Engagement Manager RoleReporting initially to the Vice President of Enterprise Partnerships (and partnering closely with the CEO), the Engagement Manager will own enterprise deployments end-to-end, from signed SOW through implementation, change management, value realization, and early expansion. As a forward-deployed, high-touch partner, you will bridge technical capability and client operational reality, weaving our solution into their daily workflow.
You will work directly with Fortune 500 customers to translate complex labor operations into clear, outcomes-driven deployment plans. Beyond delivering successful, referenceable rollouts, you will play a foundational role in ReadyOn's growth by codifying your execution into reusable playbooks, dashboards, and templates that form our Enterprise Delivery Playbook.
Ideal Candidates- Thrive in the Last Mile: You are an operator who is comfortable on the floor with clients as much as you are in the boardroom. You find energy in the ambiguity of early-stage deployments and prefer building solutions over managing status updates.
- Translate Complexity: You have an exceptional ability to simplify. You 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: You take complete ownership of the client's success. You don't wait for product requirements to be handed to you; you identify the gap, build the workaround, and then go to the Product team to advocate for the permanent fix.
- Build for Scale: You have a systems-thinking mindset. While you are happy to do the bespoke, manual work required to win a specific customer, your primary goal is to ensure you never have to do that same task manually for the next 10 customers.
- Partner, Not Vendor: You view ReadyOn as a strategic extension of the client's business. You instinctively look for ways to expand our footprint not by selling, but by delivering so much value that expansion is the natural, logical next step.
Responsibilities & Impact- 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. Move beyond standard relationship management by defining concrete success metrics (labor savings, efficiency, ROI), engineering deployment plans backward from those outcomes, and leading 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 your 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.
Your Background- 4-10+ years of experience in high-growth enterprise software environments, professional services, or management consulting.
- Technical Implementation Leadership: Proven track record of leading complex, multi-stakeholder enterprise software deployments, specifically in AI-native or high-data environments.
- Technical Fluency: Deep understanding of integrations, APIs, data flows, and system dependencies. You are comfortable navigating technical complexity and architectural trade-offs in partnership with Engineering teams, even without needing to write production code yourself.
- Team Development: Experience mentoring and developing team members around you.
- Cross-Functional Orchestrator: Demonstrated success in forward-deployed or professional services roles where you successfully bridged the gap between product/engineering teams and non-technical client operators.
- Domain Advantage: Strong interest or previous experience in labor operations or workforce management is a significant advantage
