Senior Customer Success Technical Manager

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 ensure our technology isn’t just in the hands of big brands—we aim 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 Senior 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.

Job Requirements

• Extensive experience in Customer Success, Onboarding, or Implementation within SaaS or creative technology. Must have at least 6+ years of experience.
• 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 ability to translate insights into action.
• Excellent communication and presentation skills.
• Familiarity with advertising, marketing technology, or generative AI (preferred).

You’ll Thrive Here If You...

• You see how adoption, engagement, and retention all connect to business growth.
• You act like an owner—you take accountability for client outcomes and for improving how our team delivers them.
• You’re driven by impact—you focus on what moves the needle for customers and the business.
• You value collaboration—you build strong cross-functional relationships and communicate with intent.

Job Responsibilities

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

Our Benefits

• 25 days PTO plus public holidays, although we operate a Flexible Time Off scheme.
• Health insurance / private medical cover.
• Monthly stipend towards wellness, fitness, and learning and development.
• Enhanced parental leave policies, whether you become a parent through birth, adoption, or surrogacy.
• On-site access to our customer’s New York office for collaboration and partnership.
• Flexible working hours.