Customer Success Manager - Pencil

About Pencil

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 try to help small businesses and creative individuals too.

Strong preference for candidates based anywhere on the East Coast, particularly those within the Eastern Time Zone.

About the Role

As a Customer Success Technical Manager at Pencil, you’ll lead by example: managing one of our high-impact accounts, designing scalable adoption strategies, and helping define how we deliver customer success at scale. You’ll work closely with the Head of Customer Success to build the systems, insights, and practices that ensure every client achieves measurable value from Pencil.

Key Responsibilities

• Account Leadership: Own and lead one of our largest, high-value enterprise accounts, driving deep adoption, renewal success, and long-term growth.
• Relationship Management: Build and maintain strategic relationships across multiple business units, agencies, and departments.
• Onboarding & Enablement: Design and execute scalable onboarding and training programs, tailoring bespoke approaches where needed for enterprise clients.
• Data-Driven Strategy: Drive adoption and engagement using data-led insights to inform strategy and client actions.
• Retention & Renewal: Lead renewal strategy, reduce churn, and increase customer satisfaction (NPS/CSAT).
• Account Growth: Identify and support expansion opportunities in partnership with Account Managers.
• Product Feedback: Collaborate with Product, Engineering, and Creative to advocate for customer needs and influence roadmap priorities.
• Scalable Operations: Contribute to internal enablement, playbooks, and scalable customer success initiatives.
• Community Engagement: Actively engage in the Pencil Community, supporting and celebrating customer success with GenAI.

Requirements

• 6+ years of experience in Customer Success, Onboarding, or Implementation within SaaS or creative technology.
• Experience managing a focused portfolio of 5–10 enterprise accounts with a high-touch, strategic approach (rather than a high-volume portfolio of 100+ accounts).
• Proven track record of improving adoption, retention, and satisfaction across enterprise clients.
• Experience managing or scaling programs across large brands with multiple sub-brands or business units.
• Strong data literacy and the ability to translate insights into action.
• Excellent communication and presentation skills.
• Familiarity with advertising, marketing technology, or generative AI (preferred).

Ideal Mindset

• You see how adoption, engagement, and retention all connect to business growth.
• You act like an owner — taking accountability for client outcomes and team process improvements.
• You are driven by impact and focus on what moves the needle for customers and the business.
• You value collaboration, building strong cross-functional relationships with clear intent.

Benefits & Perks

• 25 days PTO plus public holidays (Flexible Time Off scheme).
• Health insurance / private medical coverage.
• Monthly stipend towards wellness, fitness, and learning & development.
• Enhanced parental leave policies (birth, adoption, or surrogacy).
• Optional on-site access to our customer’s New York office for collaboration.
• Flexible working hours.