Job description

WHO WE ARE Help 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 articles.helpscout.com 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 ROLE 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 & 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 something. There's no mid-market playbook here yet, and you'd rather write one than inherit one. Compensation for this role is $100K base salary. OTE is $200K. COMPANY VALUES HAPPY TO HELP Help is in our first name! We show up for each other — not out of obligation, but because we’re invested in the team’s collective success. We share knowledge freely, lead with generosity, and practice empathy with our teammates, customers, and community. CRAFT OVER CONVENTION Our success relies on the quality and craft paulstamatiou.com of the work we put into the world. The status quo simply won’t work. So we insist on narrow focus, sweating every detail, and relentless pursuit of customer delight. PROGRESS NOT PERFECTION Achieving our true potential — collectively and individually — requires constant progress and forward momentum. By creating a culture of curiosity and openness, we aim to create a safe space for mistakes, the ability to identify them quickly, and use them to get better. OWN THE OUTCOME Own the outcome means taking full responsibility for the results of your work, decisions, and contributions. It reflects a mindset of accountability, proactiveness, and follow-through. If you “own the outcome,” you don’t just complete tasks, you ensure your work leads to meaningful results, and take initiative to solve problems rather than passing them along. Read more about how we define, share, and live these values here articles.helpscout.com. 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 - If you’re in the U.S. or Canada, we offer top tier health insurance for you and your dependents. HIRING GUIDELINES: All roles at Help Scout are fully remote. Some positions have specific location requirements. For roles outside the U.S. and Canada, we work with teammates as independent contractors under country-specific agreements. We do not sponsor visas. Teammates must already be authorized to work from their home country. We are an equal opportunity employer and are committed to building a company that embraces and celebrates diversity and inclusion helpscout.com. We do not discriminate on the basis of race, religion, color, national origin, gender, gender identity or expression, sexual orientation, age, marital status, veteran status, or disability status. We have read the studies and understand that diverse teams build better products, bring more perspective to the table, contribute to a company’s financial success, and help foster a more inclusive environment for all employees, but the bottom line is that it's the right thing to do. To provide you with the best experience, we can support you with accommodations or adjustments at any stage of the recruitment process. Simply inform our recruitment team during your conversation with them. A NOTE ON THE USE OF AI IN OUR INTERVIEW PROCESS While we understand that AI is an important tool in a modern skillset, we ask that you do not utilize AI assistants live on our interviews. Of course, use any tools you need to prepare! But we'd like for you to have a real human-to-human conversation with our team. On our end, we utilize a platform called Brighthire as a notetaker and review tool to ensure a fair and transparent hiring process. Beware of scammers! All legitimate communication from Help Scout regarding your application will come directly from an @helpscout.com helpscout.com email address and through our applicant tracking system, Ashby. We will never ask for personal financial information or conduct interviews outside of these official channels.

Requirements

Must-haves

Please note: For this role, we are only able to hire in the United States.
In this role, you will
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.
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.
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 something. There's no mid-market playbook here yet, and you'd rather write one than inherit one.
Compensation for this role is $100K base salary. OTE is $200K.
Read more about how we define, share, and live these values here https://articles.helpscout.com/blog/aligning-culture-with-values/.
All roles at Help Scout are fully remote. Some positions have specific location requirements. For roles outside the U.S. and Canada, we work with teammates as independent contractors under country-specific agreements.
We do not sponsor visas. Teammates must already be authorized to work from their home country.
To provide you with the best experience, we can support you with accommodations or adjustments at any stage of the recruitment process. Simply inform our recruitment team during your conversation with them.
A NOTE ON THE USE OF AI IN OUR INTERVIEW PROCESS
On our end, we utilize a platform called Brighthire as a notetaker and review tool to ensure a fair and transparent hiring process.

Nice-to-haves

None flagged.

Application prep

Use the role’s language and application details while tailoring your materials.

Keywords to mirror

Platform: ashby
Effort: quick

Benefits

Benefits detected in the listing.

Health Insurance

Parental Leave

Professional Development