[Hiring] Director of Customer Success @Deep End Talent Strategies

Role Description

The Director of Customer Success will report to the CEO and lead both customer success strategy and execution. This is a hands-on role for someone who is energized by building strong customer relationships, reducing churn, and helping customers get the full value of the platform. This is a player-coach position: you will start with a small team of direct reports while staying hands-on with customers, with the opportunity to grow the team as the business grows.

You will own customer satisfaction and retention across our global customer base. You will design and deliver customer training that drives feature adoption, identify customers who would benefit from additional products or capacity, and pass qualified expansion leads to Sales. You will help design the upsell motion with Sales and leadership, but you will not be responsible for closing upsell deals.

The role will work closely with Sales, Product, Marketing, Implementation, and Support to make sure customer insight shapes the roadmap and every customer has a clear path to more value.

Qualifications

• Successful experience in progressive B2B SaaS customer success roles, including at least several years managing and developing a team
• Demonstrated track record of improving retention and reducing churn
• Experience building customer health scoring, lifecycle programs, and CS playbooks
• Strong ability to design and deliver engaging customer training, both live and on-demand
• Experience partnering with Sales to identify and hand off expansion opportunities, and to build a repeatable upsell motion
• Proven ability to identify, measure, and report on the KPIs that matter, providing meaningful, data-driven insights to the CEO
• Comfort with CRM and customer success tools (e.g., Salesforce) and using product usage data
• Strong written and verbal communication skills, including the ability to simplify complex software and technical workflows
• Comfort working directly with executive leadership and customer stakeholders at all levels
• Willingness to travel approximately 25% as needed

Requirements

• Customer satisfaction and retention
• Own gross and net revenue retention, and build the plan to reduce churn across every region and segment.
• Build a customer health scoring model using product usage, support activity, engagement, and renewal signals.
• Identify at-risk accounts early and lead save plans with the right internal stakeholders.
• Run a regular customer feedback program (e.g., NPS or CSAT) and turn the results into action.
• Serve as the executive point of contact for key accounts and escalations.

• Customer training and adoption
• Design and deliver training programs, including webinars, live sessions, office hours, and on-demand content, so customers know what the platform can do.
• Highlight underused features and modules that solve problems customers already have.
• Build customer lifecycle touchpoints such as onboarding follow-ups, periodic business reviews, and release updates.
• Partner with Marketing on customer-facing content, case studies, and references.

• Expansion and upsell pipeline
• Identify expansion opportunities through training sessions, account reviews, and usage data, and pass qualified leads to Sales.
• Work with Sales and leadership to design the upsell motion, including lead criteria, handoff process, and follow-up expectations.
• Track expansion leads sourced by Customer Success and report on their conversion to closed revenue.
• Support Sales during expansion conversations with account context and customer relationships, without owning the close.

• Customer insight and operations
• Share customer feedback, feature requests, and churn reasons with Product and leadership.
• Build the playbooks, processes, and reporting that make Customer Success repeatable as the business scales.
• Establish regular reporting on retention, churn, health, adoption, and CS-sourced pipeline.

• Team leadership
• Lead, coach, and develop a small team of direct reports, setting clear goals and account ownership.
• Define the team's structure, roles, and hiring plan as the customer base grows.

Benefits

• The expected base salary range for this position is $170,000.
• Candidates are also eligible for an annual performance-based bonus of 20%, equity participation, and access to the company's benefits plan.
• The final offer will reflect the candidate's experience, qualifications, location, and the scope of the role.

Company Description

SimpleTrials is a SaaS company serving clinical trial teams worldwide. Our configurable CTMS (Clinical Trial Management System) and eTMF (electronic Trial Master File) platform helps sponsors, CROs, and research sites manage studies, documentation, and reporting without the cost and complexity of traditional enterprise software.

SimpleTrials has a strong product, a committed team, and a meaningful mission: helping clinical trial teams manage complex work more efficiently so treatments can reach people faster.