Mid-Market Customer Success Manager - Americas

ASHBY; Canada; On-site; CAD 90,000 - 130,000; Full time

Benefits offered by this job

Stock options

Unlimited PTO

Family leave

Equipment budget

Education budget

Job summary

Ashby is hiring a high‑touch Customer Success Manager (CSM) to support mid‑market to growth client segments in Canada. You will drive adoption, deliver strategic guidance, and conduct product trainings while collaborating with a cross‑functional team to maximize value realization.

You’ll become a product expert, tailoring trainings and guidance to each customer’s goals and challenges, handling technically complex workflows and integrations. This is a fast-growing, globally expanding team.

Qualifications

• 2+ years of Customer Success experience in B2B SaaS.
• Manage a portfolio of ~60 mid-market customers with >$1.5M ARR.
• Partner cross-functionally with Sales, Marketing, Product, Support and Operations.
• Become a product expert and tailor trainings and recommendations.
• Work with technically complex products and understand workflows.

Responsibilities

• Drive adoption and long-term value realization for high-touch customers.
• Deliver strategic guidance and product trainings.
• Conduct partnership reviews and identify expansion opportunities.
• Collaborate with CSMs to continuously evolve customer support.
• Understand customers' workflows and integrations to optimize success.

Skills

Customer Success in B2B SaaS

Portfolio management

Cross-functional collaboration

Product training/enablement

Technical product understanding

Tools

CRM platforms

Job description

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 fast. 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 and a time to hire report feels too granular, or project managing a workflow change for offer approvals feels “beneath you”, this job isn’t going to be for you.

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. Learn more on our website: https://www.ashbyhq.com/

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 (and many others who we cannot name!). 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. 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 - 1 hour

  • Rather than a traditional panel interview with a large group, we structure our panel into two focused conversations. This gives you the opportunity to meet with multiple team members in a more conversational setting centered on specific topics, instead of a formal Q&A. You'll discuss how you approach problem solving, dive into a product complexity exercise, then wrap up with a quick closing call with the hiring manager.

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. You shouldn’t feel pressure to purchase stock options if you leave Ashby - do it when you feel financially comfortable.

• 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.

• Generous equipment, software, and office furniture budget. Get what you need to be happy and productive!

• $100/month education budget with more expensive items (like conferences) 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.

Ashby is committed to a fair and transparent hiring process. We confirm that this advertisement is for an active, existing vacancy within our organization. Please be advised that we may use artificial intelligence-driven tools to assist our recruitment team in screening, assessing, and selecting candidates for this position.