Regional Sales Leader, Central

The Guardian Life Insurance Company of America

Chicago (IL)

On-site

USD 102,000 - 120,000

Full time

14 days+
Application generator

Don’t send a generic resume — generate a resume and cover letter tailored to this exact role.

Get past ATS filters

Job summary

Guardian Life Insurance Company of America in Chicago seeks a Group Benefits Regional Sales Leader to drive profitable growth through broker-led sales and retention strategies. You will lead, coach, and develop a high-performing team, aligning with underwriting, pricing, and product partners to expand market share.

The role emphasizes coaching large accounts, recruiting early-career talent, and delivering on top and bottom-line growth. Travel is modest; base pay and incentives are included.

Qualifications

  • 8+ years of group benefits industry experience.
  • An understanding of relevant functional areas including Distribution, Underwriting, Finance, Pricing, Product Development, Marketing, Operations, Risk Management, and Administration.
  • Advanced degree or equivalent experience preferred.
  • Familiarity and/or experience with group benefits product line preferred.
  • Required industry licensing within 90 days of date of hire and maintain license through Continuing Education requirements.

Responsibilities

  • Develop a sales plan to achieve corporate, financial, and market goals to maximize profitability, growth, retention, and increased market share.
  • Be a champion of bringing in new talent and developing their skills and capabilities in order for colleagues to grow their careers at Guardian.
  • Take a hands-on approach, particularly with larger accounts, coach reps in consultative selling, partnership with Underwriting, finalist presentations, and closing opportunities on new business.
  • Work collaboratively with internal cross-functional partners to achieve corporate, financial, and market objectives.
  • Identify, recommend, and champion process improvement and organizational initiatives to positively influence outcomes.
  • Cultivate strong external relationships with top brokers and distribution partners.
  • Support the general well-being of the broker and client relationships for the development and growth of Guardian sales and client retention.

Skills

Leadership
Strategic planning
Broker relations

Education

Advanced degree or equivalent experience

Job description

Guardian is seeking a Group Benefits Regional Sales Leader in the Chicago market who will be responsible for driving and executing a profitable growth strategy through ongoing sales and retention with brokers. The role will cover groups of 2–2,000 lives with a primary focus down market. The Regional Sales Leader will do this by leading, coaching, and developing a high-performing team. The role will work closely with leadership and internal partners to leverage data when delivering on Guardian’s promise to inspire well‑being, managing top and bottom‑line growth strategies, and identifying opportunities to increase broker value. Success of this role will be largely dependent on the achievement of financial results, internal and external relationships, and the ability to recruit high potential, early‑career talent.

You Will:
  • Develop a sales plan to achieve corporate, financial, and market goals to maximize profitability, growth, retention, and increased market share.
  • Be a champion of bringing in new talent and developing their skills and capabilities in order for colleagues to grow their careers at Guardian.
  • Take a hands‑on approach, particularly with larger accounts, coach reps in consultative selling, partnership with Underwriting, finalist presentations, and closing opportunities on new business.
  • Work collaboratively and create followership with internal cross‑functional partners (Underwriting, Client Management, Product, Finance, etc.) to achieve corporate, financial, and market objectives.
  • Identify, recommend, and champion process improvement and organizational initiatives to positively influence outcomes.
  • Cultivate strong external relationships with top brokers and distribution partners.
  • Support the general well‑being of the broker and client relationships for the development and growth of Guardian sales and client retention.
You Have:
  • 8+ years of group benefits industry experience; and proven leadership experience within group benefits.
  • An understanding of relevant functional areas including Distribution, Underwriting, Finance, Pricing, Product Development, Marketing, Operations, Risk Management, and Administration.
  • Advanced degree or equivalent experience preferred.
  • Familiarity and/or experience with group benefits product line preferred.
  • Required industry licensing within 90 days of date of hire and maintain license through completing Continuing Education requirements.
Soft Skills:
  • Exercise sound judgment and integrity in a changing, matrixed, and fast‑paced environment.
  • Drive discipline and hold people accountable to achieving results.
  • Persuasive presentation and communications skills with ability to influence people over whom there is no direct authority.
  • Enable and support a culture of inclusivity by treating all employees, customers, and vendors with dignity and respect.
  • Exude confidence, positivity, and proactivity.
Location and Travel Requirements:

The successful hire will be based in Chicago, IL. Approximately 20% travel associated with the position.

