Founding Sales Manager (Player-Coach)

Accountabilities:: You will lead sales execution while developing the people, processes, and performance standards needed to support sustainable revenue growth. Own the full sales cycle, including discovery calls, product demonstrations, negotiations, and deal closing, while identifying conversion bottlenecks and documenting successful sales practices. Recruit, onboard, train, and manage Sales Closers and outbound Sales Development Representatives (SDRs). Establish clear sales targets, coach representatives through live calls, monitor performance, and implement improvement strategies. Develop and refine sales messaging, follow-up sequences, pipeline management practices, conversion strategies, and forecasting processes across both brands. Take ownership of team revenue targets, convert initial projects into recurring monthly retainers, and identify opportunities for upselling and account expansion. Collaborate with Marketing, Account Management, Go-to-Market (GTM) Engineering, and the CEO to improve lead quality, sales execution, and overall revenue performance. Leverage Salesforce and existing automated GTM workflows to improve sales efficiency, pipeline visibility, and team productivity. Monitor key performance indicators, including meeting show rates, close rates, sales cycle length, and revenue per representative. Provide regular sales performance updates, forecasts, and actionable recommendations to leadership. Build scalable sales playbooks, processes, and performance standards that support long-term organizational growth. Requirements: The ideal candidate is a commercially driven sales leader who combines a strong personal record of closing deals with the ability to build, coach, and scale a high-performing sales team. At least 7 years of B2B sales experience, including 3 or more years in sales leadership. Demonstrated success exceeding sales quotas and personally closing deals. Proven experience recruiting, training, coaching, and managing sales representatives. Strong expertise in outbound prospecting, consultative selling, negotiation, pipeline development, and full-cycle sales management. Experience using Salesforce or comparable CRM platforms, along with sales performance metrics and forecasting tools. Ability to develop scalable sales processes, playbooks, and performance management frameworks. Strong analytical skills, commercial awareness, and the ability to translate sales data into actionable business decisions. A proactive, hands-on approach with a strong sense of ownership and accountability for revenue outcomes. Excellent communication, leadership, coaching, and relationship-building skills. Experience in agency, professional services, or technology sales is an advantage. Based in Florida is strongly preferred, although candidates elsewhere in the U.S. Eastern Time Zone will be considered. Ability to work remotely on a full-time basis while maintaining alignment with U.S. business hours. Benefits: Competitive compensation: Base salary plus a performance-based bonus tied to team revenue. Established lead generation: Access to a steady flow of inbound leads to support sales opportunities. Sales technology infrastructure: Work with an existing CRM system and automated go-to-market workflows. Direct leadership collaboration: Work closely with the CEO and GTM Engineering team to influence business strategy and revenue performance. Ownership and autonomy: Build, shape, and scale the sales organization from the ground up. Remote flexibility: Full-time remote work for candidates based in Florida or other eligible locations within the U.S. Eastern Time Zone.