Sr. Director, Product Management - Automation

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 Role

The Sr. Director will be a key member of Ottimate’s leadership team, responsible for defining and executing the company’s product vision and roadmap across AP, Payments, and Spend products. This executive will lead the Product Management function, with a primary focus on execution, fostering a tight, high-velocity partnership between the Product GTM and Engineering teams.

This role is for a hands-on leader who excels at translating vision into a tangible, deliverable roadmap. Our team requires a strong strategic thinker who thrives in scaling SaaS businesses, has deep experience in financial software and ERP-adjacent ecosystems, and can balance long-term vision with near-term execution.

Key Responsibilities

Roadmap Execution & Delivery

• Translate high-level strategic objectives into a clear, detailed, and prioritized product roadmap and ensure delivery in partnership with Engineering and Design.
• Implement and refine agile product management processes to improve roadmap predictability, team velocity, and cross-functional communication.
• Oversee product delivery processes, ensuring releases are high quality, timely, and aligned with customer and partner expectations.
• Prioritize product investments to balance near-term revenue goals with long-term strategic differentiation.

Product Strategy & Vision

• Translate the overarching company vision into a cohesive and actionable product strategy for Ottimate’s AP Automation, Payments, and Spend product lines.
• Drive product strategy for our core verticals (Hospitality, Retail, Healthcare), ensuring roadmap priorities align with domain-specific needs and differentiation.
• Drive innovation in AI-powered automation, real-time settlement, and ERP ecosystem integrations.

Leadership & Team Development

• Build, mentor, and scale a high-performing Product Management team, fostering a culture of customer focus, accountability, and innovation.
• Serve as a leader collaborating with peers in Revenue, Technology, Finance, Customer Success, Marketing, and People.
• Embed best-in-class product management practices, including discovery, roadmapping, and release management.

Market & Ecosystem Engagement

• Act as a thought leader for Ottimate in the AP Automation and Payments market.
• Partner with ISVs, OEMs, VARs, and System Integrators to extend Ottimate’s ecosystem reach and co-develop solutions.
• Act as a key product evangelist, communicating the value of our solutions and the direction of our roadmap to internal and external stakeholders.
• Partner with GTM teams to ensure successful product launches and support go-to-market readiness.

Metrics & Outcomes

• Define and track key KPIs, including product adoption, NDR, attach rates, and time-to-value.
• Deliver against revenue growth targets by ensuring product-market fit, competitive differentiation, and ecosystem leverage.
• Partner with Finance and Executive Leadership to ensure product decisions align with EBITDA and revenue goals.

• 15+ years in Product Management, with 7+ years in senior leadership roles in SaaS or Fintech.
• A data-driven leader with a proven ability to translate strategy into tactical execution and detailed product requirements.
• Proven track record of scaling product teams and driving significant ARR growth in a mid-market SaaS context.
• Deep understanding of ERP ecosystems (NetSuite, Sage, Infor, Microsoft Dynamics, Workday, etc.).
• Strong expertise in B2B payments, AP automation, or adjacent financial operations technology.
• Exceptional leadership skills with the ability to inspire and develop cross-functional teams.
• Strategic and analytical thinker with a customer-first mindset.
• Excellent communication skills with board-level presence.

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:

• Competitive salary range.
• 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. Nothin