PEAK6

• Process and monitor IRA contributions, Roth conversions, rollovers, Required Minimum Distributions (RMDs), and retirement plan distributions across all retirement product types including Traditional, Roth, SEP, and SIMPLE IRAs, 401(k), 403(b), pension, annuity, and HSA/ESA accounts. • Ensure all transactions comply with IRS contribution limits, distribution rules, and eligibility requirements. • Support the preparation, review, and filing of year-end tax forms including Form 1099-R (Distributions) and Form 5498 (IRA Contributions). • Identify and resolve reporting discrepancies, process corrections, and ensure timely and accurate IRS submission through FIRE/IRIS filing systems. • Manage beneficiary designation updates, excess contribution corrections, recharacterizations, and account restriction monitoring. • Ensure all retirement account activities adhere to IRC, ERISA, and FINRA/SEC requirements. • Handle a wide range of customer inquiries and requests related to retirement accounts through email and phone, providing timely and accurate information on contribution limits, distribution options, tax implications, and beneficiary rules to enhance client satisfaction. • Continuously acquire and update knowledge of IRS regulations (Internal Revenue Code), ERISA requirements, and FINRA/SEC guidelines as they apply to retirement account operations, ensuring strict compliance and operational integrity. • Actively participate in initiatives to improve procedures by reducing risks and enhancing operational efficiencies. Provide recommendations and insights that may influence the strategic direction of retirement services operations.

• Assist in identifying, validating, and processing mandatory and voluntary corporate action events, ensuring accurate and timely completion across client accounts • Distribute corporate action notifications to internal stakeholders and clients; respond to inquiries regarding upcoming or in-progress events • Support daily reconciliation of corporate action positions and entitlements against custodian and depository records to ensure data accuracy • Collect and submit client elections for voluntary corporate actions (e.g., rights offerings, tender offers, exchange offers) within required deadlines • Assist with calculating and verifying cash and stock entitlements resulting from corporate action events • Adhere to all relevant regulatory requirements and internal policies; support audit and regulatory inquiries as needed • Identify and escalate discrepancies, missing elections, or processing errors in a timely manner to mitigate risk and financial exposure • Prepare and maintain reports on corporate action events, processing status, and outstanding items for review by senior team members

• support day-to-day operations of custody and clearing services with a primary focus on Account transfers • process account transfers through multiple methods including ACATS, Non-ACATS, and direct transfers • aid in the remediation of transfer failures or errors • ensure compliance and correct supervisory oversight of the transfer process • engage in daily processes and project-oriented work to improve account transfers

• Assist in the preparation and review of investor documentation, including agreements, disclosures, and compliance-related materials • Ensure Investor Communications requests are processed while adhering to processing deadlines • Perform regular reconciliation to ensure compliance • Work with and provide assistance to internal and external stakeholders, such as Apex internal teams, third party vendors, and customers • Be responsible for ensuring that customer inquiries are completed in accordance with service level agreement guidelines • Ensure that inquiries are responded to in a professional and timely manner and escalating issues to management • Aid in the onboarding of new clients and provide supervisory oversight of communications to ensure adherence to regulatory requirements • Review and complete supervisory oversight and provide updates to management regarding any issues with client documentation or regulatory compliance • Ensure all investor communications adhere to regulatory and compliance standards • Identify documentation/processing irregularities and outline corrective measures • Identify opportunities for improving documentation processes and workflows

• Process domestic and international wire transfers, ACH transactions, check disbursements, and journal entries in accordance with Apex policy and within required processing windows. • Review and validate Letters of Authorization s (LOAs) for journals and disbursements under the guidance of senior team members. • Identify transaction exceptions and escalate to management as appropriate. • Partner with the business (e.g., AML, Legal, and Risk teams) to resolve payment exceptions within required timeframes. • Follow Apex Cash Management SOPs and disbursement policy consistently across all transactions. • Perform self-review of own work prior to submission; participate in team quality review processes as directed. • Assist with the daily completion of supervisory checklist items, ensuring all required tasks, approvals, and signoffs are documented accurately and on time. • Respond to routine and ad hoc requests from clients and internal teams in a timely and professional manner.

