Head of Sales

Location: Miami, Florida (U.S.)

Employment Type: Full-Time

StartWise is a high-end venture studio and consulting firm that helps entrepreneurs and businesses go from idea to market-ready. We provide market research, investor connections, business strategy, branding, UX/UI, product development, and advanced AI/automation solutions.

With offices in Miami and New York, StartWise partners with ambitious entrepreneurs and established companies to validate ideas, build scalable products, and secure funding.

We are seeking a Head of Sales to lead, scale, and optimize our sales organization. This role is responsible for building the sales team, setting strategy, and driving revenue growth. You will manage Account Executives, SDRs, and Sales Operations to ensure StartWise meets and exceeds revenue targets.

The Head of Sales will report directly to the CEO and collaborate closely with marketing, and client success teams.

• Build, lead, and coach a high-performing sales team (AEs, SDRs, and setters).
• Develop and execute a sales strategy aligned with StartWise’s growth goals.
• Own the full sales cycle: from pipeline development to deal closing.
• Implement and optimize sales processes, KPIs, and forecasting systems.
• Manage and improve CRM usage (HubSpot) to track performance and pipeline health.
• Work closely with marketing on lead generation and campaign alignment.
• Establish scalable outbound and inbound sales playbooks.
• Negotiate and close high-value consulting and development service contracts ($2k–$100k ).
• Represent StartWise at events, conferences, and networking opportunities.
• Report on performance, revenue forecasts, and strategic initiatives to the CEO.

• 5 years of experience in sales, with at least 2 years in a leadership role.
• Proven track record of building and scaling sales teams.
• Experience in consulting, SaaS, or professional services sales preferred.
• Strong knowledge of sales processes, CRM systems (HubSpot preferred), and pipeline management.
• Excellent leadership, coaching, and communication skills.
• Demonstrated ability to close high-ticket deals and manage long sales cycles.
• Entrepreneurial mindset, comfortable in a fast-paced, high-growth environment.

• Competitive base salary uncapped commission structure.
• Opportunity to build and scale a sales organization from the ground up.
• Work directly with visionary entrepreneurs and established businesses.
• High-impact role with direct reporting to the CEO.
• Dynamic culture focused on innovation, collaboration, and results.

• At StartWise, you’ll be at the forefront of building an elite venture studio, helping shape the future of startups and enterprises alike. If you’re a driven sales leader ready to scale revenue and lead a world-class team — we’d love to hear from you.