Remote Gig Work Strategist

About the Opportunity

Are you passionate about the gig economy and remote work culture? Do you thrive in environments that value innovation, autonomy, and long-term strategic thinking? If so, this is your moment to design impactful workforce strategies that redefine how independent professionals engage with modern work models. As a Remote Gig Work Strategist, you will lead high-level initiatives that strengthen our contractor ecosystem, align gig workflows with business goals, and empower freelance talent worldwide. This is not just a job—it’s your chance to craft the future of remote employment and champion agility across industries.

Role Overview

This role places you at the heart of operational transformation, blending human resource strategy with digital workforce planning and management. As the architect of our gig work structure, you will design, implement, and enhance strategic systems to support the growing demand for agile, project-based talent. You’ll develop programs that improve scalability, optimize freelancer utilization, and ensure smooth integration with full-time teams.

Key Responsibilities

Strategic Program Development

• Design forward-thinking gig workforce frameworks that align with company goals
• Lead cross-functional discussions to ensure freelance strategies are embedded into organizational planning.
• Develop lifecycle programs for onboarding, engagement, retention, and re-engagement of freelance professionals.

Workforce Analysis and Optimization

• Conduct labor market research and performance assessments to identify skill gaps and sourcing needs.
• Evaluate platform usage metrics to improve contractor placement efficiency
• Build talent pipeline reports to forecast gig workforce demands and align supply

Remote Experience Enhancement

• Optimize remote communication strategies to enhance contractor satisfaction and output.
• Implement inclusive policies for gig professionals to feel embedded in the broader remote team culture.
• Advocate for equity, consistency, and performance support across time zones and geographies.

Platform and Vendor Management

• Collaborate with third-party marketplaces and gig platforms to streamline sourcing processes.
• Vet tools and technologies that enhance the remote freelancer experience
• Manage compliance standards for global independent contractor relationships

Tools and Technology

This position leverages cutting-edge tools used in workforce strategy and gig resource planning. Familiarity with platforms such as Upwork Enterprise, Deel, Remote.com, or Worksome will be advantageous. You'll work with collaborative remote platforms like Notion, Miro, Slack, and Trello to manage cross-departmental projects, while utilizing analytics dashboards powered by Tableau or Power BI to inform leadership decisions.

Work Environment and Collaboration Style

You will join a highly flexible, remote-first environment that encourages autonomy, thought leadership, and continuous learning. Collaboration spans across various departments, including Operations, People Analytics, Talent Acquisition, and Compliance. Our team operates asynchronously across global time zones, allowing you to enjoy a culture of trust, accountability, and digital transparency.

Expect regular brainstorming sessions, access to mentorship circles, and thought leadership opportunities in remote workforce forums. Your work will directly support our mission to create fluid and efficient pathways for talent to thrive in the gig economy.

Qualifications and Expertise

• Demonstrated success in workforce strategy, talent operations, or remote HR leadership
• Background in managing freelance or contingent labor models, especially in distributed setups
• Experience designing contractor engagement frameworks or gig onboarding programs
• Strong analytical skills with an ability to synthesize workforce data into actionable strategies
• Working knowledge of global labor laws and freelance classification considerations
• Adept in remote-first tools and cross-functional collaboration
• A strategic mindset with excellent written and verbal communication
• Education in Human Capital Management, Business Strategy, Organizational Psychology, or a related discipline is preferred, though relevant experience may substitute

What Success Looks Like

In your first 6 months, you'll have successfully mapped our global freelance workforce, established foundational gig programs, and developed KPIs to measure agility and performance. Within the first year, you will have launched scalable gig engagement campaigns and influenced executive decisions through data-backed workforce insights. This position offers a rare opportunity to make a lasting impact, not only in optimizing gig workflows but also in shaping a new era of distributed work—a legacy, not just managing gig work, but innovating it.

Career Growth and Impact

This position opens doors to future leadership in areas such as remote work architecture, global workforce design, and talent innovation—opportunities in remote work design, workforce planning, or talent operations. As global work shifts further toward flexibility and independence, your influence will extend across organizational lines. You will build thought capital in shaping gig employment models that support fairness, agility, and innovation.

Compensation and Benefits

This role offers a competitive annual salary of $100,000, accompanied by performance bonuses tied to workforce outcomes and strategic impact. Additional benefits include:

• Fully remote flexibility with equipment provided
• Annual learning stipend to support upskilling in workforce technologies and strategy
• Access to a global coworking pass for those who prefer hybrid flexibility
• Monthly wellness credits for mental, physical, and creative enrichment
• Paid time off, inclusive of global holidays and recharge days
• Participation in quarterly innovation challenges and recognition programs

Why You Should Join Us

We are committed to redefining how people work—not just within our organization, but globally. Our approach to hiring reflects a strong belief in non-linear careers, borderless growth, and the unique value freelancers and gig professionals bring to the table. By joining our mission, you’re stepping into a role that recognizes the fluidity of modern talent and the immense potential of remote-first thinking.

Ready to Lead the Future of Gig Work?

Take charge of a dynamic, strategic role that puts you at the center of remote workforce evolution. If you have a passion for scalable solutions, human-centered planning, and future-ready strategy, this opportunity is designed for you. Your next big step starts here—apply now and shape the future of gig employment with us.