Team Lead, Onboarding
About Ottimate
Ottimate is an AI-powered AP automation platform designed to help finance teams reduce costs, prevent overpayments, detect fraud, and enforce policy compliance throughout the invoice-to-payment lifecycle.
About The Role
We are seeking 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 delivering high-impact training and strategic adoption consulting.
Key Responsibilities
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
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
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
An analytical mindset with a problem-solving attitude, high attention to detail, and working knowledge of CRM tools, preferably Salesforce
Benefits
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
Company Culture
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
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.