Team Lead, Onboarding

Ottimate

8d • $95,000 - $110,000 • Remote

About The Position

Ottimate is seeking a strategic, engaging, and leadership-oriented Team Lead, Onboarding to join their Implementation team. This player-coach position involves managing, mentoring, and developing a team of Onboarding Specialists, while also delivering high-impact training and strategic adoption consulting. The primary goal is to scale team performance and ensure new clients become experts in using the Ottimate platform to transform their financial workflows.

Requirements

• 3+ years of experience in Customer Enablement or Product Adoption within a SaaS environment.
• 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; comfortable leading a 1:1 "deep dive" as 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.
• Analytical mindset with a problem-solving attitude, high attention to detail.
• Working knowledge of CRM tools, preferably Salesforce.

Nice To Haves

• A strong understanding of the Accounts Payable lifecycle or general B2B financial operations is highly preferred.

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.

Benefits

• 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed