Optimal is seeking a Vice President of Sales, Healthcare to drive revenue growth and expand our presence across the healthcare landscape, particularly with small to mid-size independent agencies. This is a senior, highly consultative individual contributor role focused on leading complex, high-value opportunities, building executive-level client relationships, and delivering strategic, data-driven solutions. The Vice President of Sales, Healthcare will partner closely with the SVP of Sales and senior leadership to identify new business opportunities, grow key accounts, and shape go-to-market strategy within the healthcare vertical. This role is ideal for a seasoned seller who thrives in enterprise-level sales, brings a strong point of view on healthcare media, and is energized by winning and scaling meaningful client partnerships. Optimal works hard to provide our clients with innovative solutions based on the diverse perspectives of our team. To that end, we’re committed to recruiting team members from a wide range of backgrounds and experiences. We encourage applicants of all races, colors, gender identities, religions, ages, sexual orientations, national and ethnic origins, disabilities, marital status, veteran status, and all backgrounds. Optimal is an equal-opportunity employer. Optimal job offers are contingent on the results of a background check. About the Health Division Optimal pioneers the best integration of data and technology to reach and persuade audiences with the most efficient and effective digital advertising solutions in healthcare and beyond. We combine the highest quality data and brand-safe inventory to deliver the most efficient digital media solutions for consumer health brands and organizations. Fully permissioned, transparent, and trustworthy, we protect patient privacy while creating the highest quality audiences anywhere. Everyone at Optimal has the opportunity to learn, grow, and progress. We provide our team with the personal and professional development they need to achieve real career advancement. We’re always looking for exceptional people to join our team. If this sounds like you, please apply! Essential Functions, Duties, and Responsibilities: - Own and drive revenue growth within the healthcare vertical, focusing on large, complex, and high-value opportunities - Lead the full sales cycle from opportunity identification through pitch, negotiation, and close - Build and maintain senior-level client relationships, serving as a trusted advisor across key accounts - Develop and execute strategic sales approaches tailored to client objectives, competitive dynamics, and market trends - Lead the development of RFP responses, proposals, and pitch materials that reflect sophisticated targeting, activation, and measurement strategies - Translate complex healthcare measurement frameworks, including NRx, script lift, cost-per-diagnosed patient, audience quality, and direct response metrics, into clear and compelling client value - Serve as a subject matter expert in healthcare media, including endemic publishers and digital health platforms, to inform strategy and differentiate offerings - Partner cross-functionally with analytics, product, campaign management, and operations teams to ensure strong execution and performance - Identify and pursue new market opportunities, partnerships, and client segments to expand the organization’s footprint - Maintain accurate pipeline tracking, forecasting, and CRM reporting to support revenue visibility and planning - Collaborate with Finance on pricing, deal structuring, and revenue planning - Attend conferences and industry events while professionally representing Optimal - Maintain confidentiality and professionalism - Ability to travel for in-person client meetings and conferences as needed - Perform other duties as assigned Healthcare Category Fluency - Deep experience with endemic health publishers and digital platforms - Strong understanding of competitive targeting and audience activation strategies - Expertise in healthcare measurement, including NRx, script lift, cost-per-diagnosed patient, audience quality, and direct response - Deep familiarity with targeting nuances across pharmaceuticals, clinical trials, OTC products, and hospital systems - Ability to connect data, platforms, and analytics into cohesive, high-performing campaign strategies Minimum Qualifications & Skill Requirements: - 8–12+ years of experience in digital strategy, healthcare advertising sales, or agency-side business development - Proven success closing high-value, complex deals and consistently exceeding revenue targets - Strong network of healthcare clients, partners, and industry relationships - Deep understanding of platforms, analytics, campaign creation, and data strategy - Highly client-focused with a consultative, problem-solving approach and strong ability to pitch, present, and write proposals - Proficiency in CRM tools (Salesforce preferred), Google Apps, and Microsoft Office - Excellent written and verbal communication skills with strong executive presence Optimal is proud to offer the following: The base salary is commensurate with experience, depending upon factors including, but not limited to, experience, skill level, education and location with an opportunity for limitless earning potential via commissions. - Annual base salary range is $140,000 - $175,000, depending upon factors including, but not limited to, experience, skill level, education, and location.is commensurate with experience, with an opportunity for limitless earning potential via commissions. - Open leave (paid time off) - Paid Leave for new parents - Five-Year Anniversary Reward - 100% employer-paid health insurance for employees (including dental and vision) - Flex Spending Plan - Employee Assistance Program - 401K with company matching - Student Loan Repayment Program - Professional development opportunities - Rewards and recognition programs - Mobile Phone & internet reimbursement and much more Office Hours This position is based in New York metro area and is fully remote. Work hours are consistently 9:00 a.m. to 5:00 p.m. Monday - Friday, with the expectation that evening and weekend work will be required as necessary. Please visit our Notice to Applicants and Employees to learn about our information practices in the job application and employment context.

