Director Customer Success | JobSetuu

Description

Job Overview

• Source: RemoteOK

Job Description

About us:

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

Key responsibilities:

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.
  
  

Your background:

• 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
  
  

Benefits:

• 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
  
  

Expert Career Tips for Director Customer Success Roles

To succeed in a competitive market as a Director Customer Success , you need more than just technical skills. Here are some expert strategies to elevate your profile:

• Build a Strong Portfolio: For technical roles, a clean GitHub or a personal project site is essential. For non-technical roles, a case study portfolio demonstrating problem-solving and impact is equally valuable. Show, don't just tell, what you have achieved in your previous positions.
• Master the Narrative: When interviewing, use the STAR method (Situation, Task, Action, Result) to structure your answers. Quantify your results wherever possible—mentioning "increased efficiency by 20%" is much more impactful than saying "improved efficiency."
• Continuous Learning: The industry moves fast. Whether it's staying updated with the latest AI tools or mastering a new management methodology, continuous professional development is key. Consider obtaining industry-recognized certifications that align with Director Customer Success requirements.
• Networking: Connect with other professionals in similar roles. Join online communities, attend webinars, and engage in meaningful discussions on professional social networks. Often, the best opportunities come through referrals and community engagement.
• Soft Skills Matter: Communication, empathy, and leadership are often the deciding factors between two equally qualified technical candidates. Cultivate these skills as they are universally valued across all industries and seniority levels.

Additionally, research the specific company's culture and values. Tailoring your application to show how you align with their mission can significantly increase your chances of moving forward in the process.

Salary & Compensation

Salary not disclosed; typically competitive for the role.

Work Arrangement

Type: On-Site

Standard business hours at the office.

Comprehensive Application Strategy & Hiring Process

Applying for a new role is a marathon, not a sprint. Follow this strategic approach to maximize your success rate:

1. Initial Research & Tailoring

Don't send the same resume to every employer. Spend at least 30 minutes researching the company. Look for recent news, their product roadmap, and their team structure. Modify your summary and core competencies to reflect the specific keywords found in the job description.

2. The Perfect Cover Letter

If the application allows for a cover letter, use it to tell a story that your resume cannot. Explain why you are passionate about this specific company and how your unique background makes you the perfect fit for the challenges they are currently facing.

3. Navigating the Multi-Stage Interview

Most modern hiring processes involve 3-5 stages. This typically includes a recruiter screen, a technical or skill-based assessment, a peer interview, and a final leadership round. Prepare for each stage differently: focus on enthusiasm and fit for the recruiter, technical depth for the assessment, and strategic vision for the leadership round.

4. Post-Interview Follow-Up

Always send a personalized thank-you note within 24 hours of each interview. Reference a specific topic discussed during the call to demonstrate your active listening and genuine interest in the role.

By following these steps, you demonstrate a high level of professionalism and attention to detail that sets you apart from the average applicant.

Typical Interview Process

1. Resume screening
2. HR call
3. Skill interview
4. Final manager interview
5. Offer

Tip: Research the company's products and culture.

Global Market Intelligence & Relocation Insights

At JobSetuu, we specialize in helping talent navigate the global job market. Here is what you need to know about the current landscape in Global and beyond:

The demand for skilled professionals is increasingly borderless. For roles based in Global, understanding the local cost of living, visa requirements (if applicable), and cultural nuances is vital. If this is a remote role, consider the time zone alignment and the asynchronous communication culture of the hiring organization.

Relocation Support: Many forward-thinking companies offer relocation packages that include moving stipends, temporary housing, and legal assistance with work permits. When evaluating an offer, look beyond the base salary—consider the total compensation package, including equity, bonuses, and healthcare benefits.

Work-Life Balance Trends: Hybrid and remote work have become standard in many regions. Research the local labor laws and common practices regarding work hours and vacation time to ensure the role aligns with your lifestyle goals.

Leveraging JobSetuu's tools can help you compare salaries across different cities and understand the "purchasing power" of your potential offer, ensuring you make an informed decision for your long-term career path.

Skills & Competency Roadmap for Professional Development

To remain competitive in Professional Development, we recommend focusing on the following core competencies over the next 12-18 months:

• Technical Mastery: Deepen your expertise in the core tools and languages relevant to your field. For developers, this might be cloud architecture; for marketers, it might be data-driven attribution modeling.
• AI Augmentation: Learn how to leverage generative AI and automation tools to increase your productivity. Understanding how to integrate these technologies into your workflow is becoming a non-negotiable skill.
• Leadership & Strategy: Even in individual contributor roles, the ability to think strategically and lead projects from inception to completion is highly valued. Focus on stakeholder management and high-level project planning.
• Data Literacy: The ability to interpret data and use it to drive decisions is essential across all business functions. Familiarize yourself with data visualization and basic analytical concepts.

By investing in these areas, you not only prepare yourself for the role you are applying for today but also build a resilient foundation for the opportunities of tomorrow.

Apply via JobSetuu

Discover your next career milestone on JobSetuu. This Director Customer Success position is part of our commitment to bringing you the most relevant and high-impact job openings globally. At JobSetuu, we simplify your job search by aggregating premier listings and providing the tools you need to stand out. Don't miss the chance to elevate your professional journey—explore more opportunities and career insights on our platform today.