VP, Product

Our Story At Endear, we’re building the first modern CRM for retail teams, starting with the frontline. Our software empowers sales associates to have more personal, effective conversations with customers through AI-powered tools that drive measurable revenue. Despite retail being 6x larger than eCommerce, most platforms overlook the in-store experience. We’re changing that. We’re helping brands like Reformation, Gorjana, Glossier, Frame, and Mizzen+Main turn real customer relationships into growth powered by intuitive software and thoughtful design. With rapid growth ahead, we’re scaling our Product organization and need a steady, capable leader to help us get there. Position Overview Endear is hiring a VP of Product to take day-to-day ownership of the product organization during a pivotal phase of growth. Partnering closely with leadership on long-term vision, you will translate company goals into clear product priorities and lead execution against the agreed mission. This role is central to making Endear’s product team AI-native. You will improve how the team uses AI to frame problems, prototype, make decisions, and accelerate shipping—not just shape Endear’s AI product direction. You will bring a zero-to-one mindset, create clarity in ambiguous situations, and build the operating model needed for product, design, and engineering to move faster together. This is a hands-on, player-coach leadership role. You will lead and develop the product team, partner deeply with Design and Engineering, assess team structure and resourcing, and hire additional product talent as needed. We are looking for someone who has shipped products in lean environments, can go deep when needed, and knows how to build scalable processes without adding unnecessary overhead What You’ll Accomplish In your first 6 months, you’ll… Take clear day-to-day ownership of product, turning company priorities into an actionable roadmap and measurable outcomes. Align leadership, Product, Design, and Engineering around a cohesive product vision and a clear path to execution. Assess the current team, operating model, and resourcing; identify what needs to change to improve speed, ownership, and accountability. Establish stronger product rituals and decision-making systems that help the team ship with more focus and less friction. Build practical customer-feedback loops into roadmap and prioritization decisions. Make the product organization more AI-native by improving how the team uses AI to frame problems, prototype, prioritize, and ship. In your first year, you’ll… Build a high-performing product organization with clear ownership, strong psychological safety, and the right team structure for the next stage. Hire and develop product talent, including an additional PM, while evaluating the capabilities and resourcing the team needs. Deliver high-impact roadmap work that improves product adoption and business outcomes. Establish scalable planning, execution, and communication systems that keep teams aligned as Endear grows. Help shape and execute Endear’s AI product direction while ensuring the team can move quickly from idea to shipped product. You’ll Thrive in This Role If… You Have Experience With Leading product at a lean B2B SaaS company, with both strategic ownership and hands-on execution. Turning company goals into clear product priorities, success metrics, and decisions. Building and communicating product vision, then translating it into focused execution. Partnering deeply with Design and Engineering, including going technical when needed. Leading, mentoring, and growing Product Managers while maintaining a high bar for delivery. Building product processes that add clarity and speed without creating unnecessary overhead. Using AI tools in day-to-day product work—from research and problem framing to prototyping, prioritization, and execution. Transforming how product teams work in an AI-native environment. Using customer feedback, usage data, and market insight to guide roadmap decisions. Operating effectively in ambiguous, fast-moving growth-stage environments. Align With What We Value At Endear, we live by five core principles. Here’s how they translate into what we’re looking for in this role: Customer First: Prioritize real customer problems over internal assumptions. Use research, feedback, and product data to ensure the roadmap delivers meaningful value to merchants and sales associates. Take Ownership: Own outcomes, not just outputs. Take responsibility for product direction, team performance, and the impact product decisions have on the business. Enable Autonomy: Build clear product strategy, priorities, and processes so product, design, and engineering teams can execute with confidence and independence. Under Promise, Over Deliver: Set realistic expectations for product initiatives and deliver consistent, measurable improvements that build trust with customers and the team. Innovate & Deliver Value Quickly: Balance thoughtful strategy with a bias toward action. Test ideas, iterate quickly, and ship improvements that create real business impact. About the Team You’ll partner most closely with: Executive Team: Align product strategy with company goals, provide visibility into roadmap priorities and performance, and partner on key decisions around growth and product direction. Head of Product Design: strategy, feedback, and design system development Product Team: roadmap alignment, priorities, and merchant needs Engineering Team: feasibility, implementation, and iteration We’re a small team with big ambitions—collaborative, customer-obsessed, and deeply excited about the problems we’re solving in retail. Our Hiring Process Recruiter Screen Behavioral Interview with the Hiring Manager + Co-Founder Panel interview with key Product and Engineering team members Final conversation with Co-Founder + CTO Offer 🎉 Compensation & Benefits Base Salary: $190+240k Equity Eligible Fully remote team Comprehensive healthcare (medical, dental, vision) Co-working or home office stipend Flexible PTO and unlimited vacation Opportunity to shape foundational product work in a transformative industry Apply Even If You Don’t Check Every Box If this role excites you but you’re unsure if you meet every requirement, reach out anyway. We care about skills, motivation, and how you think more than we do about perfect resumes.