Jobs at PEAK6

Coordinate enterprise-wide learning and management development programs across PEAK6 and its subsidiaries. Manage program calendars, logistics, communications, participation tracking, reporting, and continuous improvement. Source, vet, and oversee external training vendors, facilitators, coaches, and content providers, including contracts, budgets, deliverables, and performance. Administer Workday Learning, maintain courses and learning paths, manage compliance training, and provide completion reports. Partner with HR leaders and business stakeholders on talent development initiatives.

Founding Head of Product responsible for defining and shipping an AI-powered agentic platform across insurance and BPO operations. The role owns the transformation roadmap, embeds with operating teams to identify high-impact workflow improvements, and delivers products that improve margins and unit economics. Responsibilities also include evaluating acquisition targets, shaping platform strategy, prototyping AI solutions, and deploying systems into live enterprise environments.

Lead the sourcing, underwriting, negotiation, and closing of acquisitions for an insurance BPO roll-up. Build the acquisition pipeline through insurance networks, brokers, and owner outreach; assess AI-driven transformation opportunities with engineers; structure transactions; support integration; and shape the long-term roll-up strategy.

Manage the Delta One portfolio, including trading activity, balance sheet and RWA utilization, funding costs, portfolio financing, and P&L reporting. Build and maintain pricing, position-management, and attribution tools using Python and SQL. Partner with Risk, Finance, Operations, and banking partners on margin efficiency, capital movement, cash management, and financing decisions. The role also supports expansion of the Middle Office function across PEAK6 entities.

Execute complex listed and OTC trades across equity options, index/ETF products, and other derivatives. Manage OTC market structure and counterparty relationships, maintain broker and sell-side relationships, analyze trading flows and performance, use proprietary tools and AI-driven analytics, and provide market research and color to the trading team.

Manage the AI Strategies group's operating cadence and own projects including acquisition diligence, new business planning, and process implementation. Build models, memos, and presentations for leadership decisions, use AI tools to improve productivity, and develop toward leading transformations, functions, or businesses. The role is an onsite apprenticeship based in Austin for a highly driven, detail-oriented recent graduate or early-career professional.

Develops and administers a firm-wide compliance program for an options market-making and proprietary trading broker-dealer. Responsibilities include maintaining policies, conducting risk assessments and compliance reviews, overseeing surveillance, managing employee disclosures and information barriers, supporting regulatory filings, maintaining FINRA CRD records, coordinating vendors, and delivering compliance training. The role requires strong knowledge of SEC, FINRA, and CBOE rules, options trading, project management, and securities licensing.

Supports and integrates SaaS and cloud-based business applications across PEAK6. Responsibilities include architecting cloud offerings, managing technology investments, implementing SaaS integrations, provisioning applications, developing support processes and documentation, evaluating software platforms, and enabling business operations through technology. The role also provides white-glove employee support and requires strong communication, problem-solving, and cloud administration skills.

Manages daily office and facilities operations, including upkeep, reception, supplies, kitchen programs, vendor coordination, budgets, inspections, repairs, conference rooms, events, safety procedures, and employee onboarding support. Supervises facilities staff and vendors, tracks inventory and expenses, maintains office standards, and serves as the local escalation point for operational issues. The role is fully onsite in New York, begins at 7 a.m., and requires a hands-on approach.

Supports high-volume accounting operations by posting cash receipts, reconciling payments and bank activity, resolving discrepancies, processing refunds and chargebacks, maintaining transaction records, and assisting with audits and financial controls. Collaborates with billing, underwriting, claims, customer service, internal teams, customers, and external partners. The role requires strong accuracy, organization, analytical problem-solving, communication, and discretion when handling sensitive financial information.

Own consumer app and web product strategy, roadmap, requirements, analytics, research, experimentation, releases, and outcomes. Lead retention and activation measurement, app store optimization, cohort analysis, qualitative user research, and cross-functional prioritization. Partner directly with the founder, Product Owner, engineering, design, marketing, and instructor operations while personally executing product strategy in a lean startup environment.

Own product roadmaps and execution for trading tools, collaborate with traders and engineers to define user stories and acceptance criteria, prioritize backlogs, run usability testing, track KPIs, and drive product improvements to boost desk performance and efficiency.

Build and manage a new student poker education business at UT Austin. Responsibilities include recruiting students, developing a community, hosting or teaching one to two weekly sessions, hiring and leading student teachers, securing venues and campus partners, executing marketing, and tracking participation and growth. Candidates should be entrepreneurial, charismatic, organized, comfortable recruiting strangers, interested in startups and leadership, and experienced enough to play, deal, and host poker games.

Lead end-to-end bi-weekly multi-state payroll processing in Workday Payroll across multiple entities; ensure compliance with federal/state laws; manage payroll tax registrations and notices; serve as SME for payroll inquiries; drive year-end W-2 processing, reconciliations, reporting, GL entries, and process improvements; partner with HR, Finance, auditors, and system implementations to maintain controls and automate payroll workflows.

Own and run finance shared services including Accounts Payable and T&E, administer Ramp and NetSuite, manage a small AP/T&E team, ensure controls and compliance, produce reporting and dashboards, and lead process improvement and AI-driven automation projects to increase efficiency and accuracy.

Process bi-weekly multi-state payroll via Workday for exempt and non-exempt employees; manage payroll tax registrations and notices; support year-end W-2s and external audits; reconcile payroll bank transactions and GL accounts; partner with HR, Finance, and Treasury; create ad hoc reporting and drive payroll process improvements and automation.

Lead product roadmaps and execution for internal HR, Finance, and support tools. Partner with cross-functional teams to define user stories, prioritize backlogs, measure impact, run usability testing, and iterate on AI-enabled and SaaS solutions to improve performance and efficiency.

One-week, fully funded trading bootcamp for undergraduate juniors introducing options trading. Participants attend educational sessions, work on deploying a real-world trading strategy, receive trader feedback, and network with firm leaders. Program offers hands-on projects, mentorship, and consideration for future full-time roles.

Hands-on convertible bonds trader focused on volatility-driven strategies. Trade convertibles emphasizing embedded optionality (gamma, vega, skew), hedge exposures in real time, identify relative-value opportunities versus equity, options, and credit, build and challenge pricing/valuation views, analyze issuer credit and fixed-income terms, and collaborate with senior traders on position sizing, risk limits, and book construction.

Structured summer trading internship designed to introduce women to options trading and volatility. Interns will learn option theory, execute trades, own a project end-to-end, rotate with traders, pitch ideas, receive mentorship and feedback, attend speaker sessions, and participate in team events. Program requires relocation to Chicago; travel and housing are provided.