Head of Sales

We’re seeking a Sales and Revenue Leader who can join Upsell.com and take full ownership of our commercial motion end to end. The goal of this role is to convert inbound demand into predictable revenue, own the full customer lifecycle from first response through renewal and expansion, and build the CRM and automation foundation that allows the business to scale with confidence.

You’ll need to:

• Own inbound leads from first response through qualification, closing, and conversion to paying customers.
• Run confident, customer-facing sales conversations with ecommerce merchants doing 25k+ orders per year.
• Design and manage the full revenue lifecycle, including trials, onboarding handoff, retention, expansion, and renewals.
• Build and maintain Pipedrive end to end, including pipelines, stages, fields, activities, automations, dashboards, and data hygiene.
• Design clear pipeline stages with enforced entry and exit criteria to keep forecasting accurate and predictable.
• Build and manage sales automations such as lead routing, follow-ups, SLA enforcement, stalled deal detection, lifecycle triggers, and renewal countdowns.
• Own pricing, packaging, annual plans, discounting logic, and commercial guardrails.
• Collaborate closely with Product, Customer Success, and Support on handoffs, escalations, and feedback loops.
• Analyse pipeline and customer data to identify risk, drive retention, and surface expansion opportunities.
• Operate comfortably across global time zones and merchant schedules.

Requirements:

• Proven experience owning the full revenue lifecycle in a B2B SaaS environment.
• Hands-on experience building and operating a CRM, including pipeline architecture, reporting, and automation.
• Strong commercial judgement across pricing, discounting, renewals, and expansion.
• Confidence running live sales calls with senior ecommerce stakeholders.
• Experience selling to or working within the Shopify ecosystem.
• Strong organisational skills and attention to detail.
• Ability to work independently in a fast-moving startup environment.
• Native-level written and spoken English.