Account Executive (Full Cycle)

Chicago, Illinois | In person

AviaryAI builds AI voice and messaging agents for credit unions and community banks.

Our agents handle real conversations with members across voice and SMS, supporting workflows like new member onboarding, card activation, dormancy reactivation, collections, loan follow up, fraud outreach, and other high value member interactions.

For us, AI communication is not a feature inside a larger product. It is the product. We are focused on getting AI powered conversations right in a highly regulated industry where reliability, compliance, and trust matter.

We are hiring two Account Executives to help build the next stage of our sales organization. Both will report directly to our CEO and will join early enough to have a meaningful impact on how we sell, who we sell to, and how we build a repeatable sales motion.

Come join us if you want to sell a product that is still early, work directly with the founder, and help build the sales playbook instead of inheriting one.

As an Account Executive at AviaryAI, you will own the full sales cycle from first outreach through signed contract.

There are no SDRs handing you meetings. You will build your own pipeline through outbound prospecting, industry conferences, referrals, and our existing network of financial institutions.

You will run discovery, demos, business cases, pricing conversations, security reviews, vendor diligence, legal negotiations, and contracting.

Our deals typically involve multiple stakeholders and take roughly four to five months to close. Buyers may include operations leaders, contact center executives, lending executives, IT, information security, compliance, finance, and executive leadership.

You will carry your own quota and work closely with the CEO, product, engineering, and client success teams to turn what you hear in the market into better messaging, positioning, pricing, and product decisions.

• Build and manage your own pipeline through outbound prospecting, conferences, referrals, and existing customer relationships

• Own the full sales cycle from initial outreach through discovery, demo, business case, vendor diligence, legal, and signature

• Sell to senior operators and executives across credit unions and community banks

• Navigate complex buying processes involving information security, compliance, procurement, legal, executive leadership, and occasionally boards

• Run multiple opportunities in parallel across four to five month sales cycles

• Attend key industry conferences and turn those events into qualified pipeline, not just badge scans

• Develop strong business cases around operational efficiency, member engagement, revenue generation, and AI adoption

• Partner closely with product and engineering to surface recurring buyer objections, competitive intelligence, and product gaps

• Help determine which messaging, outbound sequences, qualification criteria, and sales motions become the Aviary playbook

• Hit and exceed your individual sales quota

• A documented track record of sales performance. You should be able to walk us through your quota, attainment, rankings, and the deals you personally closed

• Recent experience carrying a quota in a full cycle closing role

• Experience selling at an early stage technology company where the company brand did not generate the pipeline for you

• Strong outbound experience. You know how to create opportunities instead of waiting for them to arrive

• Experience closing roughly $50K to $150K ACV deals with multiple stakeholders and a real procurement process

• Experience navigating longer, more complex sales cycles rather than primarily transactional or high velocity sales

• Strong discovery, demo, negotiation, and objection handling skills

• Comfort selling a product and category that are still evolving

• Willingness to work from our Chicago office five days per week and travel for conferences and customer meetings

• Experience selling enterprise software into regulated industries

• Experience selling AI, communications, contact center, workflow, fintech, or other infrastructure products

• Experience competing against larger or more established vendors

• Experience selling directly to VP and C level buyers

• Experience building an outbound motion from scratch

Financial services experience is helpful, but it is not required. We would rather hire someone who has repeatedly figured out how to sell difficult products than someone whose primary advantage is knowing the industry.

A recognizable company on your resume is also not a requirement. We care much more about what you personally sold, the pipeline you created, and the results you produced.

You will spend most of your time selling to credit unions and community banks in the United States.

Typical buyers and champions include:

• VP and SVP of Operations

• Contact Center leaders

• Chief Lending Officers

• Collections leaders

• Digital and Member Experience executives

• CIOs and technology leaders

• COOs and CEOs

The strongest opportunities usually involve a specific operational workflow where the financial institution wants to reach more members, improve outcomes, reduce manual work, or introduce AI without sacrificing compliance or member experience.

Our sales process is consultative. You need to understand how the workflow operates today, where the friction exists, what the economics look like, and why changing it matters.

$180,000 to $220,000 OTE with a 50/50 split between base salary and variable compensation.

Where you land within the range depends on your experience and documented track record.

Your first 60 days are paid at full OTE regardless of what closes.

This is not a draw and it is not recoverable.

Selling into a highly regulated market takes time to learn, and we want your first two months focused on understanding the product, customers, workflows, and market rather than worrying about whether a deal happens to close during your ramp.