Job Description:
The Director, Digital Customer Success Services is responsible for defining and executing the strategy, operating model, technology roadmap, and digital engagement ecosystem that enables scalable, data-driven, and AI-powered customer success at Vertex. This role leads the evolution of Customer Success Services (CSS) through intelligent automation, customer intelligence, digital engagement programs, customer community strategy, and enterprise platform optimization.
The Director oversees the technology, data, analytics, automation, and digital experience capabilities that support the entire customer lifecycle—from onboarding and adoption through renewal, expansion, and advocacy. This leader is responsible for Gainsight and the broader CSS technology ecosystem, customer community strategy and execution, customer intelligence initiatives, AI-enabled workflows, digital success programs, and scalable customer engagement models that improve customer outcomes while increasing organizational efficiency and coverage.
Partnering closely with Customer Success, Product, Marketing, Customer Experience, Data & Analytics, Operations, and Technology teams, this role drives transformation through innovative technologies, customer-centric design, operational excellence, and AI-powered decision-making.
ESSENTIAL JOB FUNCTIONS & RESPONSIBILITIES:
- Develop and execute the vision, strategy, and operating model for Digital Customer Success Services, aligning technology, customer engagement, community, intelligence, and AI capabilities to business objectives.
- Own the Customer Success Services technology ecosystem, including Gainsight, customer intelligence platforms, customer data integrations, automation tools, reporting solutions, and future-state AI capabilities.
- Lead the strategy, governance, and optimization of the Vertex Customer Community, creating a scalable digital destination that drives self-service, product adoption, peer collaboration, customer education, advocacy, and innovation.
- Design and implement AI-powered customer engagement programs that deliver personalized experiences across onboarding, adoption, value realization, renewal readiness, retention, and expansion motions.
- Develop customer intelligence capabilities including segmentation, health modeling, predictive analytics, customer risk identification, opportunity detection, propensity scoring, and next-best-action recommendations.
- Lead the development and deployment of agentic AI, intelligent automation, and digital orchestration capabilities that increase scalability, efficiency, consistency, and customer outcomes.
- Establish and optimize digital customer journeys leveraging customer health data, product telemetry, behavioral analytics, community engagement data, and customer feedback signals.
- Design scalable digital coverage models that expand Customer Success reach through automation, AI-assisted engagement, self-service experiences, and community-driven support models.
- Drive platform governance, administration, integration strategy, data quality, security, and operational standards to ensure trusted customer intelligence and scalable operations.
- Partner cross-functionally with Product, Engineering, Customer Experience, Marketing, Data & Analytics, Revenue Operations, and Technology teams to deliver integrated customer experiences and business outcomes.
- Develop and optimize Customer Success Services processes, playbooks, lifecycle workflows, and operating frameworks that improve efficiency, consistency, customer adoption, and value realization.
- Evaluate and pilot emerging technologies, AI innovations, and customer engagement capabilities while building business cases and transformation roadmaps that support organizational growth.
- Define and manage executive-level KPIs, dashboards, reporting frameworks, and success metrics that measure customer outcomes, operational performance, digital engagement effectiveness, community impact, and AI adoption.
- Serve as a champion for AI literacy, data-driven decision-making, digital transformation, and continuous innovation across Customer Success Services.
- Drive continuous improvement initiatives that enhance customer experiences, operational scalability, customer retention, advocacy, employee productivity, and business performance.
SUPERVISORY RESPONSIBILITIES:
- Serve as a champion for digital transformation by driving AI literacy, technology enablement, and best practice adoption across Customer Success & Services, elevating the organization's digital maturity and operational effectiveness.
- Lead and develop a team responsible for Customer Success technology platforms, digital engagement programs, customer community management, automation, reporting, and AI-enabled customer success capabilities.
- Establish strategic priorities, performance objectives, development plans, and accountability measures aligned to Customer Success Services goals and organizational objectives.
- Foster a culture of innovation, customer-centricity, operational excellence, continuous improvement, and responsible AI adoption.
- Serve as a player-coach leader, balancing strategic vision with hands-on leadership across transformational initiatives, platform innovation, and operational execution.
- Manage resource planning, investment prioritization, team capacity, and organizational readiness to support ongoing growth and transformation initiatives.
- Coach and develop team members in customer success technology, community strategy, AI capabilities, automation, digital engagement practices, customer experience, and operational excellence.
- Partner with executive leadership to identify future capability needs and build the technical, operational, and digital skills necessary to scale Customer Success Services.
- Lead recruiting, talent development, succession planning, and organizational design efforts that strengthen Vertex's digital customer success capabilities.
REQUIRED QUALIFICATIONS:
- Deep expertise in artificial intelligence, generative AI, agentic AI, machine learning, natural language processing, intelligent automation, recommendation engines, and advanced decisioning frameworks, with a proven track record of applying emerging technologies to transform customer success operations and business outcomes.
