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Account Executive, Mid Market

Help Scout· Sales
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Remote$100kFull-timePosted 4w ago

About the role

Outbound, mid-market account executive role focused on building and owning pipeline, running full-cycle deals, and creating a playbook for upmarket SaaS sales at Help Scout. Remote US-based position with compensation including base, OTE, and equity.

Responsibilities

  • Build and own your pipeline. We expect more than 75% of your opportunities to be self-sourced through target account campaigns, account-based targeting, referrals, events. Inbound will support you; it won't fill your calendar.
  • Run full-cycle deals. You'll land the first meeting, run tailored product demos, build compelling business cases, manage commercial negotiations and seal the deal. You own the sales motion (with support from our amazing team).
  • Build a playbook. What works for you becomes the baseline of our upmarket sales motion. You're the first person running it, and will work with GTM leadership to set our strategy for the future.
  • Collaborate cross-functionally. You'll give Product direct feedback on requirements on what mid-market support teams need from us, partner with Marketing to launch targeted campaigns & and work in lockstep with RevOps to ensure our operational process is dialed in.
  • Own numbers. You'll own and report on pipeline coverage, forecast accuracy, and progress to target with enough rigor that leadership can plan around it.

Qualifications

  • You've sourced the majority of your own pipeline — 75% or more — and you can be specific about your strategy and results
  • 8+ years in full-cycle B2B SaaS sales, working mid-market accounts at companies of roughly 250–1,000 employees.
  • You're at home in a 3-6 month cycle, closing deals with an average size of $25-$75K
  • You have a real point of view on account selection and engagement strategy
  • You are comfortable managing a modern GTM tech stack and AI solutions for prospect selection, automation, enrichment — you can build a system that works for you
  • You use AI daily to improve your output, and you can point to specific examples where AI changed the speed, quality, and scale of what you delivered.
  • You’re a problem solver, and possess a strong ability to identify customer business needs, multi-thread with key stakeholders and position relevant solutions effectively
  • You are comfortable being the first of something. There's no mid-market playbook here yet, and you'd rather write one than inherit one.

Skills

Required:Pipeline developmentFull-cycle B2B SaaS sellingAccount-based sellingAI-enabled prospecting

Benefits

  • Competitive salary and an internal, transparent salary formula based on market data
  • Flexible time off – you choose the holidays and vacations that make sense for you
  • 12 weeks of fully paid parental leave for all new parents, including adoption and foster care
  • A home office stipend to help you get set up and productive
  • A co-working stipend up to $300 a month if you choose to work out of your house
  • A yearly professional development stipend of $1,800 to help you grow in your craft
  • If you’re in the U.S. or Canada, we offer top tier health insurance for you and your dependents.
Last updated Sep 24, 2026. Interested? Apply on the company site.
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