Customer Engagement Manager

Job Description

Job Description

About The Role

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

You will serve as the primary relationship owner for enterprise customers throughout their implementation journey, commanding respect in executive conversations while rolling up your sleeves to architect solutions, unblock technical issues, and guide implementation teams. You are technical enough to challenge solution designs and give direction to engineering teams, strategic enough to navigate C-level politics and assertively manage stakeholder expectations, and operationally disciplined enough to deliver on-time, on-budget implementations.

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 the project back on track—whether that means helping team redesign the integration architecture, facilitating a difficult conversation with a frustrated CTO, or getting a prototype built to prove feasibility.

If you have led complex enterprise implementations in high-growth SaaS environments, thrive in ambiguity, can earn trust with both engineers and executives, and believe that exceptional delivery is the foundation of customer success, this role is for you.

What You Will Do

Enterprise Project Leadership & Delivery Ownership

- Own end-to-end delivery of complex enterprise implementations ($200K–$1M+ ACV) from sales handoff through successful go-live and CSM transition

- Serve as primary relationship owner and strategic advisor for 3–5 concurrent enterprise accounts, ensuring customer success and contract value realization

- Lead project planning, scope management, risk mitigation, and change management for multi-phase, multi-stakeholder rollouts

- Drive project governance: weekly status reviews, executive steering committees, escalation management, and lessons learned

- Manage project economics: ensure delivery profitability, track budget burn, forecast overruns, and negotiate scope changes when needed

- Define success criteria with customers upfront and measure progress against business outcomes, not just task completion

Executive Relationship Management & Strategic Advisory

- Build and maintain C-level and VP-level relationships with customer executives throughout the implementation lifecycle

- Conduct Executive Business Reviews (EBRs) and Steering Committee meetings, showcasing value delivered and aligning on next phases

- Serve as escalation point for at-risk projects: diagnose root cause, develop recovery plans, and facilitate difficult stakeholder conversations

- Navigate organizational politics, competing priorities, and stakeholder misalignment to drive consensus and forward progress

- Act as trusted advisor on change management, adoption strategy, and organizational readiness—not just technical implementation

- Translate business objectives into implementation strategies and communicate technical constraints in business language executives understand

Technical Solution Design & Architecture Guidance

- Lead or co-lead design workshops with customer technical teams to architect end-to-end solutions: integration flows, data migration strategies, workflow design

- Design integrations between Rocketlane and enterprise systems (NetSuite, Salesforce, Workday, SAP, HRMS, CRMs, data warehouses)

- Evaluate integration approaches and make build-vs-buy recommendations: native connectors, iPaaS platforms (Workato, Boomi), custom API development

- Review and validate solution designs created by Solution Architects; push back when designs are technically risky, over-engineered, or misaligned with customer needs

- Provide technical direction to implementation teams and partner engineering resources; unblock technical issues that arise during build phase

- Understand REST APIs, webhooks, authentication patterns (OAuth, SAML, SSO), and data flows well enough to guide technical conversations with customer IT teams and troubleshoot integration failures

Hands-On Delivery & Problem-Solving

- Jump into the details when projects are stuck: review project plans, debug integration issues, validate data migrations, test configurations

- Build prototypes or proofs-of-concept using AI tools (Claude, Cursor, MCPs) to validate technical feasibility before committing to customers

- Lead UAT planning and execution; work with customer teams to define test scenarios, track defects, and manage go-live readiness

- Manage data migration from legacy systems: validate data quality, define transformation rules, oversee cutover planning

- Use modern AI tools to accelerate delivery: automate documentation, generate project artifacts, build validation scripts, enhance productivity

Cross-Functional Collaboration & Influence

- Partner with Sales during presales phase to shape deal strategy, validate scoping accuracy, and ensure smooth handoff from AE to delivery

- Collaborate with Product and Engineering teams to prioritize roadmap items that reduce implementation complexity or unblock customer requirements

- Influence Product team on feature gaps discovered in the field; translate customer pain into actionable product requirements

- Work with Customer Success to define handoff criteria and ensure seamless transition from implementation to ongoing adoption

- Partner with India-based delivery teams and product engineering to coordinate global delivery efforts and leverage offshore capacity

- Represent voice of the customer internally, ensuring delivery insights shape product, sales, and go-to-market strategy

Team Leadership & Mentorship (Indirect)

- Provide technical and delivery guidance to Implementation Managers and Solution Architects working on your projects

- Mentor junior team members on stakeholder management, scope negotiation, technical problem-solving, and delivery discipline