• Execute day-to-day banking operations with an emphasis on accuracy and timeliness, including the processing of checks, wire transfers, and ACH transactions in accordance with Apex policy and within required processing windows • Identify transaction exceptions and escalate to management as appropriate; partner with cross-functional teams (AML, Legal, Risk, Client Services) to resolve exceptions within required timeframes, documenting all exception notes per established procedures • Follow Apex Banking SOPs and applicable regulatory requirements consistently across all transactions; seek guidance on non-standard situations and flag discrepancies or documentation gaps to senior team members • Identify and propose refinements to current operational workflows to improve efficiency and reduce risk; participate in implementation of approved process improvements under senior guidance • Perform self-review of own work prior to submission; assist with the daily completion of supervisory checklist items, ensuring all required tasks, approvals, and signoffs are documented accurately and on time • Respond to routine and ad hoc requests from clients and internal teams (Client Services, Compliance, Risk etc.) in a timely and professional manner; assess urgency, gather required information, and coordinate with appropriate teams to ensure accurate resolution within agreed service level agreements (SLAs), escalating complex matters as appropriate

• Define and execute the strategic roadmap for FOCUS’s enterprise data engineering platform, including data pipelines, ETL/ELT processes, data lakes, data warehouses, and integration frameworks • Establish architectural standards for data ingestion, transformation, storage, and access that support analytics, reporting, and AI/ML use cases • Partner with business and technology leaders to prioritize data platform investments and ensure alignment with enterprise strategy and regulatory requirements • Provide executive-level reporting on platform health, data quality, and delivery outcomes • Own the lifecycle management of FOCUS’s business application portfolio, including policy administration, agency management, billing, claims, and document management systems • Oversee vendor relationships, licensing, contract renewals, and SLA performance for all business applications • Lead application rationalization, modernization, and integration efforts to improve operational efficiency and reduce technical debt • Partner with business stakeholders to evaluate new application capabilities and drive adoption of technology solutions that improve productivity and support FOCUS’s growth strategy • Lead, grow, and develop a high-performing team of data engineers, integration developers, and business application specialists • Drive talent strategy, succession planning, performance management, and professional development across the function • Establish engineering standards, development practices, and operational KPIs for the team • Directly manages Data Engineering team leads/managers and Business Applications managers, and may directly manage senior individual contributors (e.g., Principal Data Engineers, Senior Application Analysts)

