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Career Coach

May 23, 2026

The Career Coach works as part of the program team to identify needs, deliver outcomes and facilitate successful enrollment in training, job placement, and retention activities for Connections to Success Participants. The Career Coach serves as primary coach for the development of participant resumes, cover letters, interview skills and career guidance, while working closely with the Job Developer and Education Specialist. This work will be conducted both in the community and inside prisons and jails with participants during and after the Connections to Success Personal and Professional Development training (PPD) classes. In addition, the Career Coach will serve as a Life Transformation Coach (LTC) for a small number of participants. The LTC is responsible for cultivating relationships with participants before, during and after they have completed the PPD training. LTC are participant centered, knowledgeable about community resources and act as strong advocates for participants. LTCs maintain regular contact with participants and work with them to achieve both short- and long-term goals identified in their Life Plan. The LTC provides resources, accountability and encouragement as participants pursue their goals. LTCs inspire, engage, and support participants at all stages of their transformation without judgment or prescription using coaching practices and reinforcing PPD curriculum. Essential Functions & Responsibilities <ul><li>Research local market and industry trends to identify career opportunities</li><li>Initiates and cultivates relationships with participants, building strong partnerships for career advancement</li><li>Communicates the benefits of successful resume building, interview techniques and other career advancement skills to participants</li><li>Works with participants to prepare, revise and update resumes</li><li>Works with Job Developer and Education Specialist to understand employer needs and makes appropriate participant referrals</li><li>Screens participants for employment placement and works as a liaison between participants and the Job Developer and Education Specialist to ensure participant is work ready </li><li>Works with program team to deliver employment outcomes and ensure job retention</li><li>Coordinates employment related functions including mock interviews, hiring events, tours, Career Connect, and Employer Panels</li><li>Screens participants for eligibility for participation in skill-based training</li><li>Transports participants (when necessary) to PPD class and interviews</li><li>Ability to track, manage and use data in a timely, accurate manner across a variety of database systems for grant reporting purposes</li><li>Completes all required reports and summaries on time and submits to Project Manager</li><li>Collaborates with Program Team on Connect Group activities</li><li>Engage, participate, and contribute to all assigned activities that further the goals of CtS in a variety of settings to include offices, partner organizations, correctional institutions and more </li><li>Maintain confidentiality of all participant information</li><li>Works one-on-one with participants at all stages of program participation to empower, challenge and support transformation; utilizing PPD curriculum and coaching approach to support cognitive skill development in everyday situations</li><li>Provides accountability and actionable support to participants as they pursue goals outlined in their Life Plan, offering individualized and non-prescriptive support</li><li>Makes timely and appropriate referrals to meet basic needs, advance educational goals and promote employment success; understands scope of service and refers out as needed</li><li>Supports participants in job search activities including applications, resume development, interview preparation and transportation to employers</li><li>Completes surveys, case notes, attendance records, updates employment and education information promptly when participants’ status changes. All interactions documented within 48 hours </li></ul>Experience & Qualifications <ul><li>Bachelor’s degree in the social sciences, business, or a related field, or equivalent, experience preferred but will consider experience in lieu of degree.</li><li>At least 1 year experience in direct service to a high-risk population preferred</li><li>Knowledge of labor market trends, and major private and public employers in the area</li><li>Strong interpersonal skills</li><li>Excellent verbal communication skills and ability to persuasively present program and participants needs/outcomes to audiences</li><li>Excellent written communication skills</li><li>Experience in skill-based training programs a plus</li><li>Knowledge of local workforce systems and WIOA</li><li>Ability to work some nights and weekends </li></ul>Relationships <ul><li>Reports to: Project Coordinator</li><li>Internal Relationships: All Staff, Volunteers, Mentors, Participants</li><li>External Relationships: Participants, Educational Institutions, Employers, Training Providers, Volunteers, Guest Speakers, Partner Organizations, Referring Agencies, Community Organizations and Government Agencies </li></ul>Additional Information This position is full-time, hourly, non-exempt position. Employees will be eligible for full benefits including health, retirement, and vacation benefits on the first of the month following hire date. We invite potential candidates with incarceration/ criminal justice system history to apply. This job description in no way states or implies that these are the only duties to be performed by the employee(s) incumbent in this position. Employees will be required to follow any other job-related instructions and to perform any other job-related duties requested by any person authorized to give instructions or assignments. Starting Salary Range $39,000.00-45,000.00 annually based on experience Application Instructions Interested applicants, please submit a cover letter and resume to Helen J. Hurley Regional Program Director at hhurley@connectionstosuccess.org, with job title in the subject line. Connections to Success is an Equal Employment Opportunity employer and seeks to recruit and retain a talented and diverse group of Employees. To this end, the Organization believes that diversity is important to the success of the Organization. Decisions regarding recruiting, hiring and promotions are made based on individual qualifications related to the requirements of the position.

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...