Labor & Employment Counsel

Labor & Employment Counsel

PEAK6 is a leading investment firm headquartered in Chicago. More than 20 years ago, we were one of the first firms to develop sophisticated proprietary technology in our trading business. Today, we leverage our technical ingenuity and operational ability across a number of investment areas, spanning early- to mid-stage growth capital, operational control, trading, and sports management. Over the years, we have built and operated several leading financial technology firms and today our team includes a digital wealth clearinghouse, an outsourced provider of flood insurance, an e-sports organization, a value investment arm and more.

We pride ourselves on our relentless attention to detail and place an immense value on our client services and ownership mentality. Our team is scrappy, high energy, and dedicated to maintaining high standards, while maintaining our ability to stay cool under pressure.

As a member of our Legal team, you’ll have a big impact on the firm by providing strategic L&E legal advice across our various businesses. In this role, you will work closely with PEAK6’s HR partners to accomplish the firm’s workforce objectives while minimizing risk across various personnel matters, including performance management, reductions in force, talent acquisition, leaves of absence and accommodations, EEO/affirmative action; employee benefits, compensation and rewards, and learning and development, among other areas. The Labor & Employment Counsel will also be responsible for managing outside counsel retained to represent PEAK6 in L&E litigation and providing L&E support on key business initiatives and HR projects.

You’ll be responsible for:

  • Human Resources Support: Provide employment-related legal advice and counsel to PEAK6’s HR professionals and internal business clients on a broad range of state and federal employment law issues spanning the entire employee life-cycle, from recruiting to terminations and discipline, performance management, reductions in force, leaves of absence and reasonable accommodations, drug testing and background checks, etc.; train and advise HR on recent developments in employment law; investigate employee matters, including concerns involving misconduct, harassment, and discrimination claims, and recommend remedial actions and outcomes to internal business and senior management; ensure wage and hour compliance through overtime, meal & rest break and employee classification audits.
  • Employment Documentation: Review and draft various employment-related documents, including employee agreements, offer letters, settlement agreements, separation agreements, demand letters, and responses to the same; review and update employment policies, including employee handbooks, compensation plans and guidelines and employee communications.
  • L&E Diligence: Provide direction to and collaborate with other Legal team members on employment-related projects, including due diligence reviews for M&A transactions.
  • Internal Dispute Resolution: Draft and submit position statements, responses to information requests and other responsive submissions in state and federal administrative agencies matters; represent PEAK6 and/or its portfolio companies in mediations, arbitrations and/or lawsuits; negotiate and draft settlement and separation agreements; respond to and resolve pre-litigation demands.
  • Outside Counsel Management: Supervise outside counsel in L&E matters, including establishing case strategy and overseeing other dispute management tasks; manage outside counsel spend to budget.
  • Cross-Departmental Relationships: Develop and maintain effective working relationships and open channels of communication with key members of leadership across the broader organization.

You’ll gain loads of experience in this role but before you do, you should have:

  • Minimum 4 years of labor & employment and/or benefits practice; law firm experience required.
  • Employee benefits experience strongly preferred.
  • Excellent business judgment with the ability to provide sound legal advice, which reflects an understanding of PEAK6’s overall business objectives.
  • Ability to effectively manage outside counsel.
  • Exceptional organizational and time management skills with the ability to prioritize, coordinate and satisfy numerous competing demands.
  • Strong interpersonal skills and a commitment to professionalism and integrity.
  • Self-motivated and ability to complete matters without supervision; must be able to work independently and be execution-oriented.
  • Superior written and verbal communication skills.
  • JD degree from an accredited law school; member of the Illinois State Bar in good standing.
  • Some travel required.


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