Professional Services Sales Lead

Key Responsibilities

• Own and lead the enterprise sales motion for Flywheel Services, focusing on large, multi-year transformation engagements.
• Partner with Healthcare Sales Lead to identify, shape, and close complex services opportunities across new accounts.
• Engage C-suite and senior executives to frame enterprise-wide transformation roadmaps, align stakeholders, and position Flywheel as a long-term strategic partner.
• Drive momentum in complex, multi-stakeholder sales cycles by establishing clear direction, managing executive alignment, and proactively advancing deals toward close.
• Develop and expand high-value growth channels, including strategic partnerships and deeper penetration within healthcare and other priority verticals.
• Shape commercial strategy for enterprise services engagements, including structuring multi-year proposals, defining value narratives, and aligning delivery, product, and solutions teams around a cohesive offering.
• Elevate the overall sales organization by modeling executive-level consultative selling and contributing to the evolution of Flywheel’s go-to-market strategy.
• Develop a strong pipeline and the ability to manage accurate forecasting.
• Stay well educated and informed on the robotics and automation competitive landscape, including driving new offering development where there’s a gap or noting where competitors may have an edge.

Minimum Qualifications

• 8+ years of experience selling consulting, transformation, and technology-enabled services — with a proven track record of closing complex, multi-year enterprise-wide engagements ($250K–$10M+).
• 5+ years of work experience in healthcare, ideally with established relationships across hospital systems or healthcare provider groups.
• Bachelor’s degree in business, sales, technology or other related field.
• Demonstrated ability to sell at the executive level, influence C-suite stakeholders, navigate long, complex enterprise sales cycles involving multiple decision-makers.
• Enjoy working in a fast paced, collaborative and dynamic start-up environment as part of a small team.
• Experience establishing customer trust and building strong relationships in a predominantly virtual environment - especially for first meetings.
• Highly motivated teammate with excellent oral and written communication skills.
• Enjoy working in a fast paced, collaborative and dynamic start-up environment as part of a small team.
• Willing to occasionally travel.
• Must have and maintain US work authorization.

Preferred Qualifications

• Experience in management consulting, technology transformation, digital transformation, or advisory services environments.
• Experience structuring and selling enterprise transformation programs that require close partnership between sales, strategy, and delivery teams.