Optimal is seeking a Sales Director, Health to help lead revenue growth, particularly with small to mid-size independent agencies, in our health vertical. The Director of Sales, Healthcare, plays a key role in driving revenue growth and expanding our presence across the healthcare landscape. This is a highly consultative, individual contributor role focused on building relationships, winning new business, and delivering strategic, data-driven solutions to clients. The Sales Director, Health collaborates closely with senior leadership to strengthen existing client partnerships, develop new business opportunities, and drive long-term strategic growth. Optimal works hard to provide our clients with innovative solutions based on the diverse perspectives of our team. To that end, we’re committed to recruiting team members from a wide range of backgrounds and experiences. We encourage applicants of all races, colors, gender identities, religions, ages, sexual orientations, national and ethnic origins, disabilities, marital status, veteran status, and all backgrounds. Optimal is an equal-opportunity employer. Optimal job offers are contingent on the results of a background check. About the Health Division Optimal pioneers the best integration of data and technology to reach and persuade audiences with the most efficient and effective digital advertising solutions in healthcare and beyond. We combine the highest quality data and brand-safe inventory to deliver the most efficient digital media solutions for consumer health brands and organizations. Fully permissioned, transparent, and trustworthy, we protect patient privacy while creating the highest quality audiences anywhere. Everyone at Optimal has the opportunity to learn, grow, and progress. We provide our team with the personal and professional development they need to achieve real career advancement. We’re always looking for exceptional people to join our team. If this sounds like you, please apply! Essential Functions, Duties, and Responsibilities: - Source new business through current and ever-expanding network via pitches/presentations/business discussions - Maintain and grow spend across client base - Write RFP responses and media plans - Accurately track meeting and presentation details to further deal development. - Work with campaign management and support teams to ensure client targeting and campaign needs are exceeded - Work with the finance department to complete monthly billing tasks - Attend conferences and other industry events while professionally representing Optimal - Maintain confidentiality and professionalism - Ability to travel for in-person client meetings and conferences as needed - Perform other duties as assigned Healthcare category fluency: - Experience with endemic health publishers and digital platforms - Familiarity with competitive targeting and activation offerings - Knowledge of back-end measurement (e.g. NRx, script lift, cost-per-diagnosed patient, audience quality, as well as direct response) - Familiarity of nuances in targeting needs for pharmaceuticals, clinical trials, OTC products, hospital systems and health topic/issue awareness campaigns Minimum Qualifications & Skill Requirements: - 5+ years of experience in digital strategy, programmatic platform sales, or agency-side business development, including 2+ years of experience in health-related advertising sales. Proven success reaching or exceeding sales goals with a strong network of health clients/partners - Understands platforms, analytics, campaign creation and data strategies. - Client-focused, with a collaborative problem-solving approach demonstrated through an elevated ability to pitch/present and write proposals - Proficiency in CRM tools, Salesforce preferred, familiar with Google Apps, and a strong knowledge of Microsoft Office - Excellent written and verbal communication skills - Experience with endemic health publishers and digital platforms - Familiarity with competitive targeting and activation offerings - Knowledge of back end measurement, eg NRx, script lift, cost-per-diagnosed patient, audience quality, as well as direct response - Familiarity of nuances in targeting needs for pharmaceuticals, clinical trials, OTC products, hospital systems and health topic/issue awareness campaigns Optimal is proud to offer the following: The base salary is commensurate with experience, depending upon factors including, but not limited to, experience, skill level, education and location with an opportunity for limitless earning potential via commissions. - Annual base salary range is $110,000 - $135,000, depending upon factors including, but not limited to, experience, skill level, education, and location. with an opportunity for limitless earning potential via commissions. - Open leave (paid time off) - Paid Leave for new parents - Five-Year Anniversary Reward - 100% employer-paid health insurance for employees (including dental and vision) - Flex Spending Plan - Employee Assistance Program - 401K with company matching - Student Loan Repayment Program - Professional development opportunities - Rewards and recognition programs - Mobile Phone & internet reimbursement and much more Office Hours This position is based in New York metro area and is fully remote. . Work hours are consistently 9:00 a.m. to 5:00 p.m. Monday - Friday, with the expectation that evening and weekend work will be required as necessary. Please visit our Notice to Applicants and Employees to learn about our information practices in the job application and employment context.

• Independently identify and proactively contact potential new customers via phone, virtual meetings, email and other channels • Competently support and provide long-term care to existing practices to establish DiGA (prescribable digital health applications) as a valuable supplement to standard therapy and thereby sustainably improve quality of care for patients • Support practice teams to remove barriers in prescribing so patients gain seamless access to our digital solutions • Work closely with Marketing to ensure the best possible support for our practices • Maintain and structure documentation of all activities in the CRM system: you will work with state-of-the-art tools and AI assistance to take your sales performance to the next level • Deliver trainings and other virtual events for physicians and practice teams to integrate our DiGA into existing workflows • Represent Sidekick Health at trade fairs and congresses — an ideal opportunity to expand our network and increase visibility of our solutions

• Collaborate with AI and Data Teams: Work closely with data scientists and product managers to evaluate AI models used in prospecting, lead qualification, objection handling, negotiation, and closing. • Model Evaluation & Improvement: Identify gaps, hallucinations, unnatural phrasing, and ineffective tactics in existing models and contribute domain insights to improve conversation quality and conversion potential. • Validation: Validate AI outputs against real-world sales scenarios, psychological persuasion principles, and customer experience standards to ensure interactions feel human and authentic. • Define Success Metrics: Define key metrics and success criteria to measure model performance regarding tone, empathy, objection recovery, and eventual deal progression. • Data Annotation & Context: Support data labeling and annotation by providing specific context on sales stages (e.g., differentiating between a discovery question and a closing question) to refine training datasets. • Framework Design: Assist in designing prompts and frameworks that allow the AI to adapt to different buyer personas and industries while maintaining consistency. • Industry Trends: Stay current with evolving sales methodologies (e.g., SPIN, Challenger, Sandler), CRM technologies, and ethical standards in automated selling.