Team Lead, Onboarding

About Ottimate

Ottimate is an AI-driven accounts payable automation platform built to help finance teams lower operating costs, stop duplicate or excess payments, identify fraudulent activity, and keep policy controls in place across the full invoice-to-payment workflow.

Role Overview

Ottimate is hiring a strategic and people-focused Team Lead, Onboarding for its Implementation team. This is a player-coach position: you will guide, mentor, and grow a team of Onboarding Specialists while also personally delivering high-impact training and adoption consulting. The aim is to improve team performance at scale and ensure clients become confident users of Ottimate who can use the platform to improve financial operations.

Team Leadership and Development

• Direct, coach, and support a team of Onboarding Specialists so they consistently perform at a high level and continue developing professionally.
• Welcome and train new team members, while also strengthening the consulting and presentation abilities of current staff.
• Hold regular one-on-one discussions, share actionable feedback, and manage performance to build a collaborative, high-performing group.
• Serve as the main contact for enablement-related project issues and client escalations.

Learning Strategy and Delivery

• Design and deliver tailored training programs for different user groups such as AP Clerks, Controllers, and CFOs.
• Advise client leadership directly and anticipate project risks early to keep implementations moving forward.

Success Measurement and Improvement

• Set, monitor, and report on adoption metrics as well as the effectiveness of team configuration and training efforts.
• Partner with Implementation Management to improve enablement materials, guides, and training templates that make the onboarding experience more efficient.

Requirements

• At least 3 years of experience in customer enablement or product adoption in a SaaS setting, including 1 or more years in direct management, team leadership, or formal training.
• Ability to work as a player-coach, balancing team leadership with execution of individual enablement work and project goals.
• Excellent presentation skills, with comfort leading private deep-dive discussions, speaking to executive audiences, and coaching teammates through difficult client situations.
• Strong people skills, including the ability to resolve conflict, manage competing priorities, and influence stakeholders across the organization.
• Good knowledge of the accounts payable process or broader B2B finance operations is strongly preferred.
• Analytical approach, strong problem-solving instincts, sharp attention to detail, and familiarity with CRM tools, ideally Salesforce.

Benefits and Compensation

The listed compensation range is $95,000 to $110,000 per year, with pay also influenced by skills and experience.

• Medical, dental, vision, and other company-subsidized benefits for employees and their families.
• Employer-sponsored 401(k) with company match.
• Paid time off, with clear encouragement to use it.
• Annual company retreats.
• Internal promotion culture.

Additional Information

• Ottimate emphasizes a supportive, growth-oriented workplace culture.
• The company values the chance to work at a scaling startup where individual contributions have significant impact.
• Team members are given autonomy to solve complex problems creatively and are supported with an environment that encourages ongoing learning.
• The organization works on innovative technologies including artificial intelligence, payment technology, and neural networks.
• Leadership is described as people-first, with a focus on removing obstacles, encouraging ideas, and supporting growth.
• Ottimate highlights diversity, inclusion, and psychological safety as important parts of its culture.
• It is an equal opportunity employer and does not discriminate based on race, color, national origin, religion, gender, gender expression, sexual orientation, age, veteran status, disability status, or marital status.
• Candidates who are interested in the role but do not meet every listed qualification are encouraged to apply.
• This posting is not an offer or guarantee of employment.