Director of Operations (Remote – Enterprise B2B SaaS)

Location: Remote (North America)Function: Operations / Program ManagementEmployment Type: Full-TimeAbout UsWe’re a proven leader in a specialized B2B market, delivering trusted, mission-critical software to enterprise clients for nearly 50 years. We’re now modernizing our platform with a next-generation, AI-native solution and expanding our team to support this growth.About the RoleWe’re hiring a Director of Operations to lead a team across two product lines—Business Analysts and a technical support function—while co-driving the program management behind a generational platform transformation. You’ll directly manage senior BAs and support specialists serving long-standing enterprise clients, and you’ll own the operational side of our transformation roadmap alongside the President. No Product VP layer—your operational intelligence feeds directly into the product architecture.This is a dual mandate: stabilize and optimize the legacy business that funds our future while building the operational bridge to an AI-native platform. The legacy work is not a waypoint—it’s the foundation. The right person treats both with equal seriousness.What You’ll DoDirectly manage a small team of  individual contributors across two functions: Business Analysts who scope and deliver client work, and support specialists who operate within a prescribed system across two product linesEnforce the boundary between BA and support work—your BAs do requirements, specs, and QA, not ticket triageMonitor support system health holistically: SLAs, first-response compliance, escalation quality, independent resolution rates, and knowledge base growth—without micromanaging daily ticketsOwn client tiering and differentiated service levels across the installed baseCo-own the transformation program plan with the President: manage timelines, dependencies, and delivery accountability across workstreamsProtect transformation capacity—two of your direct reports contribute institutional platform knowledge directly to the President’s product vision. Your job is to ensure legacy delivery doesn’t consume their strategic allocationGather and relay client intelligence: which accounts are strong design partners, where migration risks live, what the new platform must preserveProduce monthly operational output: capacity utilization, client health by tier, support trends, emerging risksSay no—to scope creep, to legacy mindset, to the gravitational pull of “how we’ve always done it”About You7+ years leading operations, professional services, or delivery teams in a B2B software environment—this is a leadership role that requires PM discipline, not a PM role with a leadership titleHave managed through at least one platform transition, major product shift, or technology modernization—you know what it takes to keep the lights on while building something newComfortable managing senior ICs who have deep domain expertise you won’t match for a year, including navigating the dynamics of a recently restructured team—you lead through structure, accountability, and earned trustThrive in a lean environment: no layers of middle management, no dedicated support staff, no meetings that could have been an email. You figure things out, build what’s missing, and move onDiplomatic and direct with enterprise clients, from front-desk staff to C-suiteHigh-ownership operator who builds structure where it’s missing and enforces it once it existsCan coach and develop people who need to modernize how they work—and can make the hard call when someone can’t or won’t adaptBonus: experience in hospitality, vacation ownership, property management, or similar vertical-market softwareWhy This Role Is DifferentThis is not a maintenance role at a company with an org chart full of dotted lines and a Slack channel for everything. You’ll report to a VP with a direct line to the President who owns the product vision. There’s no bureaucracy to navigate and nowhere to hide. You’ll walk into an ops team mid-transformation: recently restructured, new support system, a dual-track mission with the President relying on your operational judgment to inform what gets built. If this works, you grow into VP. The company has operated for 50 years—the next 50 depend on what gets built now, and ops is where the client reality meets the product ambition.