- Extensive experience architecting and scaling AI-powered customer success strategies leveraging predictive intelligence, customer health modeling, propensity scoring, churn forecasting, autonomous workflows, next-best-action recommendations, and real-time customer orchestration.
- Advanced expertise in enterprise data architecture, customer intelligence ecosystems, data governance, master data management, data quality frameworks, and machine learning solutions that enable trusted, scalable, and actionable customer intelligence across the enterprise.
- Deep technical proficiency in customer success technologies and digital platforms, including Gainsight, Salesforce, customer community platforms, CRM ecosystems, customer data platforms (CDPs), cloud technologies, business intelligence solutions, marketing automation platforms, and enterprise software architectures.
- Proven expertise in designing and implementing AI-powered customer experiences, intelligent journey orchestration, digital engagement ecosystems, behavioral analytics frameworks, product telemetry solutions, self-service strategies, and scalable automation capabilities that drive personalized customer interactions at scale.
- Advanced knowledge of systems architecture, API-enabled ecosystems, cloud platforms, data pipelines, integration frameworks, interoperability standards, and enterprise platform governance required to deliver connected and scalable customer success technologies.
- Demonstrated success leading enterprise platform strategy, administration, optimization, modernization, and digital transformation initiatives involving AI adoption, automation, intelligent workflows, and next-generation customer success capabilities.
- Proven experience designing, launching, and scaling enterprise customer community ecosystems, including end-to-end ownership of strategy, platform selection, implementation, governance, engagement architecture, adoption programs, customer advocacy initiatives, operational management, and long-term growth.
- Strong business and technology acumen with demonstrated success developing AI transformation strategies, operating models, technology roadmaps, business cases, innovation programs, and investment priorities that accelerate customer growth, retention, operational efficiency, and digital maturity.
- Expertise establishing AI governance frameworks, responsible AI practices, model monitoring, risk management controls, and compliance standards that ensure ethical, secure, and effective deployment of enterprise AI capabilities.
- Exceptional executive leadership, communication, and stakeholder management skills, with a proven ability to influence senior leaders, lead complex cross-functional transformation programs, drive enterprise AI adoption, and foster a culture of innovation, technical excellence, operational rigor, and continuous improvement.
- Bachelor's Degree in Computer Science, Information Systems, Data Science, Artificial Intelligence, Engineering, Business, or a related field; Master's Degree or MBA preferred.
- Minimum of 15 years of progressive leadership experience driving digital transformation, enterprise technology strategy, customer success innovation, or large-scale operational modernization within complex SaaS or technology organizations.
- Minimum of 15 years leading high-performing teams and enterprise-wide initiatives focused on AI adoption, customer technology, platform strategy, automation, digital engagement, and organizational transformation.
- Recognized expertise in artificial intelligence, including generative AI, agentic AI, machine learning, predictive intelligence, autonomous workflows, intelligent decisioning, and scalable automation, with a proven track record of translating emerging technologies into measurable business value.
- Demonstrated expertise building and scaling enterprise customer communities from strategy through implementation and long-term management, including platform selection, governance, engagement architecture, customer advocacy programs, content strategy, and community-led growth initiatives.
- Experience developing enterprise technology roadmaps, AI transformation strategies, operating models, and investment plans that align innovation, customer needs, and business objectives while establishing a foundation for future growth and scale.
- Strong executive leadership presence with demonstrated success influencing senior leaders, driving cross-functional alignment, and leading enterprise transformation initiatives spanning Product, Engineering, Customer Success, Customer Experience, Marketing, Operations, Data, and Technology organizations.
PREFERRED QUALIFICATIONS:
- Demonstrated success designing and executing enterprise AI strategies that transform customer engagement, operational efficiency, decision intelligence, customer lifecycle management, and business performance.
- Extensive experience leading the strategy, governance, architecture, and optimization of enterprise customer technology ecosystems, including CRM platforms, customer success technologies, community platforms, customer data environments, automation frameworks, and integrated digital engagement solutions.
- Proven ability to architect scalable digital customer success models that leverage AI-powered engagement, intelligent journey orchestration, automation, self-service capabilities, and data-driven customer experiences to improve adoption, retention, growth, and advocacy.
- Advanced certifications in Artificial Intelligence, Machine Learning, Cloud Technologies, Enterprise Architecture, Digital Transformation, Customer Success Platforms, or related disciplines preferred.
- Equivalent combinations of education, experience, and demonstrated leadership in AI-enabled customer technology transformation will be considered.
COMMENTS:
The above statements are intended to describe the general nature and level of work being performed by individuals in this position. Other functions may be assigned, and management retains the right to add or change the duties at any time.
Vertex Values: Together We Win
We're building a team of people who are passionate about making an impact for our customers and committed to how that impact is achieved. Our values define the behaviors, mindset, and culture that make Vertex a great place to grow and do meaningful work.
Play to Win or We Don't Play — If we choose to do something, we're choosing to do it because we plan to win. That mindset raises our bar on product quality, customer outcomes, and how we show up for one another.
