Ashby

Head of Strategic Customer Success – Americas

Ashby

full-time

Posted on:

Location Type: Remote

Location: Remote • 🇺🇸 United States

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Salary

💰 $190,000 - $225,000 per year

Job Level

Lead

About the role

  • Lead our Strategic Customer Success segment and help define how Ashby serves our Enterprise customers.
  • Ensure that our customers consistently have a remarkable experience as we continue to move upmarket.
  • Oversee and grow a highly skilled team of tenured Strategic CSMs, guiding their partnership with sophisticated organizations.
  • Work with High Touch Customer Success leaders, applying programmatic frameworks and facilitating bespoke engagements for Enterprise customers.
  • Shape how Strategic Customer Success evolves at Ashby to ensure meaningful outcomes with our platform.

Requirements

  • Proven Leadership & Coaching: You have a track record of successfully growing, leading and developing high-performing Customer Success Teams in a complex B2B SaaS environment. You know how to deliver clear, actionable feedback, and you build a culture where your team can grow and succeed.
  • Customer-Centricity with an Enterprise Focus: You bring proven experience working with upmarket B2B companies (1,000+ employees) and understand the unique opportunities of enterprise adoption. You ensure customers realize value across their lifecycle and achieve their objectives with Ashby, balancing hands-on support with scalable approaches.
  • Strategic & Operational: You proactively identify opportunities to strengthen how we serve customers — whether through process improvements, new frameworks, or fresh approaches to engagement. You balance big-picture strategy with hands-on execution, driving process improvements and frameworks that deliver measurable results.
  • Customer Impact & Product Mastery: You excel at quickly learning and navigating robust, complex products to design programs that improve the customer journey at scale. Your work drives measurable impact across onboarding, adoption, and retention — ensuring customers realize value quickly and sustain success over time.
  • Cross-functional Collaboration: You partner effectively with Sales, Product, Engineering, and Operations to align on customer needs and deliver solutions. You understand when to collaborate, when to escalate, and how to influence outcomes across teams.
  • Innovative & Principled Approach: You proactively address thematic customer opportunities and improve our processes accordingly; you’re comfortable leveraging fresh technologies to enhance the efficiency and efficacy of our team. You don’t rely on ‘I’ve seen this done’ but instead think critically to problem solve.
  • Analytical Mindset & Continuous Improvement: You use data to guide decisions and improve performance. You’re comfortable measuring what matters — both for your team and your customers — and iterating to drive better results.
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.
  • If you’re in the US, we offer top-tier health insurance for you and your dependents, with 100% of premiums covered by Ashby. We also offer a 3% 401k match.

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard skills
B2B SaaSCustomer Successprocess improvementsprogrammatic frameworkscustomer journey designonboardingadoptionretentiondata analysisperformance measurement
Soft skills
leadershipcoachingcustomer-centricitystrategic thinkingoperational executioncross-functional collaborationinnovationproblem solvinganalytical mindsetcontinuous improvement