Salary:

Salary: $120,000. The salary reflected above is a good faith estimate of base pay for the primary location of the position, which is to be based in Chicago, Illinois. The salary for this position ultimately will be determined based on the education, experience, knowledge, and abilities of the successful candidate, as well as market factors and business need. This position is also covered by a Guardian sales incentive compensation plan, making the successful candidate eligible to receive sales incentives subject to the terms and conditions of the applicable plan, in addition to base pay. The anticipated total annual compensation range inclusive of base pay and sales target incentive compensation is $316,800 to $366,000.

Our Promise

At Guardian, you’ll have the support and flexibility to achieve your professional and personal goals. Through skill-building, leadership development and philanthropic opportunities, we provide opportunities to build communities and grow your career, surrounded by diverse colleagues with high ethical standards. Inspire Well-Being As part of Guardian’s Purpose – to inspire well‑being – we are committed to offering contemporary, supportive, flexible, and inclusive benefits and resources to our colleagues. Explore our company benefits at www.guardianlife.com/careers/corporate/benefits. Benefits apply to full‑time eligible employees. Interns are not eligible for most Company benefits.

Equal Employment Opportunity

Guardian is an equal opportunity employer. All qualified applicants will be considered for employment without regard to age, race, color, creed, religion, sex, affectional or sexual orientation, national origin, ancestry, marital status, disability, military or veteran status, or any other classification protected

Get your free, confidential resume review.

or drag and drop your file here.

Similar jobs

Similar jobs worth comparing

Group Benefits Sales Executive, Advisory Market - Northern California
Group Benefits Sales Executive, Advisory Market - Northern California

The Guardian Life Insurance Company of America • California (MO)

Hybrid
USD 64,000 - 86,000
Sales Analyst, Premier Market
Sales Analyst, Premier Market

Guardian Life • Chicago (IL), Northern (KY)

On-site
USD 54,000 - 81,000
Client Executive, Advisory Market - Northern California & Pacific Northwest
Client Executive, Advisory Market - Northern California & Pacific Northwest

The Guardian Life Insurance Company of America • California (MO)

Hybrid
USD 134,000 - 185,000
Group Benefits Sales Representative - Pittsburgh, PA
Group Benefits Sales Representative - Pittsburgh, PA

Guardian Life • Pennsylvania

On-site
USD 36,000 - 44,000
Client Manager Associate - Chicago, IL & Indianapolis, IN
Client Manager Associate - Chicago, IL & Indianapolis, IN

Guardian Life Insurance • Chicago (IL)

On-site
USD 50,000 - 82,000
Group Benefits Sales Representative - Pittsburgh, PA
Group Benefits Sales Representative - Pittsburgh, PA

The Guardian Life Insurance Company of America • Pennsylvania

Hybrid
USD 38,000 - 46,000
Company benefits
Incentive compensation
Sales Analyst, Premier Market
Sales Analyst, Premier Market

The Guardian Life Insurance Company of America • United States

On-site
USD 54,000 - 81,000
Benefits for full-time employees
Hybrid work arrangement
Sales Representative, Premier Market - Denver, CO
Sales Representative, Premier Market - Denver, CO

Guardian Life • Denver (CO)

On-site
USD 36,000 - 44,000
Client Manager Associate, Premier Market - Great Lakes
Client Manager Associate, Premier Market - Great Lakes

The Guardian Life Insurance Company of America • Michigan

Hybrid
USD 50,000 - 82,000
Work from home
Chicago Regional Benefits Growth Leader
Chicago Regional Benefits Growth Leader

The Guardian Life Insurance Company of America • Chicago (IL)

On-site
USD 102,000 - 120,000