Full-Time

Senior Director

Brand & Product Marketing Strategy

Tastylive

Tastylive

51-200 employees

Real-time trading insights and education platform

Compensation Overview

$195k - $230k/yr

+ Discretionary Performance Bonus + Stock Purchase Options

Chicago, IL, USA

In Person

On-site in Chicago, IL; no remote work.

Bachelor's

Category
Growth & Marketing (2)
,
Required Skills
Market Research
Communications
Social Media

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Requirements
  • 12–15 years in leading marketing with real depth across product marketing, brand, and creative
  • 5–8 years leading teams including managers, with a track record of building and developing people
  • Experience in a regulated industry, strongly preferred in financial services or fintech
  • FINRA familiarity and willingness to obtain a Series 24 are a plus
  • A portfolio that shows high-quality creative shipped at scale and the judgment to hold a quality bar under deadline pressure
  • Fluency with brand measurement and the ability to connect brand work to business outcomes without overclaiming
  • Bachelor’s degree required
Responsibilities
  • Build a real product marketing discipline where there is ad-hoc coordination. Own the launch calendar, gate process, and cross-org dependencies so every launch runs from one master plan.
  • Translate customer segmentation into positioning that speaks to our highest-value targets. Own a live competitor matrix; in derivatives, outdated positioning is a liability.
  • Set cross-product adoption targets on every launch and produce messaging enablement, so every customer-facing team carries consistent differentiation.
  • Track launch on-time rate, gate adherence, cross-product adoption, and message consistency across customer-facing surfaces.
  • Own messaging and editorial standards across owned social and communications. Hold a brand voice consistent on every surface we control.
  • Own communications, PR announcements, brand moments, and the narrative around launches. Amplify executive voices and turn earned moments into owned content.
  • Build and operate this function
  • Track owned channel engagement, audience growth, and share of voice.
  • Own the creative quality bar and the production pipeline end to end. Compress cycle time by pairing internal leads with outside resources, scaling partner capacity to meet demand without quality drift.
  • Move to a testing framework. Run testing methodology for owned and brand creative and feed structured learnings into the Performance team’s paid-creative work.
  • Track creative production volume, on-time delivery rate, and brief-to-launch cycle time.
  • Co-own the advertising review workflow with Compliance (FINRA advertising review, including options of disclosure requirements). Build review into the timeline as a standing gate, not a surprise.
  • Own brand-health measurement: awareness, sentiment, and share of voice, reported to leadership quarterly.
  • Track brand health, compliance, first-pass approval rate, and review cycle time.
  • Support revenue, new accounts, and ARPU by contributing to the upper-funnel quality and message that make them move.
  • Support CAC and conversion by raising the quality of the message and creative that prospects encounter before they ever reach a performance channel.

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 Jobs

Simplify's Take

What believers are saying

  • Tastylive launched intraday margin coverage on June 4, 2026, expanding retail trading access.
  • The July 2026 show calendar stayed active, signaling daily programming and audience retention.
  • Free courses and over 120 segments keep top-of-funnel acquisition cheap and recurring.

What critics are saying

  • FINRA fined Tastytrade $850,000 on July 23, 2026 for best-execution failures.
  • FINRA fined Tastytrade $200,000 on June 2, 2026 for 71 unreported complaints.
  • Tastylive depends on personality-led education; Tom Sosnoff left in September 2025, weakening the franchise.

What makes Tastylive unique

  • Tom Sosnoff and ex-floor traders teach live options tactics seven days weekly.
  • Tastylive combines free streaming, courses, and brokerage distribution across YouTube, Roku, and Apple TV.
  • The brand owns niche credibility in probability-driven options education, not generic market commentary.

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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

Employee Stock Purchase Plan

Performance Bonus

Phone/Internet Stipend

Pet Insurance

Charitable Donation Matching

Flexible Work Hours