Account Executive (First GTM Hire)

Overview

You're employee #1 in go-to-market at Debbie, a Series A fintech that partners with credit unions and banks to offer their members a debt payoff and savings rewards program. You'll be selling into financial institution executives (CEOs, COOs, heads of marketing/member engagement at credit unions and community banks), running full-cycle deals with zero playbook, and building the sales process as you go. This is true 0-to-1 sales—no CRM hygiene rules, no established pitch deck, no "here's how we do it" documentation.

Role Snapshot

Company Context

Stage: Series A ($5.46M raised, March 2024)

Size: 54 employees

Growth: Just raised Series A, hiring first sales person indicates shift from founder-led sales to building a GTM team

Market Position: Category of "financial wellness platforms for FIs" is crowded (competing with neobank partnerships, existing digital banking vendors, other fintech white-label solutions). They're positioning around psychology-based debt payoff + rewards, which is differentiated but requires education.

GTM Reality

Pipeline Sources:

• 90%+ Outbound - Cold calling credit union CEOs, LinkedIn outreach, conference networking. You're building lists from NCUA data and industry directories.
• 10% Warm intros - Founders have some relationships with FIs, but those dry up fast. You'll need to create your own pipeline.
• 0% Inbound - No marketing engine. Maybe occasional conference leads.

SDR/AE Structure: No SDR. You do everything—prospecting, qualification, demos, proposals, negotiations, contracts.

SE Support: No sales engineer. Product team might join late-stage demos, but you're running most calls solo.

Partnership Motion: Some deals might come through credit union service organizations (CUSOs) or core banking vendors, but those partnerships don't exist yet.

Competitive Landscape

Main Competitors:

• Other fintech partners (neobank integrations, BNPL providers, rewards platforms)
• Existing digital banking vendors who already have relationships
• In-house solutions (many larger CUs build member engagement programs internally)
• Status quo (doing nothing, relying on traditional financial literacy content)

How They Differentiate: Psychology-based approach to debt payoff (not just budgeting tools), actual rewards for hitting milestones, proven results (3x more debt payoff than average borrower, $100/month savings). Strong mission angle with first-gen/immigrant founder story.

Common Objections:

• "We already have digital banking/financial wellness tools"
• "Our members won't use another app"
• "How do you integrate with our core system?"
• "What's the ROI? How do we measure success?"
• "We need board approval and that takes 6 months"

Win Themes: Member engagement/retention, differentiation from big banks, mission-aligned (helping members get out of debt), concrete results data.

What You'll Actually Do

Time Breakdown

Prospecting (40%) | Active Deals (30%) | Internal Building (30%)

Key Activities

• Cold outreach to FI executives: Building lists of 500-2000 member credit unions and community banks, finding the right contact (usually CEO at smaller CUs, Head of Marketing/Digital at larger ones), calling and emailing 30-40 per day. Most ignore you. You're interrupting their day to pitch a partnership they weren't looking for.

• Running discovery and demos: When someone bites, you're scheduling 30-minute intros, doing discovery about their member engagement challenges, then running product demos. You'll do these 5-10 times per week once you get traction. Explaining how the program works, how members earn rewards, what the implementation looks like.

• Managing compliance and procurement: Financial institutions are regulated. Every deal involves compliance reviews, vendor risk assessments, privacy/security questionnaires, legal contract redlines. You'll spend hours chasing down documentation, answering the same questions for different stakeholders, waiting on their procurement timelines.

• Building sales infrastructure: Creating pitch decks, writing email templates, documenting objection handling, setting up the CRM, defining what qualifies as a good lead, creating ROI calculators, building case studies. Everything is net new. You'll spend Friday afternoons writing down what you learned that week.

The Honest Reality

What's Hard

• You're completely on your own: No sales manager, no peers, no playbook. When a deal stalls, you figure it out. When you don't know pricing for a weird use case, you make it up (then check with leadership). It's liberating and terrifying.

• Credit unions are slow: Board meetings are quarterly. Compliance reviews take 2-3 months. People go on vacation and deals sit. You'll have 6-8 active deals where you're just... waiting. Lots of "checking in" emails that go unanswered.

• Unclear buyer: Sometimes it's the CEO, sometimes it's marketing, sometimes it's the head of member services. Often all three need to say yes. You'll run the same demo 3 times for different internal stakeholders at the same credit union.

• Product is still evolving: Series A means the product has gaps. You'll sell something, then learn that feature doesn't work exactly how you described it. Engineering priorities shift. You're the voice of the field but also have to manage customer expectations.

What Success Looks Like

• Close 1-2 deals per quarter once ramped (quarters 3-4)
• Build a pipeline of 20-30 active opportunities by month 6
• Document a repeatable sales process that the next AE can follow
• Get renewals/upsells from early customers (proving the model works)

Who You're Selling To

Primary Buyers:

• Credit union CEOs (at <$500M asset CUs, they make all vendor decisions)
• VPs of Marketing/Member Experience (at larger CUs, they own engagement programs)
• COOs/Heads of Digital Banking (sometimes they own fintech partnerships)

What They Care About:

• Member engagement and retention (proving value to members)
• Differentiation from big banks ("why should someone bank with us?")
• ROI and adoption metrics (how many members will use this?)
• Ease of implementation (can't disrupt operations)
• Compliance and security (non-negotiable in financial services)
• Cost (often tight budgets, need board approval for new spending)

Requirements

• 3-5 years selling B2B SaaS or fintech, ideally into financial institutions (credit unions, banks, insurance companies)
• Comfortable with full-cycle sales—you've prospected, run demos, negotiated contracts, and closed deals yourself
• Experience selling into regulated industries or complex stakeholder environments (multiple decision makers, long cycles, procurement processes)
• Self-starter who can build structure from chaos—you don't need a playbook handed to you
• Willing to be in NYC (state income tax exemption through STARTUP-NY program)
• Bonus: Existing relationships with credit union executives or experience in the credit union/community banking world