Head of Sales at Reflow AI Inc. (DBA Wayside)

As the Head of Sales, you will spearhead the commercial growth of an AI platform that integrates with existing HR systems to automate end-to-end payroll and employee life-cycle transactions. You will define the go-to-market strategy, build relationships with top PEO leaders, and drive adoption for a solution already reducing response times by 20% for enterprise clients.

• Design and execute a scalable sales playbook to target enterprise HR teams and Professional Employer Organizations (PEOs) globally.
• Manage the full sales cycle from prospecting to closing, leveraging case studies that demonstrate 40+ hours of time savings per client.
• Partner with the product team to translate client feedback into features for the AI agent, ensuring the platform continues to outperform legacy chatbot solutions.

• Proven track record in B2B SaaS sales, specifically selling complex software solutions to the HR, payroll, or PEO industries.
• Strong experience building and managing a sales pipeline from scratch within an early-stage startup environment or high-growth tech firm.
• Exceptional ability to communicate technical AI value propositions to C-suite executives while maintaining the 'human touch' essential to HR service delivery.**

• High-impact leadership role at a company backed by an advisory board of elite industry CEOs and former executives from Spirit HR and Tandem HR.
• Solve massive operational inefficiencies in the HR sector using proprietary AI that integrates bi-directionally with Salesforce and PrismHR without requiring employee change management.
• Join a SOC-2 Type II and GDPR compliant startup that is already trusted by leading organizations like Infiniti HR and Syndeo to handle sensitive HRIS data.