Sr. Manager, Intelligent Operations

HopSkipDrive

2d•Remote

About The Position

At HopSkipDrive, our goal is to create opportunity for all through mobility. We’re a technology company that solves complex transportation challenges where there is a heightened need for safety, equity, and care. Through our marketplace, we connect kids, older adults, or anyone needing extra support to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts around the country. Founded by three moms as a solution to their own transportation challenges, we’ve now facilitated more than five million rides across over 17 states around the country. We continue to expand at a rapid pace, making the Inc. 5000 list four times, as well as the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a Series D company and has raised $100M in funding to date. The Operations Excellence team is the engine behind how HopSkipDrive scales its processes, systems, and operational workflows. In 2026, this role is uniquely focused on leading the team through a pivotal transformation: shifting from manual, people-intensive operations to AI-enabled, automated workflows — all while maintaining the safety and compliance rigor our platform demands. You will be responsible for the following: Lead the AI & Automation transformation, owning the strategic roadmap to move Operations Excellence from manual oversight to intelligent, exception-based processing using Agentic AI workflows, and LLM-integrated tooling. Manage and develop the Ops Excellence team, including a manager and three direct reports, fostering growth during technical transitions. Identify, prioritize, and execute automation opportunities across central operations, supply activation, marketplace workflows, and compliance processes — working cross-functionally with Product and Engineering to build and iterate. Drive measurable improvements in throughput, yield, and cycle time, hitting or exceeding the efficiency benchmarks set for the 2026 fiscal year. Leverage 2026-standard automation tools (Agentic AI workflows, advanced OCR, automated identity verification, and internal AI orchestration platforms) to evolve process capabilities and eliminate manual friction. Synthesize complex data insights from our analytics suite to proactively identify and resolve funnel drop-off points, process bottlenecks, and operational risk areas in real-time. Partner with Product and Engineering to define the technical roadmap for intelligent process automation, including zero-touch onboarding and automated re-certification journeys. Build the AI/Automation KPI framework, establishing metrics for automation impact — time saved, error reduction, cost efficiency, and team engagement lift. Manage hybrid workforces, ensuring that onshore teams and offshore partners are up-skilled and effectively utilizing our latest AI orchestration tools. As a lean, high-impact Revenue Operations team of four we take pride in building the scalable infrastructure and strategic frameworks that power HopSkipDrive’s mission. We are the connective tissue between compensation, systems, and departmental strategy, and you will join us to sharpen our sales execution and help us build a world-class engine for growth. We do, and you will, support the business through the following responsibilities: Partner with sales leadership to translate high-level growth goals into day-to-day execution strategies and execution, incl. establishing a trusted “single source of truth” for revenue data incl. territory plans, quotas, attainment etc. Analyze sales performance & attainment data to identify bottlenecks, surface opportunities for managers, and suggest potential pivots Maintain and improve CRM hygiene, and contribute to the optimization of workflows alongside senior RevOps leadership Lead sales enablement initiatives by developing documentation that empower the team to utilize our systems and processes effectively Support refinement of end to end processes to increase velocity and improve win rates across all segments Support the sales forecasting process by maintaining pipeline standards and providing leadership with visibility into rep & customer performance. Support pricing updates, renewal workflows and incentive compensation administration, ensuring that commission structures align with sales behavior and company revenue targets You’ll report directly to the Director of Revenue Operations and work closely with senior team members to support strategic initiatives.

Requirements

Change Management Leader with experience guiding teams through technical transitions and fostering an "AI-first" mindset across the organization.
Operations Transformation Experience — you've led at least one major shift from manual to automated workflows in a high-growth or technology-driven environment.
Technical Problem-Solver proficient in leveraging modern AI/ML tools, Agentic workflows, and LLM-integrated processing to scale operations.
Data-Driven Strategist who uses advanced visualization and predictive metrics to analyze funnel health and drive continuous improvement.
Strong Cross-Functional Collaborator skilled at partnering with Product and Engineering to build and iterate on internal technical tools.
People-First Manager with 5+ years of management experience, including experience developing mid-level managers. You know how to build trust, address engagement gaps, and develop talent — especially through periods of significant change.
Strategic Project Leader with advanced project management expertise, leveraging ROI-driven analysis to prioritize process intake, optimize resource allocation, and maximize impact.
Results-Oriented Operator with a deep focus on targeted outputs, yield optimization, and reducing cycle times in a high-growth environment.
3-5 years of experience in Sales Operations or RevOps, specifically within a high-growth B2B SaaS or marketplace environment.
Exceptional analytical skills with the ability to turn raw data into a compelling narrative that influences executive decision-making.
A track record of successful stakeholder management, demonstrating the ability to challenge the status quo while maintaining strong collaborative relationships.
Strong project management discipline, with the ability to balance long-term strategic builds with the immediate, "keep-the-lights-on" needs of a sales floor.
Expertise in the tech stack, including experience with tools like Salesforce, Tableau, Coefficient etc. Salesforce proficiency on understanding of stages, workflows, validation rules, and reporting dashboards
A proactive, "owner" mindset, fueled by the desire to identify gaps before they become problems and build scalable solutions from scratch

Responsibilities

Lead the AI & Automation transformation, owning the strategic roadmap to move Operations Excellence from manual oversight to intelligent, exception-based processing using Agentic AI workflows, and LLM-integrated tooling.
Manage and develop the Ops Excellence team, including a manager and three direct reports, fostering growth during technical transitions.
Identify, prioritize, and execute automation opportunities across central operations, supply activation, marketplace workflows, and compliance processes — working cross-functionally with Product and Engineering to build and iterate.
Drive measurable improvements in throughput, yield, and cycle time, hitting or exceeding the efficiency benchmarks set for the 2026 fiscal year.
Leverage 2026-standard automation tools (Agentic AI workflows, advanced OCR, automated identity verification, and internal AI orchestration platforms) to evolve process capabilities and eliminate manual friction.
Synthesize complex data insights from our analytics suite to proactively identify and resolve funnel drop-off points, process bottlenecks, and operational risk areas in real-time.
Partner with Product and Engineering to define the technical roadmap for intelligent process automation, including zero-touch onboarding and automated re-certification journeys.
Build the AI/Automation KPI framework, establishing metrics for automation impact — time saved, error reduction, cost efficiency, and team engagement lift.
Manage hybrid workforces, ensuring that onshore teams and offshore partners are up-skilled and effectively utilizing our latest AI orchestration tools.
Partner with sales leadership to translate high-level growth goals into day-to-day execution strategies and execution, incl. establishing a trusted “single source of truth” for revenue data incl. territory plans, quotas, attainment etc.
Analyze sales performance & attainment data to identify bottlenecks, surface opportunities for managers, and suggest potential pivots
Maintain and improve CRM hygiene, and contribute to the optimization of workflows alongside senior RevOps leadership
Lead sales enablement initiatives by developing documentation that empower the team to utilize our systems and processes effectively
Support refinement of end to end processes to increase velocity and improve win rates across all segments
Support the sales forecasting process by maintaining pipeline standards and providing leadership with visibility into rep & customer performance.
Support pricing updates, renewal workflows and incentive compensation administration, ensuring that commission structures align with sales behavior and company revenue targets