Account Executive (Full Cycle)

Account Executive

Chicago, Illinois | In person | $180,000 to $220,000 OTE

AviaryAI builds AI voice and SMS agents for credit unions and community banks. Our agents call members, and the same generative AI carries the conversation over text, so someone who does not pick up the phone can finish the same task by SMS. We handle onboarding, card activation, dormancy reactivation, early collections, and loan campaigns.

We are hiring two Account Executives at the same time, both reporting directly to our CEO. You would be joining the sales team early enough to shape how we sell, with a counterpart hired alongside you to work it out with.

What you will do

Build your own pipeline. We do not have SDRs. You will run your own outbound, work the conferences we sponsor, and turn our client base into introductions.

Own the full cycle. Discovery, demo, business case, security questionnaire, vendor diligence, legal, signature. We sell into a highly regulated industry, so a deal moves through information security, compliance, and often a committee or a board. Expect a four to five month cycle, with several running in parallel.

Sell to senior operators. Your buyers are VPs of operations, contact center leaders, chief lending officers, and the executives above them.

Work the circuit. This market gathers at a handful of industry conferences a year. You will be at them, and you will be the reason those weeks produce pipeline instead of a badge scan list.

Build the playbook with us. You, the other AE, and the CEO will work out together what messaging lands, what sequences work, and what a repeatable cycle looks like here. What you hear from buyers will move our product, our positioning, and our pricing.

What we are looking for

A documented track record. Sales is one of the few roles where performance is a matter of record. Come ready to walk through your quota, your attainment, and where you ranked.

Early sales experience at a technology startup. You have sold before the brand did any of the work for you. This is the closest thing we have to a hard requirement.

Deals in the $50K to $150K range. Multiple stakeholders, a security review, a real procurement process. High volume transactional closing is a different sport.

Recent success in a full cycle closing role. You have been carrying a number and hitting it.

Chicago, in our office, four days a week. We are small enough that the fastest way to get good at selling this is to sit next to the people building it and the person running the company. Some travel for conferences and customer meetings.

Three things you do not need

You do not need a financial services background. A sharp person learns this market in a few weeks, and requiring it would rule out most of the strong salespeople in the country. If you have it, good. If you do not, it is not a mark against you.

You do not need a recognizable logo on your resume. We want to hear about the pipeline you created and the deals you won, not the brand that opened the door. Selling well as the number two or number three option in a hard market tells us more than a great brand doing half the work for you.

You do not need a network of banking buyers. We would rather you not build your pitch around one anyway. Relationships transfer less reliably than people expect. The reps who do well here are the ones who can open a cold door.

Compensation and benefits

$180,000 to $220,000 OTE , split 50/50 between base salary and variable. Where you land in the band depends on your experience and track record.

Your first 60 days are paid at full OTE regardless of what closes. Not a draw, not recoverable. Ramping in a regulated market takes time, and your first two months should go toward learning this market rather than watching a paycheck.