Director Customer Success at Pencil – Lead Enterprise Partnerships

At Pencil, we are driving innovation in advertising technology through our state-of-the-art SaaS product, which harnesses Generative AI to redefine content creation. Our mission is to make AI the default in advertising without replacing creative people. To achieve this, we need to make sure that our technology isn’t just in the hands of big brands — we need to help global enterprises transform how marketing and creative operations work at scale.

As Director, Customer Success, you will lead one of Pencil’s most strategic enterprise partnerships. You’ll oversee a dedicated cross-functional account team supporting Target’s North American business, partnering closely with Technical and Production leadership to drive adoption, operational excellence, and long-term account growth.

This role blends strategic customer leadership, operational management, and team development. You will act as the senior post-sale relationship owner for the account while ensuring the broader account pod operates effectively across customer success, technical implementation, creative production, enablement, and workflow transformation initiatives.

You’ll also directly manage a Senior Customer Success Manager, helping shape how we scale enterprise customer success at Pencil.

Preference for candidates in Eastern Time Zone

Strategic Customer Leadership

Own the overall customer relationship for the Target North America business. Build 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.

Team Leadership & Cross-Functional Management

Directly manage a Senior Customer Success, Technical Manager Report into VP, 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.

Operational Excellence & Delivery Oversight

Ensure successful onboarding, implementation, workflow adoption, and ongoing customer enablement. Partner closely with Production and Technical leadership to improve operational scalability and delivery efficiency. Monitor customer health, adoption metrics, workflow performance, and platform utilization. Identify operational bottlenecks and proactively implement scalable solutions. Support enterprise change management and transformation initiatives across the client organization.

Commercial Growth & Account Expansion

Partner with Commercial and Leadership teams to support renewals and account expansion opportunities. Help identify new use cases, workflows, and strategic opportunities for growth. Ensure customer success strategies align with broader business and revenue objectives. Contribute to strategic planning around enterprise service models and customer engagement frameworks.

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. Commercially minded with a strong customer-first approach. Experience in SaaS, AI, marketing technology, creative operations, or enterprise workflow platforms is a plus.

You’ll Thrive Here If You…

Think strategically and operationally — you can balance long-term customer vision with day-to-day execution. Lead through collaboration — you bring cross-functional teams together around shared outcomes. Are customer-obsessed — you focus on measurable client impact, adoption, and business value. Operate with ownership — you proactively solve problems and drive accountability. Are adaptable and solutions-oriented — you thrive in evolving environments and can navigate ambiguity with confidence. Communicate clearly and directly — you build trust through transparency, follow-through, and strong partnership.

KPIs & Success Measures

Adoption and platform utilization metrics Customer retention and expansion performance Workflow implementation and operational efficiency improvements Executive stakeholder satisfaction and relationship strength Team performance, collaboration, and operational alignment Strategic account growth and transformation impact

25 days PTO plus public holidays, although we operate a Flexible Time Off scheme Health insurance / private medical cover Monthly stipend towards cellphone bills Remote — work from anywhere in your home country Enhanced parental leave policies, whether you become a parent through birth, adoption or surrogacy Access to our Pencil office in The Shard, London for UK employees and SoHo in NYC Flexible working hours

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