Mid-Market Account Executive
hirewellSpringfield (IL)
Mid-Market Account Executive
Posted today
hirewellSpringfield (IL)
Sales Representatives of Services, Except Advertising, Insurance, Financial Services, and TravelComputer Systems Design Services
SENIORITY
Senior
About the role
THIS IS POSTED ON BEHALF OF A HIREWELL CLIENT, NOT A JOB AT HIREWELL ITSELF We are a high-growth, venture-backed enterprise AI company transforming how organizations manage employee benefits, optimize healthcare expenditures, and support their workforce. Backed by leading enterprise technology and digital health veterans, our proprietary intelligence platform unifies complex plan designs and claims data into an actionable, automated ecosystem trusted by industry leaders and Fortune 500 brands. By pairing real-time employee guidance with analyst-grade visibility for HR and finance leaders, we solve operating costs while delivering ROI.The ideal candidate will possess strong consultative sales, interpersonal, and deal-execution skills. They should be comfortable managing full-cycle sales processes in a fast-paced environment and be adept at pipeline planning and territory management to consistently meet and exceed assigned quotas.
Responsibilities:
Own a defined mid-market territory end-to-end, prospecting, advancing, and closing accounts from initial evaluation to contract execution.
Navigate multi-stakeholder evaluations, building relationships with HR, Total Rewards, Finance, and People leaders.
Co-sell and collaborate with channel partners, benefits brokers, and consultants to accelerate pipeline conversion.
Deliver compelling, consultative product demonstrations and manage prospective evaluations alongside technical partners.
Maintain clean pipeline management, forecast accuracy, and disciplined deal qualification using structured methodologies such as MEDDPICC.Integrate modern AI tools and automated workflows into daily research, outreach, and sales preparation.
Qualifications3–7+ years of quota-carrying B2B SaaS sales experience, with a track record closing mid-market solutions.
Proven history of meeting or exceeding revenue targets in multi-stakeholder commercial environments.
Strong written, verbal, and executive-level presentation skills.
Experience or comfort selling new-category software and educating prospective buyers on emerging platforms.
Familiarity with co-selling alongside channel partners, brokers, or consulting networks is a plus.
Exposure to HR tech, healthcare, benefits, or modern AI-native platforms is preferred.
Before you apply
Applying takes about a minute. These four things decide how fast it moves after that.
Your profile is current
It's what we read first. Occupations, seniority and locations matter more than a long history.
Two examples you can talk through
Not a portfolio — just two pieces of work where you can explain the decisions and what you'd change.
A number in mind
What you're on now and what would make you move. We negotiate better when we know both.
Your notice period
Employers plan around it, and it's the question that stalls offers most often.
Once you apply, someone reads it and calls you before anything reaches the employer — usually within two working days.