Overview
We’re seeking a Head of Sales to lead, optimize, and scale our sales function. This is a player-coach role overseeing a team of Sales Representatives while actively contributing to revenue generation. This is a hands-on leadership role at an early scaling stage, not a multi-layer management position. It’s not just about hitting numbers it’s about building repeatable systems and creating a scalable sales motion aligned with our product-led growth strategy.
Responsibilities
- Lead, coach, and develop a team of Sales Representatives to exceed individual and team targets
- Conduct regular 1:1s focused on skill development and performance improvement
- Establish clear accountability mechanisms and performance standards
- Build a culture of continuous improvement, collaboration, and customer-centricity
- Recruit and onboard additional sales talent as we scale (quality over speed)
Process Optimization & Revenue Operations
- Audit and refine the end-to-end sales process from lead qualification to close
- Define clear stage criteria, conversion benchmarks, and sales velocity metrics
- Implement best practices for opportunity management and forecasting accuracy
- Partner with Marketing and Customer Success teams to eliminate handoff friction and revenue leakage
- Leverage HubSpot (must-have) and analytics tools to drive data-informed decisions
- Use ChartMogul as a nice-to-have for revenue insights
- Apply working knowledge of outbound support tools (e.g. Apollo, Outreach, SalesLoft, or similar) to enable and scale outbound motions
Sales Strategy & Execution
- Develop and execute sales playbooks for core segments (affiliate marketers, e-commerce brands)
- Build and launch an initial outbound motion: review ICP for outbound targets, create multi-touch cadences, define outbound metrics and pipeline contribution goals
- Create competitive positioning strategies against established players (e.g. Triple Whale, Voluum, Hyros)
- Build objection-handling frameworks for pricing and ROI-driven conversations
- Optimize the balance between self-serve and sales-assisted motions, with a strong focus on performance-driven buyers
Cross-Functional Collaboration
- Work closely with the CRO on revenue strategy, capacity planning, and growth initiatives
- Collaborate with Marketing on lead quality and conversion optimization
- Partner with Product on feature prioritization based on sales feedback and competitive insights
- Align with Customer Success on handoffs and onboarding experience
Revenue Performance
- Own sales forecasting and pipeline development
- Drive improvements in key metrics such as win rate, sales cycle length, and average deal size
- Personally close strategic and complex opportunities
- Contribute 20% of team revenue through direct selling
Requirements
Must-Have
- 5+ years of experience in B2B SaaS sales, including 2+ years leading sales teams
- Proven track record of scaling sales in product-led or inbound-driven environments
- Experience operating hybrid self-serve / sales-assisted models
- Deep understanding of sales methodologies and when to apply them
- Strong process orientation - ability to diagnose and fix broken sales systems
- Strong proficiency with CRM platforms (HubSpot required)
- Experience selling technical products to analytical buyers (marketers, data analysts, technical decision-makers)
- Demonstrated coaching ability - developing reps from good to great
- Data-driven decision-making mindset with focus on metrics such as conversion rates, velocity, CAC:LTV, and pipeline quality
Highly Desirable
- Experience in MarTech, AdTech, or analytics platforms
- Familiarity with performance marketing or affiliate marketing ecosystems
- Background selling tracking, attribution or analytics solutions
- Experience competing in mid-market SaaS against better-funded players
- Comfort navigating technical evaluation processes (technical discovery, proofs of concept)
- Revenue Operations or Sales Ops experience
Personal Attributes
- Proactive rather than reactive - you spot problems before they escalate
- Process-obsessed - you believe systems drive results, not just effort
- Analytically rigorous - you validate hypotheses with data
- Direct communicator - clear, honest feedback without corporate jargon
- Resilient and comfortable with ambiguity and the pace of a growth-stage startup
- Comfortable operating without perfect data or fully defined processes
Benefits
- Base compensation + team bonus + personal bonus
- Stock option program
- Fully remote setup with flexible working hours
- 21 paid vacation days plus 10 personal paid holidays
- Paid sick leave and maternity/paternity leave
- A collaborative team culture built on ownership, clarity, and trust
- Opportunities for professional growth, experimentation, and real impact
- Team offsites and conference trips
If you enjoy building systems, not just chasing short-term numbers, we’d love to hear from you!