Strategic Customer Success Manager in Winnipeg

About this Role

My team is dedicated to building deep, consultative partnerships within the Enterprise space. Our Customer Success Team is passionate about shaping and scaling an exceptional upmarket customer experience across the Enterprise Segment. We’re thrilled to be hiring our next Strategic CSM as we continue to grow the team.

In this role, you'll guide Ashby's biggest customers - focusing on improved product adoption and increased customer health. You will shape how we serve customers ranging from high growth organizations to public companies. Ashby is designed to be powerful and flexible, allowing users to adjust it to their needs. This means that there is a lot to learn. You will become a product and domain expert in order to enable our customers to make the best use of Ashby to drive hiring excellence.

Role Requirements:

• You have a strong track record of customer success experience in B2B SaaS (at least five years), supporting the implementation and adoption of complex technologies through the customer journey.
• You’re comfortable managing a book of ~20 strategic customers, exceeding $2m in total ARR.
• You enjoy multi-threading, developing relationships across a broad set of stakeholders while supporting existing teams to drive adoption and retention.
• You have experience working closely with cross-functional stakeholders across Sales, Marketing, Product, and Operations.
• You love becoming a product and industry expert. You create ‘Ah ha!’ moments by tailoring configuration, driving product adoption, and crafting training to address a customer’s specific challenges so they achieve their intended business outcomes.
• You’ve worked with technically complex products and show a strong curiosity to explore details and understand how things work.

You Should Apply If:

• You communicate with precision and clarity. You can take something complex (like a multi-layered report or a nuanced workflow) and explain it simply and confidently.
• You are a listener first. You seek to understand what customers actually need and then advocate for them internally to shape how Ashby evolves for enterprise use cases.
• You thrive in complexity. Ashby is powerful and highly configurable; you’re energized by learning a product with depth, and you can translate that knowledge into creative solutions for your customers.
• You’re excited to help shape a new segment. Our Strategic customer motion is still evolving; you’ll be iterating on playbooks, helping us learn what works, and turning those learnings into repeatable processes for the team.
• Your peers describe you as detail oriented. You send crisp follow-up emails, on time. You take pride in internal operations, like real-time CRM updates.
• You are always looking for ways to improve your work through data.
• You may have been a recruiter, hiring manager, or interviewer before. That experience helps you quickly connect Ashby’s workflows to real-world hiring problems (though it’s not required).

Why you shouldn’t apply:

• You prefer managing a broad book of business.
• You're interested in managing customer accounts with infrequent and 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. We have tens of millions in ARR, growing >100% year over year, very low churn, and many years of runway. We’ll share more details once we meet. In short, it's the perfect time to join!

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. The process for this role is as follows:

• Intro Call with Ashby Recruiting- 30 Minutes
• Hiring Manager Interview- 45 Minutes
• Mock Customer Call- 45 Minutes
• Final Round- 2 hours

Rather than a traditional panel interview with a large group, we structure our panel into a series of smaller conversations. This gives you the opportunity to meet with multiple team members in a more conversational setting focused on specific topics, instead of a formal Q&A. You'll discuss how you approach problem solving, how you work with sales, and dive into a product complexity exercise.

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.
• If you’re in the US, we offer top-tier health insurance for you and your dependents, with 100% of premiums covered by Ashby.
• 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.
• Ashby is committed to a fair and transparent hiring process.