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Salary: USD 100,000 - 200,000 / annual
Help Scout is a customer support platform used by 10,000+ companies to manage customer relationships. Founded in 2011, the company is now integrating AI capabilities while maintaining a fully remote, 120+ person team distributed globally.
This is a true outbound sales role focused on building Help Scout's mid-market motion (100–1,000 employee companies). The company's SMB sales process is already optimized with strong inbound conversion, but mid-market prospects require a different approach: proactive outbound prospecting and account-based targeting.
You will own the full sales cycle for mid-market deals ($25–75K ACV, 3–6 month sales cycles). This includes pipeline building through self-sourced prospecting (target account campaigns, referrals, events), running tailored product demos, building business cases, managing negotiations, and closing deals. You'll be the first person running this playbook and will work with GTM leadership to define Help Scout's upmarket sales strategy going forward.
Key responsibilities include: building and owning your pipeline (75%+ self-sourced), running full-cycle deals with minimal support, developing a repeatable playbook for future hires, collaborating cross-functionally with Product and Marketing on mid-market needs, and owning pipeline coverage, forecast accuracy, and quota attainment with rigor.
Help Scout values craft, progress, ownership, and helping teammates succeed. The culture emphasizes taking ownership, staying curious, and raising the quality of work around you. The company is fully remote with flexible time off, professional development stipends, home office support, and competitive benefits including parental leave and health insurance.
REQUIREMENTS:
- 8+ years in full-cycle B2B SaaS sales, specifically working mid-market accounts (250–1,000 employees)
- Demonstrated ability to source 75%+ of your own pipeline; must be able to articulate specific prospecting strategy and results
- Comfortable with 3–6 month sales cycles and closing deals in the $25–75K range
- Strong point of view on account selection and engagement strategy
- Proficiency with modern GTM tech stacks and AI tools for prospect selection, automation, and enrichment
- Daily use of AI with specific examples of how it improved speed, quality, and scale of your work
- Strong problem-solving skills; ability to identify customer business needs, multi-thread with stakeholders, and position solutions effectively
- Comfort being the first person to build something; preference for writing playbooks over inheriting them
- Must be authorized to work in the United States; no visa sponsorship available