Title: Identity Access Manager (IAM) Engineer Location: Chicago, Illinois Work Type: Hybrid (remote up to 2 days per week) Employment Type: Full-time Travel: After-hours participation in shared identity-related security alert response; no business travel mentioned Job Description: WHO WE ARE We are PEAK6, a leading investment firm, using technology to find a better way of doing things. The company’s first tech-based solution was developed in 1997 to optimize options trading, and over the past two decades, the same formula has been used across a range of industries, asset classes, and business stages to consistently deliver superior results. Today, PEAK6 seeks transformational opportunities to provide capital and strategic support to entrepreneurs and forward-thinking businesses. PEAK6’s core brands include PEAK6 Capital Management, PEAK6 Strategic Capital, Apex Fintech Solutions, FOCUS, We Insure, Evil Geniuses, Poker Power, Zogo, and Bruce Markets. ABOUT THIS ROLE About the role You will own the identity layer that everything else depends on. That means making sure the right people have the right access at the right time, and that attackers cannot abuse credentials, tokens, or access paths to move through our environment. You will harden admin accounts, automate the joiner/mover/leaver lifecycle, clean up risky OAuth grants, and build the evidence trails that prove identity controls are working. You will partner closely with our US and Budapest teams to reduce account takeover risk and keep privileged access tight across PEAK6 and its portfolio companies. PEAK6 operates across financial services, broker-dealer, insurance, and technology sectors. The identity controls you build directly support regulatory obligations including the GLBA Safeguards Rule, SEC Regulation S-P, and SEC cybersecurity risk management requirements, so your work has real stakes and visibility. What you will do - Harden privileged access: deploy and validate phishing-resistant MFA for admin accounts (FIDO2/WebAuthn hardware keys or equivalent), maintain break-glass account procedures and test them on a defined cadence, and enforce least-privilege baselines across cloud and SaaS environments. - Own OAuth hygiene: audit and clean up risky or overprivileged OAuth grants across Google Workspace and connected SaaS platforms; define and enforce a restriction baseline that blocks high-risk scopes without breaking legitimate workflows. - Build and operate JML automation: design and implement joiner, mover, and leaver workflows with evidence trails; drive leaver access revocation to a consistent sub-24-hour SLA and mover access delivery within defined SLAs. - Apply risk-based access controls: define and implement stronger authentication and higher-scrutiny monitoring for risk cohorts (executives, finance, and IT admins) in partnership with the identity platform owners. - Maintain continuous IAM visibility: build and sustain reporting that makes access posture visible (stale accounts, standing privilege, risky grants, and JML exceptions) and route findings to owners with Jira-tracked SLAs. - Partner on identity-adjacent controls: coordinate with the Cloud/Platform team on cloud IAM policy, admin MFA enforcement, and least-privilege baselines across AWS and GCP environments. - Document and prove outcomes: maintain runbooks, process documentation, and evidence records that support audit inquiries, access certifications, and executive reporting. What you will bring - Experience: 5+ years in identity and access management, with hands-on depth in Okta (or a comparable identity provider), Google Workspace admin, and OAuth/SAML/OIDC. - Lifecycle automation: designing or operating joiner/mover/leaver workflows, ideally with evidence trails and measurable SLA tracking. - Grant and scope analysis: comfort auditing grants, scoping restrictions, and distinguishing legitimate from risky delegated access in Google Workspace or Microsoft 365 environments. - Privileged access patterns: familiarity with break-glass patterns, MFA enforcement policies, and admin account separation; experience with an enterprise password/secrets manager (we use 1Password). - Ticket discipline: you route findings, exceptions, and lifecycle tasks to tickets naturally and keep them clean. - Communication: able to write concise runbooks, explain access decisions to non-technical stakeholders, and produce audit-ready evidence. - Autonomy: you operate with high autonomy, surface blockers early, and do not wait to be handed a playbook. - After-hours response: willingness to participate in shared after-hours response to identity-related security alerts. Certifications (nice to have, not required) Okta Certified Professional or Administrator; GIAC GISF, GCIH; CompTIA Security+; Google Workspace Administrator; AWS Security Specialty or GCP Professional Cloud Security Engineer where cloud IAM is in scope. How we will measure success - Leaver access is revoked consistently within 24 hours with clean evidence trails. - Admin accounts have phishing-resistant MFA enforced and break-glass procedures are tested and documented. - Risky OAuth grants are identified, assessed, and resolved on a defined cadence, with a visible reduction in high-risk delegated access over time. - JML workflows deliver and revoke access within SLA with audit-ready records. - Identity posture is visible and improving: stale accounts, standing privilege, and exceptions are tracked and trending in the right direction. OUR REWARDS We offer a robust package of employee perks and benefits, including healthcare benefits (medical, dental and vision, EAP), competitive PTO, 401k match, parental leave, and HSA contribution match. We also provide our employees with a paid subscription to the Calm app and offer generous external learning and tuition reimbursement benefits. As a hybrid workforce, we offer our employees the ability to work remotely up to two days a week. Base pay offered may vary depending on job-related knowledge, skills, experience, and office location. This position also may be eligible for a discretionary annual bonus in addition to a range of health & wellness benefits, enhancing your overall compensation package. Base Salary Range $104,000-$130,000 PEAK6 is proud to be an equal opportunity employer that does not discriminate on the basis of race, color, religion, sex (including pregnancy, sexual orientation, and gender identity), national origin, age, disability, veteran status, marital status, or any other protected characteristic. Our hiring practices ensure that all qualified applicants receive fair consideration without regard to these characteristics. PEAK6 is committed to creating an inclusive and accessible workplace for all candidates, including those with disabilities. We are dedicated to ensuring equal employment opportunities and providing reasonable accommodations to qualified individuals with disabilities. If you require reasonable accommodations to participate in the application or interview process, please contact our HR department at hr@peak6.com. We will work with you to provide the necessary accommodations to ensure your full participation in our hiring process.

