PerkSpot is searching for an Account Executive to join our Client Sales team! At PerkSpot, our mission goes beyond discounts—it’s about empowering employees everywhere to make smarter spending decisions so they can do more of what they love. We believe every dollar saved can become a stepping stone to a brighter future, whether that’s a special family vacation, a first home, or simply extra peace of mind.
As an Account Executive, you’ll work to source and sign on new employer clients, as well as engage and convert marketing-driven inbound leads. Through research, sourcing, and building relationships, you’ll manage the sales process and eventually close deals for your assigned territory. Your work will serve to grow the PerkSpot community, ultimately providing exclusive perks and deals to a growing number of members throughout the country.
This position is required to be in the office 3 days a week on Tuesday, Wednesday, and Thursday. Our office is located in the Merchandise Mart in downtown Chicago, IL.
What you’ll accomplish:
Manage and organize your assigned geography of 250 – 500 Account prospects (Accounts, industry concentration, ICP fit, whitespace, competitors) to prioritize high-value accounts and execute targeted, multi-channel outreach that converts the territory into qualified pipeline.
Identify and target outbound activity to potential clients, creating a base of interest within accounts in your territory with the goal of influencing an evaluation of PerkSpot for their staff and converting them into clients.
Own/Manage the full acquisition sales cycle execution and lead discovery, demo, proposal calls with prospects.
Meet or exceed relevant KPIs (Pipeline Generated/Total Eligible Users Closed)
Follow PerkSpot’s defined sales processes for qualifying leads, through to contract signing and onboarding/launch
Deliver proposals and contracts; oversee negotiations, including contract redlines
Work with Sales Onboarding and Client Success teams on pre-closing calls with key prospect stakeholders
Work with team leadership to optimize PerkSpot’s sales process for the better
Attend regular team and staff meetings to go over company goals, success benchmarks, and sales strategies
What we’re looking for:
3 – 5 years of experience in a full-cycle sales role, ideally within the B2B space
Experience in the enterprise broker, insurance or healthcare industry is a big plus.
Proven knowledge in sales; must be well-versed in prospecting, selling, and negotiating
Past success meeting or exceeding monthly and quarterly KPIs
Experience using Salesforce/ZoomInfo preferred
Strong communication skills, with a self-disciplined attitude
Ability to multitask and manage your own deadlines
Curious, positive, and organized mindset
Commitment to collaboration and teamwork - when one of us succeeds, we all do!
Positive attitude and a thoughtful approach to business development and contract negotiation
Proven understanding of PerkSpot’s values as a whole and a willingness to work hard/take ownership to achieve overall company goals
Desire to learn and grow - if you’re looking to expand your enterprise sales experience, this is your chance!
About PerkSpot:
At PerkSpot, we believe that life is about getting the most out of every dollar, every moment, and every opportunity. We don’t just see a discount; we see a doorway to craft a lifestyle that balances smart choices with meaningful experiences. We celebrate the relentless pursuit of value, the satisfaction of finding that perfect deal, and the sense of confidence that comes from spending with intention. Every dollar saved is a step closer to the life you envision—one that’s rich in memories, secure in planning, and full of everyday wins that bring joy and fulfillment.
Our journey began in Chicago back in 2006 with a vision of helping employees stretch their paychecks without sacrificing what they love. What began as a small company with a big vision has evolved into a discount shopping solution…