ZipRecruiter

Log In

2

Remote Contract Leadership Development Jobs in Windsor, CT

Fisher Agencies

Remote Entry-Level Leader

Mansfield, CT · Remote

$142K/yr

This role provides an excellent opportunity to develop leadership skills while working remotely in ... Training & Development * Work From Home * Life Insurance (Basic, Voluntary & AD&D)

Aflac Incorporated

Contract Development Analyst

Windsor, CT · Remote

$60K - $80K/yr

Aflac, a Fortune 500 company, is an industry leader in voluntary insurance products that pay cash ... If the role is remote, there may be occasions that you are requested to come to the office based on ...

next page

Showing results 1-20

All JobsContract Leadership Development JobsRemote Contract Leadership Development JobsRemote Contract Leadership Development Jobs in Windsor, CT

Remote Contract Leadership Development information

See Windsor, CT salary details

$43.3K

$103.3K

$155.8K

How much do remote contract leadership development jobs pay per year?

As of Aug 25, 2026, the average yearly pay for remote contract leadership development in Windsor, CT is $103,265.00, according to ZipRecruiter salary data. Most workers in this role earn between $80,600.00 and $117,500.00 per year, depending on experience, location, and employer.

What is a remote contract leadership development professional?

A Remote Contract Leadership Development professional is someone who designs, facilitates, and manages leadership training and development programs for organizations, working remotely on a contract basis. They may create training materials, lead virtual workshops, and coach leaders to improve their skills in areas such as communication, team building, and strategic thinking. Because they work remotely and on contract, their services are flexible and adaptable to different organizations' needs. They often collaborate with HR departments and senior management to align leadership development initiatives with business goals.

What are some common challenges faced in a remote contract leadership development role, and how can they be effectively addressed?

One of the main challenges in a remote contract leadership development role is building strong relationships and trust with clients and participants without in-person interactions. Effective communication, proactive engagement, and employing various virtual collaboration tools are essential to overcome this. Additionally, adapting leadership training content to suit remote delivery and maintaining participant engagement can be demanding, so leveraging interactive digital platforms and regular feedback mechanisms is crucial. Time management and self-motivation are also important, as you may be working across multiple clients and time zones.

What are the key skills and qualifications needed to thrive in remote contract leadership development, and why are they important?

Thriving in Remote Contract Leadership Development requires a strong background in organizational development, leadership coaching, and adult learning principles, often supported by a relevant degree or certifications such as CPLP or ICF. Familiarity with virtual collaboration tools, learning management systems (LMS), and assessment platforms is typically necessary. Exceptional communication, adaptability, and self-motivation set individuals apart in this remote, client-facing role. These skills and qualities ensure effective leadership training delivery, client satisfaction, and the ability to drive measurable development outcomes in a flexible, digital environment.

What is the difference between Remote Contract Leadership Development vs Remote Contract Training Specialist?

AspectRemote Contract Leadership DevelopmentRemote Contract Training Specialist
CredentialsLeadership certifications, coaching experienceTraining certifications, instructional design
Work EnvironmentStrategic planning, leadership coachingContent creation, delivery of training programs
Employer & Industry UsageCorporate, educational, nonprofit sectorsCorporate, e-learning, professional development
Search & Comparison IntentLeadership development, executive coachingTraining delivery, instructional design

Remote Contract Leadership Development focuses on enhancing leadership skills and coaching executives or teams, often involving strategic planning. In contrast, Remote Contract Training Specialist emphasizes designing and delivering training programs, typically with a focus on instructional methods. Both roles require relevant certifications and are used across various industries, but they serve different organizational needs.

What job categories do people searching Remote Contract Leadership Development jobs in Windsor, CT look for?

The top searched job categories for Remote Contract Leadership Development jobs in Windsor, CT are:

Remote Contract Leadership Development jobs near you
Infographic showing various Remote Contract Leadership Development job openings in Windsor, CT as of June 2026, with employment types broken down into 50% Full Time, and 50% Part Time. Highlights an 100% Remote job distribution, with an average salary of $103,265 per year, or $49.6 per hour.

Entry-Level Management - Leadership and Development Track

Mansfield, CT • Remote

Fisher Agencies
Insurance Services • 11 - 50 employees
Learn more about Fisher Agenciesexternal

$142K/yr

Full-time

Posted 6 days ago

Job description

At The Fisher Organization, we represent the New England division of American Income Life, a leading provider of supplemental benefits. Our mission is simple but powerful: to protect and empower working families, especially those in labor unions, credit unions, and associations, through high-quality benefits and exceptional service

We're proud to build a legacy of leadership, growth, and service, and we're looking for passionate individuals to grow with us.

Position: Entry-Level Manager - Leadership Development Track (Remote)

If you're driven, coachable, and ready to fast-track your career, this could be your the big opportunity you have been searching for. In this role, you'll lead and mentor a team, contribute to sales strategy, and develop into a high-impact leader. All while working remotely 

This is more than a job-it's a launchpad for your leadership journey

What You'll Do:

  • Coach and support a team of agents to reach and exceed performance goals
  • Lead by example through hands-on involvement in sales and service
  • Monitor performance data and help your team strategize for success
  • Organize and lead virtual training and onboarding sessions
  • Keep communication strong, positive, and motivating across your team
  • Thrive in a fast-paced, fully remote environment

Requirements

  • Natural leadership ability and a desire to help others succeed
  • Great communication and people skills, especially over Zoom and other digital platforms
  • Strong organization, multitasking, and time-management abilities
  • A self-starter mindset with a results-driven approach
  • Experience in customer service, sales, or team leadership is a plus
  • No degree or experience required but preferred
  • Motivated go-getters who want to grow personally and professionally
  • Tech-savvy professionals who are comfortable in virtual environments

Benefits

What We Offer:

  • Accelerated career path, promotions based on merit, not tenure
  • Clear roadmap to leadership roles. Potential to advance within 60 days
  • Mentorship and support from top industry leaders
  • Flexible, remote work setup
  • 100% commission-based compensation with no cap on earnings
  • Opportunities for national and international travel
  • A culture that celebrates initiative, impact, and growth

Ready to build a career with unlimited potential-while helping families protect what matters most?
Apply now and start your leadership journey with The Fisher Organization.

Apply