Collaborate with leaders to prepare financial reports, analyze results for trends, develop budgets and forecasts, and enhance financial processes to support informed decision-making across the organization.

Senior Payroll Specialist Chicago, IL Full time JR104853 WHO WE ARE We are PEAK6, a leading investment firm, using technology to find a better way of doing things. The company’s first tech-based solution was developed in 1997 to optimize options trading, and over the past two decades, the same formula has been used across a range of industries, asset classes, and business stages to consistently deliver superior results. Today, PEAK6 seeks transformational opportunities to provide capital and strategic support to entrepreneurs and forward-thinking businesses. PEAK6’s core brands include PEAK6 Capital Management, PEAK6 Strategic Capital, Apex Fintech Solutions, FOCUS, We Insure, Evil Geniuses, Poker Power, Zogo, and Bruce Markets. ABOUT THIS ROLE PEAK6 Sr Payroll Specialist 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, with an eye toward providing value to the customer. Over the years, we have built and operated several leading financial technology firms and today our team includes a proprietary trading firm, a digital wealth clearinghouse, an outsource provider of flood insurance, a value investment arm, an incubation lab, and more. As a member of the payroll team at PEAK6, you'll have a big impact on the firm by adding your payroll and analytical experience to our organization and employees in a rapidly growing environment and team. Additionally, our diverse business streams afford you the unique opportunity to grow across a variety of verticals, engaging you in unique challenges, projects, and technologies. You'll be responsible for: Process bi-weekly multi-state and multiple location payroll for exempt and non-exempt populations via Workday. Maintain payroll information by collecting, calculating, and entering data into the payroll system. Administer all payroll tax-related tasks including registering for new states, closing old accounts, and resolving all tax notices with third-party payroll systems. Support the payroll manager with year-end W-2 preparation including processing, balancing, adjustments, and amendments. Work directly with external auditors to provide requested information for annual audits. Collaborate with internal partners in Human Resources and Finance to facilitate and improve payroll processes. Partner with Treasury to ensure accurate funding requirements for payroll, taxes, benefits, and related items. Develop ad hoc financial and operational reporting as needed. Update and reconcile monthly payroll bank transactions. Participate in financial month-end close, including preparation of accruals, booking of payroll journal entries, and reconciliation of GL accounts. Utilize technology to drive continuous improvement to PEAK6's payroll processes, reports, and controls. Before you join us, you should have: 5+ years of experience in a fast-paced payroll environment exhibiting proficiency in all aspects of day-to-day payroll operations under the financial umbrella. Strong analytical and problem-solving skills with a high level of attention to detail and accuracy. Working knowledge of federal and state payroll policies, including FLSA laws, overtime, and termination regulations. Certified Payroll Professional (CPP) or Fundamental Payroll Certification (FPC) designation is a plus. Working knowledge of Workday and related reporting tools. Familiarity with general accounting principles and accounting systems; NetSuite experience is a plus. Proficiency in Microsoft Office and payroll software programs. A tech-forward approach to managing day-to-day tasks — we love to automate and make things more efficient, and so should you. Ability to handle and prioritize multiple tasks and meet deadlines in a fast-paced environment. OUR REWARDS We offer a robust package of employee perks and benefits, including healthcare benefits (medical, dental and vision, EAP), competitive PTO, 401k match, parental leave, and HSA contribution match. We also provide our employees with a paid subscription to the Calm app and offer generous external learning and tuition reimbursement benefits. As a hybrid workforce, we offer our employees the ability to work remotely up to two days a week. Base pay offered may vary depending on job-related knowledge, skills, experience, and office location. This position also may be eligible for a discretionary annual bonus in addition to a range of health & wellness benefits, enhancing your overall compensation package. Base Salary Range $79,000-$98,750