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Head of Customer Success

Company Overview

Founded in 2008, our company is a fast-growing SaaS leader in SMS solutions designed for marketing professionals. With a robust product portfolio and a focus on scale-up growth, we currently serve diverse verticals—including Higher Education, Sports, SaaS, Financial, and more. As we continue to expand our business, we are seeking an innovative, strategic, and results-driven Head of Customer Success to lead our customer centric approach and drive sustainable growth.

Position Overview

The Head of Customer Success will be responsible for developing and executing a strategic plan for driving customer platform adoption, account retention, and long-term value by managing the post-sales relationship with customers. Reporting directly to the CEO, the ideal candidate will have a player-coach approach to lead and mentor a team primarily focused on customer adoption, usage, and success management, ensuring customers are continually maximizing the value we provide to their business.

As one of the most critical and important roles in the company, the Head of Customer Success will partner with the Sales and Finance teams for contract negotiation, identifying upsell and cross-sell opportunities, and uncovering and determining the metrics that will be crucial to forecasting, identifying churn risk, and maintaining a strong customer renewal rate and growth rate. The Head of Customer Success will also partner with the customer support team that handles day-to-day customer inquiries or escalation management. Blending people-first and data-centric approaches, this role is pivotal to customer retention, platform adoption, and partnering with marketing to turn customer experiences into case studies.

What You’ll Do:

  • Lead and mentor a team of customer success and support professionals enabling them to achieve professional growth in their roles.
  • Work directly with customers to onboarding new customers, maintain platform adoption goals, and retain customer accounts
  • Own the strategies, data, and processes that drive your work: onboarding, health checks, business reviews (QBRs), risk signals, and more
  • Partner with customers to understand their business goals, share insight into best practices, industry trends, and help them achieve measurable, repeatable self-sufficient success
  • Develop, execute, and maintain strategic account plans to drive business value and ROI. 
  • Collaborate cross-functionally to optimize new business handoffs, upsells, renewals, support experiences, customer advocacy, and product roadmap
  • Analyze customer success metrics (e.g. NPS, adoption data, churn feedback, etc.) to create a metrics-driven approach to your work and adjust your customer strategy
  • 6+ years of experience as a team lead or manager/director in Customer Success and/or Account Management in B2B SaaS companies.  
  • Experience in marketing automation, CCaaS, telephony, SMS, email marketing, carrier relations, or related field preferred.
  • Proven track record of building and leading customer-centric, high-performing, adaptable customer success teams in a fast-paced, metrics-driven environment
  • Experience with Salesforce, Gainsight or other customer success software and reporting tools
  • High degree of customer empathy
  • Critical thinking and problem-solving skills in order to envision solutions for customers.
  • Ability to thrive within a fast-paced environment that continues to evolve. 
  • Strong understanding of customer onboarding, adoption, usage, health, and retention strategies
  • Excellent communication and relationship-building skills, with the ability to collaborate cross-functionally and build strong customer relationships
  • Data-driven with a demonstrated ability to bring an analytical mindset and leverage data to improve customer and business outcomes
  • Bachelor's degree from an accredited university

What We Offer

  • Dynamic Work Environment: Join a passionate team in a company with a strong product foundation and ambitious growth plans.
  • Competitive Compensation: Attractive salary, equity, and benefits package including medical, dental and vision benefits, 401k, PTO, and professional development opportunities.
  • Growth Opportunities: Be a key player in a scale-up environment where your insights and leadership will directly impact the company’s future.
  • Innovative Culture: Work in a collaborative, forward-thinking setting that values innovation, creativity, and data-driven decision-making with a strong team and proven Executive team.

Average salary estimate

$115000 / YEARLY (est.)
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$100000K
$130000K

If an employer mentions a salary or salary range on their job, we display it as an "Employer Estimate". If a job has no salary data, Rise displays an estimate if available.

What You Should Know About Head of Customer Success, TrueDialog, Inc.

Are you ready to take the reins as the Head of Customer Success at an innovative SaaS company that has been revolutionizing the SMS solutions landscape since 2008? In this exciting role, you'll play a crucial part in developing and executing strategic plans that ensure customers not only adopt but maximize the benefits of our platform. Your mission? To lead a dynamic team dedicated to customer success, fostering relationships that translate into long-term value and retention. As you partner with various departments like Sales and Finance, you'll dive deep into contract negotiations, upsell opportunities, and uncover vital metrics to mitigate churn risk. Your analytical mindset will be pivotal as you monitor customer success metrics, leading impactful onboarding sessions and ensuring a continuous path toward customer satisfaction. With at least six years of experience in customer success management within the B2B SaaS sector, you're well-equipped to navigate this fast-paced environment while mentoring your team to excel. We're looking for someone with a deep understanding of customer behaviors, exceptional communication skills, and a passion for fostering a nurturing environment for both team members and clients. If you're ready to drive customer experiences that not only meet but exceed expectations and you thrive on innovation and collaboration, we'd love for you to bring your talents to our forward-thinking company and help us scale new heights together!

Frequently Asked Questions (FAQs) for Head of Customer Success Role at TrueDialog, Inc.
What are the main responsibilities of the Head of Customer Success at this company?

