Mid-Market Account Executive

Run Discovery That Earns the Demo:

Get into how the agency actually operates — AMS setup, document handling, carrier mix, who touches a policy change and how many times. Surface the cost of the current process before you show anything.

Run Pilots to Conversion:

Lock success criteria, scope, pricing, and the conversion path in week zero. Run the weekly check-ins. Track ROI against what the customer said mattered, and drive the conversion decision on schedule.

Multi-Thread Every Deal:

Operations, IT, and the principal or CFO each have a different reason to say yes and a different reason to stall. Build relationships with all of them to drive deals to completion.

Close and Hand Off Clean:

Negotiate commercial terms, get to signature, and give Customer Success everything they need to onboard well. A deal that churns in 60 days isn't a win.

Sharpen the Motion:

Test messaging, verticals, and sequencing. Document what works. The MM playbook gets better because you're running it.

🧠 What Makes You a Great Fit

4+ years of full-cycle AE experience

in SMB or mid-market SaaS, with quota attainment you can recite by year. Numbers matter here - know yours.

Self-sourcing is second nature.

You've built a book without a mature marketing engine behind you, and your prospecting is a system you can describe rather than a burst of activity when the quarter looks thin.

You carry volume without dropping rigor.

Managing 20+ live opportunities doesn't turn your discovery into a checklist or your CRM into a mess.

Consultative in discovery.

You ask open questions, listen more than you pitch, and connect every part of the demo to something the prospect actually told you.

ROI-driven.

You lead with business value, quantify the cost of doing nothing, and build the math that makes the decision straightforward for a budget owner.

Organized operator.

You live in your CRM (HubSpot). Your pipeline is clean, your forecast holds up, and you know where every deal stands at all times.

Resilient.

You've had good months and bad ones. You diagnose your own slumps and pull yourself out before anyone has to manage you through it.

Grit > pedigree.

You may not have sold insurance or worked at a name-brand company. You're hungry, and you deliver.

💫 Bonus Points

Experience selling to insurance agencies, or familiarity with agency management systems — Applied Epic, AMS360, ImageRight.

You've sold API, integration, or infrastructure products and can explain technical value to a non-technical buyer.

Pilot-led or POC-led selling experience — you know how to keep a trial from becoming a free consulting engagement.

Startup experience. You've built before and ambiguity doesn't slow you down.

Military or high-level athletics background. We believe that the discipline and team-first mentality translate directly to our culture.

🧩 What Success Looks Like

In 30 days:

You know the product cold, you've shadowed every deal stage, and your target account list is built. First contact is already made on your top accounts.

In 90 days:

You have a live pipeline of qualified mid-market opportunities, you've closed your first deals, and the Head of Sales trusts your forecast.

In 6 months:

You're at or ahead of pace on quota, running pilots that convert, and your notes on what works have made it into the MM playbook. At least one customer will take a reference call.

This is a career-making role for a high-output closer.

If you build your own pipeline, run deals with discipline, and close at a rate that makes other AEs ask how you do it, this is your next move. You'll work directly with the CEO and Head of Sales, close real revenue, and help modernize one of the most broken industries in the country.

Let's go close.