Join Our Team

Why Work at DSWD?

At DSWD, careers are more than jobs – they’re opportunities to grow, connect, and make a lasting impact. Since our founding in 2009, we’ve built a firm grounded in relationships, open communication, and genuine care for both our clients and our team. Our philosophy is simple: success is shared when people are supported.

We’re committed to helping our team members thrive both professionally and personally. Our flexible work options include fully remote, hybrid, and in-office arrangements at our Frankfort and Chicago, IL locations. Supported by modern technology, these options empower our teams to stay connected, collaborate effectively, and work in ways that suit their lifestyles – helping everyone feel supported and equipped for success.

Growth at DSWD is about more than numbers. It’s about people, purpose, and opportunities that last. When you join DSWD, you’re joining a firm that is committed to supporting your success today while preparing you for your future.

Join Our Team
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Benefits We Offer

We know that when our people are supported, our clients and communities thrive. That’s why DSWD offers a comprehensive benefits package designed to care or you, your family, and your future.

  • Competitive base salary plus annual discretionary bonus
  • Comprehensive benefits package including firm-paid medical and life insurance, as well as dental, vision, and an employee assistance program
  • Optional life insurance, short-term and long-term disability, and expanded EAP program through ADP PEO
  • Flexible time off
  • HSA and FSA options
  • Monthly cell phone stipend
  • 8.5 annual holidays plus firm closure from 12/25 to 1/1
  • 401(k) with annual firm-funded Safe Harbor contribution
  • Internal and external education opportunities (CPE)
  • Society or organizational membership reimbursement
  • Casual dress office
  • Hybrid work arrangement with a blend of in-office/remote work flexibility that best serves both our team and our clients

Life at DSWD

Life at DSWD is defined by one philosophy: people first. We know that the foundation of our success is not just in serving clients, but in supporting the people who make our work possible.

Beyond the office, we believe in giving back. Through our nonprofit, DSWD Fosters Hope and community involvement, we encourage our people to pursue philanthropic passions and create positive change.

But just as important as the work we do is the environment we create. Team members describe
DSWD as a place that “feels more like family than co-workers,” with camaraderie, respect, and a
healthy dose of fun woven into daily life. Our leadership team is committed to caring for people while strategically guiding the firm forward – ensuring that DSWD remains a place where careers and relationships flourish.

At DSWD, flexibility isn’t just a policy, it’s part of who we are. We’ve built a culture that balances
professional achievement with personal wellbeing, creating a workplace where people feel supported, seen, and valued.

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Together at DSWD

Embracing Your Flexibility. Empowering the Future.

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