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Head of Sales

About Intentional Outreach

Intentional Outreach is a managed marketplace connecting B2B companies with vetted commission-based sales representatives.

Our platform gives businesses the ability to scale their outbound sales efforts by connecting them with qualified appointment setters and sales professionals who generate real opportunities for their sales teams.

We're building a sales network where performance, accountability, professional development, and quality are at the center of everything we do.

About the Role

We're looking for an experienced Head of Sales to lead, develop, and oversee our growing sales organization.

This is a leadership position for someone who has extensive hands-on sales experience, understands what exceptional sales performance looks like, and can effectively teach, coach, and develop others.

You'll work directly with sales managers, oversee performance across the organization, lead weekly company-wide sales training sessions, and establish the standards that define how our sales network operates.

You'll also play an important role in creating educational and training content, including recording live sales calls, demonstrating effective sales techniques, and producing content for our YouTube channel and internal training platform.

We're looking for someone who can do more than manage a team. You should be able to demonstrate the skills you're teaching, communicate with confidence, and set an example that other sales professionals want to follow.

You'll also serve as the final level of sales approval for new representatives and sales personnel entering the organization, ensuring that everyone meets our standards before joining the network.

What You'll Be Responsible For

Sales Leadership & Team Development

Provide leadership and direction across the entire sales organization. Work directly with sales managers to develop their teams, improve performance, address challenges, and maintain consistent standards throughout the company.

You'll help managers become better leaders and ensure they have the guidance and resources necessary to develop the people they oversee.

Weekly Company-Wide Sales Meetings

Lead a weekly sales meeting with the entire organization.

Each week, you'll select a specific topic and lead an educational session designed to improve the knowledge, confidence, and performance of our sales network.

Topics may include:

  • Objection handling and overcoming resistance.
  • Discovery and qualification techniques.
  • Closing strategies and buyer psychology.
  • Building rapport and establishing trust.
  • Cold calling and outbound sales techniques.
  • Improving conversion rates and meeting quality.
  • Handling difficult conversations.
  • Sales mindset, professionalism, and consistency.
  • Reviewing real calls and identifying opportunities for improvement.

These meetings should be engaging, practical, and educational. The goal is to give everyone something they can immediately apply to their sales activities.

Sales Performance & Metrics

Oversee sales performance across the organization and work directly with managers to maintain accountability and identify opportunities for improvement.

You'll be responsible for monitoring key performance indicators, understanding what's happening across individual teams, and helping managers address performance gaps.

This includes reviewing metrics such as:

  • Calls and outreach activity.
  • Contact and engagement rates.
  • Appointments booked and held.
  • Conversion rates.
  • Closing performance.
  • Call quality and qualification standards.
  • Individual and team performance trends.
  • Overall revenue and production.

You should be comfortable interpreting sales data, identifying patterns, and turning those insights into actionable improvements.

Sales Content & Educational Development

An important part of this position is creating educational content that demonstrates what great sales execution looks like.

You'll be responsible for recording and producing sales-related content for the Intentional Outreach YouTube channel, as well as educational material used within our internal training platform.

This may include:

  • Recording live sales calls and demonstrations.
  • Walking through real-world sales scenarios.
  • Demonstrating effective objection handling.
  • Teaching prospecting, discovery, and closing techniques.
  • Reviewing recorded calls and explaining what worked and what could be improved.
  • Creating training videos and educational resources.
  • Sharing practical sales strategies that representatives can implement immediately.

You'll receive direction and content guidance, but you'll be responsible for bringing the sales expertise, presentation skills, and on-camera presence needed to produce valuable educational material.

We want someone who is comfortable being on camera, speaking to an audience, and demonstrating sales techniques naturally and confidently.

Representative Approval & Quality Standards

You'll serve as the final sales approval authority for new representatives and sales personnel entering the organization.

Before a new hire receives final approval, you'll review their qualifications, experience, audition performance, and overall suitability for the sales network.

You'll help establish and maintain the standards required to represent our clients professionally.

The quality of our sales network directly impacts the experience of our clients and the reputation of Intentional Outreach.

Sales Standards & Continuous Improvement

Help establish consistent sales standards across the organization.

Work with managers to identify weaknesses, improve training, refine processes, and ensure that the entire sales network continues developing professionally.

You'll also help identify opportunities to improve how we recruit, train, evaluate, and develop sales representatives.

Who We're Looking For

We're looking for someone who has substantial experience in sales and the ability to lead others through both instruction and example.

The ideal candidate:

  • Has extensive experience in sales, preferably B2B sales, appointment setting, and closing.
  • Has previously managed, coached, or developed sales teams.
  • Has an exceptional understanding of sales fundamentals, buyer psychology, objection handling, and closing techniques.
  • Can confidently demonstrate sales techniques rather than simply explain them.
  • Is an excellent communicator who can lead meetings, present information, and educate groups.
  • Is comfortable recording videos, conducting live demonstrations, and appearing on camera.
  • Understands sales metrics and knows how to use performance data to improve results.
  • Can work effectively with managers and hold teams accountable without micromanaging.
  • Is organized, consistent, and capable of taking ownership of the sales organization's development.
  • Maintains a calm, professional, and trustworthy presence.
  • Leads with confidence, patience, and professionalism.

We're particularly interested in someone who takes pride in developing other people and genuinely enjoys helping sales professionals become better at what they do.

Compensation & Performance-Based Earnings

This is a performance-based leadership position. Your compensation is directly tied to the overall production of the sales team.

How to Apply

This role doesn't go through our regular rep application.

Email vp@intentionaloutreach.com.

Tell us who you are and why this role. Beyond that, what you send and how you go about it is up to you. For a role built on leading and demonstrating, how you reach out tells us a lot.

Email us