Customer Engagement Manager

About the role

We're looking for an Engagement Manager to own and drive delivery of our most complex enterprise implementations, from kickoff through go-live and handoff to Customer Success. You're the strategic quarterback for high-stakes, multi-stakeholder projects where technical complexity meets organizational change.

You'll be the primary relationship owner for enterprise customers, commanding respect in executive conversations while rolling up your sleeves to architect solutions, unblock technical issues, and guide implementation teams. You're technical enough to challenge solution designs and direct engineering teams, strategic enough to navigate C-level politics and manage stakeholder expectations, and disciplined enough to deliver on-time, on-budget.

This role sits at the intersection of technical expertise, delivery excellence, and executive advisory. You own outcomes, not just activities. When a $500K implementation is at risk, you're the person who jumps in, diagnoses what's broken, realigns stakeholders, and gets it back on track, whether that means redesigning integration architecture, facilitating a hard conversation with a frustrated CTO, or building a prototype to prove feasibility.

Responsibilities

• Enterprise Project Leadership & Delivery Ownership
  • Own end-to-end delivery of complex enterprise implementations ($200K–$1M+ ACV) from sales handoff through go-live and CSM transition
  • Serve as primary relationship owner and strategic advisor for 3–5 concurrent enterprise accounts
  • Lead project planning, scope management, risk mitigation, and change management for multi-phase, multi-stakeholder rollouts
  • Drive project governance: status reviews, executive steering committees, escalation management, lessons learned
  • Manage project economics: profitability, budget burn, overrun forecasting, and scope negotiation
  • Define success criteria upfront and measure progress against business outcomes, not just tasks
• Executive Relationship Management & Strategic Advisory
  • Build and maintain C-level and VP relationships with customer executives throughout the implementation lifecycle
  • Conduct Executive Business Reviews and Steering Committee meetings, showcasing value and aligning on next phases
  • Serve as escalation point for at-risk projects: diagnose root cause, build recovery plans, facilitate difficult stakeholder conversations
  • Navigate organizational politics, competing priorities, and misalignment to drive consensus and progress
  • Act as trusted advisor on change management and organizational readiness, not just technical implementation
  • Translate business objectives into implementation strategy and technical constraints into business language
• Technical Solution Design & Architecture Guidance
  • Lead design workshops with customer technical teams to architect integration flows, data migration strategy, and workflow design
  • Design integrations between Rocketlane and enterprise systems (NetSuite, Salesforce, Workday, SAP, HRMS, CRMs, data warehouses)
  • Evaluate build-vs-buy: native connectors, iPaaS platforms (Workato, Boomi), custom API development
  • Review and validate Solution Architect designs; push back when risky, over-engineered, or misaligned
  • Provide technical direction to implementation teams and partner engineering; unblock issues during build
  • Understand REST APIs, webhooks, auth patterns (OAuth, SAML, SSO), and data flows well enough to guide customer IT conversations and troubleshoot integration failures
• Hands-On Delivery & Problem-Solving
  • Jump into stuck projects: review plans, debug integrations, validate migrations, test configurations
  • Build prototypes or POCs with AI tools (Claude, Cursor, MCPs) to validate feasibility before committing to customers
  • Lead UAT planning and execution: define test scenarios, track defects, manage go-live readiness
  • Manage legacy data migration: validate quality, define transformation rules, oversee cutover
  • Use modern AI tools to accelerate delivery: automate documentation, generate artifacts, build validation scripts
• Cross-Functional Collaboration & Influence
  • Partner with Sales presales to shape deal strategy, validate scoping, and ensure smooth AE-to-delivery handoff
  • Collaborate with Product and Engineering to prioritize roadmap items that reduce complexity or unblock requirements
  • Translate customer pain from the field into actionable product requirements
  • Work with Customer Success on handoff criteria and seamless transition to ongoing adoption
  • Partner with India-based delivery teams to coordinate global delivery and leverage offshore capacity
  • Represent voice of the customer internally, shaping product, sales, and GTM strategy
• Team Leadership & Mentorship (Indirect)
  • Provide technical and delivery guidance to Implementation Managers and Solution Architects on your projects
  • Mentor junior team members on stakeholder management, scope negotiation, and delivery discipline
  • Run project retrospectives and document lessons learned to improve delivery playbooks
  • Contribute to the PS knowledge base: solution patterns, integration playbooks, escalation frameworks, templates
• Delivery Excellence & Process Discipline
  • Maintain rigorous project hygiene: current plans, accurate status, proactive risk management, clear RACI
  • Track key metrics: milestone completion, budget burn, scope changes, CSAT
  • Implement delivery governance: phase gate reviews, quality checkpoints, go-live readiness assessments
  • Drive continuous improvement: iterate on delivery methodology and share best practices

Requirements

• 10–15 years in enterprise software delivery, professional services, technical consulting, or implementation management
• Proven track record leading complex, multi-stakeholder enterprise implementations in B2B SaaS (ideally PSA, CRM, ERP, workflow platforms)
• Deep hands-on experience across the full lifecycle: discovery, design, build, UAT, data migration, go-live, hypercare
• Experience managing high-stakes projects ($200K–$1M+ ACV) with executive visibility and complex technical requirements
• Track record of on-time go-lives, high CSAT, renewals, and expansion revenue
• Experience with global delivery teams and distributed resources across time zones

Skills

• Technical Depth & Solution Design Capability
  • Strong understanding of integration architecture: REST APIs, webhooks, iPaaS, auth protocols (OAuth, SAML, SSO)
  • Can read API docs, evaluate feasibility, and direct engineering teams (you don't write production code, but can prototype and troubleshoot)
  • Experience designing solutions for enterprise systems: PSA, CRM, ERP, HRMS, financial systems, data platforms
  • Familiarity with data modeling, ETL, migration strategy, and enterprise data flows
  • Comfortable using modern AI tools (Claude, Cursor, MCPs) to accelerate problem-solving and delivery
  • Bonus: PSA platform experience and understanding of PS operations (resourcing, time tracking, revenue recognition, margin analysis)
• Project Management & Operational Excellence
  • Expert-level PM skills: scope definition, work breakdown, risk management, dependency tracking, change control
  • Data-driven: uses metrics to diagnose problems, forecast outcomes, drive accountability
  • Strong business acumen: project economics, margin dynamics, resource utilization, delivery's impact on growth
  • Process-oriented but pragmatic: builds structure without letting it become bureaucracy
  • Proactive risk manager: sees around corners and mitigates before problems escalate
• Hands-On & High-Energy
  • Willing to get into the weeds: review a broken integration, rebuild a plan, facilitate a heated meeting, prototype a solution
  • High energy, bias toward action: moves fast, decides with incomplete information, iterates on feedback
  • Comfortable with ambiguity and shifting priorities in a fast-paced startup
  • Not precious about scope: does what's needed for customer and team success
  • Resilient under pressure: stays calm when projects are at risk