Chief Customer Officer

Job Description This is a remote position. About Webgility Webgility helps SMBs automate accounting and ecommerce operations. We make sure ecommerce books are always on and always reconciled, so every order, fee, payout, and settlement flows correctly into our customers' accounting systems, every month, without exception. Our customers are product businesses selling across Shopify, Amazon, WooCommerce, and wholesale. They need their financials right, in time to make real decisions. We don't just sell software. We sell the outcome. The Role Webgility is at an inflection point. Today we deliver our customers' outcome through software. Over the next several years, we will deliver it increasingly through agents and accounting partners, with human expertise concentrated where judgment matters most. The destination is an outcomes delivery company where software, agents, and expertise compose into the right answer for every customer. We are creating the Chief Customer Officer role to own that journey. The CCO sits on the executive team and owns the full post-sale experience: Customer Support, Customer Success, and Service Delivery. This person defines what customer success means at Webgility, builds the function, and is responsible for ensuring every customer achieves the outcomes they signed up for, with the right blend of software, agents, and human expertise behind them. They own the commercial result: gross revenue retention, expansion, and the long-term value of every account. This is a stretch role. We're hiring for caliber, not title history. If you're a VP today running customer organizations and ready to operate at the executive table, this is built for you. Requirements What You'll Own Customer Strategy Define what customer success means in an outcomes delivery model where software, agents, and human expertise combine to make the customer's books right Own gross revenue retention and drive expansion with a customer success team Bring customer intelligence into product, pricing, and GTM decisions at the executive table Customer Support Lead the support function across technical and operational queries from merchants and accountants Deploy agents and automation aggressively: intelligent triage, AI-assisted first response, self-service troubleshooting, proactive break alerts Move the function toward a posture where humans only show up for the work that requires them Customer Success Drive adoption, retention, and expansion across the customer base Run customer health and proactive intervention Use AI agents for health scoring, churn flagging, QBR prep, and trigger-based outreach so the team spends time on conversations that move the relationship Service Delivery Own the certified bookkeeping partner network today as a strategic delivery channel: outcome quality, partner economics, and capacity planning Build the bridge from a human-delivered service today to an agent-augmented service tomorrow, with human expertise concentrated where judgment matters Build the system that gives you visibility into close status across every account without asking Turn manual coordination into a system that runs itself Cross-functional Partner with Sales and Implementation on handoffs Feed customer signal into Product and Engineering You will know where things break before anyone else does Your Team and What You'll Build You'll join a distributed team of Support and Customer Success operators already serving thousands of customers. You'll have the mandate to add systems, automation, agents, and headcount to keep pace with growth, with the authority to redesign the function around what the next phase actually needs. What We're Looking For You've built and led customer organizations in B2B SaaS at a VP level and you're ready for the next step. You set strategy and execute it. You've owned a customer P&L, not just a retention score. You're credible in ecommerce and accounting workflows. 15+ years in CS, Support, or CX with 5+ years at VP-level scale Direct ownership of a customer P&L (retention + expansion revenue) at a B2B SaaS company with US customers Built and managed through managers, not just individual contributors Solid grasp of ecommerce operations: multichannel selling, marketplace fees, accounting systems workflows Experience managing third-party delivery partners or outsourced service teams to a defined quality standard Strong working knowledge of leading accounting platforms (QuickBooks, Xero, NetSuite) AI and Automation You think in workflows. You've personally led automation of business processes, not just used AI tools but designed the systems behind them. You have hands-on experience delivering service with a mix of humans and agents, and the judgment to know which work belongs to which. Demonstrated track record automating CS or Support workflows in production Comfort evaluating AI tools across vendors without loyalty to any platform Bonus: hands-on with agentic frameworks, LLM-based automation, or AI-assisted service delivery in operational settings Benefits Why Join Webgility Remote-first with flexible working Group health insurance (employee, spouse, children) Internet reimbursement Learning and development support including certification costs