Agency Development Specialist at Clearcover

| Chicago | Remote
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Our Value Proposition:

Clearcover is a venture-backed technology start-up disrupting the trillion dollar legacy insurance market. We’ve focused on building products that create confident, happy customers - and we’re flourishing. We believe in putting our people first, paying them well and working together to solve tough problems. If you’d like a high-growth opportunity with an award-winning company, let’s chat. ­­

What is an Agency Development Specialist?

We are looking for an experienced Agency Development Specialist to help us bring Clearcover insurance product solutions to evolving agency distribution channels.  

The ideal candidate for this role will bring a sales operations background in meeting the needs of various insurance distribution channels (call center, field/brick and mortar, digital, etc.).  You’ll have experience streamlining and executing training, communication, and go-to-market strategies, while also being able to tailor training solutions to meet the needs of different audiences. You’ll have experience developing and facilitating virtual agency training (and possibly in-person training). You’ll be able to effectively sell the Clearcover value proposition to drive adoption for our product offerings.

You’ll be data-savvy and be able to identify trends from our distribution channel managers and agent advocates, and deliver updated training solutions as a result. 

You’ll also have a great eye for detail and can ensure our training and communications have consistent messaging and information so we can help support our distribution channel leaders grow the business. 

As an agency support specialist, you’ll be expected to work across each of our functional areas,  understand our products, sales experience, and operational processes and then represent them externally.

 Primary Responsibilities

  • Training Development – Assist with management of agency training and support needs. Collaborate with Brand, Product, and Customer Advocacy teams to develop content and supporting media assets that meet the needs of multiple agency types. 
  • Training Coordination & Delivery – Facilitate and deliver training sessions for new and existing agents.
  • Agency Communications and Marketing – Support and deliver our agency communication and marketing strategies across multiple channels. 
  • Cross-Functional Collaboration – Work effectively with members of customer service, brand, compliance, operational teams to effectively support the channels and identify trends to guide improving training and communication materials. 
  • Agency Development – Serve a point-of-contact for best practices (i.e. agency guide and knowledge base materials) to optimize performance and profitability. 
  • Agency Onboarding & Compliance – Work with operational teams to onboard new agencies.
  • Sales Support - Handle escalated agency support questions and design operational processes that can support agencies at scale.

What are our must haves?

  • You’re a great communicator. You’re able to effectively train and communicate the features and key value propositions of our product.
  • You’re highly cross-functional.  You know how to simplify operational processes and work across multiple functional areas to address issues head-on.
  • You’ve fluent working across various insurance distribution channels.  You have experience working with various agency types.
  • You’re detail oriented- You feel comfortable diving into numbers to identify trends and propose training solutions. You can make decisions in an ambiguous context without having all the numbers. 
  • You have great relationship skills.  You’re able to build effective relationships, both internally and externally, and can navigate complex relationships and issues.
  • You understand insurance compliance.  You’re familiar with agency licensing and appointment regulations and supporting operational processes
  • You’re flexible.  You have the ability to work amidst ambiguity and adapt as we grow and expand.  
  • Occasional travel as needed: up to 20%, as needed.
  • P&C license preferred 

But wait, there’s more:

As a people-first company, your health and well-being is a priority at Clearcover. While we do offer medical (and cover the vast majority of the premium), dental, vision (and cover 100% of those premiums) and 401K (we contribute 3% even if you contribute nothing), we’ve curated a stack of perks and benefits that stretch beyond the expected. With over half of our employees remote to the Chicago HQ office, we paved the way for flexible work locations and continue to offer this flexibility. Our people also have access to unlimited vacation, monthly mental health workshops, discounted gym memberships, equity in the company and an annual bonus program. Plus, if Clearcover is available in your state, you could have access to an employee discount on auto-insurance! Excited to learn more? Complete the application below!

