Implementation & Enablement Manager

Join Ottimate as the Implementation & Enablement Manager, where you will lead a team responsible for driving customer success from contract signing to realized value. This hands-on leadership role focuses on managing outcomes rather than timelines, defining successful implementation, and building a methodology for consistent customer success. You will work cross-functionally with Sales, Customer Success, and Product & Engineering, and as Ottimate grows, this role will evolve with it.

• Lead the team responsible for bringing customers from signed contract to realized value, focusing on managing outcomes rather than timelines.
• Define what a successful implementation looks like, build the methodology that gets customers there consistently, and hold your team to a standard where implementation is complete when the customer achieves value.
• Establish clear expectations, performance standards, and growth paths for every person on the team, and build a culture of accountability, continuous improvement, and customer focus.

• Change management experience - both leading customers through operational change and leading internal teams through process transformation
• Direct and clear communicator - comfortable delivering hard feedback to your team, navigating difficult customer conversations, and representing the team in cross-functional settings
• Outcome-oriented mindset - you define implementation success by what the customer achieves, and you hold the team to that standard, not to project closure dates
• Demonstrated track record of building or meaningfully improving an implementation practice - not just inheriting and maintaining one
• Comfortable with ambiguity and organizational transformation - this function is evolving, and you'll be shaping it as much as running it
• Exceptional coaching instinct - you develop people through direct feedback, observation, and example; you make the team better as a natural byproduct of how you lead
• Experience with AP, procurement, or financial operations workflows strongly preferred; ERP or accounting system implementation experience (Sage Intacct, NetSuite, Acumatica, Microsoft BC) is a plus
• Strategic thinker who can also execute - you can hold the vision for where implementation should go while staying close enough to the work to lead through the day-to-day
• 7+ years in SaaS implementation, professional services, or customer onboarding - with at least 3-4 years in a people management or formal team lead role
• Consultative approach - to customers and to the team; you ask the right questions before jumping to solutions, and you teach others to do the same