Program Manager, Sales Readiness & Operations

Reports to: Director of Product Marketing Location: Tampa, FL (On-Site) About Us 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. The Opportunity We are seeking a strategic Program Manager to spearhead our Sales Readiness and Operations initiatives for the Tampa sales hub. In this role, you will be the architect of the programs and processes that drive sales mastery. Your dual focus will be on developing expert-level sales skills and ensuring operational excellence through the mastery of our sales technology stack. You will build the foundation that enables every representative to articulate the Ottimate story, leverage technology effectively, and generate a significant pipeline. What You Will Build & Deliver: A Structured Onboarding & Certification Program: Design an end-to-end onboarding experience for new hires that accelerates their ramp time, culminating in a formal certification that validates both their sales skills and technical proficiency. Mastery of the Sales Tech Stack: Develop and deliver training that ensures the entire team is proficient with our core sales technologies (e.g., Salesforce, Outreach, 6Sense, ZoomInfo), focusing on best practices to maximize efficiency and data integrity. Daily Skill Reinforcement Workshops: Plan and lead a calendar of daily training activities, focusing on core competencies such as prospecting for finance buyers, call execution, and foundational Accounts Payable principles. A Centralized Content Repository: Build and govern the team's single source of truth for all sales content, including e-learning modules, tech stack guides, and just-in-time training assets, ensuring all materials are current and effective. A Continuous Feedback Loop: Establish processes for analyzing team performance—in both sales conversations and tool usage—to identify opportunities for improvement and evolve the readiness programs accordingly. Sales Leadership Training - Create a development path for our SDRs to become Senior SDRs and then AEs, filling their knowledge gaps and ensuring they’re fully empowered to take the next step in their career. Requirements You have spent at least 3 years building and delivering impactful training programs specifically for high-volume sales teams (SDR/BDR). You are a power user of modern sales operations technology and are adept at teaching others how to leverage tools like CRM (Salesforce) and sales engagement platforms to their full potential. You are a natural educator and compelling storyteller, capable of crafting narratives that resonate with both new sales reps and seasoned leaders. You are fluent in the language of B2B SaaS and ideally understand the unique challenges and opportunities of selling to finance departments. You are highly organized, view enablement through a programmatic lens, and excel at managing multiple projects in a dynamic environment. You are willing to be in-person 9 to 5 in our downtown Tampa office. Previous experience carrying a quota in a sales role is a significant advantage. 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: Salary range: $105,000 - $140,000 base plus bonus compensation. Work from home in an energetic remote-first environment that supports flexible working hours and understands work-life balance. 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 none. 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.