Lead Strategist (NYC or Toronto)

About Us

At #paid, we’re on a mission to empower creators to do what they love—create. Our marketplace connects vetted creators with some of the world’s most iconic brands, like McDonald’s, Samsung, and Disney, fostering authentic collaborations that drive real business results. We’ve built a marketplace that solves big challenges in the creator ecosystem, from fair pricing to algorithmic matching and content usage rights, ensuring every partnership is seamless and impactful.

With our proprietary technology and an unwavering commitment to trust and transparency, we’re revolutionizing the way brands and creators come together to make magic. Rated #1 for customer support and managed services, #paid is leading the creator marketing space. Through innovative technology and a team of ambitious humans, we're transforming the future of the creator economy.

The Role

#paid is looking for a strategic, creative, and visionary leader to join our team as a Strategy Lead. In this high-impact role, you'll work closely with the Head of Strategy to shape the future of our Strategy team—elevating the way we pitch, win business, and build for scale. You’ll lead strategic responses to large RFPs and help design scalable materials and frameworks that position #paid as a best-in-class partner in the creator economy.

You’ll collaborate across departments—from Sales and Paid Media to Client Experience and Marketing—to deliver bold, insights-driven solutions that solve real client problems. With your strategic thinking, compelling storytelling, and creative chops, you’ll help drive 7-figure deals and cement #paid as a go-to partner for brands.

• Lead strategic development of proposals and RFP responses using insights and creativity
• Collaborate with Sales, Paid Media, Client Experience, and Measurement to build well-rounded proposals
• Present strategic recommendations and creative narratives to clients and agencies
• Own pitch work for large RFPs and Focus Accounts
• Build trusted relationships with key clients, guiding them through our process and platform
• Review and elevate proposals developed by Strategists, providing constructive feedback and coaching
• Audit and organize team workflows to increase proposal effectiveness and scalability
• Work closely with the Head of Strategy to define proposal tiers and support team enablement
• Guide team members in crafting strategic, proactive recommendations for client growth
• Build pitch templates, playbooks, and industry-specific materials for Sales enablement
• Develop vertical-specific strategies and proactive packages for tentpole moments
• Contribute to award-winning work by championing culturally relevant ideas in partnership with Marketing
• Co-create thought leadership and educational materials, including keynote presentations and inspiration decks
• Continuously identify opportunities to improve internal workflows and elevate strategic outputs

• Confidently lead high-stakes proposal work with a mix of storytelling, data, and strategy
• Provide actionable mentorship and feedback to support strategist growth and development
• Balance creativity with business needs, translating insights into real client solutions
• Thrive in a fast-paced, remote-first environment and keep projects on track with minimal oversight
• Stay on the pulse of trends in media, creators, and marketing—and bring fresh thinking to the table

• Strategic communicator: You’re a natural storyteller with strong writing and presentation skills
• Creative thinker: You’re inspired by culture and able to connect creative ideas to business outcomes
• Mentor mindset: You love helping others grow and are energized by sharing feedback, tools, and frameworks
• Highly collaborative: You know how to build relationships and navigate cross-functional teams
• Builder and optimizer: You see opportunities to scale and improve, and you don’t wait for permission to start

• We are a group of passionate and thoughtful people working together to fundamentally change the way brands are built while empowering creators to make a living doing what they love
• We are growing quickly! Plus, #paid is the highest-rated platform on the popular G2 Crowd software review website
• We have all the fun perks you’d expect—flexible vacation policy, competitive vision, dental and health benefits, team offsites and working hubs, and socials (yes, even remotely!)
• We invest in our team members, with L&D budgets and RRSP/401K Matching Programs
• We are proud of our culture and care about it deeply—we live by our team values and are always trying to make #paid a better company today than it was yesterday
• We empower learning through meaningful career progression and the autonomy to test new ideas

Equal Employment Opportunity

#paid is an equal opportunity employer and as such, we do not discriminate on the basis of race, colour, religion, sex, sexual orientation, gender identity, national origin, age, disability, or any other characteristic protected by applicable laws.

We are dedicated to growing a diverse team of highly talented individuals and creating an inclusive environment where everyone feels empowered to bring their best and authentic selves to work.

If you require any accommodations during the recruitment process, whether it be alternate forms of material, accessible meeting rooms, etc., please let us know and we will work with you to meet your needs.