Sales Director (Greater Chicago Area)

As a Director of Sales at Employment BOOST, you will oversee and support a substantial portfolio of active client accounts across our outplacement, coaching, and Careerology programs. This role blends relationship management with proactive growth activity, ensuring every client receives a high-touch, white-glove experience while also identifying new opportunities to expand our reach across the Employment BOOST, Careerology, and broader Maelstrom Global Ventures ecosystem.

Like any small, fast-moving business, this is a role where you’ll do a bit of everything, from supporting existing clients to generating new business and jumping in wherever needed to keep things running smoothly.

You’ll act as the connective tissue between clients, coaching teams, sales, and operations, making sure organizations stay engaged, informed, and supported throughout the year. This role requires both thoughtful client stewardship and the ability to drive new business through targeted outreach, cold calls, and cross-selling conversations.

Key Responsibilities

Client Relationship Management

• Serve as the day-to-day contact for a large portfolio of active accounts.
• Maintain regular check-ins to ensure clients feel supported, informed, and engaged.
• Respond promptly via email, phone, and virtual meetings.
• Build long-term trust by understanding each client’s needs, program usage, and goals.
• Conduct on-site customer visits as needed to strengthen relationships.

Retention & Success Monitoring

• Track account engagement, identify risks early, and intervene proactively.
• Gather feedback to inform continuous improvement of outplacement, coaching, and Careerology offerings.
• Surface opportunities for expanded usage or program enhancements.

New Business Development & Growth

• Generate new customers through cold calls, warm outreach, follow-ups, and targeted prospecting.
• Identify sales opportunities across multiple product lines: outplacement, coaching, Careerology, workshops, and employer branding services.
• Cross-sell across all brands within the Maelstrom Global Ventures family.
• Support pipeline building by nurturing dormant accounts back into active engagement.

Systems & Documentation

• Maintain accurate notes, tasks, and follow-ups in Salesforce.
• Track client outcomes, satisfaction trends, and participant milestones.
• Ensure all activity is documented to support sales forecasting and operational visibility.

Who You Are

• Relationship-driven, consultative, and great at building trust.
• Highly organized, with strong follow-through and the ability to manage many accounts simultaneously.
• Comfortable balancing client service with new business development.
• Strong communicator with an empathetic, professional presence.
• Motivated by growth, impact, and helping organizations thrive.
• Comfortable collaborating across multiple teams in a fast-paced, mission-driven environment.

Qualifications

• Bachelor's degree preferred.
• 7–15 years of experience in sales, account management, client success, or a related field.
• Experience in career services, HR services, staffing, or recruitment is ideal but not required.
• Background in professional services or consultative selling preferred.
• Demonstrated experience generating new business through outreach and cold calls.
• Comfortable selling multiple product lines and navigating a diversified services portfolio.
• Strong communication skills and CRM proficiency (Salesforce).
• Additional language proficiency is a plus.

What We Offer

• Rapid growth opportunities across Employment BOOST and Maelstrom Global Ventures.
• Extensive onboarding, training, and sales development support.
• Company-sponsored coaching and professional development.
• Competitive salary + performance-based bonus.
• Company-sponsored healthcare plan (medical, dental, vision, life).
• Company-sponsored 401(k).
• Generous PTO and flexible scheduling.
• Hybrid/remote work environment.

Employment BOOST is an Equal Opportunity Employer. Employment BOOST does not discriminate on the basis of race, religion, color, sex, gender identity, sexual orientation, age, physical or mental disability, national origin, veteran status or any other basis covered by appropriate law.