Senior Director Enterprise Customer Success

• Job ID: 11359BR
• Location: UK-London (Remote)
• Work Setup: Remote
• Job Category: Customer Support
• Posting Date: November 13, 2026

The Senior Director, Customer Success is responsible for leading and reshaping Deltek’s Enterprise Customer Success organisation, building a more scalable, commercially focused and customer-centric model for our most complex Professional Services customers. This is a strategic leadership and transformation role, not a traditional operational CS management position.

You will set the vision for how Enterprise Customer Success should operate, challenge inherited ways of working, and turn that vision into a practical operating model. A central part of the mandate is moving away from a product-oriented approach and towards a broader enterprise model that supports customers across the portfolio, including Maconomy, Vantagepoint and Replicon. You will own the commercial outcomes of an enterprise portfolio, lead an initial team of around eight, and remain personally credible in complex, high-stakes customer situations.

Key Responsibilities

Enterprise Customer Success Strategy

• Define the vision and strategy for Enterprise Customer Success, and what a modern, scalable model looks like across Deltek’s Professional Services business
• Assess existing processes, structures and customer-engagement models, and challenge them where they no longer serve customers or the business
• Develop an operating model covering onboarding, adoption, value realisation, account health, renewal and growth
• Determine which activities belong within Customer Success and which are better placed in adjacent teams
• Build and deliver a roadmap for moving the organisation to the future-state model

Leadership & Organisational Development

• Lead, coach and develop an Enterprise Customer Success team
• Assess current team capability and define the skills needed for the future model
• Develop CSMs beyond single-product specialisation into broader enterprise customer leaders
• Set clear expectations, accountability and performance standards
• Shape the organisation and talent roadmap so the function can grow without simply adding headcount or complexity

Complex Enterprise Customer Leadership

• Provide executive sponsorship for strategically important enterprise customers and engage directly with senior customer stakeholders
• Step into complex, high-maintenance or critical accounts and diagnose the root causes of excessive effort, poor experience, adoption problems or delivery complexity
• Move customer conversations from reactive issue management to structured, long-term improvement
• Coach CSMs to build strategic success plans appropriate to sophisticated enterprise customers
• Manage dependencies across Customer Success, Professional Services, Support, Sales, Product and Cloud teams

Commercial Ownership

• Own retention, renewal and growth performance for an enterprise portfolio of approximately $20M
• Partner with Sales on account strategy, renewals, upsell and cross-sell
• Apply a growth mindset to the portfolio while first addressing the fundamental customer and operating-model issues that drive sustainable growth
• Prioritise effort commercially, based on customer value, risk and potential

Cross-functional Collaboration

• Work closely with Sales, Product, Support, Services and Cloud leadership to deliver consistent outcomes across the customer lifecycle
• Act as the voice of the customer internally, escalating systemic risks and feeding insight into product and service improvement
• Build strong peer relationships across the senior leadership team

Operational Excellence & Insight

• Establish consistent customer health, risk, renewal and forecasting mechanisms, supported by Gainsight and Salesforce
• Provide clear, data-driven reporting and insight to senior leadership
• Apply AI and automation to improve team productivity and customer outcomes
• Senior leadership experience within Enterprise Customer Success or a closely related post-sale function in complex B2B SaaS or enterprise software
• Proven ownership of a meaningful recurring-revenue portfolio, ideally $20M or more
• Experience across a large and varied enterprise customer base (ideally 100+ accounts at organisational level), including successful, struggling and highly demanding customers
• Demonstrable experience developing Customer Success strategy and operating models, and changing how CS operates rather than only managing within an existing structure
• Strong executive presence, with the credibility to engage senior customer stakeholders and manage difficult or strategically critical relationships
• Strong commercial acumen in recurring-revenue businesses, covering retention, renewals, expansion and revenue protection
• Experience improving onboarding, adoption, retention, renewal or expansion outcomes
• Experience working cross-functionally with Sales, Services, Support and Product in complex organisations
• Proven leadership through organisational or operating-model change, and comfort with ambiguity
• Intellectual curiosity, an open mind and an adaptable approach
• AI literacy, with the ability to apply tools to improve productivity and client outcomes

Preferred

• Experience in Professional Services software or technology (Architecture, Engineering, Consulting or similar sectors)
• Experience supporting multi-product enterprise customers
• Global or multi-region Customer Success leadership
• Experience breaking down product or functional silos
• Experience designing scalable segmentation and engagement models
• Experience inheriting an established team and model and successfully challenging existing ways of working
• Familiarity with Gainsight or similar Customer Success platforms
• Bachelor’s degree or equivalent experience

Note: Deltek product knowledge (including Maconomy) is not a prerequisite. Broader enterprise Customer Success leadership capability is valued above knowledge of any single product.

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