HighlightTA

Identify and validate new growth opportunities, develop business cases, and support strategic expansion initiatives. | Experience in strategic growth, market validation, partnership development, and cross-functional collaboration at a senior level. | HighlightTA is the on-demand talent team for Zipline. About Zipline Zipline is a well-funded, rapidly growing SaaS company transforming how frontline teams work. We empower the world’s leading brands across retail, healthcare, logistics, and beyond to connect, align, and inspire their employees—from headquarters to the front lines. Our customers consistently give us best-in-class NPS and CSAT scores, and they rave about how Zipline makes their teams’ lives easier and their businesses more effective. We’re also a fully remote company, with passionate employees across the U.S., Canada, and around the globe. About the Role Zipline is entering its next phase of growth—expanding into new verticals, unlocking new revenue motions, and exploring AI-enabled and partnership-led opportunities beyond the current product footprint. The Director of Product, Strategic Ventures owns Zipline’s future growth portfolio. This role is accountable for identifying, validating, and de-risking new sources of revenue—including vertical expansion, horizontal product extensions, AI-powered commercial offerings, and strategic partnerships—before they are scaled into core product teams. This is a senior, high-impact product leadership role operating ahead of the roadmap. You will work across Product, Design, Engineering, Data, Sales, CS, RevOps, and Corporate Development to turn ambiguity into conviction. You are responsible for deciding what to bet on, why, and when, not for owning long-term execution of core product pillars. You report to the SVP of Product and act as a force multiplier for pillar Product Managers by supplying validated opportunities—not competing roadmaps. What You’ll Do Own the Strategic Growth & New Ventures Portfolio Identify, frame, and size new growth opportunities across: ○ New verticals and customer segments ○ Horizontal product extensions and modules ○ AI-powered commercial offerings ○ Strategic partnerships and ecosystem plays Maintain a transparent, prioritized portfolio of short-, mid-, and long-term bets Define clear investment theses, success criteria, and kill / scale decision points Build rigorous business cases, including TAM, ROI, cost-to-serve, and GTM implications Lead 0→1 Discovery & Validation Run early-stage discovery to understand unmet customer needs and market gaps Partner with Design to prototype and test value propositions quickly Collaborate with Engineering and Data to validate technical feasibility (without owning core platform design) Execute controlled pilots and proof points that produce executive-ready evidence For select initiatives, this role may temporarily own scoped delivery during incubation to validate customer value and commercial viability. This ownership is explicitly time-bound, limited in scope, and transitions to a core product team once the opportunity is proven Make clear recommendations to scale, pivot, partner, or stop. Drive Vertical & Market Expansion Assess and prioritize new verticals with strong commercial and strategic fit Define vertical-specific problem spaces, workflows, and value propositions Partner with Sales and CS on early customer engagement and GTM validation Recommend market entry strategies, sequencing, and success metrics. Shape AI-Enabled Growth Opportunities (Without Owning Core AI Systems) Identify AI-powered opportunities that unlock new revenue, differentiation, or market access Partner with pillar PMs and Data Science to validate feasibility and customer value Focus on commercial potential and market fit, not long-term ownership of AI platforms or intelligence layers Transition validated AI opportunities into appropriate product pillars for scaling Partnerships & Corporate Development Support Collaborate with Corporate Development on product-fit assessments for partnerships and M&A Define product strategy inputs for partner-led offerings Evaluate build vs. buy vs. partner tradeoffs from a product and revenue perspective Build Repeatable Growth Systems Establish frameworks for discovery, validation, piloting, and business casing Create operating mechanisms that accelerate decision-making and reduce risk Over time, hire and lead a small team focused on strategic growth and incubation. What This Role Explicitly Does Not Own Long-term ownership of core product pillars or platform roadmaps Execution, delivery, or optimization of in-market product experiences Ongoing ownership of analytics, AI platforms, or intelligence systems Feature-level prioritization within pillar teams Product-led growth mechanics for existing products Permanent ownership of incubation work beyond defined validation milestones Validated opportunities transition cleanly into core product teams once approved. What Success Looks Like Zipline has a steady pipeline of validated, evidence-backed growth options Executives have clarity on where to invest next and why New verticals, offerings, and partnerships launch with conviction—not hope