Director, Mid-Market Customer Success

We’re looking for a results-driven Director, Mid-Market Customer Success to own and optimize our mid-market customer segment.

This strategic leader will be responsible for overseeing our mid-market customer base, ensuring their satisfaction as customers and successfully ushering in favorable outcomes on renewal.  You will be critical in guiding our Customer Success team to greater accountability for adoption and retention outcomes.

If you're an empathetic, experienced SaaS leader with a proven track record in mid-market customer success, a data-driven mindset, and a passion for driving retention and growth, we want to hear from you.

What you will do:

As the Director of Mid-Market CS at Dscout, you are a key strategic leader, influencing the company’s growth and customer-centric initiatives. Reporting to the VP of Customer Success, you will lead a team of 6-8 Customer Success Managers, which at Dscout we call them Lead Research Advisors.  Your focus will be on ensuring customers achieve exceptional outcomes through seamless adoption and utilization of our software.

Key responsibilities:

• Business Impact & Revenue: Improve renewal rates, drive cross-sell revenue, optimize customer health metrics, and participate in forecasting rhythms with clear, data-backed updates on renewal health and expansion opportunities.
• Customer Retention & Growth: Develop and execute strategies to retain and expand the customer base, driving measurable value through proactive engagement and broadened stakeholder relationships.
• Customer Success Leadership: Oversee the Mid-Market CS function, guiding your team to drive platform adoption through customer training, research education, and methodology coaching.
• Team Management & Coaching: Manage, mentor, develop, and inspire a team of CSMs — prioritizing workload, monitoring performance, and empowering them to deliver high-impact customer engagements.
• Executive Sponsorship: Serve as executive sponsor for key accounts, cultivating senior relationships, driving successful executive-level reviews, and gathering strategic feedback.
• Operational Discipline: Hold the team accountable to activity metrics, utilization targets, and Salesforce data hygiene. Manage capacity and portfolio sizing to protect team bandwidth.
• Cross-functional Collaboration: Act as the customer voice internally, maintaining tight feedback loops with Product, Sales, Support, and Engineering.
• Process Improvement: Partner with RevOps, Enablement, and CS Leadership to continuously refine the Mid-Market customer journey and implement scalable playbooks.
• Change Management & AI Adoption: Lead your team and customers through change with confidence and empathy, championing AI tool adoption by modeling best practices and coaching CSMs and customers alike.

What you need to have:

• 7+ years in customer success, account management, or consulting within a SaaS organization, with a strong track record of hitting retention targets.
• 2+ years directly managing CS or account management teams.
• Deep expertise in CS metrics (NRR, GRR, account health, etc.), risk mitigation workflows, and activity-based accountability structures.
• Experience participating in revenue forecasting and/or cross-functional account planning with Sales and Renewals.
• Excellent communication and critical thinking skills, with a data-driven mindset and comfort with tools like Salesforce, Claude Cowork, and Gong.
• Highly organized and detail-oriented, with a passion for creative problem-solving.
• Bonus: Background in qualitative, UX, or market research is a strong plus