Head of Product

This is a remote position.

Every year, thousands of small and mid-size ecommerce businesses lose hours to the gap between where they sell (Shopify, Amazon, eBay, Walmart) and where they manage their money (QuickBooks, 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 features 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 10.

We're at an inflection point where the product is evolving from a best-in-class automation engine to an AI-powered commerce operations platform. That's why this role exists.

As Head of Product, you'll own product strategy and execution across Webgility's portfolio of products - 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:

1. 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.

2. Build and lead a high-performing PM team. You'll manage a team of Product Managers in India - 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're the kind of leader who reviews PRDs, joins customer calls, and unblocks the team.

3. 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: intelligent transaction matching, predictive inventory, proactive margin insights, anomaly detection, or entirely new value surfaces. You'll own the roadmap for taking us from sync engine to AI-powered commerce operations platform.

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 in India 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 across teams

A CEO who cares deeply about product and will be your direct manager and thought partner

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 multiple Engineering teams, Design, and GTM to ship high-impact releases on predictable timelines

Customer & UX Focus

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

Identify unmet needs and translate them into product opportunities that drive growth

Team Leadership

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 ownership, intellectual honesty, and customer obsession within the product org

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

Lead end-to-end product launches from beta through rollout and post-launch optimization

Cross-Functional Partnership

Work closely with Sales, Marketing, and Customer Success to support GTM, positioning, and adoption strategies

Communicate effectively across a US-India distributed organization - manage stakeholders with clarity and transparency

Must-haves:

10+ years in product management, with 4+ years directly managing PM teams (not just mentoring or dotted-line)

Experience managing a portfolio of multiple products or product lines simultaneously - not just a single product

Proven track record of owning and scaling B2B SaaS products, ideally in ecommerce, fintech, payments, or accounting

Hands-on leader - you still get into the details on specs, customer calls, and data analysis

Strong UX sensibility - you can evaluate design quality and push for better experiences

Deep understanding of APIs, integrations, and modern SaaS architecture

Experience working in US-India distributed teams with overlapping time zone collaboration

Excellent analytical and problem-solving skills - you default to data over opinion

Clear, structured communicator who can simplify complexity for diverse audiences

Strong advantages:

Experience with accounting systems (QuickBooks, Xero, NetSuite) or multi-channel ecommerce platforms

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 - understanding their constraints, buying behavior, and support needs

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

Webgility is an equal opportunity employer. We value diverse perspectives and encourage candidates from all backgrounds to apply.