Work As a Team, Putting the Customer At the Core — Our customers are our true north. Whatever your role, ask: how will this help a customer succeed today? We earn trust through outcomes, not promises.
Achieve Excellence With Integrity, Speed, and Agility — The market isn't slowing down. We'll move faster, adapt quickly, and never compromise on doing things the right way — for teammates, customers, and partners.
Innovate Boldly With a Growth Mindset — Progress demands smart risk. We'll try new approaches, learn fast, and keep pushing the boundaries — especially where AI can remove friction and unlock value.
Communicate with Care, Candor and Transparency — Honest, constructive conversations make us better. Let's speak plainly about what's working and what isn't and help each other improve.
Pay Transparency Statement:
Base pay offered to new hires may vary based upon factors including relevant industry and job-related skills and experience, geographic location, and business needs.* The range displayed does not encompass the full potential of the role, which allows for further growth and career progression.
In addition, as a part of our total compensation package, this role may be eligible for the Vertex Bonus Plan (VOB), a role-specific sales commission/bonus, and/or equity grants.
Learn more about Life at Vertex and connect with your recruiter for more details regarding Vertex's compensation and benefit programs.
*In no case will your pay fall below applicable local minimum wage requirements.
Skills Required
- Deep expertise in artificial intelligence, generative AI, agentic AI, machine learning, and natural language processing
- Extensive experience architecting and scaling AI-powered customer success strategies (health modeling, propensity scoring, churn forecasting)
- Advanced expertise in enterprise data architecture, customer intelligence ecosystems, data governance, master data management, and data quality frameworks
- Deep technical proficiency with customer success technologies and digital platforms, including Gainsight and Salesforce
- Proven experience designing and implementing AI-powered customer experiences, journey orchestration, behavioral analytics, and product telemetry
- Advanced knowledge of systems architecture, API-enabled ecosystems, cloud platforms, data pipelines, and integration frameworks
- Demonstrated success leading enterprise platform strategy, administration, optimization, modernization, and digital transformation initiatives
- Proven experience designing, launching, and scaling enterprise customer community ecosystems (strategy, implementation, governance, engagement)
- Bachelor's Degree in Computer Science, Information Systems, Data Science, Artificial Intelligence, Engineering, Business, or related field
- Minimum of 15 years of progressive leadership experience driving digital transformation, enterprise technology strategy, or customer success innovation
- Minimum of 15 years leading high-performing teams and enterprise-wide initiatives focused on AI adoption, customer technology, and platform strategy
- Master's Degree or MBA
- Advanced certifications in AI, Machine Learning, Cloud Technologies, Enterprise Architecture, or Customer Success Platforms
Vertex, Inc. Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Vertex, Inc. and has not been reviewed or approved by Vertex, Inc..
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Leave & Time Off Breadth — Flexible time off, including unlimited vacation for some roles, paid volunteer time, bereavement leave, sabbaticals, and observed holidays is emphasized. Occasional company shutdowns further expand time-away options.
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Parental & Family Support — Benefits span paid parental leave, adoption assistance, childcare support, fertility benefits, and structured return-to-work programs. Backup care and daycare tuition discounts reinforce family-focused support.
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Retirement Support — A 401(k) with employer matching and immediate vesting anchors long-term savings. Profit sharing and defined contribution programs complement financial security offerings.
Vertex, Inc. Insights
What We Do
The Trusted Leader in Tax Technology. We're Vertex (VERX). A pioneer in tax automation for more than 45 years. We proudly serve over 4,000 customers worldwide with distinction and provide comprehensive tax solutions that enable global businesses to transact, comply, and grow with confidence. Our collaborative, friendly culture is the foundation of everything we do and who we are. We're proud to be an employer guided by a common purpose by building trusted relationships at work, in business and in our communities. We strive to be a values-driven employer of choice who attracts, retains, and inspires talented professionals to achieve their full potential. We employ over 1,500 full-time professionals across three continents: US, Europe, and Brazil. Our software, content, and services address the increasing complexities of global commerce and compliance by reducing friction, enhancing transparency and enabling greater confidence in meeting indirect tax obligations. As a result, our software is ubiquitous within our customers’ business systems, touching nearly every line item of every transaction that an enterprise can conduct. Our software is fueled by over 300 million data-driven effective tax rules and supports indirect tax compliance in more than 19,000 jurisdictions worldwide. We partner with the world’s most respected companies and harness their strengths to deliver the best tax technology solution to businesses across the globe. We integrate with key technology partners that span ERP, CRM, procurement, billing, POS and e-commerce platforms. We also work closely with over 50 tax, accounting and consulting firms to provide the integrated tax technology solutions.
Why Work With Us
Innovative, agile, and growth-minded professionals thrive at Vertex. Our remote-first culture offers flexibility and connection, while our focus on indirect tax technology and global expansion creates real impact. With leadership development and a strong emphasis on well-being, careers flourish here.
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