Hi, I'm Kelsey 👋 – VP of Customer Success at Ashby. One of my favorite Ashby principles is Continuous Improvement. Combined with our principle of caring deeply about customers, it drives us to continually ask how we can deliver an even better customer experience.
Our product and growth are exceptional. Ashby's All-in-One recruiting platform replaces multiple disparate solutions, and we're trusted by over 5,000 customers, from early-stage Startups to sophisticated Enterprises. We're growing more than 100% year over year, with best-in-class retention and strong expansion.
As we continue scaling upmarket, our customers' needs are becoming increasingly complex. Enterprise implementations bring more integrations, data migrations, and change management needs, along with higher expectations for the expertise and partnership we provide.
That's why I'm thrilled to be hiring our
Global Head of Professional Services. This leader will shape the next chapter of our Professional Services organization, making it a competitive advantage in winning complex deals, accelerating customer time-to-value, and supporting Ashby's continued growth.
About The Role
As our Global Head of Professional Services, you'll own the strategy, performance, and evolution of Ashby's global Professional Services organization, spanning Implementation, Integrations Consulting, Build Services, and emerging technical and advisory services.
Our Professional Services organization plays a critical role across the customer journey, from helping Sales win complex Enterprise deals to ensuring customers successfully implement Ashby and are positioned for long-term success.
You'll build on a solid foundation while defining what the next generation of Professional Services looks like at Ashby. This includes further differentiating our implementation experiences by customer segment, expanding our paid services offerings, building the operational infrastructure to scale efficiently, and developing a remarkable global team.
This is a senior leadership role with accountability for customer outcomes and the commercial performance of PS. You'll partner closely with leaders across Sales, Customer Success, Product, Engineering, and Revenue Operations. As it stands today, you'll inherit a global team of: 2 directors, 2 managers (actively hiring our third and fourth), 20 Implementation Specialists, 3 Implementation Consultants (responsible for hands to keys build services), and 6 Integrations Consultants.
What You'll Do
Define and Execute Our Global Professional Services Strategy
- Own the vision and strategy for Professional Services, positioning the function as a competitive advantage for Ashby as we continue scaling upmarket.
- Evolve our services offerings to address increasingly complex customer needs, including Enterprise implementation, technical consulting, integration services, hands on build services, and change management.
- Further differentiate our High Touch and Strategic implementation motions, balancing scalable, repeatable delivery with the tailored expertise Enterprise customers expect.
Lead and Scale a High-Performing Global Organization
- Lead and scale a multidisciplinary, global organization of implementation leaders, technical consultants, and emerging services specialists.
- Hire, coach, and develop exceptional directors, managers, and individual contributors, maintaining a consistently high bar for talent, technical expertise, and customer outcomes.
- Foster a culture of ownership, intellectual curiosity, continuous improvement, and end-to-end accountability.
- Maintain a strong understanding of the team's work, from the intricacies of complex Enterprise implementations to the operational systems supporting delivery.
Own Implementation Excellence and Customer Outcomes
Establish clear standards for implementation quality, project governance, change management, and customer readiness across segments.Develop a scalable approach to managing complex Enterprise engagements, including executive stakeholder alignment, technical dependencies, project risks, and escalations.Define and inspect the metrics that matter, including implementation quality, time-to-go-live, scope adherence, customer sentiment, and successful handoffs among Sales Implementation Customer Success.
Build a Commercially Impactful Services Business
- Partner closely with Sales and Solutions Engineering to help win complex Enterprise deals through implementation expertise and clear, realistic plans for complex deployments.
- Refine our scalable pre-sales services motions, including discovery, solution scoping, Statements of Work, and commercial alignment.
- Build a commercially successful services business, expanding our offerings, establishing sustainable delivery economics, and ultimately owning the function's P&L.
- Establish appropriate commercial and operational rigor around services revenue, margin, scope management, and resource allocation.
- Balance the commercial opportunity of Professional Services with our commitment to delivering transparent, high-quality customer experiences.
Drive Operational Excellence and Scalable Delivery
- Own capacity planning and resource forecasting, partnering with Sales and Revenue Operations to translate pipeline expectations into thoughtful staffing decisions.
