Head, Sales & Market Expansion

What you will own:

• Revenue ownership & sales leadership
• Market Expansion & Go-to-Market Strategy
• Sales Operations & Performance Management
• Strategic Partnerships & Customer Growth
• Client's advocacy by proactively identifying UX gaps, usability issues, and AI opportunities.
• Surface blockers, gaps, and opportunities early for all client account.

What Makes You Fit:

• Proven track record of generating $3M+ revenue in the last 12 months
• Strong experience selling IT services/solutions
• Deep expertise across sales strategy, GTM execution, and pipeline management
• Impactful storytelling and communication skills
• Ability to translate ambiguous business problems into intuitive user experiences.
• Proactive mindset that uncovers user, product, and AI opportunities before they become requirements.
• Highly proactive with a relentless getting-things-done attitude - anticipates rather than reacts

What Success Looks Like:

30 Days - Learn & Align

• Demonstrate strong understanding of Pepper Square’s offerings, positioning, and sales motion
• Build credibility with internal teams and leadership
• Show ownership, urgency, and alignment with a performance-driven culture
• Gain visibility into pipeline, key accounts, and ongoing deals

60 Days - Execute & Improve

• Actively contribute to pipeline growth and deal movement
• Influence key deals and participate in closures
• Start identifying market expansion opportunities and GTM improvements

90 Days - Deliver Outcomes

• Close meaningful deals and contribute directly to revenue
• Build a strong, predictable pipeline
• Show measurable impact on sales performance and conversion

Qualification:

We care about your ability to own outcomes, keep clients genuinely happy, and get things done without excuses. Rest is secondary to demonstrated impact.