Ottimate

Lead large-scale design initiatives including building a company-wide design system, conduct user research to inform product strategy, collaborate with engineering and product teams, advocate for user-centric design culture, and mentor designers. | 7+ years in product design leadership with experience in complex B2B/SaaS applications, proven design system creation, strong user research skills, collaboration in agile remote teams, and excellent executive communication. | This role is open for US or Canada Ottimate is an AI-powered finance automation platform that takes the grind out of accounts payable. From scanning invoices to issuing payments and managing spend, we help finance teams cut costs, prevent overpayments, catch fraud, and stay compliant-without slowing down growth. Our AP, Payments, and Spend products share one powerful platform that handles the hard stuff: workflow orchestration, identity and access, provisioning, security, and all the accounting plumbing that keeps the money moving. Why this role matters We are at a pivotal moment of scale, and we need a design leader who can take ownership of our user experience at a fundamental level. This role is for someone who can drive large-scale design projects, establish a cohesive design system, and champion a user-centric culture throughout the organization. You will be responsible for defining the future of our product's look, feel, and usability, ensuring that it's both powerful and intuitive for our customers. Key Responsibilities Design Leadership and Systems Thinking: Lead and execute large-scale design initiatives, including the creation and implementation of a company-wide design system and a redesign of our platform's look and feel. You understand the importance of consistency, scalability, and efficiency in design. User Research & Strategy: Plan and conduct comprehensive user research (interviews, surveys, usability testing) to deeply understand user needs and inform product strategy. Translate these insights into a multi-year design plan. Cross-Functional Collaboration: Partner closely with engineering, product management, and other stakeholders to deliver exceptional user experiences. You'll provide clear specifications and high-fidelity prototypes, acting with a bias for action to get things done efficiently. Design Advocacy: Champion a strong design culture within the organization, influencing our product development process and advocating for the user at every stage. Mentorship: Guide and mentor other designers, helping to elevate the overall quality of design across the company. For this role, national/international travel is expected. 7+ years of experience in product design, with a portfolio demonstrating your work on complex B2B or SaaS applications. Proven experience leading major design projects, such as building a design system from the ground up or executing a significant product redesign. Strong expertise in user research methodologies and a track record of using research to drive strategic design decisions. Exceptional collaboration skills with a proven ability to work closely with engineering teams in an agile, and remote environment. Experience in the accounts payable, procure-to-pay, or FinTech space is a significant plus. Executive-level communication skills and the ability to inspire teams. Comfortable working with a globally distributed team across multiple geographies. Open to domestic and international travel for company retreats and team meetings. 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: $160k/ USD per year. 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 pivotal 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.

Lead and coach a sales team to exceed targets, develop sales strategies, manage pipeline, collaborate with marketing and product teams, and represent the company at industry events. | Minimum 5 years progressive sales leadership in SaaS, healthcare sales experience, strong team management, strategic thinking, CRM proficiency, and excellent communication skills. | 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. Responsibilities Team Leadership: Lead, coach, and motivate a team of 5-6 Account Executives to achieve and exceed sales targets. Sales Strategy and Pipeline Management: Develop and implement effective sales strategies to drive revenue growth within the healthcare vertical. Oversee and manage the sales pipeline, ensuring accurate forecasting and effective pipeline management. Performance Management: Monitor team performance, provide regular feedback, and conduct performance reviews to ensure continuous improvement and development. Training and Development: Identify training needs for the sales team and provide ongoing training and development opportunities. Develop and implement sales enablement strategies to equip the sales team with the tools, resources, and training they need to be successful. Customer Engagement and Success: Foster strong relationships with key clients and prospects, and partners understanding their needs and positioning our solutions to meet their business objectives. Partner with the customer success team to ensure smooth onboarding and ongoing satisfaction of new clients. Collaboration: Work closely with the Sr Director of Sales, marketing, and product teams to align sales strategies with overall company goals and product offerings. Reporting: Prepare and present regular sales reports, insights, and recommendations to the Sr Director of Sales and executive team. Market Insights: Stay informed about industry trends, competitive landscape, and emerging opportunities within the healthcare sector. Sales Process Improvement: Continuously evaluate and improve sales processes, methodologies, and tools to enhance efficiency and effectiveness. Budget Management: Assist in the development and management of the sales budget, ensuring efficient allocation of resources. Event Participation: Represent the company at industry events, conferences, and trade shows to promote our solutions and network with potential clients. Bachelor's degree in Business, Marketing, or a related field is preferred. Minimum of 5 years of progressive sales and leadership experience in a growth-stage SaaS company. Proven track record as a high-performing Enterprise Account Executive or similar role. Significant experience selling to healthcare. Strong leadership and team management skills are highly preferred. Results-oriented with a passion for exceeding sales targets. Excellent communication, negotiation, and interpersonal skills. Strong problem-solving skills and a proactive approach to challenges. Strategic thinker with the ability to execute tactically. Proficient in CRM software (e.g., Salesforce, HubSpot), sales automation, and sales analytics tools. Proven experience developing and implementing sales enablement strategies to improve sales performance. Ability to analyze sales data and market trends to make informed decisions. High level of integrity and professionalism. Strong organizational skills with the ability to manage multiple priorities. Deep understanding of the healthcare industry and its unique challenges and opportunities. Ability to thrive in a fast-paced, dynamic growth-stage startup environment 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: $130,000-155,000 USD per year. 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.

Design, build, test, and maintain fintech backend features and microservices, collaborate cross-functionally, and manage code quality and bug fixes. | 5+ years professional experience with Python and Django, strong backend and database skills, startup experience preferred, and excellent communication. | About Ottimate: Ottimate is changing the way the hospitality industry manages its finances through life-changing Accounts Payable automation. Our mission is to eliminate manual work from every aspect of business expenses and enable business operators to stay in control of their spending at all times. The Role: Ottimate's mission is to make accounts payable (AP) and payments effortless for businesses. We are looking for a Senior Backend Engineer to contribute to our new product efforts and help us take ideas to market, specifically in fintech and payments. Our stack is based on Django, Angular, Postgres, and AWS. Expertise in Django is a big plus but familiarity with other modern technologies is a solid substitute. If you have a strong background in other frameworks, we are open to that. Planning, shipping, and learning are the most important traits we are looking for. You will: Discuss, plan, build and test new features. Bring in learnings from your previous roles and experiences to help build exciting new fintech innovations for businesses everywhere Collaborate with engineers, designers, product managers, and other stakeholders in defining the user experience. Develop integrations with 3rd party APIs Triage and fix bugs, often working directly with users. Manage code reviews through Pull Requests and make sure we're moving fast while maintaining Unit Tests and quality. Help migrate some of the modules into independent micro-services. Work on product features that affect 10s of thousands of customers. You have/are: 5+ years of professional experience working on web applications using modern software engineering processes. Proficient in Python and Django. Debugging complex database performance issues. You think critically about your work and ask questions in order to improve the product, not only on its technical implementation but also on how well it’s serving the users' needs. You have built performant and scalable backends, made pragmatic tradeoffs, and can point to your prior work. You have strong communication skills and are able to explain complex technical topics to the entire team in a clear and concise way. When things inevitably break, you eagerly jump in to diagnose and fix the core issues. Experience working in an early-stage startup is a huge plus. Fluent in both written and spoken English 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. 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: $150,000 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.