Account Executive, Mid Market

Who we areHelp Scout started in 2011 with a simple premise: support software should treat customers like people, not tickets. 3+ billion conversations later, more than 10,000 companies use Help Scout to grow relationships with customers of all types, from clients to patients and beyond.

Now we’re in a new chapter: not only building AI that gives teams more space to focus on the customer experience, but also reimagining how we operate in an AI-native world. That means shipping and learning faster, without compromising on craft. Great work here carries a strong opinion and sweats the details, regardless of the tools we use to drive it.

We’ve been a fully remote team since day one, with 120+ teammates now all over the world. It’s a culture where you’ll be trusted to take ownership, stay curious, and raise the quality of work around you. It comes with clear expectations and a team that will push you to do some of the best work of your career.

If that kind of challenge gives you energy, we’d love to meet you.

About the roleToday, our SMB sales motion is dialed in. The majority of new customers find us; they visit our website, start a trial, or request a walkthrough of the platform. We’ve built a process that converts these visitors into customers at an impressive rate.

Over the past year, our product has become increasingly competitive for support teams at larger companies (100-1,000 employees), but those prospects don’t always arrive on our site ready to engage. That’s where you come in.

This is a true outbound sales role, designed for a rep with world-class prospecting skills. You’ll have the opportunity to not only craft our outbound sales motion, but lead the charge competing (and winning) new upmarket customers at a higher ACV.

Please note: For this role, we are only able to hire in the United States.

In this role, you will

• 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.

About you:- You've sourced the majority of your own pipeline — 75% or more — and you can be specific about your strategy and results

• You have 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 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 s...