Manager, Implementation & Enablement

About OttimateOttimate is a leading provider of AI-powered automation solutions that help businesses streamline financial operations and manage spend with ease. Our platform integrates seamlessly with ERP, accounting, and procurement systems, enabling organizations to work smarter and scale efficiently.We are building an implementation practice that treats go-live not as the finish line, but as the beginning of a customer's long-term relationship with value. If you want to build the playbook - not just run it this role is for you!The RoleAs Manager, Implementation & Enablement, you will lead the team responsible for bringing Ottimate customers from signed contract to realized value. This is a hands-on leadership role: you will be close enough to the work to coach through it, evolve the process around it, and remove the barriers that slow your team down - while staying accountable for the outcomes the team delivers at scale.This role is not about managing timelines. It's about managing outcomes. You will define what a successful implementation looks like at Ottimate, build the methodology that gets customers there consistently, and hold your team to a standard where implementation is complete when the customer achieves value, not when the project closes.You will work cross-functionally with Sales, Customer Success, and Product & Engineering, serving as the connective tissue between what customers were promised and what they experience. As Ottimate grows, this role grows with it - from operational leader to a key voice in how the broader Services organization evolves.ResponsibilitiesTeam leadership & talent developmentLead, develop, and retain a team of Implementation Managers and Enablement Consultants - building a culture of accountability, continuous improvement, and customer focusCoach team members through live engagement feedback, structured 1:1s, and deliberate skill-building - developing and growing talent, not just managing performanceEstablish clear expectations, performance standards, and growth paths for every person on the teamElevate the people around you: your success metric is not just what you deliver, but how much better the team gets under your leadershipModel the behaviors - ownership, consultative instinct, reliability, product depth - that define excellence in this functionImplementation methodology & delivery qualityOwn and evolve Ottimate's implementation methodology, building an outcome-driven delivery model where customer-centric milestones - not arbitrary project timelines - define valueTranslate customer goals into a structured, measurable implementation experience that creates a repeatable path to value across different customer profiles and system configurationsBuild and maintain implementation playbooks, frameworks, and escalation guides that raise baseline delivery quality and make the team faster and more efficient as it scalesServe as an escalation point for delivery risk and complex client issues - stepping in when the team needs senior judgment, not just process supportEnsure documentation standards are upheld across all active engagements; implementation knowledge should live in the system, not with individualsCustomer engagement & change managementBring a consultative approach to customer engagements - helping customers navigate the organizational change that comes with adopting new AP workflows, not just configuring softwarePartner with customers at the leadership level when needed, translating Ottimate's implementation model into their language and building confidence in the processLead through ambiguity: implementations rarely go as planned, and this role requires someone who can adapt and keep both the customer and internal teams alignedIdentify patterns where implementations stall and proactively address the root causes rather than managing symptomsCross-functional collaborationPartner closely with the Solution Architect to ensure clean transitions between pre-sales scoping and implementation executionCollaborate with Customer Success on account health, escalations, and the move from implementation to long-term customer ownershipWork with Product & Engineering on JIRA ticket prioritization, custom configuration needs, and product gaps that surface repeatedly during implementationPartner with Sales to align on customer expectations before contracts are signed - not after - so implementation begins with shared, realistic goalsRepresent the implementation function in cross-functional leadership conversations, contributing the delivery perspective to process, tooling, and roadmap decisionsOperational & strategic contributionOwn implementation team capacity planning, resource allocation, and workload management across the portfolio of active engagementsDefine and track the metrics that matter: time-to-live, utilization rates, customer satisfaction at go-live, and team delivery consistencyContribute to the broader Services org strategy - this role is not just about running implementations well today, but helping shape what the function looks like as Ottimate scalesRequirementsExperience7+ years in SaaS implementation, professional services, or customer onboarding - with at least 3-4 years in a people management or formal team lead roleDemonstrated track record of building or meaningfully improving an implementation practice - not just inheriting and maintaining oneExperience with AP, procurement, or financial operations workflows strongly preferred; ERP or accounting system implementation experience (Sage Intacct, NetSuite, Acumatica, Microsoft BC) is a plusChange management experience - both leading customers through operational change and leading internal teams through process transformationSkills & QualitiesOutcome-oriented mindset - you define implementation success by what the customer achieves, and you hold the team to that standard, not to project closure datesExceptional coaching instinct - you develop people through direct feedback, observation, and example; you make the team better as a natural byproduct of how you leadConsultative approach - to customers and to the team; you ask the right questions before jumping to solutions, and you teach others to do the sameStrategic 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-dayDirect and clear communicator - comfortable delivering hard feedback to your team, navigating difficult customer conversations, and representing the team in cross-functional settingsComfortable with ambiguity and organizational transformation - this function is evolving, and you'll be shaping it as much as running itBenefitsWe care deeply about making Ottimate an incredible place to work and invest a significant amount of time and energy into creating and maintaining a company culture that provides our team with a generous level of support whilst inspiring them to do their best work.The specific benefits/perks we offer are continually evolving, but currently include:Salary Range: USD $130,000-150,000 per yearMedical, Dental, Vision and other Company-Subsidized Benefits for you and your familyEmployer sponsored 401(k) with company matchPaid Time Off (and the encouragement to use it)Annual company retreatsPromote from within philosophyBeyond the tangible benefits though:You will be part of a growing team, at a pinnacle moment of scale for the business, and experience the excitement of working in a startup where each action makes a huge differenceYou will have the agency to solve difficult problems creatively, the freedom to explore work that inspires you, and infrastructure to ensure you're constantly challenged and developingYou will work with sharp, passionate teammates solving some of the most unique challenges and positioning our product as a premier finance automation solution. Our commitment to empowering a diverse and inclusive workforce, celebrating differences, and creating a safe space for our employees to bring their whole selves to work is second to noteWe are transforming entire industries using innovative technology including Artificial Intelligence, Payment Tech, and Neural NetworksOur leaders lead with a people-first approach; inspiring excellence, nurturing ideas, and finding creative ways to eliminate obstacles for cultivating growthWe truly love what we do and who we do it with - and we think you will too!Ottimate is an equal opportunity employer that is committed to diversity and inclusion. We do not discriminate based on race, color, national origin, religion, gender, gender expression, sexual orientation, age, veteran status, disability status, or marital status. If you are excited about the role but do not meet 100% of the qualifications listed above, we encourage you to apply. Nothing in this job posting should be construed as an offer or guarantee of employment.