Head of Outside Sales Operations Lead

3 weeks ago

Tampa, Florida, United States 360 Talent Avenue Full time

Position: Head of Outside Sales Operations

Compensation: $150K-$200K base salary, $300K OTE

We are partnering with a global leader in providing innovative restaurant point-of-sale (POS) systems and payment processing solutions, trusted by thousands of restaurants across 70+ countries. Our client is looking for a hands-on, strategic leader to drive and scale their outside sales operations across the US, with a focus on rapid expansion and market penetration.

Key Requirements:

  • Startup Experience: Proven ability to scale and lead sales teams in a high-growth, entrepreneurial environment.
  • Leadership Skills: Experience managing and mentoring teams, with a “boots on the ground” approach.
  • B2B Software Success: Demonstrated success in selling technology solutions, ideally in the SMB space.

This role is ideal for someone who thrives in fast-paced environments, enjoys getting hands-on, and is ready to build and optimize a high-performance outside sales operation. You will be instrumental in developing a repeatable sales model, expanding it across new markets, and driving significant revenue growth.

Responsibilities:

  • Lead and Build Sales Teams:
    • Start as a “Player-Coach,” actively selling while recruiting, training, and scaling high-performing outside sales teams across various US markets.
    • Foster a high-performance culture focused on accountability, collaboration, and growth.
    • Provide ongoing coaching, mentoring, and strategic direction to ensure the team meets or exceeds sales objectives.
  • Sales Strategy and Execution:
    • Develop and implement a comprehensive outside sales strategy that drives revenue and market growth.
    • Set clear sales goals, KPIs, and performance metrics, and ensure alignment with the company’s overall business objectives.
    • Identify and capitalize on new business opportunities, expanding our client base through targeted market strategies.
  • Market Expansion and Customer Acquisition:
    • Lead efforts to expand into new local markets across the US, requiring significant travel to develop and nurture client relationships.
    • Build strong relationships with restaurant owners and operators, establishing trust and credibility through tailored solutions and insights.
    • Develop a robust pipeline of qualified leads, using market research and competitive analysis to stay ahead of industry trends.
  • Sales Process Optimization:
    • Implement best-in-class sales tools, CRM systems, and methodologies to streamline operations and boost team productivity.
    • Continuously monitor sales performance, leveraging data and analytics to make informed, strategic decisions that drive improvement.
    • Refine the sales process to improve efficiency, effectiveness, and scalability.
  • Cross-Departmental Collaboration:
    • Work closely with marketing, product development, and customer support teams to ensure sales efforts are aligned with product offerings and customer needs.
    • Communicate regularly with leadership, presenting sales reports, market insights, and growth strategies.
  • Customer Relationship Management:
    • Build and maintain strong relationships with key partners in the restaurant industry, setting up a “Referral Selling System” in targeted markets.
    • Drive customer success and retention through proactive relationship management and personalized support.

Qualifications:

  • Bachelor’s degree in Business, Marketing, or a related field.
  • Minimum 4 years of experience in outside sales, with at least 2 years in a leadership role.
  • Proven track record of building and scaling successful sales teams in a startup or high-growth environment.
  • Experience selling B2B technology solutions, ideally in the SMB market.
  • Strong proficiency in CRM systems and sales analytics tools.
  • Willingness to travel extensively to support market expansion and sales efforts.

Why Work with Us:

  • Competitive base salary with a lucrative performance-based incentive structure, including stock options.
  • Comprehensive benefits package (health, dental, vision insurance).
  • Entrepreneurial culture with transparency and access to leadership, including the CEO.
  • Opportunity to scale a national sales operation and have a direct impact on the company’s growth and success.

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