Remote
SaaS
jobscollider
About this role
About Bennie:
Bennie (www.bennie.com) is an employee
benefits services and technology firm that helps companies create a healthier workplace. Bennie provides services and technology that are beyond what growing companies typically receive, yet exactly what they need.
Bennie has built the ultimate
benefits platform that connects disparate systems across the
benefits supply chain to deliver a complete experience for employees, employers, and partners. Bennie’s technology, benefit plans, and service model are designed to enable employers and their employees to experience best-in-class outcomes that reduce overall health plan costs.
Bennie’s team members use the platform and its data to supplement their market knowledge and bring innovative solutions to Bennie’s customers.
Bennie is headquartered in Stamford, CT, and is a remote-first company with employees across the U.S.
Core Values at Bennie
As an organization, we value our team members who are Optimistic, Accountable, Thoughtful, and Healthy. We believe these values, known as our O.A.T.H., are essential for our collective success. The ideal candidate for this role will embody these values by:
Maintaining a positive attitude throughout our journey of building our company. Being responsible for the quality of their work and for meeting their goals. Respecting our differences and looking out for one another. Believing in living complete lives that balance our work and personal time.
About the Role:
The Account Executive role will focus on finding and selling net new clients to our brokerage book of business in the East Coast region. You’ll manage the entire sales cycle, from prospecting to closing, leveraging the Bennie lead generation team, our business development partners, and internal and inbound prospects.
You will be responsible for building and fostering relationships with prospects, with our internal consulting team, and a variety of external partners that we work closely with.
Responsibilities inclu
Selling Motion
Prospecting
Hybrid
Mix of inbound leads and outbound prospecting
Buyer Persona
C-Suite
Selling to executive decision-makers
Territory
Greenfield
Build territory from scratch — net-new logos
Requirements at a Glance
Typical Day — Account Executive
Estimates based on role type and selling motion — actual may vary by company.
Role Signals
Green Flags
Location flexibility
SaaS — Interview Intel
Typical Sales Cycle
30–90 days (SMB) · 3–9 months (Mid-Market) · 6–18 months (Enterprise)
Common Buyer Objections
- "We're locked into a contract with [competitor]"
- "We built something in-house already"
- "We don't have budget until next quarter"
- "Our team won't adopt another tool"
Key Industry Metrics
Hot Topics to Reference
- • AI-native product disruption
- • PLG vs sales-led motion debate
- • Vertical SaaS consolidation
- • Usage-based pricing models
Use these insights to speak the buyer's language in interviews.
Tags
Walk me through your discovery process.
Template questionHow do you handle a prospect who goes silent mid-deal?
Template questionTell me about your largest closed deal and the sales cycle.
Template questionHow do you build business cases for stakeholders?
Template questionDescribe a deal you lost and what you learned.
Template questionThis Account Executive position at Bennie involves managing the full sales cycle from prospecting through close.
SaaS sales roles typically involve consultative selling with longer deal cycles.
Remote positions in sales offer flexibility but require strong self-discipline and proactive communication with distributed teams.
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