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 robust 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 explicit 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

📌 Global Head of Professional Services (Winnipeg)
🏢 Ashby
📍 Winnipeg