Director of Recruitment (Chicago)

A growing financial services organization in Chicago is seeking a relationship-driven Director of Recruitment to join their team. The total compensation for this position ranges from $100,000–$150,000, depending on experience, and offers the opportunity to take ownership of proactive recruiting and talent development initiatives that directly support the organization’s continued growth. This highly visible role is ideal for someone who thrives on building genuine professional relationships, creating opportunities through networking, and identifying talented individuals before they are actively searching for a career change. The successful candidate will be comfortable engaging with executives, business owners, sales executives, and community leaders while developing a strong pipeline of prospective talent. This is a unique opportunity for someone who is entrepreneurial, persistent, and energized by connecting people with meaningful career opportunities. A comprehensive benefits package is offered but not limited to medical and dental insurance as well as generous PTO.

Responsibilities of the Director of Recruitment:

• Develop and maintain a strong pipeline of prospective sales executives through networking, referrals, direct outreach, events, professional organizations, and other creative sourcing strategies.
• Establish and nurture relationships with business leaders, executives, community professionals, referral partners, and other influential contacts to generate new recruiting opportunities.
• Conduct meaningful conversations with prospective candidates to understand their career goals, motivations, leadership potential, entrepreneurial mindset, and overall fit.
• Partner with established sales executives to identify future staffing, growth, partnership, and succession needs while proactively developing talent aligned with those objectives.
• Guide prospective candidates through the career exploration and recruiting process, maintaining relationships with individuals who may require extended cultivation before making a career transition.
• Collaborate with internal recruiting and talent partners to identify professionals for opportunities beyond the traditional sales executive role and connect qualified individuals with appropriate teams.
• Work alongside leadership to provide insight into talent trends, strengthen recruiting strategies, expand the organization’s professional network, and support long-term growth initiatives.

Qualifications of the Director of Recruitment:

• 3–8+ years of experience in recruiting, talent acquisition, business development, relationship management, sales, or a related field.
• Demonstrated ability to proactively source talent, develop passive candidate relationships, and build a consistent pipeline through outbound efforts.
• Proven success cultivating professional networks and generating introductions, referrals, and new business or recruiting opportunities.
• Strong interpersonal skills with the ability to establish credibility and build relationships with executives, business owners, sales executives, and other senior professionals.
• Excellent communication, organization, follow-up, and relationship-management skills with strong attention to detail and sound judgment.
• Self-motivated and entrepreneurial with the persistence to develop relationships over time, the confidence to initiate conversations, and the ability to work independently.
• Experience within financial services, professional services, consulting, sales, or another relationship-driven environment is preferred, along with a professional presence and strong networking skills.

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