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Director, Digital and Scaled Customer Success

Hyland Software
parental leave, paid time off, 401(k)
United States
Aug 21, 2025

Director, Digital and Scaled Customer Success




Job ID
2025-12826

# of Openings
1


Job Locations

Remote - U.S.

Category
Support



Overview

The Director Digital and Scaled Customer Success is responsible for leading the strategy and execution of the company's digital-first customer engagement programs. This position is responsible for designing and optimizing the digital customer journey and implementing a pooled/shared model to support the company's mid-touch customer segment efficiently and effectively. The Director Digital and Scaled Customer Success is accountable for driving product adoption retention and expansion at scale by leveraging technology data automation and a customer-centric mindset.

Responsibilities



What you will be doing

    Own the end-to-end digital customer journey for mid-touch and long-tail customer segments. Select and optimize technology stack (e.g. Gainsight Catalyst Salesforce Customer.io Intercom) for automation journey orchestration and insights. Work with Ops and RevOps to ensure accurate data flows segmentation and attribution.
  • Champion a data-driven approach to customer engagement and team performance.
  • Design influence and implement lifecycle-based touchpoints (onboarding adoption value realization renewal) using email in-app messaging webinars communities and self-service content.
  • Leverage customer insights and analytics to continuously iterate and personalize journeys. Implement one-to-many programs (office hours success webinars health check campaigns).
  • Partner with Product Marketing and Customer Education to align digital experiences with customer needs. Drive cross-functional alignment with Sales Support Product and Marketing to ensure seamless customer experiences.
  • Build and lead a pooled/shared model of Customer Success Managers (CSMs) to support thousands of accounts efficiently. Develop scalable playbooks processes and KPIs for CSMs operating in a non-dedicated coverage model.
  • Establish and assure leadership adherence to budgets schedules work plans and performance requirements
  • Collaborate with senior management and executives to define and ensure success of department strategy
  • Provide managerial direction and oversee all aspects of performance management for direct reports. Measure and hold direct reports accountable for meeting defined performance standards; provide feedback to employees; ensure management team is defining and holding teams accountable for all aspects of performance management of direct reports
  • Oversee and hold management accountable for all Human Resources-related managerial functions and responsibilities associated with hiring compensation management employment relations and termination of employees. Oversee the identification and hiring of new employees
  • Oversee and ensure the development of team members; provides coaching to employees through their personal growth in: functional expertise communication skills and ability to effectively interact with clients and peers. Identify and develop future leaders.
  • Provide strategic influence to internal peers and industry groups
  • Serve as an escalation point for complex issues; provide guidance and resources to assist with resolution of issues and removing obstacles for team
  • Work with the leadership to plan and set the strategic vision organizational structure operating policies and procedures and management practices to ensure department delivers operational excellence
  • Evaluate the process and procedures used by team; Identify opportunities for process improvement and greater efficiency and serve as an advocate for change. Work collaboratively across departments with leaders


What will make you successful

  • Bachelor's degree or equivalent experience
  • 7-10+ years of experience in Customer Success Digital Success Customer Marketing or related SaaS leadership roles.
  • Proven track record of designing and executing digital customer journeys and scaled programs at scale.
  • Experience leading pooled/shared CSM teams or hybrid coverage models (in region and contracted offshore)
  • Deep understanding of customer segmentation health scoring automation and engagement strategies.
  • Familiarity with tools like Gainsight Salesforce Intercom Jira Pendo Marketo or similar.
  • Experience working in B2B SaaS with a product-led growth (PLG) motion.
  • Background in customer marketing lifecycle marketing or user education.
  • Demonstrated fiscal responsibility/accountability in managing budgets
  • Superb Problem solving critical thinking and analytical skills
  • Superb cross-functional collaboration stakeholder management and change management skills.
  • Superb attention to detail
  • Superb interpersonal skills; able to maintain solid rapport with team members as well as maintain professionalism with those outside of department
  • Superb Leadership sound judgement and business acumen skills
  • Superb oral and written communication skills that demonstrate a professional demeanor and the ability to interact with others with discretion and tact
  • Superb organizational multi-tasking and time management skills
  • Superb facilitation and project management skills
  • Superb customer service orientation
  • Self-motivated with follow through and attention to detail
  • Superb analytical mindset with the ability to translate data into action
  • Superb ability to handle sensitive information with discretion and tact
  • Superb ability to establish rapport and gain the trust of others; effective at gaining consensus
  • Able to thrive in a fast paced deadline driven environment
  • Ability to coach mentor and provide feedback to team members in a timely manner
  • Superb ability to develop use and deliver engaging informative and compelling presentation methodologies
  • Ability to provide guidance and support to developing team members
  • Sharp fast learner with technology curiosity and aptitude
  • Based on individual states' employment laws, the following details are to comply with the relevant salary posting requirements: base salary range of $156,000-$195,000 and eligible for benefits

What you can expect next

  • Hyland Recruiters thoroughly review every application and will contact you within 1 to 2 weeks regarding next steps. Be sure to add Hyland to your contacts list and check your spam folder so you never miss a message from us!
  • Any follow up questions? Email your Recruiter directly at Careers@Hyland.com.

Benefits

401(k) Retirement Savings. Flexible Schedule. Paid Time Off. Medical, Dental, Vision. Volunteer Paid Time Off. Wellness Reimbursement. Paid Parental Leave. Sabbatical Program.

Find out more by going to https://www.hyland.com/en/resources/articles/why-work-at-hyland .

Welcome to #HylandLife

Since 1991, it has been Hyland's mission to help our employees, customers and partners exceed their potential with our industry-leading content services platform. Our employees exude a contagious energy and are passionate about what they do - whether it's helping customers succeed, raising up their fellow Hylanders, or engaging in the communities where they live and work.

The #HylandLife hashtag encompasses our employee-centric culture. Our employees live our culture day in and day out by bringing their best self to work. Hyland supports them to do just that through career development resources, wellbeing programs and innovation practices. We thrive on diverse viewpoints and new ideas and believe that a positive, inclusive workplace is imperative to sustainable success.

As we've grown to a company of nearly 4,000 strong, we have the opportunity to make a significant impact on our communities. We strongly support employee initiatives and align our giving campaigns and programs to organizations that are important to them.

We are committed to a policy of Equal Employment Opportunity and will not discriminate against an applicant or employee on the basis of race, color, religion, creed, national origin or ancestry, sex, age, physical or mental disability, veteran or military status, genetic information, sexual orientation, marital status, or any other legally recognized protected basis under federal, state or local laws, regulations or ordinances. The information collected by this application is solely to determine suitability for employment, verify identity and maintain employment statistics on applicants.

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