Outbound Sales Representative (Upmarket) - Help Scout

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

Now, Help Scout is in a new chapter: building AI that gives teams more space to focus on the customer experience and reimagining how they operate in an AI-native world. This means shipping and learning faster without compromising on craft. Great work here carries a strong opinion and sweats the details.

The company has been a fully remote team since day one, with 120+ teammates worldwide. It’s a culture where you’ll be trusted to take ownership, stay curious, and raise the quality of work around you.

The Role

Today, Help Scout’s SMB sales motion is dialed in. The majority of new customers find them through their website, trials, or platform walkthroughs. Over the past year, their product has become increasingly competitive for support teams at larger companies (100-1,000 employees), but these prospects don’t always arrive on their site ready to engage.

This is a true outbound sales role, designed for a rep with world-class prospecting skills. You’ll craft the outbound sales motion and lead the charge in competing (and winning) new upmarket customers at a higher ACV.

Please note: For this role, Help Scout is only able to hire in the United States.

Key Responsibilities:

• Build and own your pipeline. Expect more than 75% of your opportunities to be self-sourced through target account campaigns, account-based targeting, referrals, and events. Inbound will support you but won’t fill your calendar.

• Run full-cycle deals. 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 the team).

• Build a playbook. What works for you becomes the baseline of Help Scout’s upmarket sales motion. You’re the first person running it and will work with GTM leadership to set future strategy.

• Collaborate cross-functionally. Provide Product with direct feedback on requirements for mid-market support teams, partner with Marketing to launch targeted campaigns, and work closely with RevOps to ensure operational processes are dialed in.

• Own numbers. You’ll own and report on pipeline coverage, forecast accuracy, and progress toward targets with enough rigor that leadership can plan around it.

About You:

• You’ve sourced the majority of your own pipeline—75% or more—and can be specific about your strategy and results.

• You have 8+ years in full-cycle B2B SaaS sales, working with mid-market accounts at companies of roughly 250–1,000 employees.

• You’re comfortable with a 3-6 month cycle, closing deals averaging $25-$75K.

• You have a strong point of view on account selection and engagement strategy.

• You’re comfortable managing a modern GTM tech stack and AI solutions for prospect selection, automation, and 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 with a strong ability to identify customer business needs, multi-thread with key stakeholders, and position relevant solutions effectively.

• You’re comfortable being the first of something. There’s no mid-market playbook here yet, and you’d rather write one than inherit one.

Benefits and Perks:

• 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.

• Top-tier health insurance for you and your dependents (if you’re in the U.S. or Canada).