Head of Sales

• Lead a team built on clearly defined roles (openers or SDRs, closers or account executives, and retention reps), each with a narrow, measurable scope.

• Bring our base-plus-variable compensation plan to life on the floor, so every rep knows the activities and behaviors that drive their earnings.

• Set clear expectations for every role, so reps know what good looks like each day, week and month.

• Run the floor on data: activities, connect and conversion rates, pipeline, approvals and funded volume, using the sales scorecard, Salesforce, Five9 and call recordings.

• Set daily and weekly targets, track them on a set cadence and act early when a rep or the team is off pace.

• Build forecasting discipline so leadership can predict monthly results before the month begins.

• Partner with Operations and Technology on lead flow, deal routing and the tools that make reps more productive, including AI call scoring and automation.

• Own the rep lifecycle: hiring, onboarding and ramp, development, and promotion through clear performance tiers.

• Partner with the Head of Enablement to deliver the Fundwell Academy in New York, from new-hire ramp to ongoing skill building.

• Coach daily through call reviews, ride-alongs, role-play and one-on-ones, so improvement is measurable and specific.

• Address underperformance quickly and fairly, with clear plans and support from HR.

• Build a steady recruiting pipeline for sales talent with HR, and hire against Fundwell’s competencies.

• Develop team leads and future managers, so the team can grow without losing quality.

• Make sure every rep recommends the financing that fits the business owner, and explains cost and terms plainly before they sign.

• Uphold compliance standards for merchant data, credit pulls, opt-outs and funder requirements.

• Team: a motivated, fully staffed New York floor where every rep knows their role, their numbers and how to win.

• Performance: a rising share of ramped reps consistently hit their targets, in line with the company goal of moving from x % to y%.

• Predictability: monthly results are forecast accurately before the month begins.

• Ramp: new hires reach productivity faster, with clear milestones through each success tier.

• Bench: a hiring pipeline and developing team leads let the floor grow on plan.

• Customer outcomes: conversion and renewal rates improve, and deals fit the business owner’s needs.

• 10+ years of sales experience, including 5+ years managing and coaching an inside sales team.

• Required: experience in high-volume, transactional sales to small and medium-sized businesses in lending, merchant cash advance, revenue-based financing and/or payments.

• Experience building or scaling a structured inside sales team, with defined roles and activity-based compensation.

• Deep comfort with sales data: dashboards, conversion funnels, activity metrics and forecasting. Experience with Salesforce and a dialer such as Five9.

• Proven coaching ability: you have built onboarding and ramp programs and moved average performers into top performers.

• Experience hiring at volume and building tiered career paths for sales reps.

• Strong ethics and judgment in selling financial products to business owners.

• A visible, energetic leadership style on the floor: you set the pace, celebrate wins and hold people to a high bar.
  

• Real ownership: build and lead the New York sales floor, with leadership backing and the tools to win.

• Join a growing fintech investing in data, AI and modern sales tools, including live dashboards and AI call scoring.

• Work in person with a New York team that moves fast and cares about doing right by small businesses.
  

Fundwell is an equal employment opportunity employer. We make employment decisions without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status or any other characteristic protected by law.