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Team Lead, Onboarding

Ottimate
CompanyOttimate
CategoryHR & Recruiting
LocationUnited States
RemoteRemote
EmploymentFull-time
LevelLead
SalaryNot stated by the employer
Posted2 Jul 2026
Last verified8 Aug 2026
SourceEmployer ATS (workable)
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Description
About Ottimate Ottimate is an AI-powered AP [Accounts Payable] automation platform that empowers finance teams to reduce costs, prevent overpayments, detect fraud, and enforce policy compliance across the entire invoice-to-payment lifecycle. About The Role The Role: We are looking for a strategic, engaging, and leadership-oriented Team Lead, Onboarding to join our Implementation team. In this player-coach position, you will manage, mentor, and develop a team of Onboarding Specialists while continuing to deliver high-impact training and strategic adoption consulting yourself. Your goal is to scale team performance and ensure that new Ottimate clients don't just "have" our software, but are experts in using it to transform their financial workflows. Key Responsibilities Team Leadership & Development: Lead, mentor, and coach a team of Onboarding Specialists to drive high performance and professional growth. Onboard new hires and successfully develop existing team members' consulting and presentation capabilities. Conduct regular one-on-one meetings, provide constructive feedback, and handle performance management to cultivate a cohesive, high-performing team. Act as the primary point of contact for enablement-related project risks and client escalations. Learning Strategy & Delivery (Player Capacity): Execute customized training programs tailored to various user personas (e.g., AP Clerks, Controllers, and CFOs). Act as a primary consultant to client leadership, proactively identifying project risks to ensure continuous momentum. Success Benchmarking & Optimization: - Define, track, and report on key adoption metrics and the overall effectiveness of the team's configuration and training interventions. Work alongside Implementation Management to develop and refine enablement resources, guides, and training templates to streamline the onboarding journey. Requirements  3+ years of experience in Customer Enablement or Product Adoption within a SaaS environment, with 1+ years of direct employee management, team leadership, or formal training experience. Proven capability to act as a player-coach: managing team dynamics while effectively executing individual enablement and project milestones. Exceptional presentation skills; you should be as comfortable leading a 1:1 "deep dive" as you are presenting to large executive groups or coaching team members through challenging client scenarios. Strong interpersonal skills with a demonstrated ability to address conflict, manage workloads, and influence stakeholders at all levels of the organization. A strong understanding of the Accounts Payable lifecycle or general B2B financial operations is highly preferred. Analytical mindset with a problem-solving attitude, high attention to detail, and working knowledge of CRM tools, preferably Salesforce. 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: Compensation: $95,000-110,000 per year. Competitive salary based on skills & experience. 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