Director, Mid-Market Sales Representative

Webster Bank

Director of Mid-Market Sales at HSA Bank using consultative sales to engage employer accounts. Selling various health-based accounts while managing the sales process for medium-sized employers.

Posted 4/17/2026full-timeRemote • California • 🇺🇸 United StatesLead💰 $130,000 - $140,000 per yearWebsite

About the role

Key responsibilities & impact

Employs a consultative based sales approach to identify, pursue, and achieve sales goals and quota of new employer accounts in the assigned sales territory
Leverage the internal assets of HSA Bank to sell health-based accounts including Health Savings Accounts (HSAs), Flexible Spending Accounts (FSAs), Health Reimbursement Arrangements (HRAs) and Commuter Benefits (Mass Transit & Parking) and COBRA to employers with 1,500 to 9,999 employees
Manage the sales process while selling to Employers directly, Insurance Consultants, Broker, Carriers, Investment Advisors, TPAs, as well as key influencers within each account

Requirements

What you’ll need

H.S. Diploma or General Education Degree (GED) required
Candidates with advanced degrees (Associates, Bachelor's, and/or Master's) preferred
8-9 years experience in cultivating relationships with existing accounts at the highest strategic level for additional sales required
Knowledge of Health Savings Accounts, Consumer Driven Health Care, Group/Individual Health Insurance sales, Managed Healthcare and the Agent/Broker distribution system
Exceptional verbal and written skills
Consistent track record in meeting and exceeding sales quotas
Proven experience in proactively identifying and closing new account opportunities in an assigned territory
Ability to manage sales through forecasting, account resource allocation, account strategy and ecosystem partnerships

