Mid-Market Customer Success Manager in Winnipeg

About this Role

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. 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 drive 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 are a great listener.
• 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 love to teach.
• Your peers describe you as detail oriented.
• You move fast.
• You’re energized by an ever-improving work environment.
• 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.
• You’re interested in managing customer accounts with well-defined touchpoints.
• You shine as an exclusively commercial CSM, motivated by variable compensation.
• You’re afraid of rolling up your sleeves.

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 are well funded and backed by great investors, including Y Combinator, Elad Gil and Lachy Groom. We have thousands of amazing customers including Snowflake, OpenAI, Shopify, Ramp, Notion, and Zapier. Our growth and retention metrics are best‑in‑class among our peers: we have tens of millions in ARR, growing >100% year over year, very low churn, and many years of runway.

Interview Process

Our interview process is thorough - we aim to ensure each person that joins the team is the right fit for Ashby and will provide ample information for you to assess if Ashby is the right fit for you.

Benefits

• You’ll get the time to do things the right way; we put a lot of emphasis on high quality work and avoid quick hacks as much as possible.
• 10-year exercise window for stock options.
• Unlimited PTO with four weeks is recommended per year.
• Twelve weeks of fully paid family leave in the US.
• Generous equipment, software, and office furniture budget.
• $100/month education budget with more expensive items covered with manager approval.

Ashby provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, genetics, sexual orientation, gender identity, or gender expression. We are committed to a diverse and inclusive workforce and welcome people from all backgrounds, experiences, perspectives, and abilities.