Head of Sales - Gatsby

Job Title: Head of Sales

Location: Remote (with occasional travel)
Employment Type: Full-Time

About Gatsby Labs

Gatsby Labs is a venture-backed startup revolutionizing how people connect and build real-world relationships with their valuable networks through engagement around events.  Our flagship product, a personalized event management tool, empowers users to effortlessly organize and grow events and to provide high value engagement with important networks. With 3x growth in customers year-over-year and over 1,000 events organized in 2023, we are poised for significant expansion.

We’re passionate about fostering genuine connections through innovative technology, and we’re looking for a dynamic Head of Sales to join our team during this exciting period of growth.

About the Role

As the Head of Sales at Gatsby Labs, you’ll lead the charge in driving revenue growth and refining our go-to-market strategy. This is a hands-on leadership role where you’ll directly build a high-performing sales function while collaborating with the leadership team to shape pricing, product strategies, and customer acquisition efforts.

This role is ideal for someone who thrives in fast-paced, high-growth environments, has scaled revenue from $0 or $1M to $5M+, and excels in a velocity sales model.  You’ll help build the foundation of our sales organization, establish processes, and help drive Gatsby to become a market leader.

Key Responsibilities

• Sales Strategy & Execution:

  • Develop and execute a comprehensive sales strategy for growing revenue.

  • Build a robust sales pipeline to achieve aggressive growth targets.

• Revenue Growth:

  • Own the entire sales cycle, from outbound prospecting to closing deals, with a focus on velocity sales ($10K-$15K ASP) and strategic contracts ($50K+).

• Team Building & Leadership:

  • This is a player/coach role, with time divided between direct customer contact, developing and executing sales strategy, and managing a team.  

  • Foster a culture of accountability, innovation, and high energy within the team.

• Pipeline Management & Metrics:

  • Establish and optimize systems to track key sales metrics, KPIs, and activities to ensure consistent pipeline health.

  • Implement tools and processes for efficient pipeline management and reporting.

• Collaborative Product Insights:

  • Work closely with the leadership and product teams to provide feedback on pricing, features, and market positioning.

  • Influence product roadmaps based on customer and market insights.

• Customer Focus:

  • Build strong relationships with customers to understand their needs and foster trust in Gatsby’s solutions.

  • Drive net new logo acquisition and develop land-and-expand strategies for long-term client partnerships.

What We’re Looking For

• Proven Sales Experience:

  • 7+ years of SaaS sales experience, with at least 2-3 years in high-growth startups in the velocity sales model with ASPs ranging from $10k-15k to $50k+.

  • Demonstrated success scaling revenue from $1M to $5M+ and  meeting/exceeding quotas consistently, preference for other roles growing sales to higher base.

  • Experience with velocity sales models with 30-90 day closes and lower side ASPs, alongside some strategic customer deals 

• Leadership:

  • Experience building and managing sales teams of 5+ with strong results.

  • Track record of fostering great sales cultures, driving accountability, and motivating teams to perform.

• Operational Excellence:

  • Expertise in pipeline management, sales metrics, and setting up systems like CRMs and ATS.

  • Strong understanding of outbound/inbound sales models and how SDRs function within a sales organization.

• Strategic Mindset:

  • Ability to contribute to pricing and product strategy, with a history of influencing GTM strategies in past roles.

  • Comfortable working as an individual contributor initially to build the foundation for future growth.

• Energy & Drive:

  • High energy, proactive, and results-driven, with a can-do attitude.

  • Passion for working in a fast-paced, dynamic environment and tackling tough challenges.

Nice-to-Have Skills

• Experience in the events space or selling to the VC/finance sector.

Why Join Gatsby Labs?

• Be part of a mission-driven company revolutionizing how people connect through events.

• Lead and shape the future of sales at a fast-growing startup with 10x customer growth.

• Collaborate with passionate, innovative leaders and make a tangible impact.