[Hiring] Manager, Implementation & Enablement @Ottimate

Role Description

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.

Qualifications

• 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

• 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.