Senior Professional Services Engagement Analyst

Join us in bringing joy to customer experience.  Five9 is a leading provider of cloud contact center software, bringing the power of cloud innovation to customers worldwide.    Living our values everyday results in our team-first culture and enables us to innovate, grow, and thrive while enjoying the journey together. We celebrate diversity and foster an inclusive environment, empowering our employees to be their authentic selves.  The Professional Services Sr. Engagement Analyst serves as the primary liaison between Sales and Professional Services. This role leads SOW strategy and lifecycle management for net new and renewal engagements ensuring that commitments made during the sales process are accurately and compliantly reflected in executed Statements of Work. Reporting to the Professional Services Engagement Director, this role combines team leadership, project planning discipline, and strong stakeholder management to partner with Sales, Legal, and Professional Services leadership in negotiating and executing SOWs that protect Five9’s interests while delivering clear value to customers. As needed, the Sr. Engagement Analyst will liaise with Engagement Director, internal SMEs and other key Five9 personnel involved in the development of SOWs to ensure all aspects of the proposal are understood and agreed upon by all parties.  This role will: Parter with Sales and Professional Services subject matter experts, ensuring seamless handoffs and alignment from pre-sales through implementation. Lead and own the full SOW lifecycle from initial scoping through execution. Apply strong project planning and organizational skills to manage multiple high-value engagements simultaneously. Articulate complex PS Sales strategies to both technical and non-technical audiences. Proactively identify and manage risk across all active engagements, developing mitigation strategies and escalate appropriately. Protect Five9 interests and exposure through skilled negotiation, stakeholder alignment, and rigorous SOW management. Communicate and document mutual obligations, assumptions, and deliverables to set clear expectations for all parties. Responsibilities : The Sr. Engagement Analyst drives SOW strategy and team leadership across the Professional Services organization, with accountability for the following areas: SOW Lifecycle Management & Strategy Managing the full SOW lifecycle for all net new and existing customers Drafting, reviews, negotiating, and monitoring SOW to ensure compliance with legal requirements, professional services implementation standards, and company policy and accurately reflect implementation requirements, delivery strategy, and project schedules Identifying potential risks associated with SOWs and developing proactive mitigation strategies to minimize exposure for Five9 and its customers Partnering with all internal and external stakeholders to negotiate SOW terms, resolve redlines, and secure favorable outcomes Recognizing commercial and legal terms requiring escalation and engages Sales Operations and/or Legal as appropriate Sales & Professional Services Partnership Serving as the connective tissue between Sales and Professional Services, translating customer commitments into executable implementation scope Partnering with Sales to support pre-sales scoping activities, ensuring that proposed solutions are accurately represented in SOW language before execution Facilitating stakeholder alignment across Sales, Legal, Connectivity, Custom Development, and PS leadership to ensure shared understanding of scope, risk, and deliverables Applying strong communication and negotiation skills to influence cross-functional alignment and drive decisions that serve both revenue goals and delivery feasibility Collaborating with the Engagement Director on complex, high-value engagements requiring executive-level coordination Participating in pipeline review, deal review and strategy sessions to provide SOW guidance that supports both commercial objectives and operational integrity SOW Development & Technical Excellence Adhering to and champions the PS SOW process for developing, tracking, and communicating all contract documentation Meeting regularly with the Engagement Director to review team SOW output, ensuring quality, timeliness, and alignment to established standards Maintaining proficiency in Five9 products and associated third-party platforms relevant to contract scoping Requirements: Demonstrated ability to operate as a strategic liaison between Sales and Professional Services, with experience navigating competing stakeholder priorities 5+ years of Contact Center or SaaS experience, with a minimum of 2 years in contract management, Professional Services, or Sales-aligned roles Proven track record managing contracts with $1M+ ACV values, including full lifecycle ownership from scoping through execution and compliance Strong negotiation skills with the ability to drive SOW redline resolution and protect organizational interests Excellent written and verbal communication skills; proven ability to translate complex technical or contractual concepts for non-technical audiences BA/BS degree or equivalent professional experience Skills: Highly organized with exceptional attention to detail; able to manage multiple complex engagements simultaneously without sacrificing accuracy or quality Proficient in project planning; skilled at structuring engagement roadmaps, tracking milestones, and keeping cross-functional work on schedule Team leadership; proven ability to inspire a team while maintaining high standards for output quality and professional growth Risk management; adept at identifying, documenting, and mitigating contractual and operational risks across high-value engagements Progress monitoring; disciplined approach to tracking deliverables, reporting engagement health, and escalating issues before they i