Head of Sales

Ladders; United States; Remote; USD 275,000 - 340,000; Full time

Benefits offered by this job

Health insurance

Unlimited PTO

Career growth

Learning stipend

Wealth planning

401k

Family leave

Fertility benefits

Equal pay

Job summary

Ladders is seeking a Head of Sales to lead our client’s revenue engine in the Information Technology space. This senior leadership role drives new business growth and expands key accounts across mid-market and enterprise segments.

You will own sales strategy, team performance, forecasting discipline, and the operating rhythm that supports revenue execution, partnering with Marketing, Product, Engineering, and customer-facing teams.

Qualifications

• 5+ years leading sales in high-growth SaaS environments.
• Proven track record selling to enterprise software buyers.
• Experience with MEDDPICC and structured deal management.
• Strong ability to build and scale sales processes.
• Experience managing mid-market and enterprise motions.

Responsibilities

• Lead and mentor sales and customer success teams to drive growth and performance.
• Own and refine sales strategy and playbooks for new business and account expansion.
• Coach teams on strategic deal qualification and negotiation techniques.
• Manage forecasts and ensure accurate qualification of opportunities using MEDDPICC.
• Identify growth within existing accounts and monitor account health.
• Collaborate with Marketing, Product, and Engineering to improve customer value.

Skills

Sales leadership

SaaS sales

Enterprise sales

Forecasting

MEDDPICC

Team building

Collaboration

Job description

For our client, we are seeking a Head of Sales to join the team of a leader in the Information Technology space.

This is a high-impact leadership role focused on driving new business growth and expanding existing accounts across both mid-market and enterprise segments. You will own sales strategy, team performance, forecasting discipline, and the operating rhythm that supports consistent revenue execution. The role partners closely with Marketing, Product, Engineering, and customer-facing teams to improve pipeline quality, strengthen deal management, and translate customer feedback into better outcomes.

Location: Remote

Compensation: $275,000 – $340,000 annually

Responsibilities

• Lead and mentor the sales and customer success teams, with a focus on growth and performance
• Own and refine the sales strategy and playbook for new business and account expansion
• Coach team members on strategic deal qualification and negotiation techniques
• Manage sales forecasts and ensure accurate opportunity qualification using MEDDPICC
• Identify growth opportunities within existing accounts and monitor account health
• Collaborate with Marketing, Product, and Engineering to enhance customer value and feedback integration

Qualifications

• 5+ years of sales leadership experience in high-growth SaaS, with a proven track record in enterprise software sales
• Experience selling to technical buyers, particularly in developer tools, DevOps, or security products
• Trained in MEDDPICC with a strong focus on deal management and detail
• Strong operational skills with a builder's mindset for optimizing sales processes
• Ability to manage both mid-market and enterprise sales motions effectively
• Proven success in building pipeline through outbound strategies
• Inclusive leadership style that fosters collaboration and empowerment

Benefits

• Premium health insurance, including medical, dental, and vision coverage
• Unlimited PTO, with a minimum of 3 weeks strongly encouraged
• Opportunities for upward mobility within the organization
• Learning and Development stipend for professional growth
• Access to a Wealth Advisor for financial planning
• 401k retirement plan
• Pregnancy and Family Leave benefits
• Fertility and Adoption benefits
• Commitment to equal compensation regardless of gender or race

Our client is an equal opportunity employer. We encourage you to apply even if you don’t meet every qualification—your background could be exactly what this team needs.