Summary
Overview
Work History
Education
Skills
Timeline
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Elliott Pen

Toronto,ON

Summary

Strategic content and partnerships executive with 15+ years of experience driving growth across streaming, transactional, and digital platforms. Proven success leading content acquisition, licensing, and editorial strategy for global companies (Apple) and cult brands (Trailer Park Boys+), with deep expertise in the Canadian media landscape. Adept at structuring high-impact deals, forecasting performance, managing multi-million-dollar portfolios, and building compelling viewer experiences across SVOD, TVOD, and FAST/AVOD distribution. Equal parts analytical and creative, with a passion for developing bold content ecosystems that deliver cultural and commercial impact.

Overview

14
14
years of professional experience

Work History

General Manager

Trailer Park Boys+
01.2025 - Current

Transformed the cult comedy franchise into direct-to-consumer streaming platform with original content, branding enhancement, and diversified revenue streams.

  • Launched OTT platform overhaul, achieving 40% YoY growth in recurring revenue through strategic pricing and interface revamp.
  • Developed comprehensive content roadmap for originals, acquisitions, and legacy IP, fostering brand engagement beyond core audience.
  • Negotiated licensing deals with producers and catalog owners, ensuring alignment with engagement-driven ROI targets.
  • Managed P&L, budgeting, performance analytics, platform migration, subscriber CRM, and agency/vendor relations.
  • Expanded TPB+ content distribution onto AVOD and FAST platforms to sync monetization with growth goals.

Business Manager (Canada)-Video

Apple
03.2019 - 11.2024
  • Pioneered go-to-market strategies for Canadian video business, enhancing reach and revenue across transactional movies, TV, and streaming channels
  • Managed a $250M (Canadian) portfolio, achieving 4-7% annual growth and growing a 2.4M+ subscriber base
  • Achieved industry-leading conversion and churn rates for Apple TV+ through targeted marketing and customer retention initiatives
  • Spearheaded business development and partner management efforts, securing high-value contracts and fostering a growth-oriented team environment

Video Partnerships Growth Lead (International)-Video

Apple
08.2021 - 06.2022
  • Successfully launched Paramount+ in seven international markets, driving 3-5% incremental sign-ups across each region
  • Orchestrated the launch of HBO Max across multiple continents, leveraging Apple's ecosystem to boost regional engagement by 5%
  • Designed data-driven user retention strategies, achieving +4% improvements against comparable distribution partners
  • Cultivated strong relationships with international and local partners, driving subscriber growth by aligning partnership goals with market trends

ITunes Store Editor

Apple
11.2017 - 03.2019
  • Curated and merchandised transactional video content, driving engagement by implementing targeted content strategies on iTunes and the TV app
  • Collaborated with cross-functional teams to optimize content operations, resulting in a 15% increase in platform engagement metrics
  • Enhanced platform content presentation, boosting user engagement by improving navigation and visual appeal by 10%
  • Devised market-specific strategies, achieving 20% growth in engagement through targeted campaigns tailored to local user preferences

Director, Sales Planning & Analysis

Entertainment One
08.2011 - 11.2017
  • Developed and managed annual budgets exceeding $300M, streamlining slate ultimates and delivering actionable insights for senior-level strategy
  • Contributed to the negotiation and execution of multi-territory Pay TV and studio output agreements, increasing Pay TV revenues by +7% yearly
  • Designed ultimate plans and led high-stakes contract negotiations, launching key franchises such as John Wick, and substantive CanCon features to-market that increased anticipated title revenue by +10% against budget
  • Assessed acquisition projects and optimized production budgets by identifying cost-saving opportunities, resulting in a minimum $150K savings across projects
  • Led strategic initiatives for the Canadian territory, increasing digital transaction revenue by 10% and mentoring a high-performing team of 3 members

Education

BA - English

University of Toronto
Toronto, ON
01.2010

Skills

  • Content acquisition & licensing strategy (SVOD, AVOD, FAST)
  • Partner negotiation & relationship management
  • Content merchandising & editorial curation
  • Strategic planning & business operations leadership
  • Financial forecasting, P&L ownership & regression analysis
  • Churn mitigation, audience retention & engagement KPIs
  • Distribution strategy across owned platforms and third-party services
  • Data-informed decision-making & performance analytics
  • Canadian media market & regulatory expertise
  • Cross-functional collaboration & executive communication
  • Vendor management & marketing coordination
  • Deal evaluation & ROI modeling for original and acquired content
  • Team development, coaching & creative leadership

Timeline

General Manager

Trailer Park Boys+
01.2025 - Current

Video Partnerships Growth Lead (International)-Video

Apple
08.2021 - 06.2022

Business Manager (Canada)-Video

Apple
03.2019 - 11.2024

ITunes Store Editor

Apple
11.2017 - 03.2019

Director, Sales Planning & Analysis

Entertainment One
08.2011 - 11.2017

BA - English

University of Toronto
Elliott Pen