Reward Gateway

Senior Sales Manager

Reward Gateway

full-time

Posted on:

Location Type: Hybrid

Location: Boston • Massachusetts • United States

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Salary

💰 $120,000 per year

Job Level

Senior

About the role

  • Own and carry an individual new-logo quota for Commuter Benefits (Transit, Parking, Mobility, and add-ons).
  • Manage the full sales cycle from first meeting through close, including discovery, solution positioning, pricing, and negotiations.
  • Execute both inbound and outbound sales motions. Ability to design, execute and continuously improve outbound prospecting strategies. This includes account targeting, messaging, activity standards and creating a scalable top-of-funnel engine that supports long term growth.
  • Partner closely with Marketing, Partnerships, Product, and Implementation to ensure a seamless buyer and customer experience.
  • Attend networking events and planned conferences to drive business development and achieve external networking alongside the Benefits SDR and our marketing team.
  • Directly manage and coach one (1) SDR responsible for outbound prospecting, meeting generation, and managing our inbound SMB clients.
  • Set clear expectations, activity targets, and quality standards for outbound efforts.
  • Conduct regular 1:1 coaching sessions, call reviews, and pipeline inspections.
  • Help the SDR develop strong discovery skills and business acumen specific to commuter benefits.
  • Collaborate on outbound strategy, account targeting, messaging, and sequencing (HubSpot).
  • Actively participate in hiring, onboarding, and ramping future SDR or Account Executive talent as the team grows.
  • Serve as a role model for consultative, value-driven selling aligned to our broader engagement and benefits portfolio.
  • Maintain accurate activity tracking, contact, account and opportunity records in Salesforce to ensure accurate forecast revenue and hygiene.
  • Support leadership with insights that inform forecasting, capacity planning, and growth initiatives.
  • Build and maintain a healthy pipeline aligned to required coverage ratios.

Requirements

  • At least 5+ years of experience in B2B sales experience, ideally with Commuter Benefits, pre-tax Benefits, SaaS, HR tech or employee benefits. Experience selling commuter benefits, payroll-adjacent products, or regulated benefits is strongly preferred.
  • 3+ years carrying a quota with consistent attainment in a closing role.
  • 2+ years of people management or player-coach experience, managing SDRs or junior sellers.
  • High levels of attention to detail with strong time management, organizational, and research skills.
  • Proven success selling complex, consultative solutions to mid-market and enterprise employers (200-10,000 employees).
  • Experience with Salesforce, HubSpot (or other cadence tool), Microsoft Suite, ZoomInfo and LinkedIn Sales Navigator preferred.
Benefits
  • Telephone interview with a member of the Talent Acquisition team.
  • 1st stage online interview with our US Sr. Director of New Business
  • 2nd stage online panel interview with our Director of Business Intelligence and VP Marketing.
  • Final stage in person interview with our US Managing Director
  • **Be comfortable. Be you.** At Reward Gateway, we want all of 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.

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard skills
B2B salesquota attainmentconsultative sellingoutbound prospectingpipeline managementdiscovery skillsbusiness acumenaccount targetingnegotiationssales cycle management
Soft skills
attention to detailtime managementorganizational skillscoachingcommunicationcollaborationleadershipnetworkingstrategic thinkingproblem-solving