Managing Director of Cara Plus

Managing Director of Cara Plus

About Cara Collective

Cara Collective seeks to fuel a courageous national movement to eradicate relational and financial poverty.

Through our four entities – Cara, Cleanslate, Cara Connects, 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 Cara Plus

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.

About the Role

We have assembled a dynamic and skilled Expansion Team dedicated to turning our vision into reality. The Managing Director of Cara Plus leads this team, introducing our model to partners nationwide and representing Cara’s expansion efforts within the organization. In just five years, Cara Plus has evolved from a start-up to a respected player in the industry. The Managing Director of Cara Plus will be instrumental in guiding us to the next phase of our growth.

Cara Plus is responsible for cultivating long-term partnerships in the non-profit and for-profit sectors, based on creative problem-solving, clear communication, and thought partnership. The goal is to increase job and retention outcomes among our affiliates and develop learning opportunities for non-profits and employers that can show measurable impacts for their stakeholders. To contribute to these outcomes, the Managing Director of Cara Plus will advance initiatives that help achieve the following outcomes:

• Change the narrative of what talent looks like and how to unlock the talent within.
• Shift how organizations create opportunities for overlooked talent to obtain, retain, or advance in gainful employment.
• Produce more jobs and higher retention rates for untapped talent.
• Help position Cara Collective as a sector leader in inclusive employment, workforce development solutions, and poverty alleviation, at a local and national level. 

Qualifications 

To perform this job successfully, an individual must demonstrate evidence of success in a previous role(s).

The requirements listed below are representative of the knowledge, skill, and/or ability required:

• 7 years of experience of successfully driving strategic planning.
• 7 years of leadership and supervisory experience
• 5 years in an external facing role, managing and building multifaceted relationships.
• Demonstrated track record of developing and implementing/operationalizing large-scale initiatives.
• Demonstrated understanding and deep knowledge of Inclusive Employment and Workforce Development ecosystem is strongly preferred.
• Proven leadership and strong interpersonal and presentation skills, and the ability to generate enthusiasm and confidence from others.
• Capacity to represent Cara Plus and effectively communicate how it benefits the continued growth and impact of Cara Collective with a variety of stakeholders (internally and externally).
• Insatiable curiosity and ability to connect with people of all walks and backgrounds – a trusted executive for our affiliates and corporate partners, but also a trusted partner to the individuals we have the honor to serve.
• Highly organized and experienced in managing multiple individuals and projects, with a broad set of goals.
• Focused on outcomes over activities.
• Ability to deepen ties with a diverse team on a non-hierarchical basis.
• Ability to motivate staff and maintain consistency during periods of innovation and growth.
• Ability to prioritize critical tasks with grace and tenacious follow up in a fast-paced startup environment.
• Occasional to moderate travel necessary

Reports to

Chief External Affairs Officer

Direct Report(s)

The Managing Director of Cara Plus directly supervises the Director of National Workforce Solutions & the Senior Director of Community & Employment Strategies.

Key Responsibilities

Expansion Strategy, Execution, and Growth (40%):      

• In partnership with CEAO and CEO, evaluate, refine, and lead the overall expansion strategy, based on a strong understanding of different expansion approaches and tradeoffs.
• Develop the capability, necessary systems, tools, and processes to ensure method fidelity and replicability across different offerings.
• Stay sharp on workforce best practices and emerging business needs and challenges, based on each market.
• Support Director of National Workforce Solutions to source and assess potential affiliation partners.
• Bring learnings from Cara Plus’s national network to Cara Collective to inform our approach and impact and ensure integration within the enterprise.
• React to and evaluate opportunities for growth, ensuring that key projects and/or initiatives clearly align with Cara Plus’ strategic vision and direction.
• Working with CEAO, devise, implement, and oversee a multi-faceted revenue strategy that secures necessary capital for expansion efforts, where needed, and ensure Cara Plus has a sustainable and diverse (both earned and philanthropic) funding stream over the long-term.  
• Manage the P&L for the Cara Plus team, with support from the CEAO, to ensure operational efficacy.

Partnership Development and Cultivation (35%):         

• Work in partnership with the CEAO and Development Team to cultivate strategic funders – both before and after securing investment – to turn them into long-term partners that can advance Cara Plus’s impact and growth.
• Identify and cultivate potential channel partners to help grow both portfolios through a one-to-many approach.
• Identify strategic partners that can augment Cara Plus’s offerings with complementary skillsets or knowledge to bring greater value to our clients.
• Identify and cultivate potential clients for each portfolio, from initial outreach to close.
• Update strategic partners through informal and formal channels, by providing updates on successes, transparency on opportunities, and uplifting learnings (e.g., annual reports, regular communications, etc.)
• Work closely with our corporate partnerships and employment services team.
• Develop strong messaging that helps convey and demonstrate Cara Plus’s role in Cara Collective and the broader ecosystem – and how our portfolios differ from but complement each other (including but not limited to staff, customers, partners, funders, board members, etc.)
• Uplift Cara Collective’s brand equity by using different media to share the Cara Method, publishing thought leadership, case studies, being a guest speaker (at conferences, on podcasts, in interviews, etc.). 

Leadership (25%):             

• Hire, train, supervise and evaluate Cara Plus Department personnel and consultants.
• Participate in Cara Collective’s Leadership Teams, providing strategic and operational input to ensure we collectively reach our goals and maximize our impact.
• Meet regularly with team members to identify priorities, discuss strategies, and review ongoing projects.
• Combine innovation with disciplined execution, turning new concepts into clear, actionable plans that drive measurable results.
• Offer direction to the team that reflects sound analysis and organizational priorities, ensuring recommendations are thoughtful and context-aligned.
• Lead the team in the development of annual workplans, and support tracking progress towards goals, and making mid-course adjustments, as necessary.
• Provide professional development opportunities and guidance to team members to help strengthen their skill sets and job satisfaction.

Starting Pay Range

We take budget and starting salary very seriously. We market our roles and use a salary analysis tool called Payscale and offer competitive, market-based compensation to all employees.

This position’s expected starting pay range is $115,000 - $120,000 annually.

Benefits

Our comprehensive benefit package include:

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,

Ø 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 a 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. 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.