Team Lead, Onboarding

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. 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. 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 developing. You will work with sharp, passionate teammates solving some of the most unique challenges and positioning our product as a premier finance automation solution. Our commitment to empowering a diverse and inclusive workforce, celebrating differences, and creating a safe space for our employees to bring their whole selves to work is second to note. 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.