Manager of Customer Success - Mid Market

Hi, I’m Denise — Head of High Touch Customer Success at Ashby. One of our core principles is “Care Deeply About Our Customers,” and we hire people who are energized by helping customers succeed and delivering high-quality experiences. That’s why I’m excited to be hiring a Manager of High Touch Customer Success. In this role, you’ll elevate the customer experience by coaching and developing a team of CSMs, while also helping them operate effectively at scale. Each CSM manages a large book of business (~60 customers), so a key part of this role is identifying what’s working, turning it into repeatable best practices, and building systems that allow the team to deliver consistently strong outcomes across many customers. You’ll partner closely with other leaders across High Touch CS, Startup CS, Implementation, as well as Support and Contract Management. ABOUT THE ROLE As the Manager of High Touch Customer Success, you will play a pivotal role in ensuring our customers have a remarkable experience with Ashby as we continue to scale. You’ll lead — and continue to grow — a team of skilled and tenured CSMs focused on driving adoption, value realization, and long-term partnership post-onboarding. In this role, you will: - Lead and coach a team of CSMs who partner with customers across adoption, optimization, and ongoing success - Uplevel team performance through 1:1 coaching, skill development, and strong operational rigor - Drive scalable approaches to customer success, helping the team translate what’s working into repeatable best practices across a large portfolio - Partner closely with Implementation, Support, and cross-functional teams to ensure a seamless customer experience across the lifecycle - Be a key voice in evolving how we deliver consistent, high-quality experiences at scale Role

Requirements

• Team Leadership & Coaching: You have experience leading and developing Customer Success Managers in a SaaS environment supporting a complex product. You know how to foster a culture of empathy, accountability, and continuous growth.
• Customer Journey Expertise: You have deep experience driving adoption, retention, and long-term value realization.

• Operational Mindset: You’ve helped implement and improve team processes, and bring a structured approach to scaling what works. You’re comfortable building systems and playbooks that enable a team to deliver consistently across a large portfolio.
• Cross-functional Collaboration: You’re comfortable partnering with teams like Implementation, Sales, Product, and Support to ensure a seamless customer experience across the lifecycle.
• Problem-Solving Orientation: You don’t rely on “what worked before” — you’re thoughtful, pragmatic, and eager to find solutions that fit the evolving needs of your team and customers.
• Data-Driven: You’re comfortable using data and metrics to inform decisions, identify trends, and continuously improve both team performance and customer outcomes.
• Customer-First Thinking: You have a deep understanding of B2B customer needs and a track record of delivering high-quality, thoughtful customer experiences.
• Lifecycle Awareness: You understand the full customer lifecycle, and know how to effectively partner with cross-functional teams to ensure strong handoffs and sustained success.

• You listen deeply. You act as both an advocate for your team and a strong voice of the customer, ensuring feedback meaningfully shapes internal decisions and product direction.
• You’re a structured problem solver.

• You value process and scale. You’re motivated to improve workflows and build systems that increase efficiency and consistency across the team.
• You operate with strong attention to detail. You bring rigor to internal operations and take pride in executing at a high standard.
• You’re a passionate coach.

• You are accustomed to defining ideas and strategies, yet not responsible for their execution.
• You thrive in environments where you lead a simple, established product rather than a dynamic, complex and evolving one.
• You prefer exclusively to build (rather than build, iterate, optimize) - You have not done this work in a growing SaaS business ABOUT ASHBY We’re building the next generation of enterprise software, and we’re starting with a suite of products that help talent leaders, recruiters, and hiring managers run their hiring process significantly better.

• We want to offer deep expertise whenever we interact with prospects and customers.
• We strongly believe that small teams with very talented people (and the right work environment) deliver much better performance than teams with large headcount.

• You get to work with a product that our prospects & customers are truly excited about.
• Competitive compensation is offered.
• 10-year exercise window for stock options.

• Unlimited PTO with four weeks is recommended per year. Expect “Vacation?” in our one-on-one agenda until you start taking it 😅 - Twelve weeks of fully paid family leave in the US. We plan to expand this to employees in other countries as situations arise.
• $100/month education budget with more expensive items (like conferences) covered with manager approval - Extended health benefits for you and your dependents (subject to availability with our Employer of Record) - Generous equipment, software, and office furniture budget.

• Showcase a data‑driven CS playbook: Bring a 1‑page dashboard (e.g., in Tableau or Google Data Studio) that tracks health scores, churn risk, and NPS for a 60‑customer book. Highlight how you used tools like Gainsight, Salesforce, and Amplitude to spot patterns and turn them into repeatable metrics‑based best practices—exactly the “identify what’s working” focus Ashby mentions.
• Prepare a scaling case study: Draft a 2‑page “CSM Scale‑Up” brief that outlines how you built a playbook, onboarding SOP, and cadence template that let a team grow from 3 to 12 CSMs while keeping each rep’s coverage at ~60 accounts. Include screenshots of the actual SOP in Notion or Confluence to give interviewers a concrete artifact.
• Demonstrate remote‑first leadership: In your interview, reference specific async communication rituals you instituted (e.g., weekly “Pulse” Slack threads, quarterly “Customer Wins” video recap, and a shared OKR board in Asana). Cite measurable outcomes such as a 20% reduction in response time or a 15% boost in CSM engagement scores.
• Align with “Care Deeply About Our Customers”: Bring a short story (150‑200 words) that shows you turned a at‑risk customer into a champion, quantifying the impact (e.g., +30% expansion revenue, 10‑point NPS lift). Quote the customer’s feedback verbatim to illustrate the deep‑care mindset Ashby values.
• Negotiate with market data: Research Glassdoor, Levels.fyi, and recent Ashby hires to confirm the typical range for a Manager of High‑Touch CS (≈ $130‑150k base + 0.10‑0.15% equity). Prepare a 3‑point justification—remote cost‑of‑living flexibility, your proven scaling track record, and the market benchmark—to confidently propose a package that meets or exceeds that range.