SENIOR EMPLOYER STRATEGY SPECIALIST

SENIOR EMPLOYER STRATEGY SPECIALIST

About Cara Collective

Cara Collective seeks to fuel a courageous national movement to eradicate relational and financial poverty. Through our three entities – Cara, Cleanslate, and Cara Plus – we engage job seekers, employers, and other organizations across the country to break the cycle of poverty through the power and purpose of employment.

At present, we produce 1,000 jobs each year; however, our results don’t just end with employment. Today, we take the insights gained over the past 30 years to equip other organizations and employers with practices to help build a more inclusive economy. Learn more at www.caracollective.org.

About the Cara Collective External Affairs Department

The External Affairs Department aims to advance Cara Collective’s mission by amplifying our brand, building strategic partnerships, attracting resources and investments, and driving public awareness and practice change. Through coordinated efforts across communications, development, and external engagement, the team ensures our message resonates with stakeholders and strengthens our impact. With a commitment to storytelling, relationship-building, and thought leadership, External Affairs connects Cara Collective to the broader community, fueling growth and deepening our influence in the workforce development field.

About the Role

This role sits within External Affairs on the Cara Plus team. Cara Plus is the expansion arm of Cara Collective, which works with organizations around the country. Our work creates inclusive employment pathways by distilling Cara Collective's best practices and tailoring them to each organization's needs. Cara Plus does this through two distinct portfolios: 

1.       Workforce Development. Where we work with non-profits and workforce development programs to help them deploy sustainable pathways to self-sufficiency in their communities.

2.       Inclusive Employment. Where we help employers shift their practices to improve how they recruit, hire, cultivate, and advance untapped talent.

The Senior Employer Strategy Specialist role sits within the Inclusive Employment portfolio. They will be responsible for working closely with employers to help them deploy inclusive workplace practices and support the necessary organizational transformation for meaningful change to take hold.

Qualifications

We’re seeking a Senior Employer Strategy Specialist who thrives at the intersection of strategy, employer engagement, and practical implementation. This is a hands-on role for someone who can support employers in adopting inclusive practices, translating ideas into actionable steps, and helping organizations make measurable progress.

The ideal candidate is a skilled facilitator, trusted advisor, and creative problem-solver who can work directly with organizations to implement meaningful change. They balance analytical thinking with strong interpersonal skills and can navigate both the business and community contexts of their work. This role is best suited for someone energized by managing multiple projects, building strong relationships, and supporting teams and organizations in achieving results.

 Requirements

• Experience working with companies to implement inclusive practices or other organizational change initiatives.
• Experience consulting or advising organizations, with the ability to translate concepts into practical solutions.
• Skilled facilitator, able to lead trainings, workshops, or one-on-one sessions with both an accessible and commanding presence.
• Strong project and portfolio management skills, able to track multiple initiatives and ensure quality outcomes.
• Excellent relationship-building skills, comfortable engaging stakeholders at all levels of an organization.
• Able to work independently and collaboratively within a small, fast-moving team, balancing strategic thinking with hands-on execution.
• Experience tracking metrics and using data to inform strategy and measure progress.
• Quick learner – can work in a small, fast-moving team and take on roles from strategy to implementation.

This is an exciting opportunity to help create and maintain the kind of space where Cara Collective’s mission—to break the cycle of poverty through the power and purpose of employment—can truly thrive.

Key Responsibilities

The Senior Employer Strategy Specialist will be responsible for leading implementation of our current Inclusive Employment offerings, including:

Employer Training Programs (60%): Training Programs can consist of multi-month engagements with groups of employers to help them increase their capacity to implement inclusive talent practices. As part of this work, you will:

• Work with the Inclusive Employment team to refine existing or develop new programming and content
• Facilitate program content and lead participants through activities that promote group learning
• Support pilot development with employers that are motivated to test and scale inclusive employment practices across their organizations
• Supplement company learning with tailored company coaching sessions, relating content to their specific environment
• Provide critical project management support, including maintaining constant communication and collaboration with clients and partners
• Collect, organize, and analyze key data from employers to fuel our learning and help the team maintain progress towards our KPIs

One-on-one Technical Assistance (25%): The Inclusive Employment team also provides companies one-on-one technical assistance outside of formal program settings, including offerings such as our "Short Advisory Session", which provide one hour of consulting to companies on scoped topics. As part of this work, you will:

• Support with individual company consulting and technical assistance as they implement inclusive employment practices and processes
• Provide research, communication, and documentation support to ensure proper preparation and follow up activities are conducted

Portfolio Team Strategy & Collaboration (15%): You will be a member of a small, agile team that is continuing to (1) adapt and grow our offerings and (2) root our work more deeply in the enterprise to achieve our broader mission. As such, you will support broader portfolio activities and:

• Work with the Inclusive Employment team to refine existing or devise new products or services to drive the inclusive employment strategy forward
• Collaborate with other team across Cara to promote cross-learning and to deepen engagement across corporate partners by supporting referrals to and from our inclusive employment team to other External Affairs and Impact teams

Reports To

Associate Director of Employer Strategy

Direct Reports

N/A

Workplace Type & Team Culture

Cara Collective has a strong team culture that values collaboration, communication, and camaraderie. We believe in the power of working together in person, which is why we expect our employees to be onsite at one of our Chicago-based locations multiple days each week. For this role, that means a minimum of three days in the office. This commitment to in-person collaboration fosters a sense of belonging and teamwork among our employees, creating a supportive and dynamic work environment. Regular travel to partner locations throughout the Chicagoland area is required, along with some occasional out-of-town travel for thought leadership, conferences, or other convenings related to Inclusive Employment or CVI initiatives.

We consistently measure staff satisfaction through employee surveys and have found that year over year, the vast majority of staff agree that Cara Collective is a great place to work and grow. This high level of employee satisfaction reflects our dedication to creating a positive and fulfilling workplace for all members of our team.

Starting Pay Range

This position’s expected starting pay range is $65,000-$68,000.

Benefits

Cara Collective is proud to offer a comprehensive, competitive benefit package, with options designed to help you make the best decision for yourself, your family, and your lifestyle. Available benefits ae based on eligibility. Our Total Rewards package includes a variety of medical and dental plans, vision coverage, disability and life insurance, 401(k)

Ø Medical, Dental, Vision Plans

Ø Basic Life Insurance

Ø Long Term Disability

Ø Personal Technology Reimbursement

Ø Starting with 17 Vacation Days, 8 Sick Days, 14 Paid Holidays

Employee Paid Benefits

Ø Pre-Tax Medical Flexible Spending Account

Ø Pre-Tax Dependent Care Account

Ø Pre-Tax Transit & Parking Options

Ø Supplemental Life and AD&D Insurance

Ø Short-Term Disability Insurance

Ø 401(k) Retirement Plan (employer match up to 4% upon hire & immediately vested)

As of this posting, we annually review our benefit offerings to meet our employees’ needs and be competitive in the market. All listed benefits offerings at the discretion of the employer.

Equal Opportunity Employer

Cara Collective is committed to creating a diverse work environment and is proud to be an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. Cara Collective does not discriminate on the basis of race, color, national origin, sex, gender identity, religion, sexual orientation, age, disability, parental status, veteran status, or any other protected status under applicable laws. We encourage individuals of all backgrounds to apply. If you are a qualified candidate with a disability, please email us at kboelkens@carachicago.org if you require reasonable accommodation to complete this application.