Head of Sales & Business Development

Summary

Join Ready Set, a high-growth creative performance agency, as their Head of Sales & Business Development. This pivotal role involves building and scaling the go-to-market engine from the ground up, leading both business development and sales execution. You will define the team structure, processes, and performance culture, transforming Ready Set into a sales-led growth machine. The position reports directly to the CEO and requires cross-functional collaboration. You will be responsible for setting targets, developing sales playbooks, and managing sales tools. This role demands experience in scaling revenue functions and building high-performing sales teams within a digital agency or AdTech environment.

Requirements

• 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
• 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
• Collaborative, accountable, and deeply motivated to win

Responsibilities

• 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
• 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
• Manage tools (CRM, automation, reporting) to support sales goals — we currently use HubSpot
• Build sales processes, pipelines, and forecasting models for repeatability and scale
• 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
• 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

Preferred Qualifications

• Familiarity with regulated industries (Finance, Healthcare, Insurance) is a plus
• Experience working in remote-first teams is a strong plus

Benefits

• 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