Engagement Manager

ReadyOn•San Francisco, CA

7d•Hybrid

About The Position

ReadyOn.AI is seeking an Engagement Manager to own enterprise deployments end-to-end, from signed SOW through implementation, change management, value realization, and early expansion. This role involves acting as a forward-deployed, high-touch partner who bridges technical capability and client operational reality, weaving the ReadyOn solution into their daily workflow. The Engagement Manager will work directly with Fortune 500 customers to translate complex labor operations into clear, outcomes-driven deployment plans. A key aspect of this role is codifying execution into reusable playbooks, dashboards, and templates to form the Enterprise Delivery Playbook, contributing to ReadyOn's growth. The role reports initially to the Vice President of Enterprise Partnerships and partners closely with the CEO.

Requirements

4-10+ years of experience in high-growth enterprise software environments, professional services, or management consulting.
Proven track record of leading complex, multi-stakeholder enterprise software deployments, specifically in AI-native or high-data environments.
Deep understanding of integrations, APIs, data flows, and system dependencies. Comfortable navigating technical complexity and architectural trade-offs in partnership with Engineering teams.
Experience mentoring and developing team members around you.
Demonstrated success in forward-deployed or professional services roles where you successfully bridged the gap between product/engineering teams and non-technical client operators.
Strong interest or previous experience in labor operations or workforce management is a significant advantage.

Nice To Haves

Thrive in the Last Mile: Operator comfortable on the floor with clients as much as in the boardroom. Finds energy in the ambiguity of early-stage deployments and prefers building solutions over managing status updates.
Translate Complexity: Exceptional ability to simplify. Can explain how an AI model or a complex data integration works to a non-technical frontline manager in a way that makes them feel empowered, not confused.
Own the Outcome: Takes complete ownership of the client’s success. Identifies gaps, builds workarounds, and advocates for permanent fixes.
Build for Scale: Systems-thinking mindset. Primary goal is to ensure tasks are not repeated manually for future customers.
Partner, Not Vendor: Views ReadyOn as a strategic extension of the client’s business. Instinctively looks for ways to expand footprint by delivering value.

Responsibilities

Own End-to-End Enterprise Deployments: Serve as the single-threaded owner for complex enterprise rollouts - from SOW signature through go-live.
Orchestrate internal workstreams across Product, Engineering, AI, and Operations to execute deployment plans, lead technical/business alignment, and maintain delivery momentum in ambiguous environments.
Drive Executive Alignment & Value Realization: Act as a trusted advisor to enterprise stakeholders. Define concrete success metrics (labor savings, efficiency, ROI), engineer deployment plans backward from those outcomes, and lead QBRs that reinforce measurable impact and set up long-term confidence.
Enable Rapid Product Innovation: Act as the voice of the customer within ReadyOn. Partner with Product and Engineering to translate deployment learnings and enterprise feedback into quantified product insights. Negotiate priorities and trade-offs to ensure our roadmap addresses high-impact customer needs without compromising delivery.
Build Scalable Delivery Systems: Turn bespoke deployment work into reusable systems. Codify execution into repeatable implementation playbooks, success frameworks, and customer health dashboards, establishing the foundational Enterprise Delivery Playbook that allows our team to grow with consistency.
Enable Enterprise Expansion: Shape expansion pathways (new sites, regions, or lines of business) based on delivery outcomes. Partner with Sales on renewals and upsells using credible impact data to position ReadyOn as a long-term strategic partner via a crawl-walk-run deployment strategy.