Head of Product Management

Job Description This is a remote position. Director of Product Management Location: India (Hybrid) — Reports to: CEO About Webgility Every year, thousands of small and mid-size ecommerce businesses lose hours to the gap between where they sell — Shopify, Amazon, Walmart, eBay — and where they manage their money — QuickBooks, NetSuite, Xero. Orders, inventory, pricing, payouts: keeping it all in sync across channels is painful, error-prone, and expensive. Webgility started by solving that sync problem, and we’ve become the market leader at it, processing $7B+ in GMV annually for 5,000+ businesses worldwide. But we’re now going beyond sync. Automation was the foundation; intelligence is the future. We’re building AI-enabled capabilities that don’t just move data between systems — they help our customers do more: surface insights they’d miss, automate decisions they’d otherwise make manually, and give small businesses the kind of operational intelligence that used to require a back-office team of ten. We’re at an inflection point. The product is evolving from a best-in-class automation engine to an AI-powered commerce operations platform. That’s why this role exists. The Role As Director of Product Management, you’ll own product strategy and execution across Webgility’s portfolio — including our cloud platform, desktop application, and Shopify-native experience — each serving distinct customer segments with dedicated engineering teams. This isn’t a single-product role, and it isn’t a “set the vision and delegate” role. We need a hands-on product leader who can operate across multiple product lines simultaneously, make smart resource allocation decisions, and drive execution at both the strategic and team level. Your core mandate is threefold: Elevate the product experience for current customers. Our users depend on Webgility daily. You’ll drive improvements to UX, reliability, and workflow efficiency that directly impact retention and expansion. You’ll spend real time with customers and in the data to understand where we’re falling short. Build and lead a high-performing PM team. You’ll manage a team of Product Managers — coaching them on discovery, prioritization, and execution rigor. You’ll set the bar for what “good” looks like in product specs, customer research, and cross-functional collaboration. You review PRDs, join customer calls, and unblock the team. Chart the path forward — beyond sync. We’ve won on automation. Now we’re building AI-enabled capabilities that help customers do more — not just move data, but act on it. You’ll identify where Webgility should place its next bets and own the roadmap for taking us from sync engine to AI-powered commerce operations platform. What You’ll Walk Into Multiple products, multiple teams: a cloud SaaS platform, a desktop application with a loyal installed base, and a Shopify-native app — each with its own customer profile, technical stack, and engineering team A product portfolio with genuine product-market fit, processing billions in transaction volume annually A customer base that is loyal but wants a more modern, intuitive experience A PM team that needs stronger leadership, process, and coaching across product lines A platform with deep integrations across QuickBooks, Shopify, Amazon, eBay, and more — technically complex and high-stakes An engineering organization structured around product lines, needing a strong product counterpart to drive clarity, prioritization, and alignment A CEO who cares deeply about product and will be your direct manager and thought partner Requirements What You’ll Do Product Strategy & Execution Own the product roadmap across multiple product lines — allocate investment across cloud, desktop, and Shopify-native based on business impact and strategic fit Drive product decisions with data: usage analytics, customer research, competitive analysis, and market trends Define and track KPIs tied to adoption, retention, NRR, and time-to-value — per product line, not just in aggregate Partner with Engineering, Design, and GTM to ship high-impact releases on predictable timelines Translate customer needs, business goals, and market insights into actionable roadmaps Align product initiatives with company growth objectives and partner with leadership on strategic opportunities Customer Experience & Discovery Be the internal champion for customer experience — drive a meaningful uplift in UX quality across the platform Run and institutionalize customer discovery: regular interviews, feedback synthesis, and data-driven insights Lead customer discovery initiatives including usability testing, surveys, and market research Identify unmet needs and translate them into product opportunities that drive growth Champion improvements in onboarding, activation, adoption, retention, and customer satisfaction Team Leadership & Development Lead, mentor, and develop Product Managers — set clear expectations for output quality and professional growth Establish product team rituals: discovery sprints, roadmap reviews, launch readiness, and retrospectives Build a culture of accountability, ownership, intellectual honesty, and customer obsession Coach PMs on prioritization, stakeholder management, and product discovery Participate in hiring and scaling the Product organization Platform & Innovation Own the integration and platform strategy across APIs, partner ecosystems, and third-party channels Drive the “beyond sync” product vision — identify and ship AI-enabled features that help customers make better decisions, not just automate data flow Identify opportunities where AI can create meaningful customer value: intelligent transaction matching, predictive inventory, proactive margin insights, anomaly detection Lead end-to-end product launches from beta through rollout and post-launch optimization Cross-Functional Leadership Work closely with Sales, Marketing, and Customer Success to support GTM, positioning, and adoption strategies Partner with Engineering and Design to deliver high-quality customer experiences Communicate product strategy, priorities, and progress across a US–India distributed organization Serve as a trusted advisor to executive leadership on product decisions Required Qualifications Experience 12+ years of Product Management experience in B2B SaaS environments 4+ years directly managing Product Managers (direct reports, not dotted-line or mentoring) Proven track record of owning and scaling complex B2B SaaS products Experience managing multiple products or product lines simultaneously — not just a single product Experience leading cross-functional product teams Background working in US-focused SaaS organizations Product Leadership Hands-on leader — you still get into the details on specs, customer calls, and data analysis Strong product strategy formulation and execution capabilities Deep customer discovery and problem-solving skills; you default to data over opinion Experience defining KPIs and measuring product success across multiple product lines Strong UX sensibility — you can evaluate design quality and push for better experiences Strong roadmap planning and prioritization experience across competing demands Technical Understanding Deep understanding of APIs, integrations, workflow automation, and modern SaaS architecture Ability to engage credibly in technical discussions with Engineering teams without overstepping Comfortable working in highly integrated, data-rich software environments Communication Clear, structured communicator who can simplify complexity for diverse audiences Strong stakeholder management across engineering, business, and executive audiences Experience working with distributed US–India teams with overlapping time zone collaboration Preferred Qualifications Experience with accounting systems (QuickBooks, Xero, NetSuite) or multi-channel ecommerce platforms (Shopify, Amazon, Walmart, eBay) Track record of shipping AI/ML-powered product features or automation workflows Experience driving PLG (product-led growth) motions: trials, onboarding, self-serve activation Familiarity with the SMB customer segment — their constraints, buying behavior, and support needs Ecommerce technology experience (marketplaces, storefronts, fulfillment) Accounting, fintech, payments, or ERP software experience Benefits Why Join Webgility Real impact: Your decisions directly affect thousands of small businesses and their ability to grow Builder’s role: This isn’t maintaining a mature product — it’s leading the evolution from sync engine to AI-powered platform Domain depth: Ecommerce + accounting is a fascinating, complex problem space with massive TAM Leadership exposure: You’ll report directly to the CEO and shape product strategy at the highest level Team you’ll build: Shape the product organization and leave your mark on how we work Category leadership: Lead product strategy for a market-leading SaaS platform used by 5,000+ businesses worldwide Ideal Candidate The ideal candidate is a hands-on SaaS product leader who has successfully managed Product Managers, shipped complex B2B software products, partnered deeply with Engineering, and driven measurable business impact. They are equally comfortable discussing strategy with executives, reviewing PRDs with Product Managers, speaking with customers, analyzing product metrics, and making difficult prioritization decisions across multiple product lines. If you’ve built and scaled B2B SaaS products, led PM teams through growth and ambiguity, and are excited about the intersection of ecommerce and AI — we’d love to talk.