Head of Sales

AI Growth Leader | B2B Digital Technology | State Department Security Clearance

Company Description

Pivot Forward.ai supports professionals and companies navigating layoffs and career disruptions by offering AI retraining, reskilling, peer community engagement, and access to valuable resources. By collaborating with professionals and leaders, we provide innovative training and tools to turn challenges into opportunities. Rooted in our belief that "Your pivot starts here," we aim to empower individuals and businesses to embrace change and transform their careers in an ever-evolving world.

We’re looking for a Head of Sales who deeply understands the assignment — someone who can bridge the gap between enterprises, professionals, graduates, and universities leveraging a modern SaaS platform.

You’ll lead our go-to-market strategy, drive revenue, and directly influence how Pivot Forward.ai grows and scales. This is a leader-level opportunity — with significant equity, autonomy, and long-term upside.

• Own and execute the B2B sales strategy for Pivot Forward.ai
• Identify and close deals from large, mid-sized, and small entities using Hubspot
• Build strategic partnerships
• Represent Pivot Forward.ai at events, expos, industry meetups, etc.
• Work closely with the tech team to shape the product around user feedback
• Build and scale the sales organization as we grow
• Weekly metrics reporting on sales insights of inflight conversations, events and revenue potential

• 7-10+ years of experience in technology, SaaS, or software
• Strong existing network within the SaaS industry
• Experience selling to enterprise level companies, and interpersonal skills to interface with university leaders
• Proven ability to close B2B deals and build relationships
• Entrepreneurial mindset — you want to build and grow revenue, not just sell
• Excellent communication, persistence, and grit – hunter mentality

• Performance-based compensation once revenue targets are hit
• Freedom to build your own sales systems and team
• Backing and support from experienced founder with multiple successful enterprise roles

• You’ll lead sales for a ready-to-scale SaaS platform with huge market potential
• Be part of a proven venture that has built and scaled multiple startups successfully
• Shape the future of technology adoption in one of the world’s largest industries — education
• Real ownership, impact, and upside

Send a resume to info with a cover letter regarding your experience and revenue achievements.