Manager, Implementation & Enablement

About Ottimate Ottimate 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 Role As 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. Responsibilities Team leadership & talent development

• Lead, develop, and retain a team of Implementation Managers and Enablement Consultants - building a culture of accountability, continuous improvement, and customer focus
• Coach team members through live engagement feedback, structured 1:1s, and deliberate skill-building - developing and growing talent, not just managing performance
• Establish clear expectations, performance standards, and growth paths for every person on the team
• Elevate the people around you: your success metric is not just what you deliver, but how much better the team gets under your leadership
• Model the behaviors - ownership, consultative instinct, reliability, product depth - that define excellence in this function

Implementation methodology & delivery quality

• Own and evolve Ottimate's implementation methodology, building an outcome-driven delivery model where customer-centric milestones - not arbitrary project timelines - define value
• Translate customer goals into a structured, measurable implementation experience that creates a repeatable path to value across different customer profiles and system configurations
• Build and maintain implementation playbooks, frameworks, and escalation guides that raise baseline delivery quality and make the team faster and more efficient as it scales
• Serve as an escalation point for delivery risk and complex client issues - stepping in when the team needs senior judgment, not just process support
• Ensure documentation standards are upheld across all active engagements; implementation knowledge should live in the system, not with individuals

Customer engagement & change management

• Bring a consultative approach to customer engagements - helping customers navigate the organizational change that comes with adopting new AP workflows, not just configuring software
• Partner with customers at the leadership level when needed, translating Ottimate's implementation model into their language and building confidence in the process
• Lead through ambiguity: implementations rarely go as planned, and this role requires someone who can adapt and keep both the customer and internal teams aligned
• Identify patterns where implementations stall and proactively address the root causes rather than managing symptoms

Cross-functional collaboration

• Partner closely with the Solution Architect to ensure clean transitions between pre-sales scoping and implementation execution
• Collaborate with Customer Success on account health, escalations, and the move from implementation to long-term customer ownership
• Work with Product & Engineering on JIRA ticket prioritization, custom configuration needs, and product gaps that surface repeatedly during implementation
• Partner with Sales to align on customer expectations before contracts are signed - not after - so implementation begins with shared, realistic goals
• Represent the implementation function in cross-functional leadership conversations, contributing the delivery perspective to process, tooling, and roadmap decisions

Operational & strategic contribution

• Own implementation team capacity planning, resource allocation, and workload management across the portfolio of active engagements
• Define and track the metrics that matter: time-to-live, utilization rates, customer satisfaction at go-live, and team delivery consistency
• Contribute 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 scales

Requirements

Experience

• 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
• Demonstrated track record of building or meaningfully improving an implementation practice - not just inheriting and maintaining one
• 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
• Change management experience - both leading customers through operational change and leading internal teams through process transformation

Skills & qualities

• 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
• 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
• 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
• 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
• Direct and clear communicator - comfortable delivering hard feedback to your team, navigating difficult customer conversations, and representing the team in cross-functional settings
• Comfortable with ambiguity and organizational transformation - this function is evolving, and you'll be shaping it as much as running it

Benefits

We 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 year.
• Medical, Dental, Vision and other Company-Subsidized Benefits for you and your family.
• Employer sponsored 401(k) with company match.
• Paid Time Off (and the encouragement to use it).
• Annual company retreats.
• Promote from within philosophy.

Beyond 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 difference.
• You 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 developing.
• You 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 note.
• We are transforming entire industries using innovative technology including Artificial Intelligence, Payment Tech, and Neural Networks.
• Our leaders lead with a people-first approach; inspiring excellence, nurturing ideas, and finding creative ways to eliminate obstacles for cultivating growth.
• We 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.