AVP, Academy Cohort Leader

Arch Insurance Group Inc.; Chicago (IL); On-site; USD 111,000 - 173,000; Full time

Benefits offered by this job

Health plans

401k match

Paid time off

Holidays & Volunteer Time

Life & disability insurance

Parental leave

Student loan assistance

Job summary

Arch Insurance Group Inc. seeks a Cohort Leader to manage the learning experience for early career underwriting associates in the MCE Academy. You will lead 18 months of intensive development, setting authority levels and shaping curriculum with innovative delivery methods.

You will coach, mentor, and provide technical leadership to accelerate time-to-authority and build a high-performing MCE underwriting organization, aligning with Arch’s growth objectives.

Qualifications

• Four-year college degree required.
• Ten years of underwriting experience in Middle Market or large commercial casualty UW.
• Technical knowledge across Property, General Liability, Commercial Auto, Workers' Comp, Umbrella, Inland Marine, and Crime.
• Experience training underwriters or learning & development tools is a plus.

Responsibilities

• Serve as the primary Academy leader, coach, and mentor for a cohort of Early Career Program underwriting associates.
• Conduct regular coaching sessions, performance discussions, and developmental feedback.
• Facilitate instructor-led training sessions, case studies, simulations, and workshops.
• Monitor development against learning objectives and authority requirements; advise readiness.
• Collaborate with supervisors on performance and progression within the cohort.
• Identify curriculum gaps and drive continuous improvement of Academy content.

Skills

Leading underwriting team

Presentation skills

Communication

Project leadership

Education

Bachelor's degree

Industry certifications (CPCU, etc.)

Tools

Learning management tools

AI-enabled delivery

Job description

With a company culture rooted in collaboration, expertise and innovation, we aim to promote progress and inspire our clients, employees, investors and communities to achieve their greatest potential. Our work is the catalyst that helps others achieve their goals. In short, We Enable Possibility℠.

Position Summary

Arch is seeking a Cohort Leader to manage the learning experience and development of early career underwriting associates within the MCE Academy, a learning program that develops technical capabilities for Arch’s Middle Market Commercial and Entertainment (MCE) underwriting organization. Delivering upon our MCE strategy, the MCE Academy will provide immersive cohort-based underwriting technical training for early career talent, bespoke onboarding for experienced new hires, and continued education and professional development for experienced MCE underwriting teams. The Cohort Leader plays a key role within the MCE Academy that will shepherd our Early Career Program Candidates through approximately 18 months of intensive learning ensuring that the associates would receive their appropriate authority levels by the conclusion of the program. This role will also take a leadership role in determining gaps in curriculum, refining content and continuous improvement of the program delivery including the use different technologies. Underwriting associates in the program will have a dotted line reporting structure to the Academy Cohort Leader. This is a unique opportunity to play a pivotal role in shaping the next generation of underwriting talent at Arch. As a Cohort Leader, you will directly influence the development, confidence, and career progression of early career underwriters while helping to build a consistent, high-performing underwriting organization. Through coaching, mentorship, and technical leadership, you will contribute to accelerating time-to-authority, strengthening underwriting excellence, and supporting Arch’s strategic growth objectives within the Middle Market Commercial business.

Responsibilities and Accountabilities

• Serve as the primary Academy leader, coach, and mentor for a cohort of Early Career Program (ECP) underwriting associates throughout their 18-month development journey, fostering professional growth, engagement, and accountability.
• Conduct regular one-on-one coaching sessions, performance discussions, and developmental feedback conversations to support participant progress, learning retention, and career readiness.
• Facilitate instructor-led training sessions, case study reviews, simulations, workshops, and cohort discussions that reinforce technical underwriting knowledge, critical thinking, and business acumen.
• Monitor participant development against established learning objectives, competency milestones, and underwriting authority requirements, providing recommendations on readiness and progression.
• Collaborate regularly with the direct reporting supervisors of each cohort member about their performance within the cohort and on the job.
• Identify curriculum gaps and lead the continuous improvement of Academy content, learning experiences, instructional methods, and assessment strategies to enhance participant outcomes.
• Leverage learning technologies, digital content, AI-enabled tools, and innovative delivery methods to improve learner engagement, scalability, and overall program effectiveness.
• Evaluate learner performance through reviews of work products, practical exercises, simulations, and on-the-job application activities, providing actionable coaching and developmental recommendations.
• Promote a culture of underwriting excellence, continuous learning, collaboration, and knowledge sharing across the Academy and broader MCE underwriting organization.
• Support the Academy’s mission of accelerating time-to-authority, developing high-performing underwriting talent, and building a sustainable pipeline of future underwriting leaders for the Middle Market Commercial business.

Required Skills and Abilities

• In depth technical knowledge of Commercial Property, Inland Marine, General Liability, Commercial Auto, Workers Compensation, and Umbrella
• Experience leading a team of underwriters
• Excellent presentation, facilitation, and communication skills
• Experience leading complex projects

Education and Experience

• Four-year college degree, preferably in Business, Economics, Risk Management, or related field.
• Ten years of prior underwriting experience in Middle Market or large commercial casualty UW business.
• Must have technical knowledge and expertise in all product lines; Property, General Liability, Commercial Auto, Workers Compensation, Umbrella, Inland Marine, and Crime.
• Candidates with prior experience as Underwriting Managers will be preferred but not necessary.
• Experience with learning and development tools a plus.
• Experience Training Underwriters a plus.
• Industry Certifications such as CPCU etc. will be a plus.

For individuals assigned or hired to work in the location(s) indicated below, the base salary range is provided. Range is as of the time of posting. Position is incentive eligible.

111,100-172,500/year

• Total individual compensation (base salary, short & long-term incentives) offered will take into account a number of factors including but not limited to geographic location, scope & responsibilities of the role, qualifications, talent availability & specialization as well as business needs. The above pay range may be modified in the future.

• multiple medical plans plus dental, vision and prescription drug coverage
• a competitive 401k with generous matching
• PTO beginning at 20 days per year
• up to 12 paid company holidays per year plus 2 paid days of Volunteer Time Offer
• basic Life and AD&D Insurance as well as Short and Long-Term Disability
• Paid Parental Leave of up to 10 weeks
• Student Loan Assistance and Tuition Reimbursement, Backup Child and Elder Care
• and more.

For Colorado Applicants - The deadline to submit your application is:

October 16, 2026

14400 Arch Insurance Group Inc.