Director, Product Management

Reports to: Chief Product Officer Location: United States

About Ottimate Ottimate is an AI-native accounts payable (AP) automation and payments platform serving mid-market, multi-location operators across hospitality, healthcare, grocery and retail, and client accounting services (CAS). We help finance teams capture, code, approve, and pay invoices with AI handling the repetitive work — across AP automation, Vendor Pay payments, and spend management. We're PE-backed (FTV Partners) and moving fast toward a more autonomous, agentic future for B2B finance. It's a great time to join and own real surface area early.

About The Role You'll own the strategy and roadmap for Ottimate's newest product initiatives — the categories that extend our platform beyond AP automation and into the rest of the purchasing lifecycle. This portfolio includes procurement, budgeting and spend planning, contract management, and adjacent capabilities that connect what our customers buy to what they ultimately pay. These are 0-to-1 and early-stage products: you'll define the vision, validate it with customers, and take it to market.

This role also leads our Design and UX function. You'll manage product managers and designers as one team, setting a high bar for craft and ensuring that new products feel coherent, intuitive, and unmistakably Ottimate from day one. This is a leadership role. You'll set direction for the new-initiatives portfolio, manage and grow a team of product managers and designers, and partner directly with engineering, data science, and go-to-market to expand what Ottimate does for the finance teams who depend on us.

Responsibilities

• Own the product vision, strategy, and roadmap for Ottimate's new-initiatives portfolio, including procurement, budgeting and spend planning, and contract management.
• Lead customer discovery and market validation for new product categories — identify the problems worth solving, size the opportunity, and build the business case for investment.
• Take new products from concept through launch: define MVPs, set success metrics, and iterate quickly based on customer and market feedback.
• Manage, mentor, and grow a team of product managers and designers; set clear goals, develop talent, and build a culture of craft and accountability.
• Lead the Design and UX function — own design quality, consistency, and the evolution of Ottimate's design system across new and existing products.
• Partner with engineering and data science leadership on prioritization, sequencing, and delivery; ensure the team ships predictably against committed milestones.
• Collaborate with sales, marketing, and customer success on positioning, pricing inputs, launch readiness, and early customer adoption.
• Define and track portfolio-level metrics; use data to make build/kill/pivot decisions and communicate progress to executive leadership.
• Represent the voice of the customer in executive planning, and represent the product externally with customers, prospects, and partners.

Required Skills & Experience

• 8+ years in product management, including 3+ years managing product managers, designers, or both.
• Deep experience with B2B SaaS platforms; fluency in workflow, data, or automation products.
• Domain experience in one or more of: procurement / procure-to-pay, budgeting and spend management, contract lifecycle management, or sourcing. This is highly valuable and will be weighted heavily.
• A track record of taking new products from concept to launch — comfort with ambiguity, customer discovery, and building the case for investment before the data exists.
• Demonstrated leadership of design and UX — either direct management of designers or a career-long, hands-on partnership with design organizations, with strong instincts for product craft.
• Strong analytical instincts — comfortable defining metrics, reading product data, and using it to drive decisions.
• Experience working with multi-entity, multi-location, or otherwise operationally complex customers.
• Clear, credible communication with executives, engineers, and customers alike.

Nice to Have

• Domain knowledge in accounts payable, source-to-pay suites, or finance operations.
• Experience shipping AI/ML-powered features and an intuition for where automation should be confident and where it should ask for help.
• Familiarity with design systems and design ops at scale.
• Exposure to agentic / MCP-based architectures.

What Success Looks Like In your first year, you've taken at least one new product category from concept to paying customers, built a validated roadmap for the broader new-initiatives portfolio, elevated the craft and consistency of Ottimate's product design, and built a combined product and design team that ships with confidence.

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: USD $175,000-190,000 per year + annual bonus.
• 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.