Clearcover is an Equal Opportunity Employer (EOE) that welcomes and encourages all applicants to apply regardless of age, race, color, religion, sex, sexual orientation, gender identify and/or expression, national origin, disability, veteran status, marital or parental status, ancestry, citizenship status, pregnancy or other reasons prohibited by law.

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Technology we use

  • Engineering
    • KotlinLanguages
    • PythonLanguages
    • RubyLanguages
    • ScalaLanguages
    • ReactLibraries
    • Ruby on RailsFrameworks
    • PostgreSQLDatabases
    • SnowflakeDatabases


33 W Monroe, Chicago, IL 60603

What are Clearcover Perks + Benefits

Clearcover Benefits Overview

Clearcover offers a comprehensive benefits package along with a number of perks in an effort to support our employees and their families. We work to align our perks with our core values and empower our employees to balance work and their personal lives.

Volunteer in local community
Intracompany committees
Daily sync
Open door policy
Team owned deliverables
Team based strategic planning
Pair programming
Open office floor plan
Dedicated Diversity/Inclusion Staff
Unconscious bias training
Hiring Practices that Promote Diversity
Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
Disability Insurance
Dental Benefits
Clearcover covers 100% of the employee's dental benefits.
Vision Benefits
Clearcover covers 100% of the employee's vision benefits.
Health Insurance Benefits
Clearcover's health insurance plan is with United Healthcare with a range of plans including PPO, HDHP and HSA. If you elect an HSA, we cover your out-of-pocket deductible as an HSA contribution.
Life Insurance
Clearcover offers voluntary life insurance.
Pet Insurance
Wellness Programs
Onsite Gym
Team workouts
Virtual yoga classes offered twice per week!
Mental Health Benefits
Monthly Mental Health Workshops 1:1 Counseling sessions with a LCSW Live, virtual yoga, 3 x week Unlimited vacation Meeting-free Fridays Access to supportive mental health community in Slack
Retirement & Stock Options Benefits
401(K) Matching
Clearcover provides employees with a 401(k) contribution of 3% of an employee's annual gross pay.
Company Equity
Performance Bonus
Annual bonus based upon company performance
Child Care & Parental Leave Benefits
Child Care Benefits
Dependent Care FSA allows you to put away pre-tax dollars towards daycare expenses for dependents under the age of 13.
Generous Parental Leave
Clearcover offers parental leave for new parents after birth or adoption of a child. Full-time employees that have been employed for six months are eligible for six weeks of paid Parental Leave.
Flexible Work Schedule
Clearcover has flexible start and end times based upon your position and your team.
Remote Work Program
Our remote work program includes work from home Full-time remote for specific positions, as well as work flexible remote work for most position.
Family Medical Leave
Employees who have been with the company for 12 months are eligible for 12 weeks of family medical leave. Other policies apply to those here less than 12 months.
Return-to-work program post parental leave
Vacation & Time Off Benefits
Unlimited Vacation Policy
Paid Volunteer Time
Paid Holidays
Paid Sick Days
Employees receive 5 paid sick days each year.
Perks & Discounts
Casual Dress
Commuter Benefits
Clearcover's offers Commuter Benefits, employees can save an average of 30 percent off their commute by contributing pre-tax dollars.
Company Outings
Clearcover celebrates company wins by organizing quarterly outings to a variety of places like the Escape Room, Punchbowl Social and Bounce.
Game Room
Clearcover's game room includes a state-of-the-art ping pong table, custom Nerf gun wall and a Pop-a-Shot to let employees enjoy breaks between work.
Stocked Kitchen
We send snack boxes monthly since we are virtual.
Home Office Stipend for Remote Employees
We offer a one-time $250 stipend to set up your work from home office. Use this for anything that will support your work from home arrangement.
Professional Development Benefits
Job Training & Conferences
Clearcover offers a stipend to each employee to invest as they choose in their own professional development.
Diversity Program
Lunch and learns
Cross functional training encouraged
Promote from within
Time allotted for learning
Online course subscriptions available

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