Head of Sales

Head of Sales

We're looking for a Head of Sales to join Railsware and lead the sales function at Coupler.io — our no-code data integration and AI analytics platform used by thousands of marketing, data, and ops teams worldwide.

This is a hands-on leadership role. You'll manage and develop a team of Account Managers, own the revenue target, and evolve our existing pipeline and sales process so they can carry enterprise deals. As Coupler.io grows, there's a real opportunity to expand your scope across Railsware's product portfolio — including Mailtrap.io, an Email Delivery Platform.

We're looking for someone with strong expertise in B2B SaaS sales, hands-on experience leading a sales team, and a track record of closing enterprise deals. Someone who knows how to build process, keep a pipeline healthy, and coach a team.

If you want real ownership over a sales function and the space to grow it, we'd love to hear from you.

What You Will Do

Own the number

• Own product revenue target: new business, expansion, and renewals
• Manage and monitor team and individual quotas
• Forecast accurately and report to leadership on performance and risks

Lead and develop the team

• Lead, mentor, and support team through regular 1:1s, pipeline reviews, and coaching sessions
• Set, track, and improve team KPIs and performance
• Hire and onboard new Account Managers as the team grows
• Coach the team on deal strategy, customer communication, and account management best practices — both inbound and outbound

Optimize sales operations

• Own pipeline health, forecast accuracy, CRM quality, and team dashboards
• Improve sales processes, identify bottlenecks, and implement scalable solutions
• Ensure consistent follow-up and high operational standards across the team

Drive cross-functional collaboration

• Partner closely with Marketing, Solutions, Support, and Product to ensure a seamless customer journey
• Share insights on lead quality, customer feedback, and process improvements
• Act as the main bridge between sales and other teams

Stay close to customers

• Lead and close complex, high-value enterprise deals across products and services
• Manage strategic customer accounts and support the team on complex deals
• Drive cross-sell and upsell opportunities and stay hands-on with customers to understand market needs and continuously improve the sales approach

What We're Looking For

• 5+ years of senior-level experience in B2B SaaS sales or/and account management, covering both inbound and outbound
• 2+ years leading, mentoring, or coaching a Sales or Account Management team
• Proven track record of closing enterprise deals and managing a mix of SMB and enterprise customers, ideally in MarTech, SaaS, or the agency space
• Strong experience building and improving sales processes, managing pipelines, and working in CRM systems at an operational level
• Data-driven mindset with hands-on experience in BI and analytics tools — Power BI, Looker Studio, Google Sheets, or similar
• Excellent communication, presentation, negotiation, and stakeholder management skills
• Comfortable using AI tools to improve productivity and customer interactions
• Experienced working cross-functionally with Marketing, Product, Support, and Solutions teams
• Fluent English

Would be a plus

• Experience with data integration, ETL, or analytics platforms
• Experience building a sales function at an early- or mid-stage SaaS company
• Exposure to a product-led growth motion where sales works on top of existing product adoption