Director Customer Success
WFA Digital Insight
As the demand for innovative advertising technology continues to rise, companies like Pencil are at the forefront, harnessing Generative AI to redefine content creation. With a growing need for skilled professionals to manage complex stakeholder relationships, the role of a Director of Customer Success is more crucial than ever. According to recent trends, the demand for customer success specialists in the tech industry has seen a significant increase. Pencil's commitment to making AI the default in advertising without replacing creative people positions this role as an exciting opportunity for those who want to be part of a revolutionary shift in the industry. Before applying, candidates should be aware of the high expectations for strategic customer leadership and the ability to drive operational excellence in a fast-paced environment.
Job Description
About the Role
The Director of Customer Success at Pencil is a pivotal role that involves leading one of the company's most strategic enterprise partnerships. This position requires a deep understanding of customer needs, the ability to build and maintain strong relationships with executive and operational stakeholders, and the capacity to drive adoption and growth through strategic planning and operational management. As a senior post-sale relationship owner, the Director of Customer Success will be responsible for overseeing a dedicated cross-functional account team, ensuring that the team operates effectively across customer success, technical implementation, creative production, enablement, and workflow transformation initiatives.The role of the Director of Customer Success is multifaceted, blending strategic customer leadership, operational management, and team development. This involves not only managing the customer relationship but also contributing to the development of the customer success organization as a whole. Given the preference for candidates in the Eastern Time Zone, the ideal candidate will be based in this region, allowing for closer alignment with key stakeholders and more effective management of the account team.
What You Will Do
- Own the overall customer relationship for the Target North America business, building trusted relationships with executive and operational stakeholders across the client organization.
- Lead strategic account planning focused on adoption, retention, workflow transformation, and growth opportunities.
- Drive quarterly business reviews, executive reporting, roadmap discussions, and escalation management.
- Identify opportunities to deepen Pencil's value across workflows, business units, and creative operations.
- Directly manage a Senior Customer Success Manager, helping shape how the company scales enterprise customer success.
- Lead the broader Target account pod in partnership with dedicated Technical and Production Leads.
- Create strong alignment across Customer Success, Technical Solutions, Production, Product, and Commercial teams.
- Establish clear operating rhythms, accountability structures, and communication processes across the account team.
- Support coaching, mentorship, and development within the Customer Success organization.
- Ensure successful onboarding, implementation, workflow adoption, and ongoing customer enablement.
- Partner closely with Production and Technical leadership to improve operational scalability and delivery efficiency.
What We Are Looking For
- Extensive experience in Customer Success, Account Management, Professional Services, or Enterprise SaaS leadership roles.
- Proven success managing large enterprise or strategic accounts with complex stakeholder structures.
- Experience leading cross-functional teams in fast-paced, high-growth environments.
- Strong operational mindset with experience building scalable processes and ways of working.
- Experience partnering closely with technical, implementation, or production/delivery teams.
- Strong executive presence and ability to lead strategic customer conversations.
- Excellent written and verbal communication skills.
- Proficiency in Excel and other relevant business applications.
- Ability to travel as required for customer meetings and company events.
Nice to Have
- Experience with Generative AI and its applications in advertising technology.
- Familiarity with SaaS products and their implementation in enterprise settings.
- Knowledge of the advertising and marketing industry, including current trends and challenges.
- Certification in customer success or a related field.
Benefits and Perks
- Competitive salary and benefits package.
- Opportunity to work with a revolutionary AI technology in advertising.
- Collaborative and dynamic work environment.
- Professional development opportunities, including training and certification programs.
- Flexible remote work arrangements, with the option to work from anywhere in the Eastern Time Zone.
- Access to cutting-edge technology and tools.
- Recognition and reward for outstanding performance.
- Comprehensive health insurance and wellness programs.
- Generous PTO and holiday policy.
How to Stand Out
- Ensure your resume and cover letter are tailored to the role, highlighting experience in customer success and account management.
- Prepare to discuss specific examples of strategic customer relationships you have managed and how you drove growth and adoption.
- Familiarize yourself with Pencil's technology and the current landscape of advertising technology to show your interest and knowledge.
- Be ready to discuss your approach to building and maintaining cross-functional teams and your experience with operational management.
- Research the company culture and values to understand how you can contribute to Pencil's mission and vision.
- Practice your presentation skills, as you may be required to present to stakeholders or lead meetings.
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