About this Role Hi, I’m Denise, and I’m the Head of High-Touch (Mid-Market) Customer Success at Ashby. Our team is passionate about shaping and scaling an exceptional customer experience for our high-touch customer segment, which primarily supports mid-market and growth-stage organizations. I’m excited to be hiring our next CSM as we continue expanding globally.

As a member of our Customer Success team, you will help us continue to grow our High-Touch Customer Success function. In this role, you’ll partner closely with customers to drive adoption, deliver strategic guidance, conduct product trainings and partnership reviews, and identify opportunities for expanded use cases and long-term value realization. You’ll also collaborate with a talented group of CSMs across the High-Touch team to continuously evolve how we support companies ranging from high-growth startups to public enterprises.

Ashby is designed to be powerful and flexible, allowing customers to tailor the platform to their unique hiring processes and workflows. Because of this, there is a lot to learn. You will become both a product and domain expert, enabling customers to make the most of Ashby and driver hiring excellence across their organizations.

Role Requirements

You have a strong track record of Customer Success experience in B2B SaaS (at least two years), supporting customers through the adoption and long-term optimization of complex technologies. You enjoy building trusted partnerships with customers and helping them realize measurable value throughout the customer lifecycle.

You have experience managing a portfolio of approximately 60 mid-market customers with over $1.5M in total ARR.



You’re comfortable balancing proactive engagement across a broad book of business while building strong relationships with a diverse set of stakeholders to drive adoption, retention, and growth.

You have experience partnering cross-functionally with teams such as Sales, Marketing, Product, Support, and Operations to advocate for customer needs and deliver a seamless customer experience.

You enjoy becoming a product expert and have demonstrated this in previous Customer Success roles. You create “aha” moments by tailoring trainings, workflow guidance, and strategic recommendations to each customer’s unique goals and challenges.

You’ve worked with technically complex products and bring strong curiosity and problem-solving skills to understanding how systems, workflows, and integrations operate in practice

You Should Apply If

You demonstrate mastery of clear communication. You ask questions with precision and can explain complex concepts in simple terms.

You are a great listener. You see your role as providing the voice of the customer to internal stakeholders so we can ensure that our product roadmap continues delivering value.

You enjoy working with a larger book of varied customers, and can effectively prioritise your time to make the biggest impact.

You’re energized by learning and supporting a complex product. You enjoy diving deep into technical details, navigating advanced configurations, and data workflows,



and you enjoy helping customers make sense of them.

You love to teach. Whether it’s a complex report to a very tenured data analyst, or a workflow to a brand new recruiter, who is new to SaaS tools, you see every teaching moment as an opportunity.

Your peers describe you as detail oriented. You obsess over sending crisp follow-up emails, on time. You take pride in internal operations, like real-time CRM updates.

You move quick. You leverage tools/technology to maximize your time. You are at home managing a wide range of customers, and prioritizing effectively.

You’re energized by an ever-improving work environment. Our team is growing, and continually iterating on processes - we live by our Operating Principle of "Implement Continuous Improvement"

You are always looking for ways to improve your work through data.

Why you shouldn’t apply

You thrive with a smaller, more focused book of customers, Our Mid-Market CSMs typically manage a book of 60+ customers, balancing personalized relationships with efficient, scalable support.

You’re interested in managing customer accounts with well-defined touchpoints (rather than excited by the fluidity required of early stage CS work)

You shine as an exclusively commercial CSM, motivated by variable compensation. While our team's north star metric is revenue retention, we focus on adoption and engagement as our leading indicators. For renewal negotiation and upsell, we have a lovely team of Contract Managers. As such, this role does not currently include variable pay.

You’re afraid of rolling up your sleeves. If the idea of getting in the weeds with a customer about the nuance between a time in process report

📌 Mid-Market Customer Success Manager (Winnipeg)
🏢 Ashby
📍 Winnipeg