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At Help Scout, the sales team serves as a trusted advisor for prospects and customers -- listening to their needs, clearly explaining what’s possible, and leading training/onboarding efforts to make sure everyone is successful for the long term. Quite simply, you’ll have the opportunity to impact small businesses in a big way on a daily basis.

About the role

  • You’ll partner with customers through the entire buying process, from initial evaluation to close, and through onboarding of the entire team. You’ll be the primary point of contact through the first year renewal.
  • You’ll team with marketing to ensure inbound campaigns are well coordinated as you follow up to qualify and close those opportunities.
  • In most cases you’ll be partnering with SMBs between 10-250 people. On a monthly basis you’ll have the opportunity to close several new deals and get them on track with the product.
  • The companies you work with will be qualified and passed to you based on the number of expected Users. They will mostly be trial signups, webinar attendees, or inbound leads we’ve talked with to get a high-level understanding of their needs. You’ll also work with existing customers on high-value upgrade and expansion opportunities.
  • Most of your time will be spent working with stakeholders over email and on the phone, and doing demos. There’s a reason we call you a trusted advisor -- this is less about the hard sell and more about having the product knowledge, passion and people skills to let the product sell itself.
  • Based on what works, you’ll experiment with, measure and document strategies that help us increase sales effectiveness. You’ll be a critical part of helping us enhance our sales playbook.
  • You’ll be proactively reporting on learnings and valuable feedback to the product team so that we can improve the product and prioritize the right projects.

About you

  • You have 2+ years of successful selling to SMBs, and have experience working on deals similar in size and volume to the ones you’d be working on at Help Scout.
  • You are in sales because you love helping people win. It energizes you to work alongside people to improve their business.
  • You are naturally curious and have a history of learning new things quickly. This is especially important in a remote company like Help Scout, as you won’t always have people nearby that you can talk to and learn from.
  • You excel at managing yourself like a successful business -- highly organized, setting and achieving goals with regularity, creating a great customer experience, and making your teammates better.
  • You have experience tracking all of your sales activity and reports with Salesforce.
  • As the primary point of contact and a trusted advisor, you’re happy to wear several hats: sales, support, customer success. Over the course of a customer’s first year, you may be point person on any one of them, mobilizing your teammates for support.
  • Above all, you’re an entrepreneur and are excited by the prospect of building your business and hitting your quarterly and annual goals.


  • Competitive Salary - We pay at or above market salary in most cases and evaluate a lot of research to make sure everyone is paid well. The formula we use to calculate all salaries is public to employees and is improved upon regularly.
  • Health and dental insurance - We cover you and your family's health/dental insurance 100%. If you are based in the US, we'll cover you on our Aetna policy. If you're based outside the US, we offer a healthcare stipend.
  • Long-term/Short-term Disability Insurance & Life Insurance - We cover 100% of the premiums for LT/ST Disability insurance and base Life Insurance. You also have the option to purchase supplementary life insurance through our provider. (currently US only)
  • Flexible vacation - Take time off when you need it, we trust you.
  • Paid parental leave, including adoption and foster care - 12 weeks for primary caretaker and 4 weeks for secondary caretaker.
  • 401k with 1% match - via Betterment for Business (currently US only)
  • Personal Development stipend - Up to $1,800 per year to improve your craft
  • Great tools - Each employee will be provided with a Mac laptop and 27'' display (or equivalent equipment of choice).
  • Home Office Stipend - You'll also receive $1,000 to spend on outfitting your home office, as well as up to $350 a month to rent a co-working space if you like.
  • Company Retreats - Twice a year, we get together to meet and work in person, covered by Help Scout.
  • Complete transparency - Everyone has full access to business metrics and financial information about the company.

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Apply for this position

Please submit an application on our website (link above). We can't wait to hear from you :)