- Conduct project retrospectives and document lessons learned to improve delivery playbooks and team capabilities

- Contribute to PS knowledge base: solution patterns, integration playbooks, escalation frameworks, project templates

Delivery Excellence & Process Discipline

- Maintain rigorous project hygiene: up-to-date project plans, accurate status reporting, proactive risk management, clear RACI structures

- Track and report on key project metrics: milestone completion, budget burn, scope change requests, customer satisfaction (CSAT)

- Implement delivery governance on your projects: phase gate reviews, quality checkpoints, go-live readiness assessments

- Drive continuous improvement: identify what's working and what's not, iterate on delivery methodology, share best practices with team

Who You Are

Experience & Track Record

- 10–15 years in enterprise software delivery, professional services, technical consulting, or implementation management roles

- Proven track record leading complex, multi-stakeholder enterprise implementations in B2B SaaS (ideally PSA, CRM, ERP, workflow platforms, or enterprise SaaS)

- Deep hands-on delivery experience across the full implementation lifecycle: discovery, design, build, UAT, data migration, go-live, hypercare

- Experience managing high-stakes projects ($200K–$1M+ ACV) with executive visibility, tight timelines, and complex technical requirements

- Track record of successful delivery outcomes: on-time go-lives, high customer satisfaction, contract renewals, expansion revenue

- Experience working with global delivery teams and managing distributed project resources across time zones

Technical Depth & Solution Design Capability

- Strong understanding of integration architectures: REST APIs, webhooks, iPaaS platforms, authentication protocols (OAuth, SAML, SSO)

- Ability to read API documentation, evaluate technical feasibility, and provide direction to engineering teams (you don't write production code, but you can prototype and troubleshoot)

- Experience designing solutions for enterprise systems: PSA, CRM, ERP, HRMS, financial systems, data platforms

- Familiarity with data modeling, ETL processes, data migration strategies, and enterprise data flows

- Comfortable using modern AI tools (Claude, Cursor, MCPs) to accelerate problem-solving, build prototypes, and enhance delivery productivity

- Bonus: Experience with Professional Services Automation (PSA) platforms and understanding of PS operations (resource management, time tracking, revenue recognition, project margin analysis)

Executive Presence & Customer Engagement

- Exceptional executive presence: comfortable presenting to and building relationships with C-level stakeholders (CTO, COO, CFO, VP-level)

- Ability to shift seamlessly between strategic conversations (business outcomes, ROI, change management) and technical conversations (integration architecture, data flows, API design)

- Command respect in the room without dominating it: you listen deeply, ask insightful questions, and guide decisions collaboratively

- Diplomatic yet direct: you push back assertively on unrealistic timelines, scope creep, and poor decisions while maintaining trust and strong relationships

- Confident managing difficult conversations: scope disputes, project delays, underperforming vendors, stakeholder misalignment, at-risk go-lives

Project Management & Operational Excellence

- Expert-level project management skills: scope definition, work breakdown structures, risk management, dependency tracking, change control

- Data-driven decision maker: you use metrics to diagnose problems, forecast outcomes, and drive accountability

- Strong business acumen: you understand project economics, gross margin dynamics, resource utilization, and how delivery impacts company growth

- Process-oriented but pragmatic: you build structure where needed but don't let process become bureaucracy

- Proactive risk manager: you see around corners, identify risks early, and develop mitigation plans before problems escalate

Leadership & Influence (Without Direct Authority)

- Lead by influence, not authority: you earn respect through expertise, empathy, and action—not org charts or titles

- Strong coach and mentor: you develop talent through real-world problem-solving, not just abstract feedback

- Comfortable with difficult conversations: performance issues with partners, scope negotiations with customers, escalations to executives

- High emotional intelligence: you read the room, adapt communication style, and build trust across diverse stakeholders (engineers, executives, operations teams)

- Collaborative mindset: you build partnerships across Sales, Product, Engineering, Customer Success, and global delivery teams

Hands-On & High-Energy

- Willing to get into the weeds when needed: review a broken integration, rebuild a project plan, facilitate a heated stakeholder meeting, prototype a solution

- High energy and bias toward action: you move fast, make decisions with incomplete information, and iterate based on feedback

- Comfortable with ambiguity and evolving priorities in a fast-paced startup environment

- Not precious about scope or job description: you do what needs to be done to ensure customer and team success

- Resilient under pressure: you thrive in high-stakes situations and stay calm when projects are at risk