Benefits and HR technology are what we do, so you'll find the workplace benefits you're looking for in a career at PeopleStrategy. Your first day as a fully remote employee gives you 100% vesting in our company-matched retirement plan, a choice of medical plan options to fit your needs, company-provided short- and long-term disability, health care concierge services, and a growing personal and professional training program to support you as a fully remote employee and maximize work/life balance.

And you'll be helping others as part of a team dedicated to building the best hire-to-retire human resources technology platform to attract, manage, and retain great people and offer benefits that improve their lives.

Enjoy top-tier benefits as a part of the solution that allows businesses to focus more on what matters most: their people.


As PeopleStrategy continues to grow, we need a hungry Regional Sales Executive who is frustrated in a small territory. With an emerging new technology product, we are striving to expand into larger territories and offer our all-in-one platform for HR, Benefits, and Payroll.


We are looking for a Regional Sales Executive (RSE) who is a self-starter, identifies potential clients through prospecting activities, consults with the potential clients to identify which PeopleStrategy products and services will solve their business challenges, and sells those solutions to new clients within assigned territories. He or she is responsible for self-generating leads through prospecting, telemarketing, sales database management (CRM), and networking.

Regional Sales Executive responsibilities include but are not limited to the following:

  • Identify potential clients in the 100+ employee band through prospecting and referrals, while leveraging tools and technology.
  • Consult with potential clients to determine solutions that solve business challenges and accommodate business needs.
  • Record all sales activity and results in HubSpot and SFDC in a timely manner, preferably daily.
  • Prospecting for new clients and new referral sources utilizing the telephone, direct mail, seminars, or other local events.
  • Represent PeopleStrategy to customers, prospects, and the public by spending time in the field, at trade shows, demonstrations, and seminars.
  • Prepare and present proposals and provide appropriate follow-up throughout the sales process.
  • Work cross-functionally with internal departments to ensure the client has a smooth transition into PeopleStrategy.
  • Respond to inbound sales leads of companies with 100 employees or more as assigned.
  • Maintain knowledge of PeopleStrategy products and services.
  • Manage an outbound selling process to generate top-of-funnel activity.
  • Other duties as assigned.


The Sales Operations team is entrusted with a diverse range of responsibilities, which includes identifying potential customers, comprehending their needs, and presenting PeopleStrategy's products and services to fulfill those needs. Acting as a liaison between PeopleStrategy, its prospects, and partners, this team collaborates with internal departments, such as marketing and client experience, to guarantee that our products and services align with the market and customer requirements. Furthermore, the team collects feedback from customers and analyzes market trends, which it shares with the Product team to enhance future offerings.


A Regional Sales Executive will possess the following education and qualifications or the equivalent:

  • 3+ years' experience in account management, sales, or quota-carrying customer success, preferably in HCM, technology, or software.
  • Track record of consistently meeting and exceeding quota via new product sales.
  • Ability to run a sales discovery, demo meeting, and run the sales process.
  • Ability to manage multiple priorities and sales opportunities at differing stages.
  • Ability and willingness to travel to prospective client sites within assigned territory.
  • Ability to represent PeopleStrategy and its product at trade events.
  • Strong presentation, organization, and time management skills.
  • Health and Life Insurance license, or willingness to acquire license within 90 days of employment.
  • Experience with Salesforce, HubSpot, ZoomInfo, and Sales Navigator.

Learn more at

The above statements are intended to describe the general nature and level of the work performed by the person assigned to this work. This is not an exhaustive list of all duties and responsibilities. PeopleStrategy management reserves the right to amend and change responsibilities to meet business and organizational needs as necessary.

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