Core product teams receive de-risked opportunities they can scale confidently. Growth decisions are faster, clearer, and more disciplined What’s in it for you: Remote-first culture: Join a high performing, fully remote team and work where you're comfortable Stock Options: Get meaningful ownership in a fast-growing, venture-backed company shaping the future of retail Time Off: Our flexible time-off policy ensures you stay refreshed and recharged. Plus, you’ll get a monthly stipend to get you out of the house—grab a coffee and work from your favorite spot Benefits: World-class medical, dental, and vision policies Team Connection: Annual company off-sites in fun locations. We've done New York, Costa Rica, Whistler, Palm Springs, San Diego, and Mexico City Sabbatical: A one-month paid sabbatical after completing five years of working at Zipline Volunteering: Every quarter, Zipliners get a paid day off to volunteer for a nonprofit of their choice Learning: We support continuous learning and provide unlimited access to our Udemy Business account Great humans, great work: Work with kind, collaborative teammates who care about doing meaningful work and making a real impact. We value diversity of all kinds and are committed to building a diverse and inclusive workplace where we learn from each other. We are an equal opportunity employer and welcome people of all different backgrounds, experiences, abilities, and perspectives Want to learn more about how we work? We may be remote, but we're anything but disconnected. Zipline is a thriving, dynamic team spread across the globe—collaborating, innovating, and having a blast along the way. Zipliners work from all over—vans, boats, Airbnbs, and everything in between. No office? No problem. Our culture still feels like one big hug. Even though we're distributed, we make space to connect—whether it's our weekly all-company social or gathering in person at our yearly retreats. We're building something meaningful together, and we're glad you're considering being a part of it. We can't wait to meet you! How We Hire We use AI tools to support our recruitment process, including helping us organize applications and identify early matches based on role criteria. That said, every rejection decision is made by a human. We encourage candidates to apply authentically and avoid relying solely on AI-generated responses, especially during interviews. This posting is for a current, open position within Zipline. This opportunity is offered through HighlightTA, the on-demand talent team supporting Zipline’s growth. Connect with us and learn more: Zipline on LinkedIn HighlightTA on LinkedIn

Lead HR operational functions including job leveling, compensation reviews, benefits program management, HRIS expertise, and data-driven reporting. | 4+ years in HR operations or total rewards in tech/SaaS, expert Google Sheets skills, HRIS platform knowledge, project management, and employment law compliance. | Description: • Optimize the entire employee experience through strategic development, implementation, and management of core HR operational functions. • Lead the administration and maintenance of the global job leveling framework and job architecture. • Manage the end-to-end annual compensation review cycle, including merit increases, bonus payouts, and equity refreshes. • Design, implement, and administer competitive, cost-effective global benefits programs. • Manage global relationships with benefits brokers, providers, and vendors. • Serve as the subject matter expert (SME) for the HRIS. • Collect, clean, analyze, and interpret complex global HR data to identify trends and provide actionable business insights. • Develop, maintain, and automate robust P&C dashboards and reports in Excel and HRIS. Requirements: • Minimum of 4+ years of progressive experience in HR/P&C Operations, Total Rewards, or HRIS Administration, ideally within a high-growth Technology or SaaS organization. • Exceptional Data Proficiency: Expert-level capability in Google sheets (e.g., VLOOKUPs, Pivot Tables, logical functions, complex data manipulation, modeling, and charting) to analyze large datasets and create comprehensive reports. • Strong Analytical Acumen: Proven ability to collect, synthesize, and interpret raw HR data into clear, concise, and actionable management reports and presentations. • HRIS Expertise: Deep functional knowledge of a major HRIS platform (e.g., Workday, SuccessFactors, UKG, Rippling, BambooHR) including reporting, maintenance, configuration, and data integration. • Operational Excellence: Demonstrated ability to manage complex, multi-faceted projects (e.g., annual enrollment, compensation cycles) with a strong focus on detail and deadlines. • Regulatory Compliance: Solid understanding of core Canadian, US and, preferably, international employment laws and compliance requirements related to compensation and benefits. Benefits: • Flexible benefit plans • Wellness programs • Parental leave top-up for growing families • Flexible paid time off • Retirement plans • 30-day work-from-anywhere program • Hybrid-flexible environment • Learning allowance • Mentorship • Leadership forums • Gig programs to grow your career