Head of Sales - Player-Coach for SaaS Growth

Grand Avenue Software Inc.; United States; Remote; USD 150,000 - 210,000; Full time

Benefits offered by this job

Health insurance

Dental & vision coverage

401(k) with employer match

Additional insurance options

10 holidays + 3 weeks PTO

Job summary

Grand Avenue Software is seeking a Head of Sales to lead a small, capable team and professionalize the function. You will optimize structure, methodology, and discipline to ramp reps and consistently hit quota while staying close to deals.

This hands-on, player-coach role reports to the CEO and owns Sales and Sales Development. You will shape GTM strategy, align with marketing, product, and implementations, and own the number.

Qualifications

• Proven, process-driven sales manager with 3+ years owning bookings.
• Hands-on leader with direct deal involvement and coaching.
• Experience in high-growth B2B SaaS with outbound and RevOps familiarity.

Responsibilities

• Professionalize the team with ramp plans and coaching cadence.
• Own bookings attainment and manage reps' performance.
• Lead live deals and guide junior reps by example.
• Install pipeline, forecast rigor, and CRM discipline.
• Collaborate with marketing, product, implementations, and partners.
• Shape growth strategy and GTM motions.

Skills

Player-coach

B2B SaaS sales

Deal involvement

Outbound sales

RevOps/data-driven

Leadership

Analytical/process-oriented

Growth-stage experience

Tools

CRM (Salesforce)

Sales analytics tools

Job description

Grand Avenue Software is seeking a Head of Sales to lead a small, capable team and professionalize the function. You will optimize structure, methodology, and discipline to ramp reps and consistently hit quota while staying close to deals.

This hands-on, player-coach role reports to the CEO and owns Sales and Sales Development. You will shape GTM strategy, align with marketing, product, and implementations, and own the number.