Senior Manager / Director, Product Marketing Contract · Embedded with PayPal Ads · Go-to-Market, Product Marketing & Sales Enablement About TOMORROW TOMORROW is where the best retail operators and advisors come together to unlock what's next for the world's leading retailers and digital platforms. That operator background is not our backstory; it is the TOMORROW difference. That is why our clients are the largest retailers and digital commerce businesses in the world: Walmart, LVMH, Ahold Delhaize, Wesfarmers, Flipkart, Uber, PayPal. Our global footprint is not decorative, it is part of our DNA - we operate across six continents because the best thinking on digital transformation does not come from one market's experience. And neither does the best talent. If you have run out of patience for work that asks less than what you have to give, this is where that changes. TOMORROW is built by restless operators who became advisors - people who saw what was possible and couldn't look away. If that sounds like you, let's chat. The engagement Tomorrow is hiring a Senior Manager / Director level independent contractor to embed with PayPal Ads as a product marketing lead. PayPal Ads is productizing its vast first-party transaction data across PayPal, Venmo, and Honey – connecting advertisers and agencies with one of the most powerful commerce audiences in the world. The team operates with startup speed and energy inside a globally recognized fintech brand, and is growing fast. This role is the narrative and go-to-market engine for PayPal Ads. You will crystallize the platform’s value proposition, translate product capabilities and campaign performance into stories that resonate with advertisers and agencies, build the proof point library that arms sales, and ensure the team can use it all effectively. The ideal candidate is a senior operator who thrives in ambiguity, moves fast, and is equally comfortable setting strategy and doing the work. This is a hands-on role for people who like to get their hands into the product, the team, and the mission. Engagement details • Type - Independent Contractor • Time commitment - Approximately 30–40 hours per week, with flexibility • Duration - H2 2026, with potential to extend • Location - Remote; East Coast hours strongly preferred • Working hours - North American business hours required • Reports to - Head of PayPal Ads Go-to-Market • Start - ASAP What you’ll work on • Crystallize the PayPal Ads pitch: distill a fast-moving, multi-surface ad platform into a clear, differentiated value proposition for advertisers and agencies; own the strategy and creation of external-facing content that drives product understanding and adoption among advertisers, and make it immediately deployable by sales. • Vertical-specific messaging & pitch customization: adapt positioning by client vertical so sales teams show up with tailored narratives that connect PayPal Ads’ unique audience and data assets to each advertiser’s specific business objectives. • Sales collateral & field tools: translate positioning into practical sales assets, one-pagers, pitch materials, and talk tracks that help teams sell through products and campaigns; brief the design agency on execution of final materials. • Build the case study & proof point library: develop and maintain a structured, searchable library of campaign results, client wins, and performance proof points; make it easy for sales to find, use, and customize for any conversation. • Enable & train sales: create the story and train sales teams on how to sell it to ensure every sales conversation is sharper and consistent. • Drive launch excellence: lead go-to-market planning and execution for new PayPal Ads products and features, from value prop definition and positioning through sales enablement, collateral, and activation; own the story from strategy through market. • Champion market intelligence: synthesize customer feedback, industry trends, and competitive dynamics to continuously sharpen positioning and inform product and GTM priorities; be the team’s lens on the market. About you • 10 - 15+ years of experience in product marketing, go-to-market, or sales enablement in ad tech, digital advertising, retail media, or a high-growth technology platform - you have been in the room where the pitch gets built and the room where it lands. • A natural storyteller and strong writer - you can take complex product capabilities, transaction data, and campaign performance and turn them into narratives that make advertisers and agencies lean in. • Experienced across the full GTM spectrum - positioning, messaging, launch planning, case study development, sales collateral, and field enablement and able to lead and execute each of these workstreams independently. • Comfortable with white space - you can break down ambiguous problems into clear workplans, move without a playbook, and build the infrastructure others will scale from; a bias towards action is non-negotiable. • A senior operator who is willing and able to pair strategic thinking with hands-on execution; this role requires someone who is energized by building and doing, not just directing. • A strong cross-functional collaborator who can drive alignment across product, sales, and an external design agency without direct authority, and who communicates with clarity at every level of the organization. Bonus points • Deep experience at a scaled ad tech platform - DSP, SSP, retail media network, or commerce media environment, where you owned GTM for complex, data-driven advertising products (e.g. The Trade Desk, Amazon Ads, Criteo, Instacart Ads, or equivalent). • Agency or client services background - you understand how media agencies and brand advertisers evaluate, plan, and buy; this fluency on both sides of the table makes your positioning sharper and your sales enablement more effective. • Experience leading or contributing to a product content platform - editorial calendars, written thought leadership, product explainers, where you were as comfortable at the keyboard as in the boardroom. • Based near New York City, where office is located. How we work Four behaviours show up in every project, every team, every conversation. • Operators who love to help: We start with the end in mind. Where are you going, and how do we help you go further? We solve real problems and craft practical solutions and we take the lead on the journey together. • Candid, with a strong point of view: Being effective advisors means having the courage to take a view. We seek and give great feedback. We care enough to be honest - that’s what helps clients (and each other) move forward. • Humble and inclusive - hearing before solving: We may be experienced, but we’re always learning. We respect the people we meet on every journey, and we embrace what makes each of us different. • Never satisfied with “good enough”: We push harder and dig for new perspectives. We’re tuned to where digital commerce is going next - and our solutions are built to actually help clients break through. Apply Click Apply on this posting to submit through our Deel application portal. Equal opportunity TOMORROW is committed to building a team that reflects the diversity of the retailers and customers we serve. We welcome applicants of every background, identity, and experience. If you need any adjustments to take part in our hiring process, just let us know - we want to make this work for you. TOMORROW · Digital Retail Delivered