Vice President of Sales

Summary

Join Raintree as the Vice President of Sales – New Logo and lead the expansion of the New Logo sales team. This high-impact role requires achieving significant revenue targets, optimizing sales processes, and building a high-performance sales organization. You will report directly to the CRO and contribute to strategic decision-making. The ideal candidate is a dynamic, proven executive with a strong analytical background and an entrepreneurial spirit. Responsibilities include developing and executing a comprehensive sales strategy, building a high-performing sales team, and standardizing the selling process. Occasional travel (25-50%) is required.

Requirements

• Proven track record as a successful B2B SaaS sales leader with a healthcare IT/EHR background, leading teams responsible for new logo sales with a history of generating $10-15M in new logo bookings annually
• Skilled in assessing existing sales teams and developing forward-looking organizational plans that swiftly manage out underperformers. Proven track record of hiring top-performing reps who consistently hit or exceed their quotas, with a history of engendering strong loyalty within the sales team—can provide examples of team members who have followed them from company to company
• Demonstrated success in selling to customers across segments, including large enterprise customers (with an average selling price of ~$750K+/ACV and a 6–12 month sales cycle), as well as middle-market ($100k/ACV) and SMB ($5k/ACV) customers
• Prior experience in designing and implementing predictable full lifecycle sales motions, including optimizing sales enablement processes, setting quotas and compensation, and segmenting customer targets thoughtfully
• Expertise in designing, instituting best practices, and ensuring adherence to sales processes and systems (CRM, performance management, territory design, etc.). Experience with Salesforce CRM
• Performance-driven management style, with a strong ability to use data to track team performance, coach reps to success, accurately forecast outcomes, and drive accountability across the team
• A culture builder and strong people leader with demonstrated experience in managing complex organizations through periods of transformation and change
• Experience in closing deals, including providing senior management sponsorship and stepping in to close key deals when necessary
• Ability to lead a fully remote sales team located across the U.S
• Demonstrated track record of collaborating with all members of an executive team to develop and refine a go-to-market approach, with a highly agile mindset

Responsibilities

• Develop and execute a comprehensive sales strategy to drive growth in new logo sales
• Implement a segmented go-to-market strategy across small, medium, and large/enterprise prospects
• Continuously assess market trends, customer needs, and competitor moves to inform strategic decisions
• Recruit, hire, develop, and mentor a high-performing sales team with a focus on achieving >$10M in Annual Recurring Revenue (ARR) from new logos
• Lead a team that consistently hits quota, with >75% of team members achieving their targets
• Standardize the selling process and guidelines to increase the sales close rate
• Set quarterly and annual sales goals, design rep territory assignments, and put in place an outbound-oriented sales motion and performance-based sales culture
• Engage directly in key deals to provide senior management sponsorship and close critical opportunities
• Partner with Rev Ops to deliver accurate sales forecasts, budgets, and performance reports
• Utilize data and metrics to track team performance, coach reps, and drive accountability
• Implement rigorous KPIs and metrics to ensure disciplined execution and continuous improvement
• Collaborate cross-functionally, particularly with marketing and product deployments, to build a predictable go-to-market model and seamless customer experience

Preferred Qualifications

Experience in healthcare SaaS and/or EHR that sells to the private post acute facilities and medical groups is highly desirable

Benefits

• Remote Work/Work From Home
• Paid Time Off/11 Paid Holidays/Year-End Holiday Break
• Health, Dental, Vision, HSA/FSA
• 401K with Company Match
• Disability & Life Insurance
• Employee Assistance Program
• Paid Parental Leave