Debtsy

Mid Market Account Executive

Debtsy$110K — $130K *
Finance & Insurance
Less than 5 years of experience
Job Overview by Ladders

Qualifications

  • 5-7 years of experience in enterprise sales or related roles.
  • Proven track record of managing complex multi-stakeholder deals.
  • Strong analytical skills with the ability to construct financial business cases.
  • Experience navigating procurement and compliance processes independently.
  • Ability to communicate effectively with various stakeholder levels.

Responsibilities

  • Run buying processes for named accounts, managing deals from outreach to close.
  • Build and empower champions within client organizations to advocate for January's solutions.
  • Develop business cases demonstrating financial impact and recovery uplift.
  • Proactively address procurement and legal hurdles throughout the sales process.
  • Prioritize and maintain engagement with high-potential leads and accounts.
  • Document insights from sales interactions to improve the GTM strategy.

Benefits

  • Collaborative company culture with a focus on transparency and candor.
  • Access to innovative AI tools that streamline processes and increase productivity.
  • Opportunity to work closely with leadership in a decentralized decision-making environment.
  • Flexible working arrangements, with in-office collaboration at least three days a week.
Full Job Description
About the Role

January's hit top growth metrics with a lean GTM org, proof the product and the motion work. We're hiring another AE to amplify it.

This isn't a role where you inherit a cookie-cutter playbook and execute it: we've codified what's worked, and we want you to make it better. We've automated the parts of this role that don't grow the business. You won't waste time on CRM updates or forecasting prep.

You'll report directly to the VP of Revenue, January's first employee. You'll own the full cycle across a named account list of banks, credit unions, and fintechs: from cold outreach to signed contract, with no BDR and no solutions engineer. We've codified that work too.

What You'll Do
  • Run enterprise-quality buying processes across a named account list, managing complex multi-stakeholder deals from cold outreach to close
  • Build champions who can defend January in rooms you're not in: equip them with materials, prepare them for internal meetings, and war-game objections before they surface
  • Construct business cases grounded in recovery rate uplift and financial impact as opposed to feature comparisons, making the cost of inaction palpable to a member of the C-suite
  • Navigate procurement, legal redlines, and compliance dependencies independently, surfacing constraints proactively rather than after signature
  • Maintain exceptional deal hygiene: work cold and warm leads, disqualify what doesn't fit, and prioritize accounts that scale as opposed to just adding another logo
  • Codify what you learn (winning messages, buyer archetypes, recurring objections) back into a GTM motion that gets sharper with every deal


What We're Looking For

We care more about how you think than where you've been. That said, the profiles that tend to thrive here share some things in common.
  • You're comfortable owning a number. You've either carried quota directly or operated close enough to revenue ownership that missing the target was a problem you constantly solved for.
  • You push past the surface signal. When a deal stalls, "they went quiet" is never a complete explanation. When a quarter comes up short, the first place you look is your own approach. You apply the same diagnostic rigor inward and outward, to your pipeline and to yourself.
  • You don't wait for all the answers. You operate at 70% confidence rather than waiting for certainty. You surface deal risks before they become surprises. You build your own structure from a cold account rather than waiting for a manager to hand it to you.
  • You understand the incentive structures underneath a deal. Not just who the buyers are, but what they're optimizing for, what organizational pressures they're navigating, and what makes a "yes" politically possible inside a regulated institution.
  • You know what to work on. With a named account list and limited time, you make deliberate choices every day about where your energy goes. You resist the pull of lower-leverage wins that feel like progress but don't compound.
  • You communicate at the altitude the room requires. You can shift from a mid-level manager to a function leader without losing the thread. You write to make people see the problem differently.


Background Signals We Look For

Strong candidates have come from conventional AE roles as well as consulting, banking, partnerships, or strategy and growth functions. We care about demonstrated ability to navigate complex, multi-stakeholder commercial processes and a track record of generating revenue without heavy structural support.

A few things we find interesting, though none are requirements: experience selling technically complex or regulated products, early employee experience at a high-growth company, and backgrounds that started in banking or consulting before moving commercial.

If you're earlier in your career but moving fast, don't self-select out.

How We Work
  • Decentralization beats control. The best calls get made by the people closest to them, not routed up a chain. You'll set the standards that let the team decide without you in the room.
  • Speed beats perfection. You run tight loops, act at 70% on reversible calls and adjust as you learn. Fast loops beat slow ones.
  • Candor beats comfort. You'd rather hear a hard truth early than a polite sidestep that wastes everyone's time.
  • Writing beats the average meeting. Clarity scales.
  • AI runs through everything here. We built our own code reviewer that beats the alternatives. Our voice AI handles most inbound calls with zero hallucinated payments. Engineers ship 3-4x the PRs they used to. You'll push it further into the work than almost any company you've worked at.
  • We operate at every altitude. No one here lives only on Mount Olympus, not even the leaders. We get into the trenches to learn the ground truth, then refine our information flows so ground truth climbs as fast as direction comes down.
  • We build in person, at least three days a week in our office in Nolita, with a growing group coming in every day. Random run-ins cross-pollinate ideas. Face time builds trust no thread can. Building alongside people makes work far more fun.


We are currently hiring for this position in our New York office.

As a New York City-based company, we are dedicated to transparent, fair, and equitable compensation practices that reflect our commitment to fostering an environment where all team members are valued and supported. We encourage individuals from all backgrounds to apply.

About Debtsy

Debtsy is a financial services company that provides a platform for users to manage their debt. The company was founded in 2019 and is based in San Francisco, California. Debtsy's platform allows users to track their debt, create a personalized payment plan, and receive personalized recommendations to help them pay off their debt faster. The company's mission is to help people take control of their finances and achieve financial freedom.
Learn more about Debtsy
Size
50 employees
Industry
Net Income
-$50,000
Founded
2019
5 Year Trend
+20%
Revenue
$100,000

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