  • Analyze market trends and identify new business opportunities.
  • Expand Berkley Select’s footprint in emerging and underserved markets.
  • Collaborate with underwriting and product teams to tailor solutions.

Pipeline Management

  • Build and maintain a robust pipeline of new business.
  • Use data-driven insights to prioritize efforts and track performance.

Product Advocacy & Collaboration

  • Serve as a subject matter expert for Berkley Select’s professional liability products.
  • Partner with underwriting, claims, and marketing teams to align on strategic initiatives.
  • Escalate key opportunities and challenges to leadership.
  • Deep knowledge and understanding of competitor product offerings and distribution.  

Relationship Building

  • Foster long-term broker and client relationships.
  • Conduct stewardship meetings and manage stakeholder engagement.
  • Invite clients to flagship events and regional programs.
  • Regular and predictable attendance

Qualifications

  • Bachelor’s degree or equivalent work experience.
  • 5-7 years of insurance marketing or sales experience, preferably within the management and professional liability space.
  • Established broker relationships and a track record of sales success.
  • Strong analytical and negotiation skills, with the ability to influence and persuade.
  • Familiarity with AI/ML tools to support strategic decisions.
  • Effective time management and organizational skills.
  • Excellent verbal and written communication skills.
  • Highly self-motivated, capable of working autonomously, but also thrives in a team-based environment.
  • Travel Requirements: This is an external-facing role with significant travel within the assigned territory. A combination of in-person and virtual agency meetings is required, with a strong preference for face-to-face interactions where feasible.

Additional Company Details

The position may be based in Arizona, Colorado, Illinois, Nevada, Pennsylvania or Texas. If located in Chicago, IL the role will be based in the office four days per week when not travelling. We do not accept any unsolicited resumes from external recruiting firms. The company offers a competitive compensation plan and robust benefits package for full time regular employees which for this role includes: Base Salary Range: $90,000 - $150,000, based on experience. The application window for this role is estimated to be open through February 13, 2026, but may be extended, if necessary, please submit your application as soon as possible prior to February 13, 2026. The actual salary for this position will be determined by a number of factors, including the scope, complexity and location of the role; the skills, education, training, credentials and experience of the candidate; and other conditions of employment. This role is eligible to participate in the annual discretionary bonus program. Benefits: Health, Dental, Vision, Life, Disability, Wellness, Paid Time Off, 401(k) and Profit-Sharing plans.

Sponsorship Details

Sponsorship not Offered for this Role

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Frequently asked questions

Chicago's insurance sector is bustling with seasoned sales professionals, making the Territory Sales Director position highly competitive. Candidates with established broker relationships and a strong grasp of professional liability products often gain an edge in this market, especially within companies like Nautilus Insurance Company.

In Illinois, holding state-specific insurance licenses such as the Property and Casualty license can significantly enhance a Territory Sales professional's credibility. Additionally, certifications like CPCU or CIC are valued, reflecting expertise in commercial lines and professional liability insurance within the Chicago area.

While both roles require strong sales acumen, a Territory Sales Director typically drives strategic growth plans, manages high-level broker partnerships, and influences regional market expansion. In contrast, a Territory Sales Manager might focus more on executing sales targets and managing day-to-day team activities.

A Territory Sales Director often leads territory-specific business planning, nurtures deep broker relationships, and collaborates cross-functionally with underwriting and claims teams. This strategic oversight and market analysis differentiate the role from standard sales positions focused mainly on direct selling.

Professionals in Territory Sales often advance by demonstrating consistent revenue growth, strategic territory development, and strong stakeholder engagement. Success in these areas can lead to regional director or sales operations roles, where broader operational leadership and decision-making become central.

Nautilus Insurance Company emphasizes a collaborative approach combining underwriting expertise with sales strategy in its Territory Sales Director role. This position offers a blend of high-impact broker engagement and data-driven decision-making, setting it apart from more traditional sales roles in insurance.

Nautilus provides robust resources, including access to AI/ML tools for strategic planning and close collaboration with underwriting and marketing teams. This environment fosters continuous learning and empowers Territory Sales Directors to expand their territories effectively and build long-lasting broker partnerships.

In Chicago, Territory Sales Directors in the insurance sector typically see base salaries ranging from $90,000 to $150,000, influenced by experience and negotiation skills. Nautilus Insurance Company aligns with this range and supplements compensation with discretionary bonuses and comprehensive benefits.

Yes, this position involves significant travel within the assigned territory, balancing in-person agency meetings with virtual sessions. For those based in Chicago, being in the office four days a week when not traveling is expected, reflecting the role’s commitment to relationship-building.

Familiarity with AI and machine learning tools is increasingly important at Nautilus to support strategic decisions and pipeline prioritization. This technical edge helps Territory Sales Directors analyze market trends and optimize growth strategies in a competitive insurance landscape.

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