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Tastylive

Real-time trading insights and education platform

Director, Business Operations - Operational Excellence

Full-TimeUpdated on 10/23/2026
$120k - $170k+ 15-20% discretionary performance bonus
Expert
Chicago, IL, USA
HybridHybrid role based in the Chicago office.
Business & StrategyBusiness Operations

About the job

Requirements
  • A qualified candidate has 8 or more years of work experience, including meaningful experience in an operations, operations strategy, or shared services role.
  • Lead complex cross-functional projects from diagnosis through implementation and measured impact in an operational context, such as tooling rollouts, process redesign, or cost structure changes.
  • Build and maintain cost-to-serve or unit economics models and use them to make concrete tradeoff recommendations to leadership.
  • Design KPI frameworks and reporting systems that operational teams use to run their business.
  • Evaluate, scope, and help implement new operational tools and systems, working closely with Engineering and Data.
  • Present analyses that help leadership make difficult decisions, including being prepared to disagree when data points in a different direction.
  • Communicate clearly with audiences ranging from the CEO and board to frontline operational managers.
  • Work hands-on with financial models, customer metrics, and operational dashboards.
  • Engage with distributed operational teams and motivate people to adopt new ways of working.
Responsibilities
  • Identify manual, duplicative, or broken workflows that slow operational teams and lead the build or rollout of tools and systems to address them.
  • Partner with Engineering, Data, and operational leaders to scope, prioritize, and implement automation that reduces cost and improves speed or quality.
  • Own the roadmap for operational tooling investments, including making build-versus-buy recommendations to leadership.
  • Define and maintain a cost-to-serve model across operational functions, down to the channel, segment, or customer level.
  • Identify costs that are out of line with value delivered and build business cases for changes to staffing, process, or technology.
  • Partner with Finance to connect operational metrics to P&L impact and inform leadership about tradeoffs.
  • Design KPIs, dashboards, and reporting cadences for operational teams to manage day-to-day work.
  • Work with the data team to build reporting infrastructure that gives leadership and frontline managers a shared source of truth in near real time.
  • Establish weekly and monthly business reviews that turn data into decisions and accountability.
  • Lead process redesigns across multiple operational teams from root-cause diagnosis through implementation and measured impact.
  • Support new product or market launches by building operational playbooks covering staffing models, service-level agreements, tooling, and performance targets before launch.
  • Take on special projects supporting the CEO's and operating leaders' priorities.
  • Contribute to company strategy, market evaluation, and planning processes with the Business Operations team.
  • Support partnership or M&A evaluations when operational integration or cost-to-serve diligence is needed.
Desired Qualifications
  • Prior experience in an operations, shared services, or operations strategy role, internally or in consulting.
  • In an operations, shared services, or operations strategy role, direct ownership of tooling and cost to serve rather than advising on them externally.

About the company

Tastylive is a real-time online financial network that provides live streams, educational content, and actionable trade ideas for options, stocks, and futures. It streams over 100 original segments with more than 20 on-air traders, available seven days a week. The platform blends entertainment with education by delivering practical market insights and strategies from experienced traders. Its goal is to help traders navigate complex markets with confidence through reliable, timely information and ongoing support.

Company Size

51-200

Company Stage

Series C

Total Funding

$1B

Headquarters

Chicago, Illinois

Founded

2011

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Simplify's Take

What believers are saying

  • FINRA's June 4, 2026 margin rule overhaul favors tastylive's trader-education positioning.
  • tastytrade announced immediate compliance readiness for FINRA's new intraday margin standards.
  • 2025 live events in London, Milan, and U.S. cities widen tastylive's acquisition funnel.

What critics are saying

  • FINRA fined tastytrade $200,000 on May 29, 2026 for 71 unreported complaints.
  • FINRA fined tastytrade $850,000 on July 22, 2026 for best-execution failures.
  • Tom Sosnoff left in September 2025; tastylive risks becoming a commoditized IG marketing asset.

What makes Tastylive unique

  • IG Group-owned tastylive pairs brokerage, media, and education in one retail-trading funnel.
  • Tom Sosnoff built a distinctive options-first brand around mechanical probability and volatility trading.
  • Seven-day live programming and archived segments keep audience engagement higher than static finance media.

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Benefits

  • Health Insurance
  • Dental Insurance
  • Vision Insurance
  • Life Insurance
  • Mental Health Support
  • Commuter Benefits
  • 401(k) Retirement Plan
  • Gym Membership
  • Paid Holidays
  • Paid Vacation
  • Paid Sick Leave
  • Wellness Program