SR Account Executive (Miami)

LendingWise — Senior Account Executive

Oct 17, 2026 · @Chris Fuelling

Remote (US) · Full-time W-2 · Eastern or Central time zone preferred

About LendingWise

LendingWise is the CRM and loan origination system (LOS) built for private lending. Lenders and brokers run their entire business on it, from first lead to closed loan.

Our customers originate bridge, fix & flip, ground-up construction, DSCR rental, and commercial real estate loans They range from small brokerages to direct lenders, small banks, and credit unions with 100+ employees.

We've been in business 10+ years and our platform has processed $100B+ in loans. We're bootstrapped, founder-led, and growing every month. We answer to customers, not investors.

The Opportunity

We're hiring a Senior Account Executive who can run two very different sales motions without blending them together.

On Monday you might close a three-person fix & flip broker in two calls. On Tuesday you might be on discovery call three with a 75-person bridge lender: mapping the COO, the processing team, the fund manager, and outsourced IT, then building a close plan with them.

Most reps are good at one of these. We need someone who knows the difference and sells each one the right way.

Private lending is a tight-knit industry. Every lender talks to every other lender, so we don't burn accounts to hit a number. You'll sell on value, protect margin, and set customers up to succeed after the signature. You'll work directly with the CEO and have real input on how our sales playbook evolves.

What You'll Own

1. Enterprise deals (50+ employee lenders, banks, credit unions)

• Run multi-stakeholder cycles of 45–120 days, from discovery to signature.

• Map the buying committee: owner, COO, processing and underwriting, loan officers, capital markets, finance, IT, and compliance.

• Build and run a mutual action plan with every enterprise prospect.

• Deliver tailored demos built on the prospect's own loan scenarios.

• Manage security reviews and vendor due diligence, with support from our technical team.

• Build business cases that justify the investment, then negotiate terms that protect margin.

2. SMB deals (brokers and small lenders)

• Work inbound and outbound SMB opportunities with a tight, disciplined follow-up cadence.

• Close efficiently without leaning on discounts.

• Hand every new customer to Customer Success with clean, complete notes.

3. Pipeline and process

• Build your own enterprise pipeline using Apollo, LinkedIn, industry events, and referrals.

• Keep HubSpot accurate: deal stages, stakeholders, next steps, and close dates.

• Forecast honestly and bring your deals to a weekly deal review.

• Feed what you hear in the market back to product and marketing.

What You Bring

Required

• 4+ years as a closing AE in B2B SaaS, including deals of $15K–$100K+ ACV with 3+ stakeholders.

• A track record of running mutual action plans or MEDDICC-style qualification, with examples you can walk us through.

• Experience selling into financial services: lending, mortgage, banking, or fintech.

• The judgment to tell a 2-call SMB close from a 6-month committee deal, and to sell each one differently.

• A habit of trading value for concessions instead of giving away price.

• A disciplined CRM practice (HubSpot preferred) and honest forecasting.

Preferred

• You've sold an LOS, loan servicing software, or lending data/technology.

• You know private lending products: bridge, DSCR, construction draws, CRE.

• You've handled vendor due diligence or security reviews with banks or credit unions.

• You have a network in the private lending and real estate investor world.

Not a fit if

• Your best quarters came from volume-closing with heavy discounts.

• You treat every prospect the same way.

Compensation

• Base salary: $(75,000–90,000)

• On-target earnings (OTE): $(140,000–170,000), uncapped.

• Commission: paid on net new ARR. Enterprise ARR earns a higher rate, to reward longer, larger deals.

• Bonuses: for annual prepay and multi-year contracts.

• Ramp: a guaranteed ramp period while you learn the platform and build pipeline.

• Benefits: (health )

Final pay depends on experience and location.

What Success Looks Like

First 90 days

• You've completed LendingWise University and passed our SMB and enterprise demo certifications.

• You're closing SMB deals independently, with clean HubSpot records and no off-policy discounts.

• You're running 3+ enterprise opportunities with active mutual action plans.

6 months

• You're fully ramped and hitting quota.

• You've closed your first enterprise deals end to end.

• Your pipeline is 3x+ your quota, built partly from your own outbound.

12 months

• You've raised our average enterprise contract value.

• Your customers go live smoothly and renew.

• You've helped shape the sales playbook the next AE will learn from.

Why This Role

• Direct access to the CEO. No layers between you and decisions.

• A product people depend on. Lenders run their whole business on LendingWise, so it isn't a nice-to-have.

• Expanding platform. Servicing, draw management, fund management, and AI tools give you more to sell into every account.

• Real influence. Your feedback shapes the playbook, the product, and our pricing.

How we sell

• We sell to an SMB broker and a 100-person lender differently, because they buy differently.

• We trade, we don't discount. Every concession earns something back.

• A deal isn't won until the customer is live and getting value.

• We protect our reputation. Private lending is a small world.

How to Apply

Send your resume and short answers (3–5 sentences each) to these three questions. Applications without them won't be reviewed.

1. Describe your largest deal with 3+ stakeholders. Who were they, who almost blocked it, and how did you get it done?

2. Tell us about a deal you walked away from, or held firm on price, instead of discounting. What happened?

3. Describe your follow up/Sales plan for a 3-person broker vs. a 75-person direct lender?

Our process: a 30-minute intro call, two scheduled role plays (one SMB, one enterprise), a short written deal plan, and a final conversation with our CEO.

Want to follow up on your application? Conact