[Hiring] Account Executive @Help Scout

Role Description

Today, 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 & 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.
• 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 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.

Compensation

• Compensation for this role is $100K base salary. OTE is $200K.

Company Values

• Happy to Help: We show up for each other — not out of obligation, but because we’re invested in the team’s collective success.
• Craft over Convention: Our success relies on the quality and craft of the work we put into the world.
• Progress not Perfection: Achieving our true potential requires constant progress and forward momentum.
• Own the Outcome: Taking full responsibility for the results of your work, decisions, and contributions.

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.