Head, Sales & Market Expansion
Drive revenue and build a high-performance sales engine.
What is this job all about?
You own the number end-to-end. You lead revenue generation, build and scale the sales team, and unlock new markets. This is a leadership role that combines sharp sales execution with strategic expansion.
Clients don’t pay for effort - they pay for outcomes. You will ensure predictable revenue, strong pipelines, and scalable growth systems.
What You Will Own:
1. Revenue Ownership & Sales Leadership:
- Own and consistently deliver revenue targets
- Lead the full sales cycle from pipeline creation to deal closure and account growth
- Build, mentor, and scale a high-performing sales team
- Drive accountability, performance metrics, and a results-first culture
- Establish strong governance across sales operations and execution
2. Market Expansion & Go-to-Market Strategy
- Identify and expand into new markets, segments, and geographies
- Define and execute go-to-market strategies aligned with business goals
- Build scalable demand generation and pipeline development systems
- Drive customer segmentation, targeting, and positioning strategies
- Continuously evaluate market trends, competition, and growth opportunities
3. Sales Operations & Performance Management
- Build predictable revenue engines through strong pipeline management
- Own forecasting accuracy, reporting, and sales analytics
- Optimize CRM systems, sales tools, and processes for efficiency
- Improve conversion rates across all stages of the sales funnel
- Align sales operations with business and financial goals
4. Strategic Partnerships & Customer Growth
- Build and nurture relationships with key clients and strategic partners
- Drive large deal closures and long-term account expansion
- Act as a trusted advisor to customers, focusing on business outcomes
- Collaborate with delivery, marketing, and leadership teams for integrated growth
- Strengthen brand positioning across target markets
What Makes You Fit:
- 12–15 years of experience in sales leadership roles
- 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
- Strong leadership presence with impactful storytelling and communication skills
What Success Looks Like:
Within 30 Days - Build Confidence & Cultural Alignment
- 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
Within 60 Days - Start Performing
- Actively contribute to pipeline growth and deal movement
- Bring structure to sales processes, forecasting, and reporting
- Influence key deals and participate in closures
- Start identifying market expansion opportunities and GTM improvements
Within 90 Days - Deliver Results
- Close meaningful deals and contribute directly to revenue
- Build a strong, predictable pipeline
- Show measurable impact on sales performance and conversion
- Establish authority as a sales leader driving outcomes, not activity
Qualification
This role demands a proven leader with a strong track record of driving revenue and delivering business outcomes. Rest is secondary to demonstrated impact.
Be the chosen one
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