Head of Sales & Business Development

About Ready Set:

• We weave AI and technology throughout our operations to enhance human creativity, not replace it
• We produce high-quality creative that stops the scroll and achieves sustainable growth
• We optimize advertising across all digital channels for consistency and performance
• We use data to inspire and refine creative concepts that drives continued efficiency across channels

Head of Sales & Business Development

Ready Set is looking for a senior sales leader to build and scale our go-to-market engine from the ground up. This is a unique opportunity to shape the full sales function at a high-growth creative performance agency, working with brands like DoorDash, Hims & Hers, and Brigit.

You’ll be responsible for leading both business development (pipeline generation) and sales execution (closing deals) — defining the team structure, processes, and performance culture that takes Ready Set from a referral-driven business to a scalable, sales-led growth machine. This role reports directly to our CEO and will work cross-functionally with leaders across the company to unlock the next phase of our growth.

Responsibilities:

• 🚀 Build & Lead the Sales Team

  • Lead and mentor the existing sales team as a player-coach.

  • Recruit, train, and manage high-performing AEs, SDRs, and Sales Ops.

  • Define and evolve team structure as we grow.

  🎯 Own Sales Strategy

  • Set targets, comp plans, and performance benchmarks aligned with 3-year growth goals.

  • Develop outbound and inbound sales playbooks tailored to DTC, B2C, and growth-stage companies — especially in regulated industries like Finance, Healthcare, and Insurance.

  • Build and refine pitches, sales decks, and collateral that align with our brand and resonate with buyers.

  ⚙️ Establish Scalable Sales Infrastructure

  • Manage tools (CRM, automation, reporting) to support sales goals — we currently use HubSpot.

  • Build sales processes, pipelines, and forecasting models for repeatability and scale.

  📈 Drive New Business Growth

  • Personally own and close high-value deals, navigating complex, multi-stakeholder buying cycles.

  • Sell into CMOs, VPs of Growth, and other senior decision-makers in a consultative, insight-driven manner.

  • Collaborate with Marketing to generate and convert pipeline.

  • Continuously refine our ICP and value proposition using insights from the market, sales data, and client conversations.

  🤝 Collaborate Cross-Functionally

  • Work closely with Client Experience, Creative Strategy, and Media Buying teams to ensure smooth client handoffs.

  • Partner with Finance and RevOps on forecasting, performance tracking, and goal-setting.

  • Provide strategic input on how we package and position our products based on buyer feedback.
    
    

Qualifications: 

• 10+ years of B2B sales experience, ideally in a high-growth, performance-driven digital agency or AdTech environment.

• Proven success scaling revenue functions from $10M+ to $50M+.

• Demonstrated ability to build, lead, and retain top-performing sales teams.

• Strong strategic thinking, operational rigor, and analytical skills.

• Experience selling creative, paid media, or performance marketing services.

• Familiarity with regulated industries (Finance, Healthcare, Insurance) is a plus.

• Skilled at adding value throughout the sales process and guiding enterprise buyers to a decision.

• Excellent communication and executive presence.

• Comfortable working in ambiguity — you thrive in build-from-scratch environments.

• Experience working in remote-first teams is a strong plus.

• Collaborative, accountable, and deeply motivated to win.
  
  

What we offer:

• • A pivotal role in shaping the next chapter of a fast-growing agency.

  • 100% remote work with a globally distributed, talented team.

  • Competitive base salary + performance-based compensation.

  • Equity participation.

  • Annual training and development budget.

  • Flexible PTO and local holidays.