Head of Strategic Customer Success, Ashby
Americas
$190-225k
OTE
Offers stock options
All-in-one recruiting software
Job no longer available
All-in-one recruiting software
201-500 employees
Job no longer available
$190-225k
OTE
Offers stock options
201-500 employees
Company mission
To redefine the applicant tracking system (ATS) category, providing talent teams with analytics, workflows and automation.
Role
Who you are
- 📣 You communicate with clarity. You ask precise questions and can distill complex concepts into simple themes
- 🎧 You see your role as both 1) an advocate for the Customer Success team, and 2) the voice of the customer to internal stakeholders so the product roadmap continues to evolve in an optimal direction
- 📈 You are a strategic problem solver. You thrive at solving complex challenges with principled, scalable solutions
- ⚡️You know process matters. You’re eager to improve workflows and operational details that enhance efficiency and consistency
- 🔍 Your peers know you for your follow-through, detail orientation, and pride in strong internal operations
- 🧑🏫 You love to coach. Whether through call shadowing, real-time feedback, or structured development, you see every moment as an opportunity to help your team grow
- You get into the weeds. You’re energized by diving into the product alongside your team, learning deeply, and modeling the type of engagement we expect from Strategic CSMs
What the job involves
- As Head of Strategic Customer Success, you will lead our Strategic Customer Success segment and help define how Ashby serves our Enterprise customers
- This role is pivotal in ensuring that, as we continue to move upmarket, our customers consistently have a remarkable experience. You’ll oversee and continue to grow a highly skilled team of tenured Strategic CSMs, guiding how they partner with some of our most sophisticated and complex organizations
- You’ll work alongside our High Touch Customer Success leaders, applying programmatic frameworks where they fit, while also facilitating bespoke engagements for Enterprise customers who require a more tailored approach
- Success in this role requires a deep product focus: we’re looking for a leader who is comfortable getting into the details of the product alongside the team, and who can partner with internal stakeholders to advocate for the product changes that matter most
- Ultimately, you will shape how Strategic Customer Success evolves at Ashby and ensure our largest customers achieve meaningful outcomes with our platform
- 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
Application process
- At Ashby, our team and interview process want to help you show your best self. Our interview process is structured to get to know you and your career as well as empower you with insight into our key focus areas. Here is the process in its entirety:
- 30 min - Recruiter Screen
- 90 min - Interviews with VP of CS and Head of Dedicated CS - 30 min, then 60 min pending previous conversation
- 60 min - Presentation & Interview with Strategic CSM(s), Head of Startup, & Head of Professional Services
- 30 min - Interview with CEO
- Deadline to Apply:
- December 11, 2025 at 5:00 PM UTC
Our take
Reportedly, 50% of employers don’t use applicant tracking systems, largely because of blockers with implementation or insufficient buy-in from top management. Ashby's co-founder and CEO, Benji Encz, experienced first-hand how existing solutions failed to support hyper-growth hiring needs whilst working at PlanGrid, which is in part what led to the creation of the company.
Ashby is looking to redefine the ATS category - providing talent teams with analytics, workflows and automation - and intends to replace solutions from well-established vendors like Greenhouse and Lever with algorithms. The company's AI can schedule interviews and infer demographic data, which clients use for aggregate analyses of DEI hiring metrics.
The market for recruitment software could potentially reach $3.5 billion by 2030. Unsurprisingly, there is now a growing number of startups emerging to compete for a slice of it. Despite the crowded market and having only emerged from stealth in 2022, Ashby has already secured over 500 clients (including high-profile customers like Notion and Figma). The company has also attracted impressive funding, which will be used to expand its product offering beyond what is typically expected from an ATS and grow its customer success and community initiatives.
Kirsty
Company Specialist at Welcome to the Jungle
Insights
32% employee growth in 12 months
Company
Funding (last 2 of 6 rounds)
Jul 2025
$50m
SERIES D
Jun 2024
$30m
SERIES C
Total funding: $114.7m
Company benefits
- Unlimited PTO with four weeks recommended per year
- 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
- Generous equipment, software, and office furniture budget
- $100/month education budget with more expensive items (like conferences) covered with manager approval
- Twelve weeks of fully paid family leave
Company HQ
SoMa, San Francisco, CA
Leadership
Benjamin Encz
(Co-Founder & CEO)Previously the Director of Engineering and Part-Time Recruitment Operations at PlanGrid. They also worked as a Software Engineer at Make School and was a Lecturer at Baden-Wuerttemberg Cooperative State University (DHBW).
Abhik Pramanik
(Co-Founder & VP of Engineering)VP of Engineer at Ashby. Previously a Senior Product Manager at Lob and a Senior Product Manager at PlanGrid.
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