Benefits

Comp & perks

🌐 Worldwide ❌ Jobs You've Hidden ⭐️ Saved Jobs ✅ Applied Jobs ✉️ Email Alerts 👤 Account Webster Bank Website LinkedIn All Job Openings 1001 - 5000 employees Founded 1935 🏦 Banking 💸 Finance 💳 Fintech Banking
Finance
Fintech Webster Bank is a financial services company that offers a wide range of banking solutions for individuals, small business owners, and commercial entities. It provides personal and business checking and savings accounts, loans, mortgages, and investment services, as well as wealth management and retirement planning. Webster Bank emphasizes digital convenience through mobile and online banking platforms while also providing personalized assistance from dedicated relationship managers. The bank is committed to serving diverse industries and communities, with specialized offerings in areas like healthcare, manufacturing, and government banking. Webster Bank is dedicated to helping clients achieve their financial goals through tailored solutions and expert guidance, ensuring security and trust are maintained at all times. Director, Mid-Market Sales Representative Job not on LinkedIn 🔥 2 minutes ago 🏄 California – Remote 💵 $130k - $140k / year ⏰ Full Time 🔴 Lead 🧑‍💼 Account Executive 🦅 H1B Visa Sponsor Apply Now Find Hiring Managers Customize resume for this job Report problem ☆ Save ☑️ Mark as applied ❌ Hide 📋 Description
Employs a consultative based sales approach to identify, pursue, and achieve sales goals and quota of new employer accounts in the assigned sales territory
Leverage the internal assets of HSA Bank to sell health-based accounts including Health Savings Accounts (HSAs), Flexible Spending Accounts (FSAs), Health Reimbursement Arrangements (HRAs) and Commuter Benefits (Mass Transit & Parking) and COBRA to employers with 1,500 to 9,999 employees
Manage the sales process while selling to Employers directly, Insurance Consultants, Broker, Carriers, Investment Advisors, TPAs, as well as key influencers within each account 🎯 Requirements
H.S. Diploma or General Education Degree (GED) required
Candidates with advanced degrees (Associates, Bachelor's, and/or Master's) preferred
8-9 years experience in cultivating relationships with existing accounts at the highest strategic level for additional sales required
Knowledge of Health Savings Accounts, Consumer Driven Health Care, Group/Individual Health Insurance sales, Managed Healthcare and the Agent/Broker distribution system
Exceptional verbal and written skills
Consistent track record in meeting and exceeding sales quotas
Proven experience in proactively identifying and closing new account opportunities in an assigned territory
Ability to manage sales through forecasting, account resource allocation, account strategy and ecosystem partnerships Apply Now 📊 Check your resume score for this job Improve your chances of getting an interview by checking your resume score before you apply. Check Resume Score Similar Jobs AI Sales Executive 🔥 3 hours ago Thomson Reuters 10,000+ employees 💸 Finance 📱 Media ☁️ SaaS Website LinkedIn All Job Openings AI Sales Executive responsible for market growth and strategy at Thomson Reuters legal products. Focusing on customer partnerships, sales enablement, and product feedback to drive success. 🇺🇸 United States – Remote 💵 $199.5k - $370.5k / year ⏰ Full Time 🟠 Senior 🔴 Lead 🧑‍💼 Account Executive 🦅 H1B Visa Sponsor Account Executive – Enterprise 🔥 5 hours ago DevRev 51 - 200 🤝 B2B ☁️ SaaS Website LinkedIn All Job Openings Account Executive responsible for scaling business in the US market for AI-driven SaaS company. Managing customer relationships from concept to implementation and driving paid conversions. 🇺🇸 United States – Remote 💰 Seed Round on 2022-09 ⏰ Full Time 🟠 Senior 🔴 Lead 🧑‍💼 Account Executive 🦅 H1B Visa Sponsor Enterprise Account Executive 🔥 7 hours ago Abnormal Security 501 - 1000 Website LinkedIn All Job Openings Enterprise Account Executive at Abnormal selling security solutions in the Mid Atlantic territory. Managing enterprise accounts and prospecting for new business opportunities. 🇺🇸 United States – Remote 💵 $144.5k - $170k / year ⏰ Full Time 🟠 Senior 🔴 Lead 🧑‍💼 Account Executive 🦅 H1B Visa Sponsor Account Director 🔥 7 hours ago SBM - Website LinkedIn All Job Openings Account Director responsible for customer retention and growth strategies at SBM Management Services. Collaborating with teams to align with corporate plans and market trends in California. 🇺🇸 United States – Remote 💵 $140k - $170k / year ⏰ Full Time 🔴 Lead 🧑‍💼 Account Executive 🦅 H1B Visa Sponsor Account Executive 🔥 7 hours ago Brown & Brown Insurance 10,000+ employees 💸 Finance Website LinkedIn All Job Openings Account Executive supporting Senior Broker on large accounts and leading strategy for smaller clients. Overseeing client service and coordinating junior members in a dynamic insurance brokerage environment. 🇺🇸 United States – Remote ⏰ Full Time 🟠 Senior 🔴 Lead 🧑‍💼 Account Executive View More Account Executive Jobs 🌐 Worldwide Built by Lior Neu-ner. I'd love to hear your feedback — Get in touch via DM or support@remoterocketship.com Search Search Jobs by country Search jobs by city Search jobs by job title Search entry-level jobs Search junior-level jobs Search senior-level jobs Search jobs by tech stack Search jobs by contract type Search remote internships Search remote part-time jobs Remote jobs Anywhere in the World Companies Hiring Anywhere in the World Companies Hiring Sales People Anywhere in the World Companies Hiring Software Engineers Anywhere in the World Resources Advice Tips for finding remote jobs Interview questions and answers Resume examples Cover letter examples Post a job Affiliates Privacy policy Terms of service Job board SEO course AI Apply Copilot OpenClaw job finder Jobs by Country Remote jobs anywhere in the world (Worldwide remote jobs) Remote jobs United States Remote jobs Australia Remote jobs Brazil Remote jobs Canada Remote jobs France Remote jobs Ireland Remote jobs Germany Remote jobs Netherlands Remote jobs Spain Remote jobs UK Popular Jobs Remote data analyst jobs Remote customer support jobs Remote executive assistant jobs Remote marketing jobs Remote product designer jobs Remote product manager jobs Remote project manager jobs Remote recruiter jobs Remote sales jobs Remote software engineer jobs Jobs by Type Remote full-time jobs Remote part-time jobs Remote contract jobs Remote internship jobs Remote entry-level jobs Remote jobs with no experience required Remote junior jobs (1-3 years of experience) Digital nomad jobs Remote jobs with no degree required Freelance remote jobs Temporary remote jobs Remote jobs hiring now Stay at home mom jobs

ATS Keywords

✓ Tailor your resume

Applicant Tracking System Keywords

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

Hard Skills & Tools

Health Savings AccountsFlexible Spending AccountsHealth Reimbursement ArrangementsCommuter BenefitsCOBRAGroup Health Insurance salesIndividual Health Insurance salesManaged HealthcareSales forecastingAccount resource allocation

Soft Skills

consultative sales approachrelationship cultivationverbal communicationwritten communicationstrategic account managementproactive identification of opportunitiesclosing salesmeeting sales quotasaccount strategyecosystem partnerships

Certifications

H.S. DiplomaGeneral Education Degree (GED)Associates degreeBachelor's degreeMaster's degree