<img height="1" width="1" style="display:none;" alt="" src="https://dc.ads.linkedin.com/collect/?pid=557769&amp;fmt=gif https://dc.ads.linkedin.com/collect/?pid=557769&amp;fmt=gif ">

Mid Market/Enterprise Account Executive

Sales, Boston, Full Time, $90,000 - $130,000 / year + OTE

Job Description

Since 2006, we’ve helped the most innovative companies and HR leaders transform the employee experience to attract and retain top talent through employee benefits, strategic reward and recognition, wellbeing, and much more.
Across the globe, over 600 of us work together to make the world a better place to work. As an ambitious, fast-growth, private-equity backed, HR Tech SaaS company we’re flexible, inclusive, and keen to meet talented individuals who are passionate about positively impacting the future of work.

Your role in our Mission
Our mission is to make the world a better place to work and to achieve this mission, you will partner with HR leaders in mid-market enterprise organizations all over North America to improve their employees’ everyday experience and engagement. You will build new partnerships to help us drive this mission, play your part in an elite sales team and achieve annual revenue targets.

Key Responsibilities

  • Delivering a consultative sales approach with a focus on adding insights aligned to solutions to key business challenges, identified through a detailed discovery process
  • Partnering with Sales Researchers and Representatives to develop a targeted account strategy for your territory and increase lead generation, qualification, and conversion
  • Delivering quality and consistency in all sales calls, online and face-to-face sales presentations
  • Delivering insights and engaging prospects into a business conversation about solutions to their unique business challenges
  • Storytelling via live platform demonstrations and client case studies
  • Making recommendations on alternative employee engagement solutions to prospects
  • Developing tailored solution-focused documents including proposals, executive summaries, RFP/RFI’s, and specific prospects demonstration sites, aligned to business challenges
  • Collaborating with our Client Success team to demonstrate existing client case studies and implementing strategies to bring the voice of the customer to life throughout the sales process
  • Developing effective win strategies to ensure the momentum of each opportunity in your pipeline
  • Managing your sales funnel with the implementation of strategies to address key friction points and improve sales conversion rates
  • Negotiating commercial and contract terms in conjunction with your VP of Sales
  • Being an ambassador for Reward Gateway including representing Reward Gateway at HR events
  • Accurately forecasting the sales pipeline in line with Reward Gateway global Salesforce forecasting
  • Contributing to a strong USA and Global Sales culture with a mission to be an extraordinary sales team, aligned to RG’s mission and values


  • Proven sales success within consultative B2B sales with a focus on the Corporate mid-market or Enterprise space.
  • Experience selling HR Technology to HR executives is preferred
  • Experience in a consultative sales cycle, including influencing and negotiating with C-suite executives
  • An experienced storyteller with strong presentation and written skills and a preference to showcase solutions via the voice of the customer and client case studies
  • A proven innovator with a strong bias for action and the ability quickly adapt to change in a fast-paced environment
  • Excellent collaboration skills, with experience working within a team and with cross-functional teams to support and leverage growth
  • Demonstrate success ‘owning it’, developing tools and strategies to address sales friction points, and increase deal velocity and momentum in longer sales cycles (4+ months)

The Interview Process

  • Telephone call with a member of the Talent Acquisition Team 
  • 1st Round interview with the North America VP of Sales and a member of the sales team
  • 2nd Round Pitch Assessment style interview with the North America VP of Sales and a member of the sales team
Be comfortable. Be you.
At Reward Gateway, we want our employees to feel comfortable bringing their passion, creativity, and individuality to work. We value all cultures, backgrounds, and experiences, as we truly believe that diversity drives innovation. Express yourself, join our community and help us Make the World a Better Place to Work.
We hire BETTER.  
From perks to people, our BETTER approach to hiring earns us more trust, happier people, and more world-class talent that help us to make the world a better place to work. Find out more about Reward Gateway's approach to benefits, equality, talent, technology, empathy, and what you’ll get in return for joining our Mission at rg.co/lifeatrg.
Apply Now


8th Floor
141 Tremont Street

Visit our Boston office

Other jobs you may be interested in

register for job alerts

Can't find what you're looking for?

If you can't see a job that interests you, why not register for our job alerts by email service? And we'll email you when a job that matches what you're looking for is uploaded onto the site.

Join our talent community