Fast Facts

The Digital CX Lead will drive digital transformation in Customer Success by leveraging automation and analytics to enhance customer engagement throughout the post-sales journey.

Responsibilities: Lead digital programs supporting the Customer Success lifecycle, optimize customer engagement through analytics, and collaborate across teams for a unified customer experience.

Skills: Proven program management, analytical proficiency with data visualization tools (e.g., Tableau), and strong communication and stakeholder management skills.

Qualifications: 8+ years of relevant experience in Program Management or Customer Success, with familiarity in SaaS or HR tech and comfort with AI tools.

Location: Chicago, IL, US

Compensation: Not provided by employer. Typical compensation ranges for this position are between $90,000 - $150,000.

Champion a digital-first mindset across Customer Success — train and enable CSMs to leverage automation, content, and analytics to reach more customers efficiently and effectively. Lead end-to-end ownership of digital programs that support the Customer Success lifecycle — from onboarding through expansion. Own and drive cross-functional digital experience programs that directly impact the post-sales customer journey - including initiatives like community experience expansion, communications automation, and alignment of customer-facing touch points. Map, design, and continuously improve post-sales digital engagement programs that enhance onboarding, adoption, retention, and expansion across customer segments. Develop and maintain dashboards using data visualization tools (e.g., Tableau) to measure program impact and inform iteration. Analyze and synthesize customer data to surface trends and drivers of health, then apply insights to optimize digital touch points and lifecycle programs. Partner with GTM Systems to align tools, data, and workflows that scale Customer Success operations and customer engagement. Experiment with AI and automation, including custom agent pilots, to streamline internal CS processes and create faster, more personalized customer experiences. Build and maintain playbooks, documentation, and governance models to ensure digital programs are sustainable, measurable, and continuously improved. Collaborate with Sales and Solution Delivery to ensure consistent handoffs and unified customer experience across post-sale phases. 8+ years of relevant professional experience, including 3-5 years of experience in Program Management, Customer Success, or Consulting, ideally within a SaaS or HR tech environment. Proven ability to manage cross-functional projects with measurable business outcomes. Strong operational and execution mindset, translating strategy into structured, scalable programs. Analytical fluency with data visualization tools such as Tableau. Comfort working with technical and data teams, and openness to learning new technical skills as needed. Curiosity and hands-on experience with AI tools or automation, with a perspective on how AI can enhance internal workflows and customer engagement. Excellent communication and stakeholder management skills. A collaborative, proactive, and learning-oriented mindset. Experience in customer experience design or scaled success programs, with a focus on lifecycle management. Comfort configuring and working within technical systems (e.g., platform settings, integrations, workflow automation, and data structures). Experience partnering closely with developers & data teams, including the ability to translate business needs into clear technical requirements and participate in technical discussions. Technical fluency such as SQL, scripting, light coding, or prior experience building simple tools, automations, or prototypes. Demonstrated “builder” mindset with a track record of experimentation, rapid iteration, and shipping improvements with speed and measurable impact. Experience piloting or prototyping new tools (including AI-enabled tools), evaluating what works, and scaling successful solutions into repeatable programs. Self-starter who proactively explores novel technologies and learns independently to stay ahead of emerging solutions and best practices. Experience our comprehensive benefits with family medical, vision and dental coverage, a competitive base salary, and eligibility for equity awards and discretionary bonuses or commissions.