5-7 years of sales experience with a proven track record of exceeding quotas
Experience in coaching or mentoring sales teams
Strong consultative selling skills, particularly with business owners and HR leaders
Ability to create and document training materials and playbooks
Experience in fast-paced, startup environments with adaptability to change
Responsibilities
Carry a full book of business against a quota for the first 1-2 quarters
Manage the entire sales process from discovery to ongoing service
Collaborate with AI agents to improve operational efficiency
Document learnings to create a ramp playbook for new hires
Hire and train new Account Executives in batches
Monitor and optimize ramp time for new hires
Partner with leadership on organizational design and career path development
Benefits
Opportunity to shape the future of a growing team
Direct impact on the sales process and team performance
Collaborative environment with a focus on innovation
Access to advanced AI tools to streamline operations
Potential for rapid career advancement in a dynamic setting
Full Job Description
Why this role exists
Small group health insurance is the bedrock of our business, and it's about to get much bigger.
The motion works. A new advisor at a traditional brokerage takes three years to build a $400K book. Our first advisor built a seven-figure book in under a year. If that holds, every advisor we hire compounds faster than traditional brokerages ever could. The question for 2027 is how we can turn it into a machine.
That means hiring, onboarding, and mentoring AEs in batches through 2027. So we're hiring the person who will lead them.
But we're hiring them to sell first. You cannot teach this motion without having run it. Our advisors close and serve - they run the sales process, then own the client relationship through enrollment and renewal, with AI agents doing the work that used to take a team of ten. So you'll carry your own book through your first 1-2 quarters, then build and scale the team behind you.
What you'll own Your first 1-2 quarters - you're a player
Carry a full book against a real quota. Inbound demand is handed to you; you're a closer, not a hunter.
Run the complete motion end to end: discovery, quoting through our GA and carrier network, plan design, proposal, close, enrollment, and ongoing service.
Work alongside our AI agents and tell us where they break. Every advisor here is also the quality bar on the system doing most of the work, and your feedback goes straight to the product team.
Write down what you're learning as you learn it. The ramp playbook for the January cohort is the artifact you build while you sell.
From Q1 2027 onward - you're a coach
Hire and ramp the small group AE cohorts, and help us size each batch off how the last one performed.
Own ramp time as a number. How fast a new AE reaches first close, and then $500K, is your metric.
Run the coaching cadence - pipeline reviews, call reviews, deal strategy - the weekly ritual that makes a team better rather than just measured.
Be a thought partner to the CEO and our business operations lead on org design: territories, commission structures, cohort sizing, and what a career path looks like for a Corridor advisor. These questions are genuinely unanswered and you'll have real authorship over them.
What we're looking for
A great player coach. You've carried a number and beaten it, and you've managed or mentored people who then beat theirs.
Strategic, consultative selling. Our buyers are owners and HR leaders making a decision that affects every employee they have. The motion looks like a consultative closing approach.
Strong pattern-matches. A sales leader who built the enterprise motion on top of a product-led one; a consultant with managerial experience and some carried-quota exposure who wants to own a number rather than advise on one; someone from hospitality or high-touch client services who learned the trade by apprenticeship and knows what going beyond what was asked actually costs.
You teach by writing things down. You can build artifacts: playbooks, call libraries, objection docs, scorecards.
You move at startup speed and change direction without friction. Priorities here shift monthly. People who need a stable mandate to be effective struggle at this stage, and we'd rather be honest about that up front.
