Manager of Technical Services Hi, I’m John and I’m the Head of Professional Services at Ashby. One of my favorite aspects of Ashby is our operating principle of Continuous Improvement. Coupled with our principle of caring deeply about our customers, we often find ourselves wondering ‘what is a better way to accomplish this’. That’s why I am thrilled to be hiring our first Technical Services Manager As a leader on our growing Professional Services team (within Ashby’s Customer Success organization), you’ll have the opportunity to play a key role early in our customers’ journey, ultimately up-leveling the overall customer experience. The Ashby team has grown rapidly over the last few years, and we're not slowing down: we now support thousands of customers, with ARR growing much faster than 100% year over year. To meet this demand, our technical services function is expanding quickly, and we are looking for our first dedicated leader to guide this talented group of individual contributors through our next phase of scale. The RoleWe’re looking for our first Manager of Technical Services to be the strategic anchor for Ashby’s expanding technical integration services. This role bridges two distinct technical engines: you will oversee specialized integration consultants dedicated to deep Workday integrations, as well as a team of technical solution consultants who build bespoke API solutions, craft custom recommendations, and deliver hands‑on technical builds for our customers. Six months in, success looks like having a highly efficient, scaled team that seamlessly handles multiple concurrent complex integrations, successfully troubleshoots mid‑flight technical challenges, and consistently delivers high‑value technical consulting.



you will help shape ourtechnical services strategy and ensure all customers can cohesively integrate Ashby into their complex HR tech stacks. Building and scaling a high-performing team, supporting both specialized Integration Consultants and Technical Solution Consultants; empowering them to comfortably manage high‑volume portfolios while maintaining Ashby's high standards for quality. Building the operational infrastructure required to scale technical services, including capacity planning, project prioritization, quality standards, and repeatable delivery processes. You know when to standardize, when to customize, and how to balance speed, quality, and customer outcomes. Acting as a senior escalation point, leveraging your foundational knowledge of Workday architecture and complex API capabilities to guide your team. Diving into active integrations, troubleshooting roadblocks, and translating ambiguity into explicit technical paths, helping your team scope solutions. Owning the evolution of our technical services offerings, identifying recurring customer needs, evaluating opportunities to standardize solutions, and determining where new technical capabilities will deliver the greatest customer and business impact. Partnering closely with Product, Engineering, Sales, and Implementation to distinguish product gaps from services opportunities, establish clear ownership of complex technical challenges,



and ensure customer commitments are both technically feasible and commercially sound. 8+ years of experience in technical consulting, integration services, or technical implementations, with at least 3+ years directly managing and scaling a team of technical resources. Strong working knowledge of enterprise integrations, including Workday architecture, APIs, authentication, data mapping, and integration design. You can critically evaluate proposed solutions, identify technical risks, and guide consultants through complex implementation challenges, ultimately translating these concepts into clear, actionable strategies for non‑technical audiences and executive stakeholders. You know how to orchestrate moving pieces, keep a mixed‑discipline team on track, and balance bandwidth across concurrent enterprise projects. Experience actively building a team by anticipating future gaps, looking around the corner to determine what technical capabilities or services we will need next before the demand even hits. Dive into the technical details; if you prefer to managefrom a distance rather than understand the underlying architecture and challenge technical decisions, this isn't a fit. when a customer suddenly requires a custom build instead of a standard integration, you must be able to step in and define that technical path. Manage the reality of scale; if you are only comfortable overseeing singular, monolithic deployments rather than a high‑volume portfolio of concurrent projects across your team. We spend a lot of time building best‑in‑class products since we believe a highly differentiated product is a lot easier to sell. We want to offer deep expertise whenever we interact with prospects and customers. We strongly believe that small teams with very talented

📌 Head of Technical Service and Customer Experience (Winnipeg)
🏢 Ashby
📍 Winnipeg