- Develop repeatable delivery methodologies, playbooks, and quality standards while maintaining flexibility for complex customer requirements.
- Establish clear visibility into project health, resource allocation, delivery performance, and operational risks.
- Identify opportunities to improve efficiency through process design, automation, and technology without compromising customer outcomes.
- Partner with Product and Engineering to translate implementation insights into product improvements and reduce recurring sources of delivery complexity.
You Could Be a Great Fit If
- You're a strategic builder. You've built or meaningfully transformed a Professional Services organization within a high growth B2B SaaS company. You can articulate a compelling long-term vision and translate it into a clear plan for getting there.
- You understand the business of Professional Services. You have experience commercializing services, designing offerings, managing delivery economics, and balancing revenue generation with customer outcomes. You understand how PS can enable software growth, not just generate services revenue.
- You're an exceptional people leader. You have deep experience hiring, developing, and managing leaders and technically sophisticated teams. You set a high bar, provide direct and thoughtful feedback, and are comfortable making difficult performance decisions.
- You're technically fluent. You've led services for a complex B2B SaaS platform involving sophisticated integrations, data migration, configuration, or Enterprise workflows. You can engage credibly in technical discussions and know when to go deeper.
- You're an effective cross-functional partner. You have a strong track record of partnering with Sales, Product, Engineering, and Customer Success to solve complex problems and move toward shared business outcomes.
- You pair strategic thinking with operational rigor. You understand the details behind capacity models, project economics, implementation methodology, and delivery metrics. You're equally comfortable defining a multi-year strategy and pressure-testing the assumptions behind a staffing forecast.
- You're a principled problem solver. You think in systems, challenge conventional approaches, and build solutions that scale. You bring strong judgment and intellectual curiosity rather than relying exclusively on what worked at your last company.
- You communicate with exceptional clarity. You can distill technical and operational complexity into crisp recommendations, influence executive stakeholders, and build confidence with sophisticated Enterprise customers.
This Role May Not Be a Great Fit If
- You prefer managing an established playbook over building one. We've established a solid foundation, but much of our future Professional Services strategy and operating model is still ours to define.
- Your experience is primarily with low-complexity implementations or transactional services. Our customers increasingly have sophisticated technical ecosystems, complex workflows, and Enterprise change management requirements.
- You view Professional Services exclusively as a delivery function. We expect this leader to think commercially and strategically about how PS influences win rates, services revenue, customer outcomes, and long-term growth.
- You prefer to operate exclusively at the strategic level. Even our most senior leaders are expected to traverse the elevation, understanding the details of their organizations and engaging directly when circumstances warrant.
- You don't enjoy hiring, coaching, and performance management. Building an exceptional global team and developing the next generation of leaders will be central to your success.
- You rely on headcount as the primary solution to scaling challenges. We value leaders who can build sustainable systems, improve efficiency, and make thoughtful tradeoffs without compromising quality.
Our Philosophy
Here are a few principles that shape how we operate:
- We believe exceptional products and exceptional customer experiences reinforce one another.
- We bring deep expertise to customer interactions and believe our teams should understand both the technical and business context of the problems they're solving.
- We prioritize principled thinking over rigid adherence to prior playbooks.
- We value strong ownership, thoughtful communication, and continuous improvement.
- We invest in doing things the right way, building systems that scale rather than relying on individual heroics.
You can learn more about our Customer Success philosophy and Operating Principles.
The Interview
At Ashby, our interview process is designed to help you show your best self while giving you meaningful insight into the opportunities and challenges ahead.
- 30 min – Recruiter Screen
- 45–60 min – Hiring Manager Interview with VP of Customer Success
- 45–60 min – Leadership Interview
- 60 min – Practical Exercise & Presentation
- Final Round – Cross-functional leadership conversations, including our CEO, Sales leader, and closing questions with the Hiring Manager
About Ashby
We’re building the next generation of recruiting software and we’re starting with a suite of products that help talent leaders, recruiters, and hiring managers run an efficient and data-driven hiring process. 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! 🚀
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.
Compensation Range: $215K - $300K