The Head of Customer Success at our company is responsible for developing and executing strategic plans that focus on customer platform adoption, retention, and value. This role involves managing post-sales relationships with clients, mentoring a dedicated team, and working closely with other departments like Sales and Finance to identify upsell opportunities and forecast metrics. Engaging directly with customers to understand their needs and providing valuable insights into best practices is crucial for ensuring continued success.

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What qualifications are required for the Head of Customer Success role?

To be considered for the Head of Customer Success position, candidates should have at least six years of experience in a team lead or managerial role within customer success or account management in B2B SaaS companies. Preferred qualifications include familiarity with marketing automation, telephony, and customer success software such as Salesforce or Gainsight. Strong communication skills, a customer-centric mindset, and proven team leadership abilities are essential for this role.

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How does the Head of Customer Success collaborate with other teams?

Collaboration is key in this role. The Head of Customer Success works with cross-functional teams including Sales, Marketing, and Customer Support to optimize customer handoffs, improve upsell and renewal processes, and enhance overall customer advocacy. By maintaining open communication channels and aligning strategies, the Head of Customer Success ensures that all teams are focused on delivering exceptional customer experiences and achieving company goals.

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What type of work culture can a Head of Customer Success expect at this company?

The work culture at our company is dynamic, innovative, and collaborative. Employees thrive in an environment that values creativity and data-driven decision-making. As part of a passionate team, the Head of Customer Success will have the opportunity to contribute directly to the company’s ambitious growth plans while developing their own professional skills in a supportive atmosphere.

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What benefits does the Head of Customer Success role offer?

The Head of Customer Success role offers a competitive compensation package that includes an attractive salary, equity options, and comprehensive benefits like medical, dental, and vision coverage. Additionally, opportunities for professional development, paid time off, and a dynamic work environment contribute to a well-rounded experience for employees.

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Common Interview Questions for Head of Customer Success
How do you approach onboarding new customers as the Head of Customer Success?

When onboarding new customers, it's essential to foster relationships right from the start. Begin by understanding their unique business goals. Implement structured onboarding processes that include personalized training sessions and check-ins to ensure customers feel supported. Your goal should be to equip them with the tools and knowledge they need for immediate success and adoption.

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What strategies do you use to manage customer retention?

Successful customer retention strategies combine building strong relationships with data-driven insights. Regularly assess customer health metrics such as NPS and usage statistics to identify potential churn risks. Maintaining frequent communication and soliciting feedback can help address issues proactively and strengthen customer loyalty.

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Can you describe your experience leading a team in customer success?

In my previous roles, I've led diverse teams by cultivating an environment where team members feel empowered to share ideas and drive customer satisfaction. Encouraging professional growth through training and mentoring has been a focus, as well as promoting a strong team culture where everyone collaborates toward shared goals.

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How would you define success in a customer success role?

Success in a Head of Customer Success role can be defined by key metrics such as customer retention rates, overall customer satisfaction scores, and the successful adoption of the platform by clients. Alongside quantitative data, success is also measured through qualitative feedback from customers about their experience and the value they derive from the product.

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What tools and systems do you leverage to monitor customer success metrics?

To monitor customer success metrics effectively, I rely on tools such as Salesforce and Gainsight. These platforms provide insights into customer engagement, usage, and health scores. By integrating various reporting tools and dashboards, I can keep track of these metrics in real-time, allowing for proactive management of customer relationships.

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How do you handle customer complaints or escalations?

Handling customer complaints requires a calm and strategic approach. I believe in listening actively to understand the root cause of the issue. From there, I work collaboratively with the customer to offer solutions and set clear expectations for resolution. Following up after an escalation is crucial to ensure satisfaction and prevent future concerns.

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What role do customer insights play in shaping your strategies?

Customer insights are invaluable in shaping successful strategies. By gathering and analyzing feedback, I can identify trends, pain points, and opportunities for improvement. This data-driven approach allows me to tailor our services to meet customer needs more effectively while showcasing how our products can evolve based on real-world use cases.

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How do you balance strategic planning with day-to-day customer support?

Balancing strategic planning with daily operations involves creating a well-structured workflow. Establishing priorities for both short-term support needs and long-term initiatives helps ensure neither is neglected. Regularly assessing and adjusting workflows based on team feedback and customer demands keeps us agile and responsive.

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What steps do you take to foster a customer-centric culture within your team?

Fostering a customer-centric culture starts with leading by example; I prioritize understanding customer needs and expectations. Training sessions focused on empathy and relationship building are crucial, as well as celebrating successes and learning from failures collectively. Encouraging team input on customer strategy emphasizes the importance of each role in contributing to overall customer satisfaction.

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Could you explain how you would conduct a business review with a customer?

Conducting a business review involves preparing a comprehensive analysis of the customer’s usage, successes, challenges, and goals. I typically start by confirming the agenda and objectives of the meeting. During the review, I present insights backed by data, discuss successes, identify opportunities for further value, and collaboratively set goals for the next phase of our partnership.

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DATE POSTED
March 25, 2025

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